Vacations in Chicago
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Attraction
45-minute Chicago River Architecture Boat Tour
Chicago, United States of America
A discovery of the city's most iconic buildings and landmarks
From $28
From $79 per day
Best places to stay in Chicago
Find the perfect stay for your trip
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 7,941 reviews
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Scored out of 10, guest rating 7.2
Good - What previous guests thought, 4,918 reviews
From $273.92 per night
Scored out of 10, guest rating 8.1
Very Good - What previous guests thought, 3,470 reviews
From $355.28 per night
Scored out of 10, guest rating 8.1
Very Good - What previous guests thought, 3,727 reviews
Scored out of 10, guest rating 8.1
Very Good - What previous guests thought, 3,268 reviews
From $254.86 per night
Scored out of 10, guest rating 8.2
Very Good - What previous guests thought, 5,425 reviews
From $355.28 per night
Scored out of 10, guest rating 8.3
Very Good - What previous guests thought, 5,938 reviews
From $256.05 per night
Scored out of 10, guest rating 7.5
Good - What previous guests thought, 1,741 reviews
From $213.30 per night
Scored out of 10, guest rating 7.9
Good - What previous guests thought, 1,609 reviews
From $220.41 per night
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Cheapest flights to Chicago
The cheapest flights available in the next 60 days – prices are updated regularly
Vacations in Chicago: Things to know
Most booked car type | Premium car |
|---|---|
Avg. daily price for Premium car | $62 per day |
Avg. cost of stay | $223 per night |
Best time to visit | October and May |
Avg. price for a round-trip flight | $417 |
Most popular flight route | LGA LaGuardia 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 of America
Visit on a boat to see the architecture of the buildings along the river
From $45
45-minute Architecture River Cruise
Chicago, United States of America
A chance to take a leisurely river cruise to explore Chicago's iconic architecture
From $28
360 CHICAGO Observation Deck
Chicago, United States of America
Admission to the sky-high lookout platform with panoramic views over the city
From $30.30
Chicago City Pass Experience
Chicago, United States of America
A nine-day pass to choose and visit three iconic Chicago attractions
From $109
Admission to Skydeck Chicago
Chicago, United States of America
A ticket to access the attraction in Chicago for views over the city
From $44
CityPASS Ticket
Chicago, United States of America
A ticket that grants entry to some of Chicago's most iconic attractions
From $144
Two-hour Chicago Sunset Cruise
Chicago, United States of America
A short cruise to admire the Chicago skyline at sunset
From $45
Architecture River Cruise
Chicago, United States of America
A scenic river cruise to explore Chicago's iconic architecture and famous landmarks by water
From $46
360 Chicago Observation Deck Tickets
Chicago, United States of America
A chance to appreciate soaring views of the Chicago skyline from over 984 feet high
From $30
Flyover in Chicago
Chicago, United States of America
A 30-minute multimedia presentation combining on-ground stories, aerial drone and helicopter footage with scents and music
From $27.95
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