Vacations in Chicago

Vacations in Chicago

2 travellers

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Cheap Chicago package deals

These are the best prices for May 18 - 21.
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BreakfastHalf boardSelf cateringAll inclusiveMeals not included

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C$ 308 - C$ 575C$ 575 - C$ 843C$ 843 - C$ 1,110C$ 1,110 - C$ 1,378C$ 1,378+ 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
7.9 Good
Near North Side
Pool
Pet friendly
San Francisco
Meals not included
3 nights + flight
C$ 585
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
San Francisco
Meals not included
3 nights + flight
C$ 552
Hilton Chicago - Chicago - Living room
Hilton Chicago - Chicago - Living room
Hilton Chicago
7.9 Good
Downtown
Free Wi-Fi
Pool
Pet friendly
San Francisco
Meals not included
3 nights + flight
C$ 531
River Hotel - Chicago - Property amenity
River Hotel - Chicago - Property amenity
River Hotel
8.4 Very good
Downtown
Free Wi-Fi
Pet friendly
San Francisco
Meals not included
3 nights + flight
C$ 502
Hotel Saint Clair - Magnificent Mile - Chicago - Bedroom
Hotel Saint Clair - Magnificent Mile - Chicago - Bedroom
Hotel Saint Clair - Magnificent Mile
8 Very good
Near North Side
Free Wi-Fi
Pet friendly
San Francisco
Meals not included
3 nights + flight
C$ 467
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
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
C$ 658
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
San Francisco
Meals not included
3 nights + flight
C$ 543
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
San Francisco
Meals not included
3 nights + flight
C$ 546
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
San Francisco
Meals not included
3 nights + flight
C$ 565
Hampton Inn Chicago Downtown/N Loop/Michigan Ave - Chicago - Lobby
Hampton Inn Chicago Downtown/N Loop/Michigan Ave - Chicago - Lobby
Hampton Inn Chicago Downtown/N Loop/Michigan Ave
7.9 Good
Downtown
Free Wi-Fi
Pet friendly
San Francisco
Breakfast
3 nights + flight
C$ 517
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
9.2 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
San Francisco
Meals not included
3 nights + flight
C$ 1,008
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago
8.6 Very good
Downtown
Free Wi-Fi
San Francisco
Meals not included
3 nights + flight
C$ 671
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
San Francisco
Meals not included
3 nights + flight
C$ 642
Hampton Inn Chicago Downtown/Magnificent Mile - Chicago - Lounge
Hampton Inn Chicago Downtown/Magnificent Mile - Chicago - Lounge
Hampton Inn Chicago Downtown/Magnificent Mile
7.5 Good
Near North Side
Free Wi-Fi
Pet friendly
San Francisco
Breakfast
3 nights + flight
C$ 561
The Peninsula Chicago - Chicago - Lobby
The Peninsula Chicago - Chicago - Lobby
The Peninsula Chicago
9.4 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
San Francisco
Meals not included
3 nights + flight
C$ 1,234
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel
7.3 Good
Downtown
Free Wi-Fi
San Francisco
Meals not included
3 nights + flight
C$ 521

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
Lambert-St Louis
All inclusive
3 nights + flight
C$ 1,227

Last minute vacation packages to Chicago

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Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.7 Very good
Near West Side
Free Wi-Fi
Pet friendly
Santa Ana J. Wayne/Orange Cnty
Breakfast
3 nights + flight
C$ 1,157
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown
9 Wonderful
South Side
Free Wi-Fi
Santa Ana J. Wayne/Orange Cnty
Breakfast
3 nights + flight
C$ 987

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$ 104; Family vacation C$ 401; Romantic vacation C$ 238; Luxury vacation C$ 498; Budget vacation C$ 265.

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$ 104
Family vacation (Flight+Hotel)C$ 401
Romantic vacation (Flight+Hotel)C$ 238
Luxury vacation (Flight+Hotel)C$ 498
Budget vacation (Flight+Hotel)C$ 265