Vacations in Chicago

Vacations in Chicago

2 travelers

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$222 - $429$429 - $636$636 - $843$843 - $1,049$1,049+ per night

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Most popular Chicago flight and hotel deals

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Thompson Chicago - Chicago - Lobby
Thompson Chicago - Chicago - Lobby
Thompson Chicago
8.9 Very good
Near North Side
Free Wi-Fi
Pet friendly
Denver Intl
Meals not included
3 nights + flight
$513
The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
7.9 Good
Near North Side
Pool
Pet friendly
Denver Intl
Meals not included
3 nights + flight
$412
Hyatt Regency Mccormick Place - Chicago - Patio
Hyatt Regency Mccormick Place - Chicago - Patio
Hyatt Regency Mccormick Place
8.5 Very good
Near South Side
Free Wi-Fi
Newark
Meals not included
3 nights + flight
$589
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
Newark
Meals not included
3 nights + flight
$532
Admiral Motel By OYO Chicago I-94 - Chicago - Building
Admiral Motel By OYO Chicago I-94 - Chicago - Building
Admiral Motel By OYO Chicago I-94
2.6 Poor
Chatham
Parking
Pet friendly
Nashville Intl
Meals not included
3 nights + flight
$223
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
Denver Intl
Meals not included
3 nights + flight
$402
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
Denver Intl
Breakfast
3 nights + flight
$539
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
Denver Intl
Meals not included
3 nights + flight
$469
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Denver Intl
Meals not included
3 nights + flight
$380
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
8 Very good
Loop
Free Wi-Fi
Pet friendly
Denver Intl
Breakfast
3 nights + flight
$424
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
Newark
Meals not included
3 nights + flight
$771
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
Newark
Meals not included
3 nights + flight
$429
The Westin Michigan Avenue Chicago - Chicago - Front desk
The Westin Michigan Avenue Chicago - Chicago - Front desk
The Westin Michigan Avenue Chicago
8.2 Very good
Near North Side
Pet friendly
Spa
Newark
Meals not included
3 nights + flight
$562
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
$498
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
Newark
Meals not included
3 nights + flight
$962
Wrigleyville Suites - Chicago - Living room
Wrigleyville Suites - Chicago - Living room
Wrigleyville Suites
7.8 Good
Wrigleyville
Free Wi-Fi
Newark
Meals not included
3 nights + flight
$778

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
Nashville Intl
All inclusive
3 nights + flight
$834

Last minute vacation packages to Chicago

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The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy
Near West Side
Philadelphia
Meals not included
3 nights + flight
$920
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
Newark
Breakfast
3 nights + flight
$502

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 $105; Family vacation $278; Romantic vacation $324; Luxury vacation $426; Budget vacation $251.

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)$105
Family vacation (Flight+Hotel)$278
Romantic vacation (Flight+Hotel)$324
Luxury vacation (Flight+Hotel)$426
Budget vacation (Flight+Hotel)$251