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
MDW
Chicago
$82 Roundtrip, found 9 hours ago
$82
Roundtrip
found 9 hours ago
ATL
Atlanta
ORD
Chicago
$95 Roundtrip, found 2 days ago
$95
Roundtrip
found 2 days ago
LGA
New York
ORD
Chicago
$111 Roundtrip, found 1 day ago
$111
Roundtrip
found 1 day ago
Top rated hotels for your Chicago vacation
Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.97 mi from city center
$125 nightly
The price is $148 total per night
$148 total
May 25 - May 26
Total with taxes and fees
Hotel Felix River North/Magnificent Mile is centrally located in Chicago, a 5-minute walk from Holy Name Cathedral and 10 minutes by foot from Chicago Water Tower.
Pet friendly
Free WiFi
River Hotel
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.5 mi from city center
$144 nightly
The price is $171 total per night
$171 total
May 26 - May 27
Total with taxes and fees
A stay at River Hotel places you in the heart of Chicago, steps from Michigan Avenue and Chicago Riverwalk.
Pet friendly
Free WiFi
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.19 mi from city center
$116 nightly
The price is $138 total per night
$138 total
May 25 - May 26
Total with taxes and fees
With a stay at Club Quarters Hotel, Central Loop, Chicago, you'll be centrally located in Chicago, just a 5-minute walk from Willis Tower and 9 minutes by foot from Millennium Park.
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
- 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
- Flights from Budapest to Chicago
- Flights from Rapid City to Chicago
- Flights from Killeen to Chicago
- Flights from Terre Haute to Chicago
- Flights from Charlotte to Chicago
- Flights from Lima to Chicago
- Flights from St. Augustine to Chicago
- Flights from Seoul to Chicago
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- Flights from Portland to Chicago
- Flights from Buenos Aires to Chicago
- Flights from Sarasota to Chicago
- Flights from Minneapolis - St. Paul to Chicago
- Flights to Chicago
- Flights from Vilnius to Chicago
- Flights from Newark to Chicago
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- Flights from Mexico City to Chicago
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- Flights from Jacksonville to Chicago
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- Flights from Harrisburg - Hershey to Chicago
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- Flights from Traverse City to Chicago
- Flights from Bengaluru to Chicago
- Flights from New York to Chicago
- 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.
