Vacations in Chicago

Vacations in Chicago

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Cheap Chicago package deals

These are the best prices for Aug 4 - 7.
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BreakfastHalf boardSelf cateringAll inclusiveMeals not included

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C$ 263 - C$ 507C$ 507 - C$ 751C$ 751 - C$ 994C$ 994 - C$ 1,238C$ 1,238+ per night

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Free breakfastFree internetFree airport shuttleFree parking

Most popular Chicago flight and hotel deals

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The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
7.9 Good
Near North Side
Pool
Pet friendly
Los Angeles Los Angeles
Meals not included
3 nights + flight
C$ 585
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Building
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Building
Intercontinental Hotels Chicago Magnificent Mile By IHG
8.1 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Los Angeles Los Angeles
Meals not included
3 nights + flight
C$ 634
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
Los Angeles Los Angeles
Meals not included
3 nights + flight
C$ 569
River Hotel - Chicago - Property amenity
River Hotel - Chicago - Property amenity
River Hotel
8.4 Very good
Loop
Free Wi-Fi
Pet friendly
Los Angeles Los Angeles
Meals not included
3 nights + flight
C$ 501
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
Los Angeles Los Angeles
Breakfast
3 nights + flight
C$ 579
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 Very good
Near West Side
Free Wi-Fi
Pet friendly
Fort Lauderdale
Meals not included
3 nights + flight
C$ 696
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
Los Angeles Los Angeles
Meals not included
3 nights + flight
C$ 532
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Los Angeles Los Angeles
Meals not included
3 nights + flight
C$ 803
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
Los Angeles Los Angeles
Meals not included
3 nights + flight
C$ 586
The Royal Sonesta Chicago Downtown - Chicago - Building
The Royal Sonesta Chicago Downtown - Chicago - Building
The Royal Sonesta Chicago Downtown
8.8 Very good
Loop
Pet friendly
Los Angeles Los Angeles
Meals not included
3 nights + flight
C$ 624
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Los Angeles Los Angeles
Meals not included
3 nights + flight
C$ 530
Hotel Lincoln - Chicago - Balcony
Hotel Lincoln - Chicago - Balcony
Hotel Lincoln
7 Good
Lincoln Park
Free Wi-Fi
Pet friendly
Los Angeles Los Angeles
Meals not included
3 nights + flight
C$ 559
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
Loop
Pet friendly
Los Angeles Los Angeles
Meals not included
3 nights + flight
C$ 579
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
Los Angeles Los Angeles
Meals not included
3 nights + flight
C$ 991
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago
8.4 Very good
Loop
Free Wi-Fi
Los Angeles Los Angeles
Meals not included
3 nights + flight
C$ 648
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
Los Angeles Los Angeles
Meals not included
3 nights + flight
C$ 739

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
Los Angeles Los Angeles
All inclusive
3 nights + flight
C$ 1,195

Last minute vacation packages to Chicago

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Admiral Motel By OYO Chicago I-94 - Chicago - Building
Admiral Motel By OYO Chicago I-94 - Chicago - Building
Admiral Motel By OYO Chicago I-94
2.7 Poor
Chatham
Parking
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
C$ 724
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Meeting room
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Meeting room
Courtyard by Marriott Chicago Downtown/Magnificent Mile
8.2 Very good
Near North Side
Free Wi-Fi
Pool
Charlotte Douglas
Meals not included
3 nights + flight
C$ 1,493

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$ 235; Romantic vacation C$ 247; Luxury vacation C$ 516; Budget vacation C$ 257.

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$ 235
Romantic vacation (Flight+Hotel)C$ 247
Luxury vacation (Flight+Hotel)C$ 516
Budget vacation (Flight+Hotel)C$ 257