Vacations in Chicago

Vacations in Chicago

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C$ 350 - C$ 548C$ 548 - C$ 747C$ 747 - C$ 945C$ 945 - C$ 1,144C$ 1,144+ per night

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Most popular Chicago flight and hotel deals

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The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
7.9 Good
Near North Side
Pool
Pet friendly
Cleveland Hopkins Intl
Meals not included
3 nights + flight
C$ 494
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Building
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Building
Intercontinental Hotels Chicago Magnificent Mile By IHG
8 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Los Angeles
Meals not included
3 nights + flight
C$ 576
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
Orlando
Meals not included
3 nights + flight
C$ 647
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites
8.4 Very good
Near North Side
Pool
Pet friendly
Orlando
Meals not included
3 nights + flight
C$ 506
Hilton Chicago - Chicago - Living room
Hilton Chicago - Chicago - Living room
Hilton Chicago
7.9 Good
Loop
Pool
Pet friendly
Cleveland Hopkins Intl
Meals not included
3 nights + flight
C$ 533
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
7.9 Good
Near North Side
Pool
Pet friendly
Orlando
Breakfast
3 nights + flight
C$ 549
The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel - Chicago - Restaurant
The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel - Chicago - Restaurant
The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel
8.3 Very good
Near North Side
Free Wi-Fi
Pet friendly
Cleveland Hopkins Intl
Meals not included
3 nights + flight
C$ 467
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Los Angeles
Meals not included
3 nights + flight
C$ 1,019
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Pool
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Pool
Hampton Inn & Suites by Hilton Chicago Medical District UIC
9.3 Wonderful
Near West Side
Pool
Pet friendly
Cleveland Hopkins Intl
Breakfast
3 nights + flight
C$ 416
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
Los Angeles
Meals not included
3 nights + flight
C$ 591
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Orlando
Meals not included
3 nights + flight
C$ 470
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
Cleveland Hopkins Intl
Meals not included
3 nights + flight
C$ 482
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
Orlando
Meals not included
3 nights + flight
C$ 918
The Westin Michigan Avenue Chicago - Chicago - Front desk
The Westin Michigan Avenue Chicago - Chicago - Front desk
The Westin Michigan Avenue Chicago
8.1 Very good
Near North Side
Pet friendly
Spa
Cleveland Hopkins Intl
Meals not included
3 nights + flight
C$ 473
Hotel Riu Plaza Chicago - Chicago - Lounge
Hotel Riu Plaza Chicago - Chicago - Lounge
Hotel Riu Plaza Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Orlando
Breakfast
3 nights + flight
C$ 508
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.8 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Orlando
Meals not included
3 nights + flight
C$ 1,104

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$ 99; Family vacation C$ 217; Romantic vacation C$ 245; Luxury vacation C$ 487; Budget vacation C$ 255.

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$ 99
Family vacation (Flight+Hotel)C$ 217
Romantic vacation (Flight+Hotel)C$ 245
Luxury vacation (Flight+Hotel)C$ 487
Budget vacation (Flight+Hotel)C$ 255