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Vacations in Chicago

Vacations in Chicago

2 travelers

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$242 - $408$408 - $574$574 - $741$741 - $907$907+ per night

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Most popular Chicago flight and hotel deals

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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
2.5 Poor
Chatham
Parking
Pet friendly
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$242
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites
8.5 Very good
Near North Side
Pool
Pet friendly
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$373
City Suites Hotel - Chicago - Bedroom
City Suites Hotel - Chicago - Bedroom
City Suites Hotel
8.1 Very good
Lake View
Free Wi-Fi
Denver Intl
Meals not included
3 nights + flight
$427
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
Dallas/Fort Worth
Breakfast
3 nights + flight
$417
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
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$394
The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel - Chicago - Restaurant
The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel - Chicago - Restaurant
The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel
8.3 Very good
Near North Side
Free Wi-Fi
Pet friendly
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$348
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
8.9 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$565
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
9.4 Wonderful
Near West Side
Pool
Pet friendly
Dallas/Fort Worth
Breakfast
3 nights + flight
$417
Motel Edgebrook Chicago North Shore By OYO - Chicago - Bedroom
Motel Edgebrook Chicago North Shore By OYO - Chicago - Bedroom
Motel Edgebrook Chicago North Shore By OYO
5.5 Fair
Forest Glen
Parking
Free Wi-Fi
Dallas/Fort Worth
Meals not included
3 nights + flight
$254
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$337
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
Denver Intl
Meals not included
3 nights + flight
$619
Chicago South Loop Hotel - Chicago - Building
Chicago South Loop Hotel - Chicago - Building
Chicago South Loop Hotel
6.1 Okay
Douglas
Parking
Free Wi-Fi
Spa
Dallas/Fort Worth
Meals not included
3 nights + flight
$390
The Drake - Chicago - Lobby
The Drake - Chicago - Lobby
The Drake
8.3 Very good
Near North Side
Pet friendly
Denver Intl
Meals not included
3 nights + flight
$418
Central Loop Hotel - Chicago - Lobby
Central Loop Hotel - Chicago - Lobby
Central Loop Hotel
8.1 Very good
Loop
Free Wi-Fi
Pet friendly
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$350
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.8 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$819
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel
7.1 Good
Loop
Free Wi-Fi
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$340

Last minute vacation packages to Chicago

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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
Hartford Bradley Intl
Meals not included
3 nights + flight
$941

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