Chicago City Tour 11 options
From US$ 35 · departures between 08:00 and 22:00 · live guides in 3 languages
No experiences match those filters.
Chicago City Cruise Tour: Minibus, river boat & skyline stopsSmall-group Chicago tour with expert guide in minibus, three photo stops and optional 75-minute Architecture River Cruise.
- 747 reviews
- 4.77★
- Duration
- 2h–4h
- start times · Every day
- 4
Chicago Private City Tour: Millennium Park & Lincoln Park with PickupPrivate Chicago city tour with hotel pickup, guide & driver for up to 5 passengers. Covers Millennium Park, Lincoln Park, Museum Campus & architecture.
- 211 reviews
- 4.93★
- Duration
- 3h–4h
- start times · Every day
- 2
Chicago: Elevated Architecture Tour & "L" Train TicketFeel the pulse of Chicago’s Loop from above on an architecture tour riding the iconic “L” train, with station stops, city stories, and your ticket included.
- 103 reviews
- 4.77★
- Duration
- 2h
- start times · Tue, Fri and Sun
- 2
Chicago: Willis Tower & Cloud Gate Half-Day Architecture TourHalf-day Chicago architecture tour covering Willis Tower, Marina City, Cloud Gate & Millennium Park. Small groups, expert guide, bottled water included. Starts 9am downtown.
- 46 reviews
- 4.96★
- Duration
- 2h 30m
- start times · Tue–Sun
- 2
Chicago: 2-Hour Luxury Minibus Tour & Skyline ViewsTwo-hour guided minibus tour of Chicago's skyline, Grant Park, Cloud Gate and Lake Michigan views. Climate-controlled comfort, live guide, photo stops included.
- 20 reviews
- 4.90★
- Duration
- 2h
- start times · Every day
- 4
Chicago to Milwaukee: Harley Museum & Brewery TourDay trip from Chicago to Milwaukee with Harley-Davidson Museum, Miller Brewery tour and tasting, Milwaukee Art Museum, and Public Market. Expert guide and transport included.
- 13 reviews
- 4.38★
- Duration
- 8h–10h
- Fri and Sat
- 08:00
Chicago: 360 Observation Deck & 48-Hour Hop-on Hop-off Bus48-hour hop-on hop-off bus tour of Chicago with 360 CHICAGO Observation Deck admission. Includes audio commentary, digital walking tours, and 11 stops across neighborhoods.
- 5 reviews
- 4.20★
- Duration
- 2h
- start times · Every day
- 27
Chicago to Milwaukee Day Trip: Harley-Davidson Museum & ArtDay trip from Chicago to Milwaukee with professional guide and driver, exploring the Harley-Davidson Museum, Public Market.
- 4 reviews
- 5.00★
- Duration
- 1d
- Fri and Sat
- 08:00
Chicago: Cloud Gate, Architecture & Grant Park Full DayChicago full-day tour: Cloud Gate, architecture tour, Grant Park & Buckingham Fountain. Optional Art Institute or 360 Chicago views. Professional guide.
- 4 reviews
- 4.00★
- Duration
- 8h–10h
- Mon
- 08:00
Chicago: Hop On Hop Off Bus Tour & Walking ToursOpen-top double-decker bus tour of Chicago with 11 stops: Millennium Park, Willis Tower, Navy Pier & more. Includes walking tours and sunset ride with real-time app tracking.
- 2,445 reviews
- 3.89★
- Duration
- 2h
Chicago City Tour: 20+ Stops & Skyline Views No FillerChicago city tour covering 20+ landmarks: Millennium Park, Riverwalk, Willis Tower, Grant Park & more. Shared tour, air-conditioned vehicle, bottled water & snacks included.
