Things To Do In Chicago

River architecture, lakefront sunsets, legendary venues, and deep dish detours. Compare tickets, book must-do tours, and stitch together a Chicago trip you will actually brag about.

Top Deals In Chicago

Concerts & Venues

Historic theaters, new arenas, and summer nights by the lake. Big tours hit Chicago year round. Weekends sell first.

• United Center
• Wrigley Field (select concerts) and Soldier Field (select concerts)
• Huntington Bank Pavilion at Northerly Island
• Chicago Theatre and Auditorium Theatre
• Aragon Ballroom, Riviera Theatre, The Salt Shed
• Allstate Arena (Rosemont)

Sports

Day games at Wrigley, night games on the South Side, buzzer beaters on the West Side. Grab seats early for rivalry series.

• Chicago Cubs at Wrigley Field
• Chicago White Sox at Guaranteed Rate Field
• Chicago Bears at Soldier Field
• Chicago Bulls and Blackhawks at United Center
• Chicago Fire FC at Soldier Field
• Chicago Red Stars at SeatGeek Stadium

Chicago River & Lake Cruises

Architecture cruises, sunset sails, and fireworks nights from the lake. Book timed departures during summer weekends.

• Chicago Architecture River Cruise
• Lake Michigan dinner or fireworks cruise
• Speedboat thrill rides (summer only)
• Private charters for groups and celebrations

Museums & Views

World class collections and sky high observatories. Check for timed entry and city pass bundles to skip lines.

• Art Institute of Chicago
• Field Museum, Shedd Aquarium, Adler Planetarium
• Skydeck Chicago (Willis Tower) and 360 CHICAGO (Hancock)
• Museum of Science and Industry
• Millennium Park and Cloud Gate (The Bean)

Neighborhood & Food Tours

Loop architecture walks, Riverwalk tastings, Chinatown and Pilsen food tours, and Wicker Park nightlife. Each area has its flavor.

• Deep dish pizza and local eats tours
• Chinatown or Pilsen cultural tours
• Street art and craft brewery tours
• Architecture walking tours along the Riverwalk

Beaches & Outdoors

Lakefront Trail miles, skyline beaches, and kayaking under bridges. Summer in Chicago belongs outside.

• North Avenue and Oak Street Beach
• Kayak the Chicago River (guided)
• Bike the Lakefront Trail
• Lincoln Park Conservatory and Zoo (free)

Festivals & Big Weekends

Chicago's calendar is loaded. Book hotels early for major events and holidays.

• Lollapalooza in August, Grant Park's signature music festival
• Chicago Blues Fest in June, world's largest free blues festival
• Taste of Chicago in summer, local eats, live music, lakefront vibes
• Air & Water Show in August, jets over Lake Michigan
• St. Patrick's Day in March, river dyeing and citywide parades
• Chicago Marathon in October, world major event weekend
• Christkindlmarket in November and December, holiday market and winter lights

Chicago By Month

Winters sparkle inside. Summers live outside. Book early for prime weekends.

• January through March: Museums, theater, and skating at Millennium Park
• April through June: River cruises reopen, patio season returns
• July through September: Peak festivals, fireworks, and rooftop nightlife
• October through December: Marathon, holiday lights, and winter markets

Chicago FAQ

No. Stay central and use CTA, rideshare, or tour shuttles. Parking downtown can be pricey.

Loop or River North for theaters and Riverwalk. Wrigleyville for games. South Loop for museums.

Skydeck and 360 CHICAGO, or free from Adler Planetarium and the Riverwalk at blue hour.

Bundle attractions, visit midweek, and compare ticket sites for the best deals.