Holidays in Chicago

Holidays in Chicago

2 travellers

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$260 - $445$445 - $631$631 - $817$817 - $1,003$1,003+ per night

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Most popular Chicago flight and hotel deals

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Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Lobby
Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Lobby
Residence Inn by Marriott Chicago Downtown Magnificent Mile
9.1 Wonderful
Near North Side
Free Wi-Fi
Pet-friendly
Baltimore/Washington
Breakfast
3 nights + flight
$436
Admiral Motel By OYO Chicago I-94 - Chicago - Bedroom
Admiral Motel By OYO Chicago I-94 - Chicago - Bedroom
Admiral Motel By OYO Chicago I-94
3.6 Poor
South Side
Parking
Pet-friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$304
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical - Chicago - Lounge
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical - Chicago - Lounge
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
8.1 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
$360
Pendry Chicago - Chicago - Balcony
Pendry Chicago - Chicago - Balcony
Pendry Chicago
8.9 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Baltimore/Washington
Meals not included
3 nights + flight
$511
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.5 Very Good
Near West Side
Free Wi-Fi
Pet-friendly
Baltimore/Washington
Breakfast
3 nights + flight
$415
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
8 Very Good
Near North Side
Pool
Pet-friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
$489
Chinatown Hotel Chicago - Chicago - Dining room
Chinatown Hotel Chicago - Chicago - Dining room
Chinatown Hotel Chicago
5.7 Fair
South Side
Free Wi-Fi
New York LaGuardia
Meals not included
3 nights + flight
$341
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
Baltimore/Washington
Meals not included
3 nights + flight
$516
Hampton Inn & Suites Chicago-Downtown - Chicago - Lobby
Hampton Inn & Suites Chicago-Downtown - Chicago - Lobby
Hampton Inn & Suites Chicago-Downtown
8.5 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Philadelphia
Breakfast
3 nights + flight
$574
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
8.8 Very Good
Downtown
Pool
Pet-friendly
Spa
Dallas/Fort Worth
Meals not included
3 nights + flight
$1,531
Residence Inn by Marriott Chicago Downtown/Loop - Chicago - Bar
Residence Inn by Marriott Chicago Downtown/Loop - Chicago - Bar
Residence Inn by Marriott Chicago Downtown/Loop
8.9 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Baltimore/Washington
Breakfast
3 nights + flight
$461
The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Living room
The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Living room
The Allegro Royal Sonesta Hotel Chicago Loop
8.3 Very Good
Downtown
Pet-friendly
Baltimore/Washington
Meals not included
3 nights + flight
$399
Hotel Chicago West Loop, SureStay Collection by Best Western - Chicago - Living room
Hotel Chicago West Loop, SureStay Collection by Best Western - Chicago - Living room
Hotel Chicago West Loop, SureStay Collection by Best Western
7.5 Good
Near West Side
Free Wi-Fi
Pet-friendly
New York LaGuardia
Meals not included
3 nights + flight
$324
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
Baltimore/Washington
Meals not included
3 nights + flight
$683
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
8.4 Very Good
Near North Side
Free Wi-Fi
Pool
Dallas/Fort Worth
Meals not included
3 nights + flight
$401
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown
8.9 Very Good
South Side
Free Wi-Fi
New York LaGuardia
Breakfast
3 nights + flight
$465

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
Columbia Metropolitan
All-inclusive
3 nights + flight
$1,669

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.

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

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