Holidays in Chicago
Get inspired to book your holiday with us
Plan your next holiday in Chicago
From flights to stays, discover great offers for cheap holidays
Get more for less
Unlock better prices on flights and places to stay with Genius.
Attraction45-minute Chicago River Architecture Boat Tour
Chicago, United StatesA discovery of the city's most iconic buildings and landmarksFrom US$28
From US$78 per day
Best places to stay in Chicago
Find the perfect stay for your holiday
Scored out of 10, guest rating 8.3Very good - What previous guests thought, 6,407 reviewsFrom US$216.02 per night
Sign in to save 10% or more
Unlock members-only discounts with a free Booking.com account and start saving with Genius.
From US$139.71 per night
Scored out of 10, guest rating 8.3Very good - What previous guests thought, 6,834 reviewsFrom US$240.67 per night
Scored out of 10, guest rating 8.1Very good - What previous guests thought, 5,201 reviewsFrom US$257.25 per night
Scored out of 10, guest rating 7.4Good - What previous guests thought, 5,707 reviewsFrom US$268.85 per night
Scored out of 10, guest rating 8.0Very good - What previous guests thought, 2,662 reviewsFrom US$257.25 per night
Scored out of 10, guest rating 7.3Good - What previous guests thought, 3,495 reviewsFrom US$207.80 per night
Scored out of 10, guest rating 7.9Good - What previous guests thought, 2,878 reviewsFrom US$215.92 per night
Scored out of 10, guest rating 7.3Good - What previous guests thought, 3,287 reviewsFrom US$163.19 per night
Reasons to book holidays with Booking.com
Build your perfect trip
Book the best flights, stays and more – all in one place
Stay flexible
Keep your travel plans flexible with free cancellation options
Get 24/7 support
Contact us anytime and get support in multiple languages
Cheapest flights to Chicago
The cheapest flights available in the next 60 days – prices are updated regularly
- Tue 28 OctUS$90.83One wayEconomy1 traveller
- Tue 21 OctUS$92.93One wayEconomy1 traveller
- Wed 22 OctUS$96.25One wayEconomy1 traveller
Holidays in Chicago: things to know
Most booked car type | Premium car |
|---|---|
Avg. daily price for Premium car | US$78 per day |
Avg. cost of stay | US$224 per night |
Best time to visit | May and October |
Avg. price for a round-trip flight | US$441 |
Most popular flight route | LAX Los Angeles International Airport to ORD Chicago O'Hare International Airport |
Weekend car rentals in Chicago
- Hyundai Santa Feor similar SUV
Chicago O'Hare International AirportPrice for 2 days fromFri 17 Oct – Sun 19 Oct - Ford Fiestaor similar Small carChicago O'Hare International AirportPrice for 2 days fromFri 17 Oct – Sun 19 Oct
- Volkswagen Jettaor similar Large car
Chicago O'Hare International AirportPrice for 2 days fromFri 17 Oct – Sun 19 Oct - Nissan Sentraor similar Medium car
Chicago O'Hare International AirportPrice for 2 days fromFri 17 Oct – Sun 19 Oct - Cadillac XTSor similar Premium car
Chicago O'Hare International AirportPrice for 2 days fromFri 17 Oct – Sun 19 Oct
Best places to visit in Chicago
Make the most out of your holidays with tours, activities and more
90-minute Tour of the Chicago River
Chicago, United StatesVisit on a boat to see the architecture of the buildings along the riverFrom US$45
Chicago River Architecture Tour
Chicago, United StatesA 90-minute cruise to admire the city's architecture from the waterFrom US$45
Chicago Architecture River Cruise
Chicago, United StatesExperience the stunning beauty of Chicago on a captivating cruise along the historic Chicago Rive...From US$44.43
360 Chicago Observation Deck Tickets
Chicago, United StatesA chance to appreciate soaring views of the Chicago skyline from over 300 metres highFrom US$29
45-minute Architecture River Cruise
Chicago, United StatesA chance to take a leisurely river cruise to explore Chicago's iconic architectureFrom US$28
Two-hour Chicago Sunset Cruise
Chicago, United StatesA short cruise to admire the Chicago skyline at sunsetFrom US$45
Sightseeing River and Lake Cruise Experience
Chicago, United StatesA guided boat tour to explore some of Chicago's most iconic buildings and landmarksFrom US$45
Admission to Skydeck Chicago
Chicago, United StatesA ticket to access the attraction in Chicago for views over the cityFrom US$44
Flyover in Chicago
Chicago, United StatesThe Flyover experience takes 30 minutes from beginning to end. First, on-the-ground stories conne...From US$38.03
CityPASS Ticket
Chicago, United StatesA ticket that grants entry to some of Chicago's most iconic attractionsFrom US$142
Popular alternatives to Chicago
Explore more holiday destinations in the United States
