Vacations in Chicago

Vacations in Chicago

2 travellers

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Cheap Chicago package deals

These are the best prices for Jul 25 - 28.
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BreakfastHalf boardSelf cateringAll inclusiveMeals not included

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C$ 340 - C$ 651C$ 651 - C$ 961C$ 961 - C$ 1,272C$ 1,272 - C$ 1,584C$ 1,584+ per night

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Most popular Chicago flight and hotel deals

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Thompson Chicago - Chicago - Lobby
Thompson Chicago - Chicago - Lobby
Thompson Chicago
8.9 Very good
Near North Side
Free Wi-Fi
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 888
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
8.1 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Philadelphia
Meals not included
3 nights + flight
C$ 694
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
Pool
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 727
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.8 Very good
Near West Side
Free Wi-Fi
Pet friendly
Philadelphia
Breakfast
3 nights + flight
C$ 482
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton
8.9 Very good
Downtown
Free Wi-Fi
Spa
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 952
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North
8.6 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Philadelphia
Meals not included
3 nights + flight
C$ 654
Palmer House a Hilton Hotel - Chicago - Lounge
Palmer House a Hilton Hotel - Chicago - Lounge
Palmer House a Hilton Hotel
8 Very good
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Philadelphia
Meals not included
3 nights + flight
C$ 573
The Whitehall Hotel, BW Premier Collection - Chicago - Lounge
The Whitehall Hotel, BW Premier Collection - Chicago - Lounge
The Whitehall Hotel, BW Premier Collection
7.9 Good
Near North Side
Free Wi-Fi
Pet friendly
Philadelphia
Meals not included
3 nights + flight
C$ 405
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Philadelphia
Meals not included
3 nights + flight
C$ 558
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
San Francisco
Meals not included
3 nights + flight
C$ 1,243
Best Western River North Hotel - Chicago - Balcony
Best Western River North Hotel - Chicago - Balcony
Best Western River North Hotel
7.3 Good
Near North Side
Free Wi-Fi
Pool
Philadelphia
Meals not included
3 nights + flight
C$ 480
Central Loop Hotel - Chicago - Lobby
Central Loop Hotel - Chicago - Lobby
Central Loop Hotel
8.1 Very good
Downtown
Free Wi-Fi
Pet friendly
Philadelphia
Meals not included
3 nights + flight
C$ 440
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
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 820
Sofitel Chicago Magnificent Mile - Chicago - Gym
Sofitel Chicago Magnificent Mile - Chicago - Gym
Sofitel Chicago Magnificent Mile
8.8 Very good
Near North Side
Free Wi-Fi
Pet friendly
Philadelphia
Meals not included
3 nights + flight
C$ 823
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
Pet friendly
Spa
Philadelphia
Meals not included
3 nights + flight
C$ 1,268
Club Quarters Hotel Central Loop, Chicago - Chicago - Lobby
Club Quarters Hotel Central Loop, Chicago - Chicago - Lobby
Club Quarters Hotel Central Loop, Chicago
8.2 Very good
Downtown
Free Wi-Fi
Pet friendly
Philadelphia
Meals not included
3 nights + flight
C$ 439

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$ 1,275

Last minute vacation packages to Chicago

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SpringHill Suites by Marriott Chicago Chinatown - Chicago - Meeting room
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Meeting room
SpringHill Suites by Marriott Chicago Chinatown
9 Wonderful
South Side
Free Wi-Fi
Huntsville
Meals not included
3 nights + flight
C$ 1,435
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Pool
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Pool
Hampton Inn & Suites by Hilton Chicago Medical District UIC
9.3 Wonderful
Near West Side
Pool
Pet friendly
Huntsville
Meals not included
3 nights + flight
C$ 1,337

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$ 91; Family vacation C$ 236; Romantic vacation C$ 248; Luxury vacation C$ 519; Budget vacation C$ 258.

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$ 91
Family vacation (Flight+Hotel)C$ 236
Romantic vacation (Flight+Hotel)C$ 248
Luxury vacation (Flight+Hotel)C$ 519
Budget vacation (Flight+Hotel)C$ 258