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
$68 Roundtrip, found 21 hours ago
$68
Roundtrip
found 21 hours ago
ATL
Atlanta
ORD
Chicago
$73 Roundtrip, found 5 days ago
$73
Roundtrip
found 5 days ago
LAX
Los Angeles
ORD
Chicago
$78 Roundtrip, found 6 days ago
$78
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
$137 nightly
The price is $161 total per night
$161 total
Apr 26 - Apr 27
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
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
$119 nightly
The price is $140 total per night
$140 total
Apr 26 - Apr 27
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.
Pool
Pet friendly
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
0.83 mi from city center
$139 nightly
The price is $163 total per night
$163 total
Apr 26 - Apr 27
Total with taxes and fees
With a stay at Embassy Suites by Hilton Chicago Downtown River North, you'll be centrally located in Chicago, just a 4-minute walk from Michigan Avenue and 9 minutes by foot from Chicago Riverwalk.
Pool
Breakfast included
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
- Flights from Medellin to Chicago
- Flights from Salt Lake City to Chicago
- Flights from Washington to Chicago
- 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
- Flights from Columbus to Chicago
- Flights from Mexico City to Chicago
- Flights from San Antonio to Chicago
- Flights from Wichita to Chicago
- Flights from Warsaw to Chicago
- Flights from Jacksonville to Chicago
- Flights from Miami to Chicago
- Flights from Manila to Chicago
- Flights from Bucharest to Chicago
- Flights from Munich to Chicago
- Flights from Cleveland to Chicago
- Flights from Oakland to Chicago
- Flights from Sao Paulo to Chicago
- Flights from Dallas to Chicago
- Flights from Tampa to Chicago
- Flights from San Juan to Chicago
- Flights from Atlanta to Chicago
- Flights from Lisbon District to Chicago
- Flights from Rome to Chicago
- Flights from Harrisburg - Hershey to Chicago
- Flights from Spokane to Chicago
- Flights from St. Louis to Chicago
- Flights from Detroit to Chicago
- Flights from Raleigh to Chicago
- Flights from Memphis to Chicago
- Flights from Amritsar to Chicago
- Flights from Providence to Chicago
- Flights from Fort Lauderdale to Chicago
- Flights from Allentown to Chicago
- 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.
