Vacations in Chicago

Vacations in Chicago

2 travellers

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C$ 290 - C$ 625C$ 625 - C$ 960C$ 960 - C$ 1,294C$ 1,294 - C$ 1,629C$ 1,629+ per night

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Most popular Chicago flight and hotel deals

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The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
7.8 Good
Near North Side
Pool
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
C$ 536
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel - Chicago - Restaurant
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel - Chicago - Restaurant
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
8 Very good
Loop
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
C$ 432
River Hotel - Chicago - Property amenity
River Hotel - Chicago - Property amenity
River Hotel
8.4 Very good
Loop
Free Wi-Fi
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
C$ 452
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel
8.1 Very good
O'Hare
Airport shuttle
Pool
Nashville Intl
Meals not included
3 nights + flight
C$ 523
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
8.9 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
C$ 799
The Whitehall Hotel, BW Premier Collection - Chicago - Lounge
The Whitehall Hotel, BW Premier Collection - Chicago - Lounge
The Whitehall Hotel, BW Premier Collection
7.8 Good
Near North Side
Free Wi-Fi
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
C$ 465
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Los Angeles
Meals not included
3 nights + flight
C$ 510
Aloft Chicago Mag Mile - Chicago - Pool
Aloft Chicago Mag Mile - Chicago - Pool
Aloft Chicago Mag Mile
8.2 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
C$ 549
La Quinta Inn & Suites by Wyndham Chicago Downtown - Chicago - Bar
La Quinta Inn & Suites by Wyndham Chicago Downtown - Chicago - Bar
La Quinta Inn & Suites by Wyndham Chicago Downtown
8 Very good
Loop
Free Wi-Fi
Pet friendly
Spa
Baltimore/Washington
Breakfast
3 nights + flight
C$ 524
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
Meals not included
3 nights + flight
C$ 957
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
8.1 Very good
Near North Side
Free Wi-Fi
Pool
Baltimore/Washington
Meals not included
3 nights + flight
C$ 588
SpringHill Suites by Marriott Chicago O'Hare - Chicago - Patio
SpringHill Suites by Marriott Chicago O'Hare - Chicago - Patio
SpringHill Suites by Marriott Chicago O'Hare
8.1 Very good
Norwood Park
Airport shuttle
Free Wi-Fi
Pool
Pet friendly
Philadelphia
Breakfast
3 nights + flight
C$ 449
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago
8.3 Very good
Loop
Free Wi-Fi
Philadelphia
Meals not included
3 nights + flight
C$ 630
Central Loop Hotel - Chicago - Lobby
Central Loop Hotel - Chicago - Lobby
Central Loop Hotel
8.1 Very good
Loop
Free Wi-Fi
Pet friendly
Denver Intl
Meals not included
3 nights + flight
C$ 433
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel
7.2 Good
Loop
Free Wi-Fi
Los Angeles
Meals not included
3 nights + flight
C$ 464
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection
8.2 Very good
Near North Side
Free Wi-Fi
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
C$ 571

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
All inclusive
3 nights + flight
C$ 1,018

Last minute vacation packages to Chicago

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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
Philadelphia
Meals not included
3 nights + flight
C$ 830
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy
Near West Side
Philadelphia
Meals not included
3 nights + flight
C$ 1,268
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.9 Very good
Near West Side
Free Wi-Fi
Pet friendly
Philadelphia
Breakfast
3 nights + flight
C$ 767

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$ 85; Family vacation C$ 202; Romantic vacation C$ 242; Luxury vacation C$ 480; Budget vacation C$ 252.

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$ 85
Family vacation (Flight+Hotel)C$ 202
Romantic vacation (Flight+Hotel)C$ 242
Luxury vacation (Flight+Hotel)C$ 480
Budget vacation (Flight+Hotel)C$ 252