Chicago Events, Tours & Things to Do 2025

River architecture, lakefront sunsets, legendary venues, and deep-dish detours. Use this guide to compare tickets, book must-do tours, and stitch together a Chicago trip you’ll actually brag about.

Top Deals in Chicago

Jump to: Concerts & Venues · Sports · River & Lake Cruises · Museums & Views · Neighborhood & Food Tours · Beaches & Outdoors · Festivals & Big Weekends · By Month · FAQ

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) · Soldier Field (select concerts)
• Huntington Bank Pavilion at Northerly Island
• Chicago Theatre · 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 — Wrigley Field
• Chicago White Sox — Guaranteed Rate Field
• Chicago Bears — Soldier Field
• Chicago Bulls / Blackhawks — United Center
• Chicago Fire FC — Soldier Field
• Chicago Red Stars — 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 & 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) · 360 CHICAGO (Hancock)
• Museum of Science and Industry
• Millennium Park & “Cloud Gate” (The Bean)

Neighborhood & Food Tours

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

• Deep-dish pizza & local eats tours
• Chinatown or Pilsen cultural tours
• Street art & 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 & Oak Street Beach
• Kayak the Chicago River (guided)
• Bike the Lakefront Trail
• Lincoln Park Conservatory & Zoo (free)

Festivals & Big Weekends

Chicago’s calendar is loaded—book hotels early for major events and holidays.

• Lollapalooza (Aug): Grant Park’s signature music festival
• Chicago Blues Fest (Jun): world’s largest free blues festival
• Taste of Chicago (summer): local eats, live music, lakefront vibes
• Air & Water Show (Aug): jets over Lake Michigan
• St. Patrick’s Day (Mar): River dyeing & citywide parades
• Chicago Marathon (Oct): world major event weekend
• Christkindlmarket (Nov–Dec): holiday market & winter lights

Chicago by Month

Winters sparkle inside; summers live outside—book early for prime weekends.

• Jan–Mar: Museums, theater, and skating at Millennium Park.
• Apr–Jun: River cruises reopen; patio season returns.
• Jul–Sep: Peak festivals, fireworks, and rooftop nightlife.
• Oct–Dec: Marathon, holiday lights, and winter markets.

Chicago FAQ

Do I need a car?

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

Where should I stay?

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

Best skyline views?

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

How do I save?

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