Go City Chicago Explorer Pass: Choose from 39 Attractions
From$84
Most booked
Most booked in Chicago in May 2026
Skydeck Chicago: Entry Ticket
From€36.12
45-min Chicago River Architecture Cruise by Wendella
Wendella Tours & Cruises
From$28
Combo (Save 10%): Chicago Hop-on Hop-off Bus Tour + 360 Chicago Observation Deck Skip-the-Line Tickets
From$71.1
The Art Institute of Chicago: Fast Pass
From€34.2
90-min Chicago River Architecture Cruise by Wendella
Wendella Tours & Cruises
From$45
Big Bus: Chicago Hop-on Hop-off Bus Tour
From$45
The Field Museum of Natural History: Entry Ticket
From€24.8
Chicago attractions
Iconic landmarks, museums and galleries — book entry tickets in advance to skip the line where supported.
Go City Chicago Explorer Pass: Choose from 39 Attractions
From$84
Skydeck Chicago: Entry Ticket
From€36.12
The Art Institute of Chicago: Fast Pass
From€34.2
The Field Museum of Natural History: Entry Ticket
From€24.8
360 Chicago Observation Deck: Entry Ticket
From€25.65
360 Chicago Observation Deck Skip-the-Line Tickets
360 CHICAGO
From$30
Chicago tours
Guided walking tours, hop-on-hop-off buses and small-group experiences led by local guides.
45-min Chicago River Architecture Cruise by Wendella
Wendella Tours & Cruises
From$28
Combo (Save 10%): Chicago Hop-on Hop-off Bus Tour + 360 Chicago Observation Deck Skip-the-Line Tickets
From$71.1
90-min Chicago River Architecture Cruise by Wendella
Wendella Tours & Cruises
From$45
Big Bus: Chicago Hop-on Hop-off Bus Tour
From$45
Chicago: Architecture River Cruise from Navy Pier
From€33.35
Official Chicago Architecture Cruise by First Lady
First Lady
From$57
Curated
First time in Chicago?
The must-dos — start here
Curated
Chicago hidden gems
High-rated experiences that haven't gone viral (yet)
45-min Chicago River Architecture Cruise by Wendella
Wendella Tours & Cruises
From$28
90-min Chicago River Architecture Cruise by Wendella
Wendella Tours & Cruises
From$45
Chicago: Architecture River Cruise from Navy Pier
From€33.35
Chicago: Architecture River Cruise from Michigan Avenue
From€39.33
The Art Institute of Chicago: Fast Pass
From€34.2
Official Chicago Architecture Cruise by First Lady
First Lady
From$57
Official venue partner
Direct from the venue
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Chicago · May 2026
Chicago in May 2026
Long daylight, warmer evenings, and Chelsea Flower Show. Garden tours at Kew and Hampton Court come into their own. 121 experiences in Chicago are confirmed bookable in May 2026 — book ahead for the best seats at West End theatre shows and flagship attractions.
Top picks for May 2026: Go City Chicago Explorer Pass: Choose from 39 Attractions, Skydeck Chicago: Entry Ticket, and 45-min Chicago River Architecture Cruise by Wendella.
Average rating across these Chicago experiences sits at 4.0 stars.
Before you book
Frequently asked questions
Answers to the most common questions about booking experiences in Chicago.
- Go City Chicago Explorer Pass: Choose from 39 Attractions, Skydeck Chicago: Entry Ticket, and 45-min Chicago River Architecture Cruise by Wendella lead the line-up. 121 experiences in total across West End theatre, attractions, tours and Thames cruises.
From the tickadoo blog
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Hand-picked travel guides, show reviews, and itineraries — all free, all written by our editorial team.