Vacations in Chicago

Vacations in Chicago

2 travellers

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C$ 120 - C$ 357C$ 357 - C$ 592C$ 592 - C$ 828C$ 828 - C$ 1,064C$ 1,064+ per night

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Most popular Chicago flight and hotel deals

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Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Lobby
Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Lobby
Residence Inn by Marriott Chicago Downtown Magnificent Mile
8.9 Very good
Near North Side
Free Wi-Fi
Pet friendly
Charlotte Douglas
Breakfast
3 nights + flight
C$ 386
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
7.7 Good
Near North Side
Free Wi-Fi
Phoenix Sky Harbor Intl
Breakfast
3 nights + flight
C$ 321
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
8.2 Very good
Near West Side
Free Wi-Fi
Pet friendly
Philadelphia
Meals not included
3 nights + flight
C$ 308
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.6 Very good
Near West Side
Free Wi-Fi
Pet friendly
Philadelphia
Breakfast
3 nights + flight
C$ 312
Hotel Chicago Downtown, Autograph Collection - Chicago - Building
Hotel Chicago Downtown, Autograph Collection - Chicago - Building
Hotel Chicago Downtown, Autograph Collection
8.6 Very good
Near North Side
Spa
Philadelphia
Meals not included
3 nights + flight
C$ 423
Hotel 55 Chicago Downtown - Chicago - Restaurant
Hotel 55 Chicago Downtown - Chicago - Restaurant
Hotel 55 Chicago Downtown
8.2 Very good
Near North Side
Free Wi-Fi
Pet friendly
Philadelphia
Meals not included
3 nights + flight
C$ 420
The Wicker Park Inn - Chicago - Bedroom
The Wicker Park Inn - Chicago - Bedroom
The Wicker Park Inn
8.9 Very good
Free Wi-Fi
Philadelphia
Breakfast
3 nights + flight
C$ 594
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites by Hilton Chicago Medical District UIC
9.3 Wonderful
Near West Side
Pool
Pet friendly
Philadelphia
Breakfast
3 nights + flight
C$ 305
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
Philadelphia
Meals not included
3 nights + flight
C$ 350
DoubleTree by Hilton Chicago Midway Airport - Chicago - Lobby
DoubleTree by Hilton Chicago Midway Airport - Chicago - Lobby
DoubleTree by Hilton Chicago Midway Airport
8.6 Very good
Airport shuttle
Free Wi-Fi
Pool
Philadelphia
Meals not included
3 nights + flight
C$ 429
Eurostars Magnificent Mile - Chicago - Living room
Eurostars Magnificent Mile - Chicago - Living room
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Philadelphia
Meals not included
3 nights + flight
C$ 297
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
8.3 Very good
Downtown
Pet friendly
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
C$ 339
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
Charlotte Douglas
Meals not included
3 nights + flight
C$ 308
Chicago Marriott Ohare - Chicago - Building
Chicago Marriott Ohare - Chicago - Building
Chicago Marriott Ohare
7.6 Good
O'Hare
Airport shuttle
Free Wi-Fi
Pool
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
C$ 426
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
Philadelphia
Breakfast
3 nights + flight
C$ 322
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Philadelphia
Breakfast
3 nights + flight
C$ 404

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
Philadelphia
All inclusive
3 nights + flight
C$ 1,319

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$ 730; Family vacation C$ 662; Romantic vacation C$ 771; Luxury vacation C$ 764; 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$ 730
Family vacation (Flight+Hotel)C$ 662
Romantic vacation (Flight+Hotel)C$ 771
Luxury vacation (Flight+Hotel)C$ 764
Budget vacation (Flight+Hotel)C$ 544