Chicago is a city full of surprises, with something exciting around every corner. From world-famous museums to tasty local food, there’s always something new to try.
Whether you’re visiting for the first time or you live nearby, this list of things to do in Chicago will help you make the most of your time. Get ready to explore, have fun, and find your new favorite spot!
🏠 Where to Stay in Chicago
- 💎 Luxury Hotel: Nobu Hotel Chicago, Chicago
- ✨ 5-Star: Trump International Hotel & Tower Chicago, Chicago
- 🏨 4-Star: Riu Plaza Chicago, Chicago
- 🛏️ 3-Star: The Willows Hotel, Chicago
- 💸 Cheap: Congress Plaza Hotel Chicago, Chicago
- 🏢 Apartment: Homewood Suites by Hilton Chicago Downtown - Magnificent Mile, Chicago
- 👨👩👧👦 For Families: Central Loop Hotel, Chicago
- 🏩 For Couples: River Hotel, Chicago
💁 Best Guided Tours
- Chicago River Narrated Architecture Indoor-Outdoor Boat Tour from € 42 (⭐4.9/5)
- Chicago River Architecture Cruise History and Sightseeing Tour from € 45 (⭐4.8/5)
- Chicago River 45-Minute Architecture Tour from Magnificent Mile from € 30 (⭐4.7/5)
- Chicago River and Lake Michigan Sunset Boat Tour from € 50 (⭐4.9/5)
Best Things To Do in Chicago
1. Art Institute of Chicago
Iconic Masterpieces. The Art Institute of Chicago is where I found myself face-to-face with classics like Seurat’s “A Sunday on La Grande Jatte,” Hopper’s “Nighthawks,” and Grant Wood’s “American Gothic.” The Modern Wing, designed by Renzo Piano, gave me a fresh look at contemporary art and stunning city views.
Special Exhibitions. I timed my visit for the Frida Kahlo show, which needed a special $5 ticket on top of regular admission. Joining the virtual line was easy with a quick scan at the entrance. The museum often hosts big-name exhibitions-always check what’s on before you go.
Admission Prices
| Ticket Type | Price (USD) | Price (EUR) |
|---|---|---|
| Adult (non-resident) | $32 | €30 |
| Senior/Student (non-res.) | $26 | €24 |
| Adult (Chicago resident) | $20 | €19 |
| Adult (Illinois resident) | $27 | €25 |
| Teen (Chicago) | Free | Free |
| Child (under 14) | Free | Free |
Practical Tips. I used public transport to reach 111 S Michigan Ave-buses and the ‘L’ stop nearby. Free admission is available for children, Chicago teens, and Illinois residents on select days. I recommend grabbing the CityPASS if you plan to visit multiple Chicago attractions-it saved me both time and money.
My Highlights. I loved the Thorne Miniature Rooms and the armor collection-great for families. The Ryan Learning Center lets kids (and adults) create their own art adventure. The museum’s free app made my visit smoother, with audio tours and interactive maps.
⭐ Best Activities
- Tour: Skip-the-Line Art Institute of Chicago Guided Tour – Enjoy a guided tour of the Art Institute of Chicago, skipping the lines and exploring masterpieces by Picasso, Monet, van Gogh, and more with expert commentary.
- Ticket online: The Art Institute of Chicago: Fast Pass – Secure fast-track entry to America’s second-largest art museum and see iconic works by Monet, Hopper, Dalí, and many more, with a free audio guide included.
2. Navy Pier and Centennial Wheel
Lakefront Fun. Navy Pier is my go-to spot when I want a mix of city energy and lake views. I walked along the 3,300-foot pier, passing gardens, shops, and street performers, all with Lake Michigan sparkling beside me.
Centennial Wheel Experience. The Centennial Ferris Wheel lifts you nearly 200 feet above the city. I rode in a comfy, enclosed gondola, enjoying three full revolutions with sweeping 360-degree views of downtown Chicago and the lake. The LED lights at night are a bonus.
Price Comparison.
| Ticket Type | Price (USD) | Price (EUR) |
|---|---|---|
| Centennial Wheel | $18–$21 | €17–€20 |
| Fastpass Express | $28–$35 | €26–€32 |
| Navy Pier Entrance | Free | Free |
Practical Tips. There’s no fee to enter Navy Pier itself-just pay for rides or attractions. I recommend public transport or rideshare, as parking can be expensive and crowded. The pier is at 600 E Grand Ave, and everything from boat cruises to the Children’s Museum is right there.
My Highlights. I caught a live concert and watched street artists perform. The pier is perfect for families, couples, or anyone who likes people-watching, food, and fun. For a real treat, I tried a sunset ride on the Centennial Wheel-the city lights were unforgettable.
⭐ Best Activities
- Tour: Private Day Sailing on Lake Michigan – Sail Lake Michigan on a private yacht, enjoying skyline views and a relaxing cruise with your own captain.
- Ticket online: Navy Pier: Play the Park Pass – Get access to Chicago’s iconic Centennial Wheel, carousel, and more fun rides at Navy Pier with this all-in-one park pass.
3. Willis Tower Skydeck and 360 Chicago
Sky-High Thrills. Standing on the Skydeck at Willis Tower, I stepped onto The Ledge-a glass box 1,353 feet above the city. My stomach did a little flip as I looked straight down at the streets below. The panoramic views stretched from Lake Michigan to the distant suburbs.
