Vacations in Chicago

Vacations in Chicago

2 travellers

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Cheap Chicago package deals

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C$ 280 - C$ 631C$ 631 - C$ 982C$ 982 - C$ 1,331C$ 1,331 - C$ 1,682C$ 1,682+ 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
Fort Lauderdale
Meals not included
3 nights + flight
C$ 470
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
New Orleans Louis Armstrong
Meals not included
3 nights + flight
C$ 670
City Suites Hotel - Chicago - Bedroom
City Suites Hotel - Chicago - Bedroom
City Suites Hotel
8.2 Very good
Lake View
Free Wi-Fi
Fort Lauderdale
Meals not included
3 nights + flight
C$ 565
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
New Orleans Louis Armstrong
Meals not included
3 nights + flight
C$ 550
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.9 Very good
Near West Side
Free Wi-Fi
Pet friendly
Boston Logan Intl
Breakfast
3 nights + flight
C$ 671
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel
8.2 Very good
O'Hare
Airport shuttle
Pool
Fort Lauderdale
Meals not included
3 nights + flight
C$ 463
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
New Orleans Louis Armstrong
Meals not included
3 nights + flight
C$ 1,180
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
New Orleans Louis Armstrong
Breakfast
3 nights + flight
C$ 795
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
7.9 Good
Loop
Pool
Pet friendly
Spa
Los Angeles
Meals not included
3 nights + flight
C$ 1,778
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
New Orleans Louis Armstrong
Meals not included
3 nights + flight
C$ 601
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
New Orleans Louis Armstrong
Meals not included
3 nights + flight
C$ 993
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Meeting room
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Meeting room
Courtyard by Marriott Chicago Downtown/Magnificent Mile
8.1 Very good
Near North Side
Free Wi-Fi
Pool
Fort Lauderdale
Meals not included
3 nights + flight
C$ 649
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Meeting room
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Meeting room
SpringHill Suites by Marriott Chicago Chinatown
9 Wonderful
Chinatown
Free Wi-Fi
Fort Lauderdale
Breakfast
3 nights + flight
C$ 793
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago
8.3 Very good
Loop
Free Wi-Fi
Denver Intl
Meals not included
3 nights + flight
C$ 624
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.9 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
New Orleans Louis Armstrong
Meals not included
3 nights + flight
C$ 1,414
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago
8.6 Very good
Loop
Free Wi-Fi
Pet friendly
New Orleans Louis Armstrong
Meals not included
3 nights + flight
C$ 681

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
New Orleans Louis Armstrong
All inclusive
3 nights + flight
C$ 977

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
8.5 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
C$ 1,447
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
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
C$ 1,314
Wrigleyville Suites - Chicago - Living room
Wrigleyville Suites - Chicago - Living room
Wrigleyville Suites
7.8 Good
Wrigleyville
Free Wi-Fi
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
C$ 1,762

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$ 85; Family vacation C$ 202; Romantic vacation C$ 242; Luxury vacation C$ 481; Budget vacation C$ 252.

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$ 85
Family vacation (Flight+Hotel)C$ 202
Romantic vacation (Flight+Hotel)C$ 242
Luxury vacation (Flight+Hotel)C$ 481
Budget vacation (Flight+Hotel)C$ 252