Vacations in Chicago

Vacations in Chicago

2 travelers

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Cheap Chicago package deals

These are the best prices for Aug 5 - 8.
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$187 - $360$360 - $533$533 - $706$706 - $879$879+ 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
Los Angeles
Meals not included
3 nights + flight
$415
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
8.1 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Los Angeles
Meals not included
3 nights + flight
$450
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites
8.6 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Los Angeles
Meals not included
3 nights + flight
$404
River Hotel - Chicago - Property amenity
River Hotel - Chicago - Property amenity
River Hotel
8.4 Very good
Loop
Free Wi-Fi
Pet friendly
Los Angeles
Meals not included
3 nights + flight
$356
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.8 Very good
Near West Side
Free Wi-Fi
Pet friendly
Lambert-St Louis
Breakfast
3 nights + flight
$349
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
Los Angeles
Meals not included
3 nights + flight
$416
Millennium Hotel Knickerbocker Chicago - Chicago - Bedroom
Millennium Hotel Knickerbocker Chicago - Chicago - Bedroom
Millennium Hotel Knickerbocker Chicago
7.8 Good
Near North Side
Lambert-St Louis
Meals not included
3 nights + flight
$389
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Los Angeles
Meals not included
3 nights + flight
$376
Hotel Lincoln - Chicago - Balcony
Hotel Lincoln - Chicago - Balcony
Hotel Lincoln
7 Good
Lincoln Park
Free Wi-Fi
Pet friendly
Los Angeles
Meals not included
3 nights + flight
$397
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
Los Angeles
Meals not included
3 nights + flight
$411
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
Los Angeles
Meals not included
3 nights + flight
$704
Marriott Chicago O'Hare - Chicago - Building
Marriott Chicago O'Hare - Chicago - Building
Marriott Chicago O'Hare
7.5 Good
O'Hare - International
Airport shuttle
Free Wi-Fi
Pool
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$402
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago
8.4 Very good
Loop
Free Wi-Fi
Los Angeles
Meals not included
3 nights + flight
$460
Sofitel Chicago Magnificent Mile - Chicago - Gym
Sofitel Chicago Magnificent Mile - Chicago - Gym
Sofitel Chicago Magnificent Mile
8.8 Very good
Near North Side
Free Wi-Fi
Pet friendly
Los Angeles
Meals not included
3 nights + flight
$524
Club Quarters Hotel Wacker at Michigan, Chicago - Chicago - Building
Club Quarters Hotel Wacker at Michigan, Chicago - Chicago - Building
Club Quarters Hotel Wacker at Michigan, Chicago
8.3 Very good
Loop
Free Wi-Fi
Pet friendly
Los Angeles
Meals not included
3 nights + flight
$355
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel
7.2 Good
Loop
Free Wi-Fi
Los Angeles
Meals not included
3 nights + flight
$377

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
Los Angeles
All inclusive
3 nights + flight
$849

Last minute vacation packages to Chicago

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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
8.2 Very good
Near North Side
Free Wi-Fi
Pool
Toronto Pearson Intl
Meals not included
3 nights + flight
$1,064

When to book a vacation in Chicago

Price includes flights and 3 nights accommodation for 2 travelers. 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 travelers: Top vacation $111; Family vacation $308; Romantic vacation $324; Luxury vacation $390; Budget vacation $256.

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)$111
Family vacation (Flight+Hotel)$308
Romantic vacation (Flight+Hotel)$324
Luxury vacation (Flight+Hotel)$390
Budget vacation (Flight+Hotel)$256