Vacations in Chicago

Vacations in Chicago

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Cheap Chicago package deals

These are the best prices for Jul 15 - 18.
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BreakfastHalf boardSelf cateringAll inclusiveMeals not included

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C$ 401 - C$ 695C$ 695 - C$ 988C$ 988 - C$ 1,281C$ 1,281 - C$ 1,574C$ 1,574+ 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
Washington, D.C. Dulles Intl
Meals not included
3 nights + flight
C$ 875
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
Boston Logan Intl
Meals not included
3 nights + flight
C$ 708
Warwick Allerton Chicago - Chicago - Building
Warwick Allerton Chicago - Chicago - Building
Warwick Allerton Chicago
8.1 Very good
Near North Side
Free Wi-Fi
Boston Logan Intl
Meals not included
3 nights + flight
C$ 622
Omni Chicago Hotel - Chicago - Building
Omni Chicago Hotel - Chicago - Building
Omni Chicago Hotel
8.9 Very good
Near North Side
Free Wi-Fi
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
C$ 706
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites
8.6 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Orlando
Meals not included
3 nights + flight
C$ 694
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
Dallas/Fort Worth
Breakfast
3 nights + flight
C$ 574
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel
8.2 Very good
O'Hare
Airport shuttle
Pool
Boston Logan Intl
Meals not included
3 nights + flight
C$ 588
Hotel 55 Chicago Downtown - Chicago - Restaurant
Hotel 55 Chicago Downtown - Chicago - Restaurant
Hotel 55 Chicago Downtown
8.3 Very good
Near North Side
Free Wi-Fi
Pet friendly
Washington, D.C. Dulles Intl
Meals not included
3 nights + flight
C$ 694
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
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 672
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
7.9 Good
Downtown
Pool
Pet friendly
Spa
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 1,574
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop
8.9 Very good
Downtown
Free Wi-Fi
Pet friendly
Spa
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 771
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Washington, D.C. Dulles Intl
Meals not included
3 nights + flight
C$ 621
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
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 1,088
Chicago Marriott Ohare - Chicago - Building
Chicago Marriott Ohare - Chicago - Building
Chicago Marriott Ohare
7.5 Good
O'Hare
Airport shuttle
Free Wi-Fi
Pool
Boston Logan Intl
Meals not included
3 nights + flight
C$ 653
The Westin Michigan Avenue Chicago - Chicago - Front desk
The Westin Michigan Avenue Chicago - Chicago - Front desk
The Westin Michigan Avenue Chicago
8.2 Very good
Near North Side
Pet friendly
Spa
Washington, D.C. Dulles Intl
Meals not included
3 nights + flight
C$ 690
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
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
C$ 828

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
Dallas/Fort Worth
All inclusive
3 nights + flight
C$ 1,265

Last minute vacation packages to Chicago

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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
New Orleans Louis Armstrong
Meals not included
3 nights + flight
C$ 817
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Building
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Building
Courtyard by Marriott Chicago Downtown/Magnificent Mile
8.2 Very good
Near North Side
Free Wi-Fi
Pool
New York John F Kennedy Intl
Meals not included
3 nights + flight
C$ 856
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
New York John F Kennedy Intl
Breakfast
3 nights + flight
C$ 792

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$ 92; Family vacation C$ 237; Romantic vacation C$ 249; Luxury vacation C$ 521; Budget vacation C$ 260.

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$ 92
Family vacation (Flight+Hotel)C$ 237
Romantic vacation (Flight+Hotel)C$ 249
Luxury vacation (Flight+Hotel)C$ 521
Budget vacation (Flight+Hotel)C$ 260