Vacations in Chicago

Vacations in Chicago

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Cheap Chicago package deals

These are the best prices for Jun 13 - 16.
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BreakfastHalf boardSelf cateringAll inclusiveMeals not included

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$227 - $437$437 - $647$647 - $857$857 - $1,066$1,066+ per night

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Free breakfastFree internetFree airport shuttleFree parking

Most popular Chicago flight and hotel deals

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Warwick Allerton Chicago - Chicago - Meeting room
Warwick Allerton Chicago - Chicago - Meeting room
Warwick Allerton Chicago
8.1 Very good
Near North Side
Free Wi-Fi
San Antonio
Meals not included
3 nights + flight
$430
Pendry Chicago - Chicago - Balcony
Pendry Chicago - Chicago - Balcony
Pendry Chicago
8.8 Very good
Downtown
Free Wi-Fi
Pet friendly
San Antonio
Meals not included
3 nights + flight
$590
Kimpton Gray Hotel - Chicago - Lobby
Kimpton Gray Hotel - Chicago - Lobby
Kimpton Gray Hotel
8.9 Very good
Downtown
Pet friendly
San Antonio
Meals not included
3 nights + flight
$590
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
San Antonio
Meals not included
3 nights + flight
$622
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
San Antonio
Meals not included
3 nights + flight
$496
The Royal Sonesta Chicago Downtown - Chicago - Building
The Royal Sonesta Chicago Downtown - Chicago - Building
The Royal Sonesta Chicago Downtown
8.8 Very good
Downtown
Pet friendly
San Antonio
Meals not included
3 nights + flight
$514
JW Marriott Chicago - Chicago - Lobby
JW Marriott Chicago - Chicago - Lobby
JW Marriott Chicago
8.7 Very good
Downtown
Pool
Spa
San Antonio
Meals not included
3 nights + flight
$575
Waldorf Astoria Chicago - Chicago - Restaurant
Waldorf Astoria Chicago - Chicago - Restaurant
Waldorf Astoria Chicago
9.2 Wonderful
Near North Side
Pool
Pet friendly
Spa
Washington, D.C. Dulles Intl
Meals not included
3 nights + flight
$670
Hampton Inn Chicago Downtown/N Loop/Michigan Ave - Chicago - Lobby
Hampton Inn Chicago Downtown/N Loop/Michigan Ave - Chicago - Lobby
Hampton Inn Chicago Downtown/N Loop/Michigan Ave
7.9 Good
Downtown
Free Wi-Fi
Pet friendly
San Antonio
Breakfast
3 nights + flight
$429
The Langham Chicago - Chicago - Lounge
The Langham Chicago - Chicago - Lounge
The Langham Chicago
9.3 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Newark
Meals not included
3 nights + flight
$923
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bedroom
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bedroom
Hilton Garden Inn Chicago Downtown Riverwalk
8.5 Very good
Downtown
Free Wi-Fi
Pet friendly
San Antonio
Meals not included
3 nights + flight
$468
Best Motel By OYO Chicago I-90 - Chicago - Bedroom
Best Motel By OYO Chicago I-90 - Chicago - Bedroom
Best Motel By OYO Chicago I-90
2.2 Poor
South Side
Parking
Pet friendly
Nashville Intl
Meals not included
3 nights + flight
$227
The Drake - Chicago - Lobby
The Drake - Chicago - Lobby
The Drake
8.3 Very good
Near North Side
Free Wi-Fi
Pet friendly
San Antonio
Meals not included
3 nights + flight
$463
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago
8.6 Very good
Downtown
Free Wi-Fi
San Antonio
Meals not included
3 nights + flight
$512
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.7 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
San Antonio
Meals not included
3 nights + flight
$917
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel
7.2 Good
Downtown
Free Wi-Fi
San Antonio
Meals not included
3 nights + flight
$416

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
Phoenix Sky Harbor Intl
All inclusive
3 nights + flight
$905

Last minute vacation packages to Chicago

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The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
7.9 Good
Downtown
Pool
Pet friendly
Spa
Wichita Eisenhower National
Meals not included
3 nights + flight
$2,363
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
Downtown
Pet friendly
Wichita Eisenhower National
Meals not included
3 nights + flight
$1,152
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.7 Very good
Near West Side
Free Wi-Fi
Pet friendly
Wichita Eisenhower National
Breakfast
3 nights + flight
$1,208

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 $120; Family vacation $343; Romantic vacation $324; Luxury vacation $390; Budget vacation $253.

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)$120
Family vacation (Flight+Hotel)$343
Romantic vacation (Flight+Hotel)$324
Luxury vacation (Flight+Hotel)$390
Budget vacation (Flight+Hotel)$253