Choose your trip length, interests, and pace to build a flexible Chicago itinerary. Add other destinations, compare experiences, and reserve time for travel between stops.
Plan my Chicago trip →Explore more in Illinois.
May–June and September–October
Seasonal guidance is a starting point; check weather and dates for your chosen experiences.
The Loop: Central location, walkable to major museums, theaters, and transit hubs. River North: Dense restaurant and nightlife options, close to the Magnificent Mile and galleries. Lincoln Park: Lakefront parks, family-friendly attractions, and quieter residential feel.
Browse these experiences as a starting point. The planner considers your interests, pace, and published schedules when building your days.
Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of the river, up the nort…
Approx. 90 minutesView on Viator →
Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy C…
Approx. 45 minutesView on Viator →
Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Explore historic crime scenes with great photo opportunities. Hea…
Approx. 120 minutesView on Viator →
Discover Chicago at your own pace with Big Bus. Travel aboard an open-top, double-decker bus and enjoy panoramic views of the city's most famous landmarks, including the Magnificen…
Approx. 120 minutesView on Viator →
The perfect Food Tour of Chicago for first timers or anyone eager to explore Chicago's famous foods & top attractions—all in one tour. Stroll the beautiful streets of downtown & ta…
Approx. 180 minutesView on Viator →
Gaze upon the city sights from the pinnacle of Chicago, the Skydeck. Located on the 103rd floor of Willis Tower, formerly Sears Tower -- the third-tallest building in the world -- …
Approx. 90 minutesView on Viator →Start with the number of days you have, then choose an unhurried, balanced, or fuller pace. Review the suggested route before generating your daily plan. Transport allowances are estimates; confirm services and meeting points before booking.
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