Cheap Vacations in Chicago
- Chicago vacations
- 3-night Chicago vacations
- 4-night Chicago vacations
- 5-night Chicago vacations
- 6-7 night Chicago vacations
Chicago vacations
Price found within the past 48 hours. Click for updated prices.
3-night Chicago vacations
Price found within the past 48 hours. Click for updated prices.
4-night Chicago vacations
Price found within the past 48 hours. Click for updated prices.
5-night Chicago vacations
Price found within the past 48 hours. Click for updated prices.
6-7 night Chicago vacations
Price found within the past 48 hours. Click for updated prices.
Flight deals to Chicago
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
ATL
Atlanta
MDW
Chicago
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
LGA
New York
ORD
Chicago
$71 Roundtrip, found 6 days ago
$71
Roundtrip
found 6 days ago
EWR
New York
ORD
Chicago
$74 Roundtrip, found 1 day ago
$74
Roundtrip
found 1 day ago
Top rated hotels for your Chicago vacation
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.43 mi from city center
$97 nightly
The price is $114 total per night
$114 total
Jan 19 - Jan 20
Total with taxes and fees
With a stay at Congress Plaza Hotel, you'll be centrally located in Chicago, steps from Columbia College Chicago and Museum of Contemporary Photography.
Free WiFi
Restaurant
Hilton Chicago
720 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.6 mi from city center
$155 nightly
The price is $182 total per night
$182 total
Feb 1 - Feb 2
Total with taxes and fees
With a stay at Hilton Chicago, you'll be centrally located in Chicago, within a 10-minute walk of Buckingham Fountain and Art Institute of Chicago.
Pool
Hot Tub
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.35 mi from city center
$80 nightly
The price is $94 total per night
$94 total
Jan 25 - Jan 26
Total with taxes and fees
With a stay at Hilton Chicago/Magnificent Mile Suites, you'll be centrally located in Chicago, steps from Michigan Avenue and 8 minutes by foot from Lake Michigan.
Pool
Pet friendly
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Picks
Hotels
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- Hotels near Allstate Arena
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- Hotels near University of Chicago
- Hotels in North Chicago
- Hotels near Schaumburg Convention Center
- Hotels near Six Flags Great America
- Hotels near Northwestern University
- Hotels in Schaumburg
- Hotels near Donald E. Stephens Convention Center
- Hotels in Hoffman Estates
- Hotels near Navy Pier
- Hotels near Loyola University Chicago
- Hotels in Wrigleyville
- Hotels near Griffin Museum of Science and Industry
- Hotels near Concordia University Chicago
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- Hotels in Downtown Chicago
- Hotels in Magnificent Mile
^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.
