Things to Do in Chicago. Activities, Experiences, Adventures

Outdoor Adventures

Embrace Chicago's outdoor spaces, from its lakefront to its urban trails.

Land & Water Activities

Hiking & Cycling

The Lakefront Trail, an 18-mile paved path along Lake Michigan, popular for walking, running, and cycling. The 606 Trail urban cycling. Forest Preserves offer unpaved trails.

Water Sports

Kayaking and paddleboarding are available on the Chicago River and Lake Michigan. Boating and swimming (seasonal) on Lake Michigan are popular.

Adrenaline Experiences

Skydeck Ledge at Willis Tower (glass box on 103rd floor) and 360 Chicago Tilt!

Wildlife & Nature Escapes

Lincoln Park Zoo: Free admission, with close encounters with various animals.
Peggy Notebaert Nature Museum: Exhibits on local wildlife and ecosystems.
Forest Preserves of Cook County: Numerous unpaved trails for hiking and nature walks.
Urban Birding: Spots along the lakefront attract migratory birds.

Trail Exploration

Lakefront Trail for urban walks.
606 Trail for unique city cycling.
Forest Preserves for nature walks.
Mountain biking trails outside the city.

Waterway Activities

Kayaking on Chicago River.
Paddleboarding on Lake Michigan.
Boat tours from Navy Pier.
Seasonal swimming at city beaches.

Scenic Views

Skydeck for city panoramas.
360 Chicago for unique downward views.
Lakefront Track for city skyline.
North Avenue Beach for sunset vistas.

Safety Advisory

Always check weather conditions before engaging in outdoor water activities on Lake Michigan, as conditions can change rapidly.

Cultural Immersion

Dive into Chicago's rich cultural fabric through hands-on experiences and performances.

Workshops & Classes

Cooking Classes: Learn culinary skills at The Chopping Block or Read It & Eat.
Art Classes: Various local art studios offer workshops for different mediums.
Dance Classes: Numerous dance studios across the city offer drop-in classes.
Language Learning: Schools in Chicago offer short-term courses.

Cultural Performances

Theater

Catch touring Broadway shows, Steppenwolf Theatre Company, or Goodman Theatre productions.

Music & Dance

Experience world-renowned Chicago Symphony Orchestra, Lyric Opera, or Joffrey Ballet.

Comedy

See improvisational comedy at The Second City, where many famous comedians started.

Community Tourism

Explore diverse neighborhoods like Chinatown, Pilsen, Little Italy, or Bronzeville for authentic cultural experiences.

Cultural Festivals

Chicago hosts numerous ethnic festivals throughout the year, especially in the summertime, with a soundtrack, food, and cultural celebrations.

Major Events

The Taste of Chicago, Chicago Jazz Festival, Lollapalooza, and Chicago Blues Festival are popular annual events.

Relaxation & Wellness

Find moments of calm and rejuvenation amidst the urban energy.

Spas & Wellness

A lot of luxury accommodations feature excellent spas with a selection of treatments.
Independent spas throughout the city offer massages and facials.
Yoga studios offer drop-in classes.
Nature retreats are typically outside the city.

Waterfront Relaxation

City Beaches

Beaches along Lake Michigan are popular for relaxation during summer.

Hotel Pools

A lot of hotels have indoor or outdoor pools for swimming and unwinding.

Riverwalk Strolls

Enjoy a relaxing walk along the Chicago Riverwalk, with scenic views.

Entertainment & Nightlife

Live Music

Experience jazz/blues at Green Mill, Kingston Mines, Buddy Guy's Legends, and Andy's Jazz Club.

Nightclubs

River North, West Loop, and Wicker Park host numerous nightclubs and dance venues.

Bar Districts

River North for upscale bars; Wicker Park/Bucktown/Logan Square for trendy spots; Wrigleyville for sports bars.

Shopping & Markets

Discover everything from luxury brands to unique artisan crafts.

Traditional Markets

Maxwell Street Market (Sundays): Eclectic outdoor market featuring a range of food vendors and merchandise.
French Market (daily): Indoor food market with an European feel, prepared foods and specialty items.
Green City Market (seasonal): Popular farmers market vending local produce and artisanal goods.
Artisan Workshops: Explore independent boutiques in Lincoln Park, Andersonville, and Wicker Park for handcrafted items.