Vacations in Chicago

Vacations in Chicago

2 travellers

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Cheap Chicago package deals

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C$ 268 - C$ 461C$ 461 - C$ 655C$ 655 - C$ 848C$ 848 - C$ 1,041C$ 1,041+ 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
Fort Lauderdale
Meals not included
3 nights + flight
C$ 451
Le Méridien Essex Chicago - Chicago - Bedroom
Le Méridien Essex Chicago - Chicago - Bedroom
Le Méridien Essex Chicago
8.2 Very good
Downtown
Fort Lauderdale
Meals not included
3 nights + flight
C$ 327
The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
8.1 Very good
Near North Side
Pool
Pet friendly
New York John F Kennedy Intl
Meals not included
3 nights + flight
C$ 401
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
Fort Lauderdale
Meals not included
3 nights + flight
C$ 487
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
Orlando
Breakfast
3 nights + flight
C$ 467
Admiral Motel By OYO Chicago I-94 - Chicago - Balcony
Admiral Motel By OYO Chicago I-94 - Chicago - Balcony
Admiral Motel By OYO Chicago I-94
3.4 Poor
South Side
Parking
Pet friendly
New York John F Kennedy Intl
Meals not included
3 nights + flight
C$ 292
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
New York John F Kennedy Intl
Meals not included
3 nights + flight
C$ 350
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel
8 Very good
O'Hare
Airport shuttle
Pool
Fort Lauderdale
Meals not included
3 nights + flight
C$ 383
Hampton Inn Majestic Chicago Theatre District - Chicago - Building
Hampton Inn Majestic Chicago Theatre District - Chicago - Building
Hampton Inn Majestic Chicago Theatre District
8.5 Very good
Downtown
Pet friendly
Orlando
Breakfast
3 nights + flight
C$ 381
Silversmith Hotel Chicago Downtown - Chicago - Restaurant
Silversmith Hotel Chicago Downtown - Chicago - Restaurant
Silversmith Hotel Chicago Downtown
8.7 Very good
Downtown
Free Wi-Fi
New York John F Kennedy Intl
Meals not included
3 nights + flight
C$ 411
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
Fort Lauderdale
Meals not included
3 nights + flight
C$ 432
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy
Near West Side
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 574
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
Fort Lauderdale
Meals not included
3 nights + flight
C$ 431
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
Fort Lauderdale
Meals not included
3 nights + flight
C$ 267
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Fort Lauderdale
Breakfast
3 nights + flight
C$ 432
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago
8.6 Very good
Downtown
Free Wi-Fi
Pet friendly
New York John F Kennedy Intl
Meals not included
3 nights + flight
C$ 336

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
Houston George Bush Intcntl
All inclusive
3 nights + flight
C$ 1,389

Last minute vacation packages to Chicago

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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
New York John F Kennedy Intl
Meals not included
3 nights + flight
C$ 539

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$ 735; Family vacation C$ 667; Romantic vacation C$ 777; Luxury vacation C$ 770; Budget vacation C$ 548.

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$ 735
Family vacation (Flight+Hotel)C$ 667
Romantic vacation (Flight+Hotel)C$ 777
Luxury vacation (Flight+Hotel)C$ 770
Budget vacation (Flight+Hotel)C$ 548