Observation Decks Compared. I also visited 360 Chicago at 875 N Michigan Ave, home of the Tilt platform. I felt a rush as the glass moved forward, giving me a unique angle on the skyline. Both decks offer different vibes: Willis Tower feels dramatic, while 360 Chicago is more interactive.
Ticket Prices.
| Attraction | Price (USD) | Price (EUR) |
|---|---|---|
| Willis Tower Skydeck | $32–$44 | €30–€41 |
| 360 Chicago General | $30–$44 | €28–€41 |
| 360 Chicago Tilt | +$9 | +€8 |
Insider Advice. I bought tickets online to skip the line. Both towers are busy on weekends, so I went midweek for a quieter experience. Each deck has its own café and souvenir shop-great for a quick break or a gift.
Memorable Moments. I snapped photos of the city’s famous grid and spotted Wrigley Field in the distance. If you love cityscapes, both towers are must-sees, but if you want an adrenaline kick, try the Tilt at 360 Chicago.
⭐ Best Tickets
- 360 CHICAGO Observation Deck Ticket – Take in breathtaking panoramic views of Chicago and Lake Michigan from the 94th floor of the John Hancock Center.
- Skydeck Chicago at Willis Tower Ticket – Step out onto The Ledge for a thrilling glass-floor experience and unbeatable city views from the Willis Tower.
4. Chicago Riverwalk and Architectural Boat Tours
Riverside Walks. The Chicago Riverwalk is my favorite place for a relaxed walk with city views. I wandered past public art, cozy cafés, and boat docks, feeling the buzz of downtown without the traffic noise.
Tour Adventures. I joined an architectural boat tour, gliding along the river as guides explained the stories behind the Wrigley Building, Tribune Tower, and Marina City. The open-air deck was perfect for photos, and I learned how the city rebuilt itself after the Great Fire.
Price Guide.
| Experience | Price (USD) | Price (EUR) |
|---|---|---|
| Riverwalk Access | Free | Free |
| Standard Tour (60–90 min) | $45–$55 | €42–€51 |
| Kayak Rental (per hour) | $25–$35 | €23–€32 |
Personal Favorites. My highlights included seeing the city’s bridges open for passing boats and spotting murals under the viaducts. The Riverwalk is a lively, ever-changing part of Chicago-perfect for people-watching, relaxing, or learning something new about the city’s architecture.
⭐ Best Activities
- 75-Minute Guided Architecture Cruise – Discover Chicago’s world-famous architecture from the water on this popular guided river cruise.
5. Wrigley Field Game
Atmosphere. Wrigley Field is a Chicago icon, and stepping into the stadium at 1060 West Addison Street always gives me a rush. The ivy-covered outfield walls, hand-turned scoreboard, and the smell of popcorn make every game feel special. The neighborhood buzzes with fans, and local bars fill up before and after the game.
Seating Choices. There’s a seat for every budget and mood. Bleacher seats are for the loudest fans, while the 400 level is more relaxed and budget-friendly. I’ve found tickets for as low as $7 online, but they can go up to $150 for the best spots. Rooftop experiences across the street are unique, with food and drinks included, but expect to pay between $89 and $149.
| Ticket Type | Price (USD) | Price (EUR) |
|---|---|---|
| Cheapest (online) | $5–$14 | €5–€13 |
| Average | $67 | €62 |
| Rooftop Experience | $89–$149 | €82–€137 |
Game Day Tips. Gates usually open 90 minutes before the first pitch. I always check the Cubs’ social media for batting practice times. If you catch a home run ball from the visiting team, tradition says you should throw it back! Public transport is the best way to get here; the Red Line stops right at Addison.
My Experience. I love the energy in the bleachers, but the upper deck offers great views for less money. Food and drinks inside are pricey, so I sometimes grab a bite from a street vendor before heading in. The crowd is friendly, and the old-school vibe makes every visit memorable.
Extra Details. The stadium is not just about baseball. Statues, party areas like Gallagher Way, and nearby shops add to the fun. Bring a jacket, even in summer-the wind can surprise you.
⭐ Best Activities
- Chicago Cubs Baseball Game Ticket at Wrigley Field – Experience the excitement of a live Cubs game at historic Wrigley Field with your reserved seat.
6. Field Museum
Immersive. The Field Museum at 1400 S Lake Shore Drive is a place where I lose track of time. I’ve wandered through ancient Egyptian tombs, stood beneath Máximo the Titanosaur, and stared up at SUE, the famous T. rex fossil. The Evolving Planet gallery took me on a journey from early life to the age of dinosaurs.
Permanent Collections. My favorites include the Cyrus Tang Hall of China, with centuries-old jade and pottery, and the Ancient Americas exhibit, where I walked through an 800-year-old pueblo. The Grainger Hall of Gems sparkles with rare stones, and the Underground Adventure lets you experience life as a bug.
Admission Prices
| Ticket Type | Price (USD) | Price (EUR) |
|---|---|---|
| Basic Admission | $26 | €24 |
| All Access Pass | $37 | €34 |
Family Friendly. The Crown Family PlayLab is perfect for kids, with hands-on activities like digging for fossils and playing instruments from around the world. The museum is fully accessible, with wheelchair rentals and sensory guides.
