Vacations in Chicago

Vacations in Chicago

2 travellers

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Cheap Chicago package deals

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C$ 232 - C$ 487C$ 487 - C$ 741C$ 741 - C$ 995C$ 995 - C$ 1,251C$ 1,251+ 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
8.7 Very good
Near North Side
Free Wi-Fi
Pet friendly
Cleveland Hopkins Intl
Meals not included
3 nights + flight
C$ 474
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
Baltimore/Washington
Breakfast
3 nights + flight
C$ 467
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
Baltimore/Washington
Meals not included
3 nights + flight
C$ 367
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
8.2 Very good
Near North Side
Free Wi-Fi
Pet friendly
Las Vegas Harry Reid Intl
Breakfast
3 nights + flight
C$ 422
River Hotel - Chicago - Lobby
River Hotel - Chicago - Lobby
River Hotel
8.3 Very good
Downtown
Free Wi-Fi
Pet friendly
Cleveland Hopkins Intl
Meals not included
3 nights + flight
C$ 340
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
Baltimore/Washington
Breakfast
3 nights + flight
C$ 411
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites by Hilton Chicago Medical District UIC
9.3 Wonderful
Near West Side
Pool
Pet friendly
Dallas/Fort Worth
Breakfast
3 nights + flight
C$ 423
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton
9 Wonderful
Downtown
Free Wi-Fi
Spa
Cleveland Hopkins Intl
Meals not included
3 nights + flight
C$ 445
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
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
C$ 454
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
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
C$ 470
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
8.8 Very good
Downtown
Pool
Pet friendly
Spa
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 1,249
Homewood Suites by Hilton - Chicago Downtown South Loop - Chicago - Living room
Homewood Suites by Hilton - Chicago Downtown South Loop - Chicago - Living room
Homewood Suites by Hilton - Chicago Downtown South Loop
8.1 Very good
Downtown
Free Wi-Fi
Pool
Houston George Bush Intcntl
Breakfast
3 nights + flight
C$ 368
The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Living room
The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Living room
The Allegro Royal Sonesta Hotel Chicago Loop
8.3 Very good
Downtown
Pet friendly
Orlando
Meals not included
3 nights + flight
C$ 420
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Cleveland Hopkins Intl
Meals not included
3 nights + flight
C$ 735
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
8.4 Very good
Near North Side
Free Wi-Fi
Pool
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 339
Central Loop Hotel - Chicago - Front desk
Central Loop Hotel - Chicago - Front desk
Central Loop Hotel
8 Very good
Downtown
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 416

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
Nashville Intl
Meals not included
3 nights + flight
C$ 859

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$ 748; Family vacation C$ 678; Romantic vacation C$ 790; Luxury vacation C$ 783; Budget vacation C$ 557.

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$ 748
Family vacation (Flight+Hotel)C$ 678
Romantic vacation (Flight+Hotel)C$ 790
Luxury vacation (Flight+Hotel)C$ 783
Budget vacation (Flight+Hotel)C$ 557

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