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.
Attraction
90-minute Tour of the Chicago River
Chicago, United States
Visit on a boat to see the architecture of the buildings along the river
From US$45
From US$50 per day
Best places to stay in Chicago
Find the perfect stay for your holiday
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 6,527 reviews
From US$154.97 per night
Sign in to save 10% or more
Unlock members-only discounts with a free Booking.com account and start saving with Genius.
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 6,860 reviews
From US$217.19 per night
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 5,183 reviews
From US$184.93 per night
From US$139.71 per night
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 5,660 reviews
From US$186.67 per night
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 2,707 reviews
From US$184.93 per night
Scored out of 10, guest rating 7.3
Good - What previous guests thought, 3,488 reviews
From US$132.66 per night
Scored out of 10, guest rating 7.2
Good - What previous guests thought, 3,287 reviews
From US$117.67 per night
Scored out of 10, guest rating 7.9
Good - What previous guests thought, 2,921 reviews
From US$143.60 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 4 Nov
US$96.34
One way
Economy
1 traveller
Wed 5 Nov
US$103.83
One way
Economy
1 traveller
Sat 20 Dec
US$107.94
One way
Economy
1 traveller
Holidays in Chicago: things to know
Most booked car type | Premium car |
|---|---|
Avg. daily price for Premium car | US$75 per day |
Avg. cost of stay | US$224 per night |
Best time to visit | May and June |
Avg. price for a round-trip flight | US$431 |
Most popular flight route | LAX Los Angeles International Airport to ORD Chicago O'Hare International Airport |
Weekend car rentals in Chicago
Best places to visit in Chicago
Make the most out of your holidays with tours, activities and more
45-minute Chicago River Architecture Boat Tour
Chicago, United States
A discovery of the city's most iconic buildings and landmarks
From US$28
45-minute Architecture River Cruise
Chicago, United States
A chance to take a leisurely river cruise to explore Chicago's iconic architecture
From US$28
360 CHICAGO Observation Deck
Chicago, United States
Admission to the sky-high lookout platform with panoramic views over the city
From US$29
CityPASS Ticket
Chicago, United States
A ticket that grants entry to some of Chicago's most iconic attractions
From US$142
Two-hour Chicago Sunset Cruise
Chicago, United States
A short cruise to admire the Chicago skyline at sunset
From US$45
Architecture River Cruise
Chicago, United States
A scenic river cruise to explore Chicago's iconic architecture and famous landmarks by water
From US$44.43
Admission to Skydeck Chicago
Chicago, United States
A ticket to access the attraction in Chicago for views over the city
From US$44
360 Chicago Observation Deck Tickets
Chicago, United States
A chance to appreciate soaring views of the Chicago skyline from over 300 metres high
From US$29
Sightseeing River and Lake Cruise Experience
Chicago, United States
A guided boat tour to explore some of Chicago's most iconic buildings and landmarks
From US$45
Chicago River Architecture Tour
Chicago, United States
A 90-minute cruise to admire the city's architecture from the water
From US$45
Popular alternatives to Chicago
Explore more holiday destinations in the United States