Practical Advice. I always wear comfortable shoes-there’s a lot of ground to cover. Tickets are cheaper if you buy online, and CityPASS or GoCity passes can save money if you plan to visit other Chicago attractions. The museum is part of the Museum Campus, so it’s easy to combine with a visit to the Shedd Aquarium or Adler Planetarium.
⭐ Best Activities
- The Field Museum Chicago Ticket – Explore one of the world’s largest natural history museums, home to Sue the T. rex and fascinating global exhibits.
7. Griffin Museum of Science and Industry
Hands-On Wonders. At the Griffin Museum of Science and Industry in Hyde Park, I felt like a kid again, surrounded by massive machines. The museum is housed in the historic Palace of Fine Arts at 5700 S DuSable Lake Shore Drive, making it a must-see for science and history fans.
Unforgettable Exhibitions. My highlights included walking through the full-size WWII U-505 submarine, exploring the Coal Mine, and watching the 40-foot tornado in Science Storms. I got lost in the Numbers in Nature mirror maze and marveled at the Pioneer Zephyr train and Boeing 727 jet. The Great Train Story’s model railroad, Colleen Moore’s Fairy Castle, and the Henry Crown Space Center were also standouts.
Admission Prices
| Ticket Type | Price (USD) | Price (EUR) |
|---|---|---|
| Adult | $25.95 | €24 |
| Child (3–11) | $14.95 | €14 |
| Special Exhibits | +$12–$18 | +€11–€17 |
Personal Favorites. I loved the Science Storms area-controlling lightning and avalanches was unforgettable. The museum’s seasonal “Christmas Around the World” is magical, with decorated trees and cultural displays. Plan for at least half a day-there’s so much to see, you’ll want to stay longer.
⭐ Best Activities
- Chicago Museum of Science and Industry Ticket – Dive into interactive science, a WWII submarine, and hands-on fun at this top Chicago museum.
8. Grant Park
Urban Oasis. Grant Park’s 319 acres stretch from the Loop to Lake Michigan, offering a blend of open lawns, gardens, and cultural landmarks. I wandered to see Cloud Gate and Crown Fountain, then crossed to Maggie Daley Park with its skating ribbon and playgrounds.
Landmarks and Events. The park is home to the Art Institute of Chicago, Museum Campus, and the iconic Buckingham Fountain. I’ve joined crowds at the Taste of Chicago food festival and listened to music at the Grant Park Music Festival. The park’s wide paths are perfect for jogging, cycling, or a peaceful walk.
Facilities and Activities.
| Activity/Facility | Cost (USD/EUR) | Details |
|---|---|---|
| Park Entry | Free | Open daily 6am–11pm |
| Sports Courts | Free | Tennis, baseball |
| Events | Free–Ticketed | Seasonal, various fees |
⭐ Best Activities
- 1-Day Chicago City Tour – See Chicago’s highlights in a single day with a guided city tour covering major landmarks and neighborhoods.
9. The Chicago Theatre
Grand Entrance. The Chicago Theatre at 175 N State St is impossible to miss with its famous red marquee. Walking into the ornate lobby, I was wowed by the sweeping staircase, French Baroque details, and murals that set the stage for a night out in the Loop.
Live Events. I’ve seen everything here, from comedy shows and concerts to Broadway tours and special events. The theater seats 3,600 and every seat feels close to the action. Guided tours are available for those who want to explore behind the scenes and learn about the building’s history.
Ticket Prices.
| Event Type | Price (USD) | Price (EUR) |
|---|---|---|
| Tour Experience | $33 | €30 |
| Concerts/Shows | $30–$105+ | €28–€97+ |
Personal Highlights. My favorite memory is seeing a jazz band play under the grand arch, the sound filling the historic auditorium. Even if you’re not catching a show, the tour is worth it for a look at one of Chicago’s most beautiful buildings.
⭐ Best Activities
- Chicago Theatre Marquee Tour – Go behind the scenes at the legendary Chicago Theatre with a guided tour of its historic stage and iconic marquee.
10. Clarence F. Buckingham Memorial Fountain
Spectacle. Watching the hourly water shows at Buckingham Fountain, I was amazed by the center jet shooting 150 feet into the air. The fountain’s 133 jets create a powerful display, and after dusk, lights and music transform the scene into something magical. The evening light show, with its soft, moonlit glow, draws crowds who gather along the edges for the best view.
Design Details. The fountain sits at the heart of Grant Park and is made from Georgia pink marble. Four sets of sea horses represent the states bordering Lake Michigan. The fountain’s structure, inspired by Versailles, gives it a grand, wedding-cake look. I noticed the subtle color changes in the lights, a result of careful planning to create a dreamy, fairy-tale effect.
Operation Schedule.
| Feature | Time/Details |
|---|---|
| Water Shows | Every hour, 20 min |
| Light/Music Shows | Dusk–10:55 p.m. |
| Fountain Season | May–October |
| Entry | Free |
Visitor Experience. Free Wi-Fi is available around the fountain, making it easy to share photos instantly. The open plaza is perfect for relaxing, people-watching, or enjoying a picnic. The sound of the jets and the cool mist on warm days make this a favorite spot for both locals and visitors.
11. Chicago Architecture Center
Exhibition. At One Illinois Center, the Chicago Architecture Center (CAC) offers a deep dive into the city’s design legacy. The Chicago City Model Experience, with over 4,200 miniature buildings, let me trace the city’s growth and see how the skyline has changed.
