Vacations in Chicago

Vacations in Chicago

2 travellers

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C$ 180 - C$ 456C$ 456 - C$ 732C$ 732 - C$ 1,007C$ 1,007 - C$ 1,282C$ 1,282+ per night

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Most popular Chicago flight and hotel deals

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Le Méridien Essex Chicago - Chicago - Bedroom
Le Méridien Essex Chicago - Chicago - Bedroom
Le Méridien Essex Chicago
8.2 Very good
Downtown
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 339
The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
8.1 Very good
Near North Side
Pool
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 323
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Lobby
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Lobby
Intercontinental Hotels Chicago Magnificent Mile By IHG
8 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 460
Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Lobby
Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Lobby
Residence Inn by Marriott Chicago Downtown Magnificent Mile
8.9 Very good
Near North Side
Free Wi-Fi
Pet friendly
Austin Bergstrom
Meals not included
3 nights + flight
C$ 472
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites
8.5 Very good
Near North Side
Free Wi-Fi
Pet friendly
Austin Bergstrom
Meals not included
3 nights + flight
C$ 368
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical - Chicago - Lounge
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical - Chicago - Lounge
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
7.7 Good
Near North Side
Free Wi-Fi
Houston George Bush Intcntl
Breakfast
3 nights + flight
C$ 329
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.6 Very good
Near West Side
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Breakfast
3 nights + flight
C$ 340
Crowne Plaza Chicago West Loop By IHG - Chicago - Lobby
Crowne Plaza Chicago West Loop By IHG - Chicago - Lobby
Crowne Plaza Chicago West Loop By IHG
8.2 Very good
Near West Side
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 337
Hampton Inn Majestic Chicago Theatre District - Chicago - Building
Hampton Inn Majestic Chicago Theatre District - Chicago - Building
Hampton Inn Majestic Chicago Theatre District
8.3 Very good
Downtown
Pet friendly
Austin Bergstrom
Meals not included
3 nights + flight
C$ 390
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 967
The Wicker Park Inn - Chicago - Bedroom
The Wicker Park Inn - Chicago - Bedroom
The Wicker Park Inn
8.9 Very good
Free Wi-Fi
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 704
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North
8.5 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Austin Bergstrom
Meals not included
3 nights + flight
C$ 409
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop
9 Wonderful
Downtown
Free Wi-Fi
Pet friendly
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 482
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
8.3 Very good
Downtown
Pet friendly
Austin Bergstrom
Meals not included
3 nights + flight
C$ 419
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
9.2 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Austin Bergstrom
Meals not included
3 nights + flight
C$ 769
Four Seasons Hotel Chicago - Chicago - Lounge
Four Seasons Hotel Chicago - Chicago - Lounge
Four Seasons Hotel Chicago
8.7 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 989

All inclusive vacation packages to Chicago

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The Wheeler Mansion - Chicago - Dining room
The Wheeler Mansion - Chicago - Dining room
The Wheeler Mansion
9.8 Wonderful
Near South Side
Free Wi-Fi
San Francisco
All inclusive
3 nights + flight
C$ 1,216

Last minute vacation packages to Chicago

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The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy
Near West Side
San Francisco
Meals not included
3 nights + flight
C$ 945
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard by Marriott Chicago Downtown/Magnificent Mile
8.3 Very good
Near North Side
Free Wi-Fi
Pool
San Francisco
Meals not included
3 nights + flight
C$ 906

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$ 733; Family vacation C$ 664; Romantic vacation C$ 774; Luxury vacation C$ 767; Budget vacation C$ 546.

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$ 733
Family vacation (Flight+Hotel)C$ 664
Romantic vacation (Flight+Hotel)C$ 774
Luxury vacation (Flight+Hotel)C$ 767
Budget vacation (Flight+Hotel)C$ 546