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
$48 Roundtrip, found 14 hours ago
$48
Roundtrip
found 14 hours ago
DFW
Dallas
ORD
Chicago
$55 Roundtrip, found 1 hour ago
$55
Roundtrip
found 1 hour ago
ATL
Atlanta
MDW
Chicago
$58 Roundtrip, found 4 days ago
$58
Roundtrip
found 4 days 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
The price is $143 per night
$143
includes taxes & fees
$122 per night
Dec 8 - Dec 9
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
River Hotel
75 East Wacker Drive, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.5 mi from city center
The price is $120 per night
$120
includes taxes & fees
$102 per night
Jan 2 - Jan 3, 2025
With a stay at River Hotel, you'll be centrally located in Chicago, steps from Michigan Avenue and 5 minutes by foot from Chicago Riverwalk.
Pet friendly
Free WiFi
The Westin Michigan Avenue Chicago
909 North Michigan Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
1.29 mi from city center
The price is $184 per night
$184
includes taxes & fees
$160 per night
Dec 15 - Dec 16
With a stay at The Westin Michigan Avenue Chicago, you'll be centrally located in Chicago, steps from Michigan Avenue and 4 minutes by foot from State Street.
Spa
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
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More ways to book
^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.