— Private & premium
Luxury experiences in Chicago
Sometimes the whole point of a trip is to splurge. These Chicago experiences go beyond standard admission — private guides, after-hours access, skip-the-line everything, and small-group sizes that put you in the room with the curator instead of the crowd.
See all Chicago
VIP access, private guides, zero queues.
Matches
103
City
Chicago
Total in city
75
Min rating
4.5
About this list
Why this shortlist
Every listing is rated 4.5★ or higher and starts at €100+ per person. We've included the full range — from private evening tours of major museums to helicopter transfers, yacht charters, and Michelin-starred tasting menus paired with Chicago's best experiences.
Booking is instant, but for anything time-sensitive we recommend reserving several weeks ahead.
Shortlist
Luxury experiences in Chicago
Skydeck Chicago: Entry Ticket
From€36.07
The Art Institute of Chicago: Fast Pass
From$40
The Field Museum of Natural History: Entry Ticket
From$29
Big Bus: Chicago Hop-on Hop-off Bus Tour
360 Chicago Observation Deck: Entry Ticket
From$30
The Field Museum of Natural History: Pass
From$42
Chicago: Architecture River Cruise from Navy Pier
From$39
360 Chicago Observation Deck Skip-the-Line Tickets
Chicago C3® CityPASS®: 3 Attractions of your choice
From$109
Chicago: 45 Minute Architectural Sightseeing Cruise
From$28
Museum Of Contemporary Art (MCA): Entry Ticket
From$22
Lake Michigan & Chicago River: 1.5-Hr Sightseeing Cruise
From$46
Navy Pier Centennial Wheel: Entry Ticket
From€21.1
Museum of Illusions Chicago: Entry Ticket
From$43
Museum of Ice Cream Chicago: Entry Ticket
From$43
Chicago: 90 Minute Architecture Sightseeing Cruise
From$45
Flyover Experience in Chicago
From$27.95
Medieval Torture Museum: Entry Ticket
From$35.83
Chicago CityPASS®
From$144
Chicago: Architecture Foundation Center River Cruise aboard Chicago's First Lady
From$57
Chicago Explorer Pass: 2 to 7 Attractions including 360 Chicago
From$84
Chicago: 90-Minute Architecture Tour on the Lake & River
From$45
Chicago Crime & Mob Bus Tour: Criminals, Mobsters and Gangsters
From$49
Before you book
FAQ
- Is gratuity included?
- Usually not — a 10–15% tip for private guides and drivers is standard and appreciated.