Cheap Vacations in Chicago

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Chicago vacations

Price found within the past 48 hours. Click for updated prices.
Motel 6 Prospect Heights, IL
Bridgeview Inn Chicago Area
The Chicago Hotel Collection River North
Best Western Plus Chicago Hillside
Best Western Oakbrook Inn
Crowne Plaza Lombard Downers Grove, an IHG Hotel
Red Roof Inn PLUS+ Chicago - Willowbrook
Quality Inn & Suites near I-80 and I-294
Chicago Club Inn & Suites
Motel 6 Glenview, IL - Chicago North

3-night Chicago vacations

Price found within the past 48 hours. Click for updated prices.
The Chicago Hotel Collection River North
Level Chicago - River North
Found Chicago powered by Sonder
Hyatt House Chicago Medical/University District
Courtyard Chicago Elmhurst/Oakbrook Area
Freehand Chicago
Four Points by Sheraton Mt Prospect O'Hare
Hampton Inn Chicago Downtown/Magnificent Mile
Holiday Inn Express & Suites Chicago North Shore - Niles, an IHG Hotel
Courtyard by Marriott Chicago Wood Dale
The Hoxton Chicago
Holiday Inn Chicago O'Hare Area, an IHG Hotel

4-night Chicago vacations

Price found within the past 48 hours. Click for updated prices.
Extended Stay America Suites Chicago Elmhurst O'Hare
Holiday Inn Express & Suites Prospect Heights, an IHG Hotel
W Chicago - Lakeshore
Hyatt Place Chicago/River North
DoubleTree by Hilton Chicago - Magnificent Mile
Country Inn & Suites by Radisson, Bolingbrook, I-55
Comfort Suites Oakbrook Terrace near Oakbrook Center
Hilton Chicago/Magnificent Mile Suites
Sonesta ES Suites Chicago - Schaumburg
Springhill Suites by Marriott Chicago Downtown/ River North
Courtyard Chicago Elmhurst/Oakbrook Area
Residence Inn Chicago Downtown/Loop

5-night Chicago vacations

Price found within the past 48 hours. Click for updated prices.
21c Museum Hotel Chicago
Hilton Chicago
Hotel Chicago Downtown, Autograph Collection by Marriott
The Allegro Royal Sonesta Hotel Chicago Loop
Hyatt Centric The Loop Chicago
Sheraton Grand Chicago Riverwalk
Level Chicago – Old Town
AC Hotels by Marriott Chicago Downtown
Pendry Chicago
Congress Plaza Hotel
Aloft Chicago Downtown River North
Trump International Hotel & Tower Chicago

6-7 night Chicago vacations

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Level Chicago – Old Town
Congress Plaza Hotel
Aloft Chicago Downtown River North
Hilton Chicago
W Chicago - Lakeshore
The Emily Hotel
Hotel Riu Plaza Chicago
Virgin Hotels Chicago
Pendry Chicago
Fairmont Chicago at Millennium Park
Embassy Suites by Hilton Chicago Downtown River North

Flight deals to Chicago

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Top rated hotels for your Chicago vacation

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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.

^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.