Tours. The CAC is the launch point for more than 85 tours. I joined the river cruise, ranked among the best in the U.S., and learned the stories behind over 50 iconic buildings while gliding past them on the Chicago River. There are also walking, bus, and “L” train tours, each led by expert docents.
Admission and Tours.
| Experience | Price (USD) | Price (EUR) |
|---|---|---|
| General Admission | $15 | €14 |
| River Architecture Cruise | $54–$59 | €50–€55 |
| Walking/Bus Tours | $30–$45 | €28–€41 |
⭐ Best Activities
- Chicago Architecture Foundation Center River Cruise – Cruise the Chicago River with expert guides and learn about the city’s architectural marvels.
12. Garfield Park Conservatory
Green Escape. Stepping into the Garfield Park Conservatory, I felt like I’d left the city behind. The Palm House, with soaring ceilings and dozens of palm varieties, set the tone for a lush, tropical adventure. The Fern Room, with its lagoon and ancient cycads, offered a glimpse into prehistoric Chicago.
Gardens. Eight indoor rooms showcase everything from cacti in the Desert House to seasonal blooms in the Show House. The Aroid House features Dale Chihuly’s glass lily pads floating in the Persian Pool. Outside, 12 acres of gardens bloom in summer, and the Elizabeth Morse Genius Children’s Garden is a hit with families.
Admission and Features.
| Feature/Exhibit | Price (USD/EUR) | Notes |
|---|---|---|
| General Admission | Free | Donations welcome |
| Special Events | $5–$15 | Some ticketed |
Community Connections. The conservatory hosts events like the Spring Flower Show, County Fair, and Fleurotica. Educational programs engage visitors of all ages, and there’s always something new to discover, from hands-on science to art installations. The peaceful Horticulture Hall is ideal for a quiet break or attending a workshop.
Things to Do in Chicago with Kids
1. Shedd Aquarium
Underwater Worlds. At Shedd Aquarium, 1200 S DuSable Lake Shore Drive, I watched beluga whales glide by and saw reef sharks circling in the Caribbean Reef. The Amazon Rising exhibit put me eye-to-eye with piranhas and colorful frogs, while the Wild Reef’s coral tanks felt like a slice of the ocean.
Interactive Experiences. Kids and adults can touch stingrays, watch penguin feedings, and see divers interact with sea turtles. The aquatic show in the Abbott Oceanarium is a highlight, featuring dolphins and sea lions performing with trainers.
Admission Prices
| Ticket Type | Price (USD) | Price (EUR) |
|---|---|---|
| Adult | $39.95 | €37 |
| Child (3–11) | $29.95 | €28 |
| 2 & under | Free | Free |
Visitor Resources. Stroller rentals and family restrooms are available. I found the aquarium easy to navigate with clear signs and friendly staff. The Shedd is part of Museum Campus, so it’s easy to combine with the Field Museum or Adler Planetarium.
⭐ Best Activities
- Chicago C3 CityPASS – Save on top attractions like the Art Institute, Shedd Aquarium, and Skydeck with this all-in-one city pass.
2. Lincoln Park Zoo
City Wildlife. Lincoln Park Zoo, at 2001 N Clark St, is one of the country’s last free zoos. I walked through lush gardens and watched gorillas, lions, and polar bears in spacious habitats. The Regenstein African Journey and Farm-in-the-Zoo are especially popular with families.
Seasonal Activities. The zoo hosts ZooLights in winter, with thousands of twinkling lights, and Summer Wine Fest for adults. The carousel and train rides add extra fun for kids.
Admission and Extras.
| Feature | Price (USD/EUR) | Notes |
|---|---|---|
| General Admission | Free | Donations welcome |
| Carousel/Train | $4 | €4 per ride |
Good to Know. The zoo offers free wildlife talks and animal feedings throughout the day. Downloading the zoo’s app helped me find my way and check for special programs, making my visit smoother and more fun.
⭐ Best Activities
- Lincoln Park Zoo Scavenger Hunt – Explore Lincoln Park Zoo in a fun and interactive way with a self-guided scavenger hunt adventure.
3. Maggie Daley Park
Active Play. Maggie Daley Park, just east of Millennium Park, is a wonderland for families. The Play Garden is massive, with towers, slides, and bridges. I watched kids race down the giant slides and climb the suspension bridge.
Seasonal Fun. In winter, the Skating Ribbon is a favorite, winding through the park with city views. In summer, mini golf and climbing walls are open. There’s also a picnic grove and plenty of shaded benches for a break.
Activity Prices.
| Activity | Price (USD) | Price (EUR) |
|---|---|---|
| Skating Ribbon | $16–$20 | €15–€19 |
| Mini Golf | $12 | €11 |
| Climbing Wall | $16 | €15 |
Family Tips. Restrooms and water fountains are easy to find. I recommend arriving early on weekends, as the playground gets busy. The park is stroller-friendly and close to public transport.
Accessibility Note. The entire park is wheelchair accessible, and adaptive equipment is available for the climbing wall. Staff are happy to help with any special needs, making it a welcoming spot for everyone.
4. Chicago Children’s Museum
Hands-On Learning. Located on Navy Pier, the Chicago Children’s Museum is packed with interactive pieces. I watched kids build skyscrapers, climb through the Treehouse Trails, and splash in the WaterWays zone. The Tinkering Lab lets children use real tools to make their own creations.
