Vacations in Chicago

Vacations in Chicago

2 travellers

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C$ 310 - C$ 517C$ 517 - C$ 724C$ 724 - C$ 931C$ 931 - C$ 1,137C$ 1,137+ per night

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Most popular Chicago flight and hotel deals

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The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
7.9 Good
Near North Side
Pool
Pet friendly
Denver Intl
Meals not included
3 nights + flight
C$ 466
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Building
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Building
Intercontinental Hotels Chicago Magnificent Mile By IHG
8 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 526
Omni Chicago Hotel - Chicago - Building
Omni Chicago Hotel - Chicago - Building
Omni Chicago Hotel
8.9 Very good
Near North Side
Free Wi-Fi
Pet friendly
Fort Lauderdale
Meals not included
3 nights + flight
C$ 643
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites
8.4 Very good
Near North Side
Pool
Pet friendly
Fort Lauderdale
Meals not included
3 nights + flight
C$ 497
Hilton Chicago - Chicago - Living room
Hilton Chicago - Chicago - Living room
Hilton Chicago
7.9 Good
Loop
Pool
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 556
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.9 Very good
Near West Side
Free Wi-Fi
Pet friendly
Spa
Fort Lauderdale
Breakfast
3 nights + flight
C$ 429
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
7.9 Good
Near North Side
Pool
Pet friendly
Dallas/Fort Worth
Breakfast
3 nights + flight
C$ 551
The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel - Chicago - Restaurant
The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel - Chicago - Restaurant
The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel
8.3 Very good
Near North Side
Free Wi-Fi
Pet friendly
Denver Intl
Meals not included
3 nights + flight
C$ 497
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop
8.9 Very good
Loop
Free Wi-Fi
Pet friendly
Spa
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 574
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Fort Lauderdale
Meals not included
3 nights + flight
C$ 461
The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Lobby
The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Lobby
The Allegro Royal Sonesta Hotel Chicago Loop
8.4 Very good
Loop
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 480
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
9.3 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Fort Lauderdale
Meals not included
3 nights + flight
C$ 919
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Building
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Building
Courtyard by Marriott Chicago Downtown/Magnificent Mile
8.1 Very good
Near North Side
Free Wi-Fi
Pool
Spa
Denver Intl
Meals not included
3 nights + flight
C$ 443
Hotel Riu Plaza Chicago - Chicago - Lounge
Hotel Riu Plaza Chicago - Chicago - Lounge
Hotel Riu Plaza Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Fort Lauderdale
Breakfast
3 nights + flight
C$ 535
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago
8.1 Very good
Loop
Free Wi-Fi
Fort Lauderdale
Meals not included
3 nights + flight
C$ 512
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.9 Very good
Near North Side
Free Wi-Fi
Pool
Spa
Fort Lauderdale
Meals not included
3 nights + flight
C$ 1,096

Last minute vacation packages to Chicago

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SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown
9 Wonderful
Chinatown
Free Wi-Fi
Raleigh-Durham
Breakfast
3 nights + flight
C$ 1,187

When to book a vacation in Chicago

Price includes flights and 3 nights accommodation for 2 travellers. Prices are not fixed and may vary with time.

Tips for finding Chicago package deals

  • There are loads of types of vacations in Chicago and the cost will depend on what type of trip you’re taking and for how long you’d like to stay. Here are the latest prices for a 3 night trip for 2 travellers: Top vacation C$ 94; Family vacation C$ 205; Romantic vacation C$ 245; Luxury vacation C$ 487; Budget vacation C$ 255.

Where to stay in Chicago

Our map will help you find the perfect place to stay for your vacation in Chicago by showing you the exact location of each hotel.

Everything you need to know for your vacation in Chicago

Chicago vacation information

Top vacation (Flight+Hotel)C$ 94
Family vacation (Flight+Hotel)C$ 205
Romantic vacation (Flight+Hotel)C$ 245
Luxury vacation (Flight+Hotel)C$ 487
Budget vacation (Flight+Hotel)C$ 255