Vacations in Chicago

Vacations in Chicago

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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
7.8 Good
Near North Side
Pool
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$304
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel - Chicago - Restaurant
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel - Chicago - Restaurant
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
8 Very good
Loop
Pet friendly
Philadelphia
Meals not included
3 nights + flight
$290
River Hotel - Chicago - Property amenity
River Hotel - Chicago - Property amenity
River Hotel
8.4 Very good
Loop
Free Wi-Fi
Pet friendly
Nashville Intl
Meals not included
3 nights + flight
$326
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel
8.1 Very good
O'Hare - International
Airport shuttle
Pool
Seattle/Tacoma Intl
Meals not included
3 nights + flight
$357
The Whitehall Hotel, BW Premier Collection - Chicago - Lounge
The Whitehall Hotel, BW Premier Collection - Chicago - Lounge
The Whitehall Hotel, BW Premier Collection
7.8 Good
Near North Side
Free Wi-Fi
Pet friendly
Nashville Intl
Meals not included
3 nights + flight
$260
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Nashville Intl
Meals not included
3 nights + flight
$360
La Quinta Inn & Suites by Wyndham Chicago Downtown - Chicago - Bar
La Quinta Inn & Suites by Wyndham Chicago Downtown - Chicago - Bar
La Quinta Inn & Suites by Wyndham Chicago Downtown
8 Very good
Loop
Free Wi-Fi
Pet friendly
Spa
Nashville Intl
Breakfast
3 nights + flight
$366
The Langham Chicago - Chicago - Lounge
The Langham Chicago - Chicago - Lounge
The Langham Chicago
9.4 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Seattle/Tacoma Intl
Meals not included
3 nights + flight
$676
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
Seattle/Tacoma Intl
Meals not included
3 nights + flight
$511
SpringHill Suites by Marriott Chicago O'Hare - Chicago - Patio
SpringHill Suites by Marriott Chicago O'Hare - Chicago - Patio
SpringHill Suites by Marriott Chicago O'Hare
8.1 Very good
Norwood Park
Airport shuttle
Free Wi-Fi
Pool
Pet friendly
Philadelphia
Breakfast
3 nights + flight
$299
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago
8.3 Very good
Loop
Free Wi-Fi
Philadelphia
Meals not included
3 nights + flight
$412
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
Seattle/Tacoma Intl
Meals not included
3 nights + flight
$446
Central Loop Hotel - Chicago - Lobby
Central Loop Hotel - Chicago - Lobby
Central Loop Hotel
8.1 Very good
Loop
Free Wi-Fi
Pet friendly
Nashville Intl
Meals not included
3 nights + flight
$284
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
Nashville Intl
Meals not included
3 nights + flight
$354
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection
8.3 Very good
Near North Side
Free Wi-Fi
Pet friendly
Seattle/Tacoma Intl
Meals not included
3 nights + flight
$393
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel
7.1 Good
Loop
Free Wi-Fi
Nashville Intl
Meals not included
3 nights + flight
$341

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
Seattle/Tacoma Intl
All inclusive
3 nights + flight
$508

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
Newark
Meals not included
3 nights + flight
$846
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
Newark
Meals not included
3 nights + flight
$728
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
Los Angeles Los Angeles
Meals not included
3 nights + flight
$781
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
$908

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