Special Programs. Story times, art workshops, and science demonstrations run daily. The museum is designed for ages 2–10, but older siblings often join in the fun.
Admission Prices
| Ticket Type | Price (USD) | Price (EUR) |
|---|---|---|
| Adult/Child (1+) | $21 | €19 |
| Under 1 | Free | Free |
Visitor Essentials. There are quiet spaces for sensory breaks and a family-friendly café. The museum is fully accessible and offers free admission on select Thursday evenings. I found it a perfect spot for a rainy day or when kids need to burn off energy.
⭐ Best Activities
- Chicago Children's Museum Entry Ticket – Let kids explore, play, and learn at Chicago’s top museum on Navy Pier.
Free Things to Do in Chicago
1. Millennium Park and Cloud Gate
Iconic Art and City Life. Millennium Park, right in downtown Chicago, is famous for Cloud Gate-known as “The Bean.” This shiny, stainless steel sculpture is a favorite for photos. Walking under it, I noticed how the curved surface distorts reflections, making every angle unique. The park also features Crown Fountain, where kids splash in the water, and the Jay Pritzker Pavilion, with its bold architecture and open-air concerts.
Events and Activities. There’s always something happening here. In summer, I joined crowds on the Great Lawn for free music and movie nights under the stars. Outdoor yoga, Pilates, and tai chi classes are offered for free, and in winter, the park hosts Chicago’s official Christmas tree and festive markets. Lurie Garden is a peaceful spot for a walk among native plants and flowers.
Practical Details.
| Feature/Activity | Cost (USD/EUR) | Notes |
|---|---|---|
| Park Entry | Free | Open daily |
| Cloud Gate | Free | Photo spot |
| Concerts/Movies | Free | Seasonal |
| Crown Fountain | Free | Splash zone in summer |
| Lurie Garden | Free | Gardens open to all |
Getting Around. The park is accessible by public transport and has underground parking. Free WiFi is available, making it easy to share your photos instantly. I found plenty of benches for resting, and the park is stroller- and wheelchair-friendly.
2. Chicago Cultural Center
Architectural Treasure. The Chicago Cultural Center is a landmark building with two of the world’s largest stained-glass domes. I was amazed by the Tiffany dome’s colors and the marble mosaics throughout the halls. The building’s Classical Revival style and historic details make it worth visiting even if you’re not attending an event.
Free Arts and Culture. Admission is always free. I explored art exhibitions featuring local and international artists, and caught a live music performance in the Preston Bradley Hall. The center also hosts film screenings, lectures, dance, and family workshops. The Learning Lab offers interactive experiences for all ages, and the Buddy shop supports local artists and makers.
Visitor Information.
| Feature/Activity | Cost (USD/EUR) | Notes |
|---|---|---|
| General Admission | Free | Open daily |
| Concerts | Free | Check calendar for events |
| Guided Tours | Free | In-person or virtual |
| Buddy Shop | Free entry | Pay for items |
Amenities. The Welcome Center provides orientation and event info. Public restrooms, elevators, and seating areas are available. The building is centrally located, making it easy to combine both in one visit.
3. Lakefront Trail and Beaches
Outdoor Adventure. The Lakefront Trail is Chicago’s 18-mile paved path along Lake Michigan. I biked from Ardmore Avenue to 71st Street, passing parks, gardens, and beaches with views of the lake’s blue water. The trail is popular for walking, running, biking, and rollerblading, and connects neighborhoods like Edgewater and Hyde Park.
Beaches and Recreation. There are 24 public sand beaches along the trail, including North Avenue Beach and Oak Street Beach. Admission is free, and lifeguards are on duty from 11 a.m. to 7 p.m. during the summer. I stopped at Montrose Dog Beach to watch playful pups and grabbed a snack at a lakeside café. Volleyball courts, playgrounds, and water sports rentals are available at many beaches.
Trail and Beach Details.
| Feature/Activity | Cost (USD/EUR) | Notes |
|---|---|---|
| Trail Access | Free | Open 6am–11pm daily |
| Public Beaches | Free | Lifeguards on duty in summer |
| Bike Rental | $10–$20/hr | Divvy bikes available |
| Beach Facilities | Free | Restrooms, concessions, playgrounds |
Safety and Tips. The trail can get busy, so I stayed to the right and watched for signs marking pedestrian and bike lanes. Public restrooms are available at most parks and beaches, but some close in fall. Swimming is only allowed when green or yellow flags are flying, and red flags mean no swimming due to safety concerns.
5. The 606/Bloomingdale Trail
Elevated Greenway. The 606, also known as the Bloomingdale Trail, is a 2.7-mile elevated park and trail running from Ridgeway Avenue to Ashland Avenue. I walked above city streets, passing through Bucktown, Logan Square, Humboldt Park, and Wicker Park, with city views and public art around every bend. The trail is lined with native plants and features 37 bridges, each with its own character.
Activities and Access. Walking, biking, running, and skating are all welcome here. I found Divvy bike stations nearby and noticed families, joggers, and even dogs enjoying the space. There are twelve access points, making it easy to hop on or off and explore connected parks like Walsh Park and Churchill Park. The trail is open daily from 6 a.m. to 11 p.m.
