Holidays in Chicago

Holidays in Chicago

2 travellers

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Cheap Chicago package deals

These are the best prices for 6-9 Jun.
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$308 - $484$484 - $659$659 - $833$833 - $1,008$1,008+ per night

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Free breakfastFree internetFree airport shuttleFree parking

Most popular Chicago flight and hotel deals

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Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Lobby
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Lobby
Intercontinental Hotels Chicago Magnificent Mile By IHG
8.1 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
Baltimore/Washington
Meals not included
3 nights + flight
$603
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
3 Poor
South Side
Parking
Pet-friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$312
Hilton Chicago - Chicago - Living room
Hilton Chicago - Chicago - Living room
Hilton Chicago
7.8 Good
Downtown
Free Wi-Fi
Pool
Pet-friendly
Baltimore/Washington
Meals not included
3 nights + flight
$561
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
8.2 Very Good
Near West Side
Free Wi-Fi
Pet-friendly
Charlotte Douglas
Meals not included
3 nights + flight
$534
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Baltimore/Washington
Meals not included
3 nights + flight
$704
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton
8.8 Very Good
Downtown
Free Wi-Fi
Spa
Baltimore/Washington
Meals not included
3 nights + flight
$620
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
Baltimore/Washington
Meals not included
3 nights + flight
$625
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
Baltimore/Washington
Meals not included
3 nights + flight
$570
Hyatt Place Chicago Downtown/The Loop - Chicago - Bedroom
Hyatt Place Chicago Downtown/The Loop - Chicago - Bedroom
Hyatt Place Chicago Downtown/The Loop
8.3 Very Good
Downtown
Free Wi-Fi
Pool
Pet-friendly
Baltimore/Washington
Meals not included
3 nights + flight
$547
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
8.1 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Spa
Baltimore/Washington
Breakfast
3 nights + flight
$550
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
Baltimore/Washington
Breakfast
3 nights + flight
$580
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
Baltimore/Washington
Meals not included
3 nights + flight
$748
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago
8.6 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Baltimore/Washington
Meals not included
3 nights + flight
$590
Sofitel Chicago Magnificent Mile - Chicago - Building
Sofitel Chicago Magnificent Mile - Chicago - Building
Sofitel Chicago Magnificent Mile
8.9 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Little Rock
Meals not included
3 nights + flight
$667
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.6 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$932
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel
7.2 Good
Downtown
Free Wi-Fi
Baltimore/Washington
Meals not included
3 nights + flight
$504

All inclusive holiday 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
Austin Bergstrom
All-inclusive
3 nights + flight
$832

Last minute holiday packages to Chicago

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Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard by Marriott Chicago Downtown/Magnificent Mile
8.3 Very Good
Near North Side
Free Wi-Fi
Pool
Houston George Bush Intcntl
Meals not included
3 nights + flight
$1,177
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
Houston George Bush Intcntl
Breakfast
3 nights + flight
$1,206
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown
9 Wonderful
South Side
Free Wi-Fi
Houston George Bush Intcntl
Breakfast
3 nights + flight
$1,571

When to book a holiday in Chicago

Price includes flights and 3 nights accommodation for 2 travellers. Prices are not fixed and may vary with time.

Tips for finding Chicago package deals

  • There are loads of types of holidays 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 travellers: Top holiday $549; Family holiday $1,647; Romantic holiday $1,647; Budget holiday $2,575.

Where to stay in Chicago

Our map will help you find the perfect place to stay for your holiday in Chicago by showing you the exact location of each hotel.

Everything you need to know for your holiday in Chicago

Chicago holiday information

Top holiday (Flight+Hotel)$549
Family holiday (Flight+Hotel)$1,647
Romantic holiday (Flight+Hotel)$1,647
Budget holiday (Flight+Hotel)$2,575