Vacations in Chicago

Vacations in Chicago

2 travellers

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Cheap Chicago package deals

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BreakfastHalf boardSelf cateringAll inclusiveMeals not included

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C$ 270 - C$ 534C$ 534 - C$ 798C$ 798 - C$ 1,063C$ 1,063 - C$ 1,327C$ 1,327+ 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
Los Angeles
Meals not included
3 nights + flight
C$ 631
Admiral Motel By OYO Chicago I-94 - Chicago - Bedroom
Admiral Motel By OYO Chicago I-94 - Chicago - Bedroom
Admiral Motel By OYO Chicago I-94
4.1 Mediocre
South Side
Parking
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 316
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$ 599
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel
7.9 Good
O'Hare
Airport shuttle
Pool
Philadelphia
Meals not included
3 nights + flight
C$ 487
L7 Chicago by LOTTE - Chicago - Lounge
L7 Chicago by LOTTE - Chicago - Lounge
L7 Chicago by LOTTE
9.1 Wonderful
Downtown
Free Wi-Fi
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 553
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
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 506
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
San Francisco
Meals not included
3 nights + flight
C$ 1,186
Homewood Suites by Hilton Chicago Downtown West Loop - Chicago - Living room
Homewood Suites by Hilton Chicago Downtown West Loop - Chicago - Living room
Homewood Suites by Hilton Chicago Downtown West Loop
9 Wonderful
Near West Side
Free Wi-Fi
Pool
Pet friendly
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
C$ 592
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
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
C$ 679
Eurostars Magnificent Mile - Chicago - Lounge
Eurostars Magnificent Mile - Chicago - Lounge
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Los Angeles
Meals not included
3 nights + flight
C$ 476
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
New York LaGuardia
Meals not included
3 nights + flight
C$ 578
Marriott Chicago O'Hare - Chicago - Building
Marriott Chicago O'Hare - Chicago - Building
Marriott Chicago O'Hare
7.2 Good
O'Hare
Airport shuttle
Free Wi-Fi
Pool
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 550
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel
8.8 Very good
Downtown
Pet friendly
Spa
Richmond Byrd Intl
Meals not included
3 nights + flight
C$ 684
SpringHill Suites by Marriott Chicago Downtown/River North - Chicago - Lounge
SpringHill Suites by Marriott Chicago Downtown/River North - Chicago - Lounge
SpringHill Suites by Marriott Chicago Downtown/River North
8.7 Very good
Near North Side
Free Wi-Fi
Pet friendly
Dallas/Fort Worth
Breakfast
3 nights + flight
C$ 629
Holiday Inn & Suites Chicago-Downtown By IHG - Chicago - Lounge
Holiday Inn & Suites Chicago-Downtown By IHG - Chicago - Lounge
Holiday Inn & Suites Chicago-Downtown By IHG
8.1 Very good
Near West Side
Free Wi-Fi
Pool
Los Angeles
Meals not included
3 nights + flight
C$ 496
Virgin Hotels Chicago - Chicago - Building
Virgin Hotels Chicago - Chicago - Building
Virgin Hotels Chicago
8.6 Very good
Downtown
Free Wi-Fi
Pet friendly
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
C$ 800

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
Pet friendly
Los Angeles
All inclusive
3 nights + flight
C$ 1,110

Last minute vacation packages to Chicago

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Sonder by Marriott Bonvoy The Burnham Apartments Loop - Chicago - Living room
Sonder by Marriott Bonvoy The Burnham Apartments Loop - Chicago - Living room
Sonder by Marriott Bonvoy The Burnham Apartments Loop
8.1 Very good
Near West Side
Free Wi-Fi
Fort Myers SW Florida Intl
Meals not included
3 nights + flight
C$ 754

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$ 729; Family vacation C$ 661; Romantic vacation C$ 771; Luxury vacation C$ 763; Budget vacation C$ 544.

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$ 729
Family vacation (Flight+Hotel)C$ 661
Romantic vacation (Flight+Hotel)C$ 771
Luxury vacation (Flight+Hotel)C$ 763
Budget vacation (Flight+Hotel)C$ 544

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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