Vacations in Chicago
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Attraction
45-minute Chicago River Architecture Boat Tour
Chicago, United States
A discovery of the city's most iconic buildings and landmarks
From $28
From $51 per day
Best places to stay in Chicago
Find the perfect stay for your trip
Scored out of 10, guest rating 8.3
Very Good - What previous guests thought, 6,740 reviews
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From $139.71 per night
Scored out of 10, guest rating 8.1
Very Good - What previous guests thought, 5,211 reviews
From $319.23 per night
Scored out of 10, guest rating 8.3
Very Good - What previous guests thought, 6,852 reviews
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 4,264 reviews
Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 3,016 reviews
Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 3,071 reviews
From $568.22 per night
Scored out of 10, guest rating 7.9
Good - What previous guests thought, 4,160 reviews
Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 2,765 reviews
From $319.23 per night
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Cheapest flights to Chicago
The cheapest flights available in the next 60 days – prices are updated regularly
Sat, Dec 20
$101.37
One-way
Economy
1 traveler
Wed, Dec 17
$114.45
One-way
Economy
1 traveler
Wed, Dec 24
$118.53
One-way
Economy
1 traveler
Vacations in Chicago: Things to know
Most booked car type | Premium car |
|---|---|
Avg. daily price for Premium car | $76 per day |
Avg. cost of stay | $229 per night |
Best time to visit | May and June |
Avg. price for a round-trip flight | $452 |
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 of your vacation with tours, activities, and more
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 $45
45-minute Architecture River Cruise
Chicago, United States
A chance to take a leisurely river cruise to explore Chicago's iconic architecture
From $28
360 CHICAGO Observation Deck
Chicago, United States
Admission to the sky-high lookout platform with panoramic views over the city
From $30
CityPASS Ticket
Chicago, United States
A ticket that grants entry to some of Chicago's most iconic attractions
From $142
Two-hour Chicago Sunset Cruise
Chicago, United States
A short cruise to admire the Chicago skyline at sunset
From $45
Architecture River Cruise
Chicago, United States
A scenic river cruise to explore Chicago's iconic architecture and famous landmarks by water
From $44.43
Admission to Skydeck Chicago
Chicago, United States
A ticket to access the attraction in Chicago for views over the city
From $44
360 Chicago Observation Deck Tickets
Chicago, United States
A chance to appreciate soaring views of the Chicago skyline from over 984 feet high
From $30
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