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.
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
$53 Roundtrip, found 4 days ago
$53
Roundtrip
found 4 days ago
ATL
Atlanta
MDW
Chicago
$58 Roundtrip, found 4 days ago
$58
Roundtrip
found 4 days ago
DFW
Dallas
ORD
Chicago
$63 Roundtrip, found 2 days ago
$63
Roundtrip
found 2 days ago
Top rated hotels for your Chicago vacation
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.83 mi from city center
$94 nightly
The price is $111 total per night
$111 total
Dec 18 - Dec 19
Total with taxes and fees
With a stay at Embassy Suites by Hilton Chicago Downtown River North, you'll be centrally located in Chicago, steps from State Street and 4 minutes by foot from Michigan Avenue.
Pool
Breakfast included
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
$90 nightly
The price is $106 total per night
$106 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
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.05 mi from city center
$128 nightly
The price is $145 total per night
$145 total
Dec 28 - Dec 29
Total with taxes and fees
Palmer House a Hilton Hotel is centrally located in Chicago, a 3-minute walk from Millennium Park and 5 minutes by foot from Art Institute of Chicago.
Pool
Spa
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.
