Vacations in Chicago

Vacations in Chicago

2 travelers

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$267 - $502$502 - $736$736 - $971$971 - $1,205$1,205+ 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
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$401
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
Los Angeles Los Angeles
Meals not included
3 nights + flight
$640
The Godfrey Hotel Chicago - Chicago - Lobby
The Godfrey Hotel Chicago - Chicago - Lobby
The Godfrey Hotel Chicago
7.9 Good
Near North Side
Free Wi-Fi
Spa
Denver Intl
Meals not included
3 nights + flight
$465
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
Newark
Meals not included
3 nights + flight
$467
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Philadelphia
Meals not included
3 nights + flight
$754
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
$491
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
Denver Intl
Meals not included
3 nights + flight
$370
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
$455
Aloft Chicago Mag Mile - Chicago - Pool
Aloft Chicago Mag Mile - Chicago - Pool
Aloft Chicago Mag Mile
8.2 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$531
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
Denver Intl
Meals not included
3 nights + flight
$430
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
Denver Intl
Meals not included
3 nights + flight
$889
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 Los Angeles
Meals not included
3 nights + flight
$802
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
$580
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
Philadelphia
Meals not included
3 nights + flight
$972
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
Denver Intl
Meals not included
3 nights + flight
$514
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel
7.2 Good
Loop
Free Wi-Fi
Fort Lauderdale
Meals not included
3 nights + flight
$433

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 Los Angeles
All inclusive
3 nights + flight
$872

Last minute vacation packages to Chicago

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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
Austin Bergstrom
Breakfast
3 nights + flight
$981
Wrigleyville Suites - Chicago - Living room
Wrigleyville Suites - Chicago - Living room
Wrigleyville Suites
7.8 Good
Wrigleyville
Free Wi-Fi
Austin Bergstrom
Meals not included
3 nights + flight
$789

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 $106; Family vacation $279; Romantic vacation $324; Luxury vacation $407; 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)$106
Family vacation (Flight+Hotel)$279
Romantic vacation (Flight+Hotel)$324
Luxury vacation (Flight+Hotel)$407
Budget vacation (Flight+Hotel)$251