- 21 reviews
- 3.81★
- Duration
- 4h–8h
All 11 options, side by side
✓ 2026-11-03| Option | Price | Duration | Rating | Days and times | Guide languages |
|---|---|---|---|---|---|
| Chicago City Cruise Tour: Minibus, river boat & skyline stopsOur pickGroup of up to 12 | US$ 50 per person | 2h–4h | 4.77★ · 747 | Every day · 4 start times | English |
| Chicago Private City Tour: Millennium Park & Lincoln Park with PickupTop ratedPrivate · Pickup offered | US$ 108 per personUS$ 539 per group (split 5 ways) | 3h–4h | 4.93★ · 211 | Every day · 2 start times | English |
| Chicago: Elevated Architecture Tour & "L" Train TicketBest valueGroup of up to 10 | US$ 35 per person | 2h | 4.77★ · 103 | Tue, Fri and Sun · 2 start times | English |
| Chicago: Willis Tower & Cloud Gate Half-Day Architecture TourGroup of up to 12 · Pickup offered | US$ 48 per person | 2h 30m | 4.96★ · 46 | Tue–Sun · 2 start times | English |
| Chicago: 2-Hour Luxury Minibus Tour & Skyline ViewsGroup of up to 14 | US$ 65 per person | 2h | 4.90★ · 20 | Every day · 4 start times | English |
| Chicago to Milwaukee: Harley Museum & Brewery TourGroup of up to 14 | US$ 125 per person | 8h–10h | 4.38★ · 13 | Fri and Sat · 08:00 | English |
| Chicago: 360 Observation Deck & 48-Hour Hop-on Hop-off Bus | US$ 84 per person | 2h | 4.20★ only 5 reviews | Every day · 27 start times | — |
| Chicago to Milwaukee Day Trip: Harley-Davidson Museum & Art | US$ 125 per person | 1d | 5.00★ only 4 reviews | Fri and Sat · 08:00 | English |
| Chicago: Cloud Gate, Architecture & Grant Park Full DayPickup offered | US$ 194 per person | 8h–10h | 4.00★ only 4 reviews | Mon · 08:00 | English |
| Chicago: Hop On Hop Off Bus Tour & Walking Tours | US$ 49 per person | 2h | 3.89★ · 2,445 | Every day | — |
| Chicago City Tour: 20+ Stops & Skyline Views No FillerGroup of up to 10 · Pickup offered | US$ 150 per person | 4h–8h | 3.81★ · 21 | Next departure: 31 Jan 2027 | English, Arabic, French |
By what you need
- Private (1): Chicago Private City Tour: Millennium Park & Lincoln Park with Pickup (US$ 539)
- With pickup (4): Chicago Private City Tour: Millennium Park & Lincoln Park with Pickup (US$ 539) · Chicago: Willis Tower & Cloud Gate Half-Day Architecture Tour (US$ 48) · Chicago: Cloud Gate, Architecture & Grant Park Full Day (US$ 194)
Chicago City Tour at a glance
- Our pick: Chicago City Cruise Tour: Minibus, river boat & skyline stops, US$ 50 (2h–4h, 4.77★ · 747).
- Top rated: Chicago Private City Tour: Millennium Park & Lincoln Park with Pickup, US$ 108 (3h–4h, 4.93★ · 211).
- Best value: Chicago: Elevated Architecture Tour & "L" Train Ticket, US$ 35 (2h, 4.77★ · 103).
Real price per person across the 11 options: US$ 35–US$ 194 (median US$ 84). With 100+ reviews: 4 of 11.
Of the 11 options: 9 with live guides in English, 11 with free cancellation, 7 with instant confirmation, 4 with hotel pickup, 9 kid-friendly, 1 private and 6 bookable last-minute.
How we rank: quality, number of reviews and relevance to the topic. In the comparison table, our top 3 comes first. Real price per person: the group price divided by the seats it includes.
More things to do in Chicago
360 Chicago Tickets5 optionsBoat Tours in Chicago13 optionsArchitecture Tour Chicago25 optionsChicago Food Tour19 optionsChicago Ghost Tour8 optionsChicago Walking Tour30 optionsChicago Bus Tour7 optionsLake Michigan Boat Tour9 optionsBike Tours in Chicago5 optionsChicago Crime Tour8 optionsMuseums in Chicago9 optionsChicago Airport Taxi27 optionsChicago Segway Tour5 optionsE-Bike Tours in Chicago6 options