Vacations in Chicago

Vacations in Chicago

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Cheap Chicago package deals

These are the best prices for May 24 - 27.
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BreakfastHalf boardSelf cateringAll inclusiveMeals not included

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C$ 346 - C$ 567C$ 567 - C$ 788C$ 788 - C$ 1,009C$ 1,009 - C$ 1,229C$ 1,229+ per night

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Most popular Chicago flight and hotel deals

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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
Los Angeles
Meals not included
3 nights + flight
C$ 532
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
3 Poor
South Side
Parking
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 369
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
8.3 Very good
Near North Side
Free Wi-Fi
Pet friendly
Miami
Breakfast
3 nights + flight
C$ 513
Holiday Inn Express Chicago - Magnificent Mile By IHG - Chicago - Lobby
Holiday Inn Express Chicago - Magnificent Mile By IHG - Chicago - Lobby
Holiday Inn Express Chicago - Magnificent Mile By IHG
7.7 Good
Near North Side
Free Wi-Fi
Phoenix Sky Harbor Intl
Breakfast
3 nights + flight
C$ 621
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
Raleigh-Durham
Breakfast
3 nights + flight
C$ 598
Homewood Suites by Hilton Chicago - Downtown - Chicago - Lounge
Homewood Suites by Hilton Chicago - Downtown - Chicago - Lounge
Homewood Suites by Hilton Chicago - Downtown
8.4 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Miami
Breakfast
3 nights + flight
C$ 550
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
Miami
Meals not included
3 nights + flight
C$ 531
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Miami
Meals not included
3 nights + flight
C$ 493
Aloft Chicago Mag Mile - Chicago - Lounge
Aloft Chicago Mag Mile - Chicago - Lounge
Aloft Chicago Mag Mile
8.3 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Los Angeles
Meals not included
3 nights + flight
C$ 554
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
Los Angeles
Meals not included
3 nights + flight
C$ 555
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
Los Angeles
Breakfast
3 nights + flight
C$ 464
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
Miami
Meals not included
3 nights + flight
C$ 727
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard by Marriott Chicago Downtown/Magnificent Mile
8.3 Very good
Near North Side
Free Wi-Fi
Pool
Raleigh-Durham
Meals not included
3 nights + flight
C$ 569
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel
8.7 Very good
Downtown
Pet friendly
Spa
Los Angeles
Meals not included
3 nights + flight
C$ 658
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.6 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Los Angeles
Meals not included
3 nights + flight
C$ 1,107
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel
7.3 Good
Downtown
Free Wi-Fi
Miami
Meals not included
3 nights + flight
C$ 493

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
Phoenix Sky Harbor Intl
All inclusive
3 nights + flight
C$ 1,202

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
8.6 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
London Heathrow
Breakfast
3 nights + flight
C$ 2,461
The Neighborhood Hotel Little Italy - Chicago - Living room
The Neighborhood Hotel Little Italy - Chicago - Living room
The Neighborhood Hotel Little Italy
Near West Side
London Heathrow
Meals not included
3 nights + flight
C$ 2,313

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$ 105; Family vacation C$ 404; Romantic vacation C$ 240; Luxury vacation C$ 501; Budget vacation C$ 266.

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$ 105
Family vacation (Flight+Hotel)C$ 404
Romantic vacation (Flight+Hotel)C$ 240
Luxury vacation (Flight+Hotel)C$ 501
Budget vacation (Flight+Hotel)C$ 266