Vacations in Chicago

Vacations in Chicago

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Cheap Chicago package deals

These are the best prices for 30 Jul - 2 Aug.
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BreakfastHalf boardSelf cateringAll inclusiveMeals not included

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C$ 253 - C$ 608C$ 608 - C$ 964C$ 964 - C$ 1,318C$ 1,318 - C$ 1,673C$ 1,673+ 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$ 602
Warwick Allerton Chicago - Chicago - Building
Warwick Allerton Chicago - Chicago - Building
Warwick Allerton Chicago
8.1 Very good
Near North Side
Free Wi-Fi
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
C$ 699
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
Los Angeles
Meals not included
3 nights + flight
C$ 717
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites
8.5 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Los Angeles
Meals not included
3 nights + flight
C$ 629
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
8.1 Very good
Near North Side
Free Wi-Fi
Pet friendly
Los Angeles
Breakfast
3 nights + flight
C$ 633
River Hotel - Chicago - Property amenity
River Hotel - Chicago - Property amenity
River Hotel
8.4 Very good
Loop
Free Wi-Fi
Pet friendly
Los Angeles
Meals not included
3 nights + flight
C$ 732
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
Los Angeles
Breakfast
3 nights + flight
C$ 601
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton
8.9 Very good
Loop
Free Wi-Fi
Spa
Los Angeles
Meals not included
3 nights + flight
C$ 791
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
Loop
Free Wi-Fi
Pet friendly
Spa
Baltimore/Washington
Meals not included
3 nights + flight
C$ 803
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$ 592
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
Meals not included
3 nights + flight
C$ 610
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$ 995
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
Los Angeles
Meals not included
3 nights + flight
C$ 683
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
Meals not included
3 nights + flight
C$ 674
Club Quarters Hotel Wacker at Michigan, Chicago - Chicago - Building
Club Quarters Hotel Wacker at Michigan, Chicago - Chicago - Building
Club Quarters Hotel Wacker at Michigan, Chicago
8.3 Very good
Loop
Free Wi-Fi
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
C$ 737
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection
8.5 Very good
Near North Side
Free Wi-Fi
Pet friendly
Los Angeles
Meals not included
3 nights + flight
C$ 816

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
Seattle/Tacoma Intl
All inclusive
3 nights + flight
C$ 862

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
Columbus
Meals not included
3 nights + flight
C$ 1,163
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
Columbus
Meals not included
3 nights + flight
C$ 1,198
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
Columbus
Breakfast
3 nights + flight
C$ 1,280

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$ 90; Family vacation C$ 234; Romantic vacation C$ 246; Luxury vacation C$ 515; Budget vacation C$ 256.

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$ 90
Family vacation (Flight+Hotel)C$ 234
Romantic vacation (Flight+Hotel)C$ 246
Luxury vacation (Flight+Hotel)C$ 515
Budget vacation (Flight+Hotel)C$ 256