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.
EWR
New York
ORD
Chicago
$69 Roundtrip, found 3 days ago
$69
Roundtrip
found 3 days ago
ATL
Atlanta
ORD
Chicago
$78 Roundtrip, found 2 days ago
$78
Roundtrip
found 2 days ago
ATL
Atlanta
MDW
Chicago
$88 Roundtrip, found 3 days ago
$88
Roundtrip
found 3 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
$134 nightly
The price is $157 total per night
$157 total
May 26 - May 27
Total includes 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
Warwick Allerton - Chicago
701 North Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
1 mi from city center
$125 nightly
The price is $147 total per night
$147 total
May 27 - May 28
Total includes taxes and fees
With a stay at Warwick Allerton - Chicago, you'll be centrally located in Chicago, steps from Michigan Avenue and 11 minutes by foot from Chicago Riverwalk.
Air conditioning
Gym
Ambassador Hotel Chicago
1301 N State Pkwy, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
1.73 mi from city center
$166 nightly
The price is $195 total per night
$195 total
May 28 - May 29
Total includes taxes and fees
You'll be centrally located in Chicago with a stay at The Chicago Hotel Collection Ambassador Gold Coast, within a 15-minute walk of Chicago History Museum and 900 North Michigan Shops.
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
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^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.