Trail Etiquette and Features.
| Feature | Details |
|---|---|
| Length | 2.7 miles (4.3 km) |
| Hours | 6am–11pm |
| Entry | Free |
| Activities | Walk, run, bike, skate |
| Access Points | 12, with parks and playgrounds |
Community Connection. The 606 links diverse areas and hosts events like art installations and family-friendly runs. I enjoyed stopping at the Damen Arts Plaza for a break and watching local artists at work. Humboldt Overlook gave me a great view of the city’s historic boulevards.
Safety Note. The path can get busy, especially on weekends. I kept to the right, passed on the left, and watched for fast-moving cyclists. Dogs are welcome but must be leashed. There’s security and lighting at night, but I felt safest during daylight hours.
6. Old Town Walks
Historic Area. Exploring Old Town, I wandered tree-lined streets filled with vintage homes, cobblestone alleys, and landmarks like St. Michael’s Church, a survivor of the Great Chicago Fire. The area’s mix of German and Irish immigrant history, artists’ studios, and Civil War–era cottages gives it a unique, lived-in feel.
Walking Tour Highlights. My route started on Wells Street, famous for its restaurants, pubs, and the legendary Second City comedy club. I turned onto West Burton Place, where Depression-era artists transformed old houses into creative studios. Menomonee Street, with its rare “fire relief” shanties, offered a glimpse of resilience after 1871.
Tour Information.
| Feature | Details |
|---|---|
| Distance | 1.6–1.75 miles (2.6–2.8 km) |
| Entry | Free (self-guided) |
| Notable Stops | Wells St, St. Michael’s, Second City, West Burton Place, Menomonee St |
| Art Fairs | Old Town Art Fair (June), Wells Street Art Festival (June) |
Local Flavor. I stopped at Marge’s Still, a historic tavern, for a pot pie and a pint. The area is dotted with boutiques, coffee shops, and galleries. Annual art fairs fill the streets with music, food, and creativity.
Getting There. Old Town is easy to reach by CTA Red or Brown Line (Clark/Division or Sedgwick stops). Walking is the best way to see the area, and the Old Town Triangle Tours app offers extra stories and hidden gems from local residents.
7. Promenades
Chase Promenade. The Chase Promenade is an 8-acre, tree-lined walkway stretching from Randolph Street to Monroe Street. I enjoyed strolling past outdoor art exhibitions, festival tents, and pop-up events. The promenade is divided into North, Central, and South sections, each hosting different activities throughout the year.
Events. The space is known for large-scale art installations, like the Burnham Pavilions and the Museum of Modern Ice. Seasonal events, family activities, and open-air markets make it lively and ever-changing. I once caught a photography exhibition that stretched the length of the Central Promenade.
Promenade Details.
| Feature | Details |
|---|---|
| Location | Millennium Park |
| Size | 8 acres (3.2 ha) |
| Entry | Free |
| Events | Art, markets, rentals |
| Public Transit | Metra, CTA Red, Brown, Blue Lines |
Atmosphere. The wide paths and shade from mature trees make the promenade a relaxing escape from city noise. Benches and open lawns invite picnics and people-watching. It’s a favorite spot for locals and visitors alike.
Practical Info. The promenade is fully accessible and close to major attractions like Cloud Gate and the Art Institute. Restrooms, water fountains, and plenty of seating are available, making it a convenient stop during a day in downtown Chicago.
Seasonal Activities
Christmas in Chicago
Festive Lights and Parades. Chicago comes alive with the Magnificent Mile Lights Festival, kicking off the season with over one million lights and a dazzling parade on Michigan Avenue (Nov. 23, 5:30–7:30 p.m.). The city’s official Christmas Tree Lighting takes place in Millennium Park on Nov. 22 at 6 p.m., with the tree glowing through Jan. 8.
Holiday Markets and Experiences. The Christkindlmarket (Nov. 22–Dec. 24, Daley Plaza and Aurora) brings German treats, artisan gifts, and the famous boot mug. Wrigley Field’s Winterland offers skating, rides, and Santa’s Workshop, while Navy Pier hosts Light Up the Lake (Nov. 29–Jan. 5) with outdoor lights and fireworks on Saturdays. Hop on the CTA Holiday Train or Bus for a festive ride with Santa, or visit the Jack Frost Pop-Up for bumper cars.
Cultural Traditions and Shows. Don’t miss “Christmas Around the World” at the Griffin Museum of Science and Industry (Nov. 16–Jan. 6), featuring 50+ decorated trees. The Goodman Theatre’s “A Christmas Carol” (Nov. 16–Dec. 30) and the Beatrix Potter Holiday Party (Nov. 23–Dec. 29, Chicago Children’s Theatre) are family favorites.
Summer Festivals and Events
Music and Dance. Chicago’s summer is packed with world-class music events. The Chicago Blues (June 5–8) is the world’s largest free blues fest. The Summer Music Series (Mondays & Thursdays, June 26–Aug. 7) and Grant Park Music Festival (June–Aug.) offer free outdoor concerts. Chicago SummerDance (select dates June–Sept.) transforms parks into open-air dance floors with free lessons and live bands.
Major Events. Lollapalooza (July 31–Aug. 3, Grant Park) brings top artists and huge crowds. The Chicago Jazz (Aug. 28–31) and Chicago House Music Festival (Aug. 22–23) showcase the city’s musical roots. Don’t miss Taste of Chicago (Sept. 5–7, Grant Park) for food from dozens of local vendors.
