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.
Flight deals to Chicago
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
ATL
Atlanta
MDW
Chicago
$56 Roundtrip, found 5 days ago
$56
Roundtrip
found 5 days ago
ATL
Atlanta
ORD
Chicago
$56 Roundtrip, found 5 days ago
$56
Roundtrip
found 5 days ago
EWR
New York
MDW
Chicago
$56 Roundtrip, found 6 days ago
$56
Roundtrip
found 6 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
$101 nightly
The price is $118 total per night
$118 total
Apr 1 - Apr 2
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
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
$122 nightly
The price is $143 total per night
$143 total
Mar 22 - Mar 23
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
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.91 mi from city center
$156 nightly
The price is $183 total per night
$183 total
Mar 30 - Mar 31
Total with taxes and fees
With a stay at Hotel Riu Plaza Chicago, you'll be centrally located in Chicago, steps from Michigan Avenue and 10 minutes by foot from Chicago Riverwalk.
Breakfast included
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
- Romantic Getaways & Hotels in The Loop
- Chicago Hotels
- Hotels near Navy Pier
- 5 Star Hotels in Downtown Chicago
- Hyatt Hotels in Chicago
- Hotels near Art Institute of Chicago
- Hotels with a Wedding Venue in Magnificent Mile
- Hotels near Millennium Park
- Cheap Hotels in The Loop
- Hotels with Kitchenettes in River North
- Hotels with WiFi in The Loop
- Flights from Guangzhou to Chicago
- Flights from Monroe to Chicago
- Flights from Nairobi to Chicago
- Flights from Seattle to Chicago
- Flights from Providenciales to Chicago
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- Schaumburg Vacations
- Field Museum of Natural History
- Adler Planetarium and Astronomy Museum
- Glenview Vacations
- Museum of Contemporary Art Chicago
- Glencoe Vacations
- Wrigley Field
- Legoland® Discovery Center
- Lincolnshire Vacations
- Schiller Park Vacations
- Thornton Junction Vacations
- Tribune Tower
- Hyde Park Vacations
- Magnificent Mile Vacations
- Cloud Gate
- Allstate Arena
- Oakbrook Terrace Vacations
- Goodman Theater
- Addison Vacations
- Navy Pier
- Chicago Cultural Center
- Donald E. Stephens Convention Center
- Wood Dale Vacations
- Pilsen Vacations
- Mccormick Place
- Bridgeview Vacations
- Skokie Vacations
- Aragon Ballroom
- Griffin Museum of Science and Industry
- Montrose Beach
^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.
