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
$137 Roundtrip, found 12 hours ago
$137
Roundtrip
found 12 hours ago
EWR
New York
ORD
Chicago
$158 Roundtrip, found 2 days ago
$158
Roundtrip
found 2 days ago
EWR
New York
MDW
Chicago
$168 Roundtrip, found 1 day ago
$168
Roundtrip
found 1 day 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
$175 nightly
The price is $208 total per night
$208 total
Aug 30 - Aug 31
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
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.74 mi from city center
$152 nightly
The price is $181 total per night
$181 total
Aug 9 - Aug 10
Total with 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 Oak Street Beach and Chicago History Museum.
Pet friendly
Free WiFi
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Free Cancellation
Reserve now, pay when you stay
15.67 mi from city center
$212 nightly
The price is $248 total per night
$248 total
Aug 29 - Aug 30
Total with taxes and fees
With a stay at Hilton Chicago O'Hare Airport in Chicago (O'Hare), you'll be within a 10-minute drive of Donald E. Stephens Convention Center and Rosemont Theatre.
Free airport shuttle
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
- 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
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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.
