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
ORD
Chicago
$68 Roundtrip, found 2 days ago
$68
Roundtrip
found 2 days ago
JFK
New York
ORD
Chicago
$70 Roundtrip, found 18 hours ago
$70
Roundtrip
found 18 hours ago
LGA
New York
ORD
Chicago
$82 Roundtrip, found 1 day ago
$82
Roundtrip
found 1 day ago
Top rated hotels for your Chicago vacation
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
$89 nightly
The price is $105 total per night
$105 total
Jan 5 - Jan 6, 2026
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.
Pet friendly
Free WiFi
Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.12 mi from city center
$127 nightly
The price is $149 total per night
$149 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Silversmith Hotel Chicago Downtown is in the heart of Chicago, within a 5-minute walk of Millennium Park and CIBC Theatre.
Free WiFi
Air conditioning
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.5 mi from city center
$88 nightly
The price is $103 total per night
$103 total
Dec 25 - Dec 26
Total with taxes and fees
With a stay at Club Quarters Hotel Wacker at Michigan, Chicago, you'll be centrally located in Chicago, steps from Chicago Riverwalk and 5 minutes by foot from Michigan Avenue.
Pet friendly
Free WiFi
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
- Hotels near Naval Base Great Lakes
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- Hotels near Allstate Arena
- Hotels near Wrigley Field
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- Hotels in Rosemont
- 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
- Hotels in Lincoln Park
- Hotels in Buffalo Grove
- 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.