Neighborhood Fun and Family Events. From the Old Town Art Fair (June 14–15) to Andersonville Midsommarfest (June 13–15) and Northalsted Market Days (Aug. 9–10), every area has its own street party. The Air and Water Show (Aug. 16–17, North Avenue Beach) and Navy Pier’s summer fireworks (Wednesdays & Saturdays, Memorial Day–Labor Day) are crowd-pleasers.
Spring Blooms in Parks
Best Flower Spots. Spring in Chicago means tulips on Michigan Avenue and cherry blossoms in Jackson Park (peak bloom: late April–early May). Garfield Park Conservatory’s Spring Flower Show (March–early May) fills the glasshouse with tulips, hyacinths, and daffodils.
Gardens and Hidden Gems. The Alfred Caldwell Lily Pool in Lincoln Park is a peaceful spot for wildflowers and water lilies. Ping Tom Memorial Park in Chinatown offers cherry blossom views with skyline backdrops. Columbus Park and Washington Park burst with blooms and historic gardens. The Chicago Botanic Garden (Glencoe) is a spring highlight, with 27 themed gardens and special events like Blooming Fest (May 17, West Chicago).
Family Activities. Many parks host spring plant sales. The Model Railroad Garden (May–Oct.) and Butterflies & Blooms (end of May–Labor Day) at the Botanic Garden are especially popular with kids.
Autumn Foliage Walks
City Parks and Trails. Lincoln Park’s Nature Boardwalk and the gardens near the Conservatory offer stunning fall color, while Millennium Park and Lurie Garden are filled with reds and golds by late September through October. Stroll Jackson Park’s Garden of the Phoenix for Japanese maples, or walk the Lakefront Trail for a mix of lake views and changing leaves.
Top Leaf-Peeping Destinations. The 606/Bloomingdale Trail provides an elevated view of neighborhood trees and boulevards. Garfield Park Conservatory’s outdoor gardens and the Chicago Botanic Garden’s “Autumn-Hued Wonderland” (peak color: first two weeks of October) are must-sees. Morton Arboretum (Lisle) hosts the Fall Color 5k and Glass Pumpkin Patch, drawing families and photographers.
Seasonal Events. Zoo Fall Fest (select weekends in October) features a pumpkin patch, corn maze, and crafts. The Great Highwood Pumpkin Festival (Oct. 4–6) and Oaktoberfest (Sept. 13–14, Oak Park) blend local food, music, and autumn fun. For a unique perspective, visit 360 Chicago for panoramic views of the city’s fall colors.
Day Trips from Chicago
1. Frank Lloyd Wright’s Robie House
Prairie Style Masterpiece. At 5757 S. Woodlawn Avenue, the Robie House stands as a landmark of American design. Completed in 1910, this UNESCO World Heritage Site is celebrated for its sweeping horizontal lines, cantilevered roof, and art glass windows. Guided tours, available Thursday to Monday from 10 a.m. to 2:30 p.m., explore both public and private spaces, revealing Wright’s vision for modern living.
Tour Details. Entry is by guided tour only, with groups limited to 10–14 people for an intimate experience. Tickets cost $27 for adults, $24 for students, and $22 for seniors. The “Inside and Out” tour combines interior exploration with a self-guided outdoor audio walk along 58th Street, available in multiple languages. Children under 8 and strollers are not permitted inside.
Visitor Experience. The house is not wheelchair accessible, but service animals are allowed. Photography is permitted, and the on-site shop offers Wright-themed souvenirs. Advance booking is highly recommended, as tours fill quickly. Arrive at the Museum Shop at least 15 minutes before your scheduled time.
Nearby Sights. After your visit, explore the University of Chicago campus or stop by the Rockefeller Memorial Chapel. The area is rich in history and architectural gems, making it easy to spend a full afternoon discovering Hyde Park’s treasures.
Highlights at Robie House:
- Original art glass windows and doors
- Cantilevered roof and open floor plan
- Guided tours with expert docents
- Museum Shop with unique gifts
- Proximity to other Wright buildings in Hyde Park
⭐ Best Activities
- Frank Lloyd Wright Robie House Tour – Tour the iconic Robie House and discover the genius of Frank Lloyd Wright’s Prairie School architecture.
2. Hyde Park and University of Chicago
Campus Landmarks. The University of Chicago’s campus is a blend of Gothic architecture and peaceful green spaces. Highlights include the Harper Memorial Library Reading Room, Bond Chapel, and the Main Quadrangles, which double as a botanic garden.
Cultural Stops. Art lovers can visit the Smart Museum of Art, featuring American, Asian, and European works, or the Renaissance Society for contemporary exhibitions. The Oriental Institute Museum houses ancient artifacts from Egypt and Mesopotamia. For theater, Court Theatre offers innovative productions year-round.
Outdoor Relaxation. Botany Pond is a quiet spot for watching turtles and goldfish, while the Garden of the Phoenix in Jackson Park offers a peaceful Japanese garden experience. Promontory Point is popular for picnics and lake breezes.
Getting Around. Hyde Park is about 7 miles south of downtown, accessible by regular train service from Van Buren Street station. Cafés and independent bookstores line 57th Street, making it easy to linger for an afternoon.
