Vacations in Chicago

Vacations in Chicago

2 travellers

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BreakfastHalf boardSelf cateringAll inclusiveMeals not included

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C$ 172 - C$ 416C$ 416 - C$ 658C$ 658 - C$ 901C$ 901 - C$ 1,144C$ 1,144+ per night

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Most popular Chicago flight and hotel deals

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Thompson Chicago - Chicago - Living room
Thompson Chicago - Chicago - Living room
Thompson Chicago
8.8 Very good
Near North Side
Free Wi-Fi
Pet friendly
Orlando
Meals not included
3 nights + flight
C$ 471
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
Pet friendly
New York LaGuardia
Meals not included
3 nights + flight
C$ 336
Renaissance Chicago Downtown Hotel - Chicago - Building
Renaissance Chicago Downtown Hotel - Chicago - Building
Renaissance Chicago Downtown Hotel
8.7 Very good
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Washington, D.C. Dulles Intl
Meals not included
3 nights + flight
C$ 731
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.5 Very good
Near West Side
Free Wi-Fi
Pet friendly
Dallas/Fort Worth
Breakfast
3 nights + flight
C$ 376
Fairfield Inn and Suites Chicago Downtown-River North - Chicago - Lobby
Fairfield Inn and Suites Chicago Downtown-River North - Chicago - Lobby
Fairfield Inn and Suites Chicago Downtown-River North
8.4 Very good
Near North Side
Free Wi-Fi
Orlando
Breakfast
3 nights + flight
C$ 499
Hampton Inn Majestic Chicago Theatre District - Chicago - Building
Hampton Inn Majestic Chicago Theatre District - Chicago - Building
Hampton Inn Majestic Chicago Theatre District
8.3 Very good
Downtown
Pet friendly
Orlando
Breakfast
3 nights + flight
C$ 459
21c Museum Hotel Chicago - Chicago - Restaurant
21c Museum Hotel Chicago - Chicago - Restaurant
21c Museum Hotel Chicago
8.5 Very good
Near North Side
Free Wi-Fi
Pet friendly
Orlando
Meals not included
3 nights + flight
C$ 445
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
Downtown
Free Wi-Fi
Spa
Denver Intl
Meals not included
3 nights + flight
C$ 454
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
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 518
Eurostars Magnificent Mile - Chicago - Lounge
Eurostars Magnificent Mile - Chicago - Lounge
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
New York LaGuardia
Meals not included
3 nights + flight
C$ 478
Hyatt Place Chicago Downtown/The Loop - Chicago - Bedroom
Hyatt Place Chicago Downtown/The Loop - Chicago - Bedroom
Hyatt Place Chicago Downtown/The Loop
8.2 Very good
Downtown
Free Wi-Fi
Pool
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 554
Aloft Chicago Mag Mile - Chicago - Lounge
Aloft Chicago Mag Mile - Chicago - Lounge
Aloft Chicago Mag Mile
8.2 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 483
The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Living room
The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Living room
The Allegro Royal Sonesta Hotel Chicago Loop
8.4 Very good
Downtown
Pet friendly
Orlando
Meals not included
3 nights + flight
C$ 426
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bar
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bar
Hilton Garden Inn Chicago Downtown Riverwalk
8.4 Very good
Downtown
Free Wi-Fi
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 443
Courtyard Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard Chicago Downtown/Magnificent Mile
8.4 Very good
Near North Side
Free Wi-Fi
Pool
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 383
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
Orlando
Meals not included
3 nights + flight
C$ 635

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
San Francisco
All inclusive
3 nights + flight
C$ 1,175

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$ 734; Family vacation C$ 666; Romantic vacation C$ 776; Luxury vacation C$ 768; Budget vacation C$ 547.

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$ 734
Family vacation (Flight+Hotel)C$ 666
Romantic vacation (Flight+Hotel)C$ 776
Luxury vacation (Flight+Hotel)C$ 768
Budget vacation (Flight+Hotel)C$ 547

Chicago vacation: Search Chicago vacation packages on KAYAK. KAYAK is a travel tool that searches Chicago trips on hundreds of travel sites to help you find the Chicago package that suits you best. Discover Chicago deals now and book your Chicago flight and hotel today.

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