Vacations in Chicago

Vacations in Chicago

2 travellers

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Cheap Chicago package deals

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C$ 296 - C$ 520C$ 520 - C$ 746C$ 746 - C$ 971C$ 971 - C$ 1,196C$ 1,196+ per night

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Most popular Chicago flight and hotel deals

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Thompson Chicago - Chicago - Living room
Thompson Chicago - Chicago - Living room
Thompson Chicago
8.8 Very good
Near North Side
Free Wi-Fi
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 430
The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
8.1 Very good
Near North Side
Pool
Pet friendly
Charlotte Douglas
Meals not included
3 nights + flight
C$ 445
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
9 Wonderful
Near North Side
Free Wi-Fi
Pet friendly
New York John F Kennedy Intl
Breakfast
3 nights + flight
C$ 415
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
Charlotte Douglas
Meals not included
3 nights + flight
C$ 372
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
8.3 Very good
Near North Side
Free Wi-Fi
Pet friendly
Dallas/Fort Worth
Breakfast
3 nights + flight
C$ 404
Holiday Inn Express Chicago - Magnificent Mile By IHG - Chicago - Lobby
Holiday Inn Express Chicago - Magnificent Mile By IHG - Chicago - Lobby
Holiday Inn Express Chicago - Magnificent Mile By IHG
7.6 Good
Near North Side
Free Wi-Fi
Dallas/Fort Worth
Breakfast
3 nights + flight
C$ 399
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.7 Very good
Near West Side
Free Wi-Fi
Pet friendly
Dallas/Fort Worth
Breakfast
3 nights + flight
C$ 464
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
Orlando
Meals not included
3 nights + flight
C$ 532
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop
9 Wonderful
Downtown
Free Wi-Fi
Pet friendly
Spa
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 498
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
8.2 Very good
Downtown
Pool
Pet friendly
Spa
New York John F Kennedy Intl
Meals not included
3 nights + flight
C$ 1,195
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
New York John F Kennedy Intl
Meals not included
3 nights + flight
C$ 311
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
Downtown
Pet friendly
Charlotte Douglas
Meals not included
3 nights + flight
C$ 446
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
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 352
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown
9 Wonderful
South Side
Free Wi-Fi
New York John F Kennedy Intl
Breakfast
3 nights + flight
C$ 328
Homewood Suites by Hilton Chicago Downtown/Magnificent Mile - Chicago - Lounge
Homewood Suites by Hilton Chicago Downtown/Magnificent Mile - Chicago - Lounge
Homewood Suites by Hilton Chicago Downtown/Magnificent Mile
7.8 Good
Near North Side
Free Wi-Fi
Pet friendly
Charlotte Douglas
Breakfast
3 nights + flight
C$ 447
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Dallas/Fort Worth
Breakfast
3 nights + flight
C$ 465

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
Charlotte Douglas
All inclusive
3 nights + flight
C$ 1,574

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$ 724; Family vacation C$ 656; Romantic vacation C$ 764; Luxury vacation C$ 757; Budget vacation C$ 539.

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$ 724
Family vacation (Flight+Hotel)C$ 656
Romantic vacation (Flight+Hotel)C$ 764
Luxury vacation (Flight+Hotel)C$ 757
Budget vacation (Flight+Hotel)C$ 539