Don’t Miss in Hyde Park:
- Harper Memorial Library’s reading room
- Smart Museum of Art
- Oriental Institute Museum
- Botany Pond and Garden of the Phoenix
- 57th Street Books and local cafés
3. Chicago Suburbs (Oak Park, Evanston)
Oak Park Highlights. Just 10 miles west of downtown, Oak Park is renowned for its concentration of Frank Lloyd Wright buildings. The Frank Lloyd Wright Home and Studio and Unity Temple are open for tours, with tickets starting at $20. The Oak Park Conservatory offers year-round greenery, and Scoville Park is perfect for a quiet break.
Local History. Visit the Ernest Hemingway Birthplace House or the Oak Park River Forest Museum for stories about local legends, from writers to inventors. The village also hosts walking tours like the Spring Housewalk and Forest Preserve Walking Tour.
Evanston Discoveries. On Chicago’s North Shore, Evanston is home to Northwestern University and the Block Museum of Art, which features outdoor sculptures and rotating galleries. The Halim Time & Glass Museum showcases stained glass and historic timepieces, while the Dawes House offers guided tours of a 25-room mansion.
Nature and Recreation. Evanston’s parks and gardens are ideal for a picnic or a calming yoga session. Grosse Point Lighthouse is open for tours on weekends from June to September, and Centennial Park’s sandy beach is a local favorite.
Top Picks in Oak Park & Evanston:
- Frank Lloyd Wright Home and Studio
- Unity Temple
- Oak Park Conservatory
- Ernest Hemingway Birthplace House
- Block Museum of Art (Evanston)
- Grosse Point Lighthouse (Evanston)
⭐ Best Activities
- Chicago Suburbs Movie Sites Tour – Visit famous filming locations in the Chicago suburbs on this fun movie-themed tour.
4. Lake Michigan Beaches
Beach Season. Chicago’s sandy stretches open the Friday before Memorial Day and close on Labor Day. Admission is free, and lifeguards are on duty daily from 11 a.m. to 7 p.m. Popular spots include North Avenue Beach (1600 N), Oak Street Beach (1000 N), Foster Beach (5200 N), and Montrose Beach (4400 N).
Amenities and Activities. Most beaches offer restrooms, concessions, volleyball courts, and chair rentals. Oak Street Beach Café and The Dock at Montrose Beach provide food and drinks. Foster Beach is known for its peaceful atmosphere and dog-friendly area, while Montrose Beach is a hub for kayaking and volleyball.
Family-Friendly Options. South Shore Beach features a cultural center, playgrounds, and picnic areas. 63rd Street Beach is popular for its playground and summer events. All locations have accessible walkways and bike paths nearby.
Tips for Visitors. Arrive early on weekends to secure a spot. Swimming is only allowed when lifeguards are present and green or yellow flags are flying. Bring your own snacks or enjoy local beach cafés for a relaxing day by the water.
Popular Beach Features:
- Free entry and lifeguards on duty
- Volleyball courts and kayak rentals
- Beachside cafés and concessions
- Dog-friendly areas (Foster, Montrose)
- Accessible walkways and bike paths
⭐ Best Activities
- Lake Michigan Skyline Kayak Rental at Ohio Street Beach – Paddle along the Chicago shoreline and enjoy unique views of the city’s skyline from Lake Michigan.
FAQ
What are the top things to do in Pilsen?
Pilsen is known for vibrant murals, Mexican bakeries, and the National Museum of Mexican Art. Join a food tour or stroll 18th Street for authentic tacos and lively street art.
Which Chicago neighbourhoods are best for a family-friendly visit?
Lincoln Park and the Gold Coast offer parks, zoos, and playgrounds, while Streeterville has easy access to the Magnificent Mile and LEGOLAND Discovery Center. These areas feature attractions and activities for all ages.
Where can I find the best observation deck for the skyline?
Skydeck Chicago and 360 CHICAGO both offer panoramic skyline views from towering heights. Each observation deck has unique features like The Ledge or TILT for thrill seekers.
What are the best brewery experiences in Logan Square?
Logan Square is home to Revolution Brewing and Maplewood Brewery, both with taprooms and rotating craft beer selections. Many breweries in this neighbourhood also serve food and host trivia nights.
How do I book a cruise to see Chicago’s architecture?
Architecture cruises depart daily from downtown docks and last about 90 minutes. Advance ticket purchase is recommended, especially on weekends and holidays.
Which food tour highlights deep dish pizza and local eats?
Food tours in River North and Streeterville take you to legendary spots for deep dish pizza, Italian beef, and Chicago-style hot dogs. Guides share stories about the Windy City’s food culture along the way.
What are some must-see attractions on the Magnificent Mile?
The Magnificent Mile features upscale shopping, historic landmarks, and the TILT experience at 875 N Michigan Ave. Don’t miss Water Tower Place and the Chicago Sports Museum for interactive fun.
Where can I catch a show at Chicago Shakespeare Theater?
Chicago Shakespeare Theater is located on Navy Pier and hosts classic plays, new works, and family-friendly performances. Group discounts are available for parties of ten or more.
Is Adler Planetarium suitable for kids and families?
Adler Planetarium offers hands-on activities and immersive sky shows. It’s a popular destination for school groups and families with curious kids.
How can I find things to do in different neighbourhoods?
Check local guides or tourism websites for neighbourhood highlights, from Pilsen’s murals to brewery tours in Logan Square. Each area has its own unique attractions and food experiences to discover.
