Holidays in Chicago

Holidays in Chicago

2 travellers

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$252 - $530$530 - $807$807 - $1,084$1,084 - $1,362$1,362+ per night

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Most popular Chicago flight and hotel deals

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Thompson Chicago - Chicago - Living room
Thompson Chicago - Chicago - Living room
Thompson Chicago
8.7 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$516
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 Wonderful
Near North Side
Free Wi-Fi
Pet-friendly
Baltimore/Washington
Breakfast
3 nights + flight
$509
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
Free Wi-Fi
Pet-friendly
Baltimore/Washington
Meals not included
3 nights + flight
$399
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
8.2 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Las Vegas Harry Reid Intl
Breakfast
3 nights + flight
$460
River Hotel - Chicago - Lobby
River Hotel - Chicago - Lobby
River Hotel
8.3 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$370
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.6 Very Good
Near West Side
Free Wi-Fi
Pet-friendly
Baltimore/Washington
Breakfast
3 nights + flight
$447
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites by Hilton Chicago Medical District UIC
9.3 Wonderful
Near West Side
Pool
Pet-friendly
Dallas/Fort Worth
Breakfast
3 nights + flight
$461
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton
9 Wonderful
Downtown
Free Wi-Fi
Spa
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$485
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
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$495
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop
9 Wonderful
Downtown
Free Wi-Fi
Pet-friendly
Spa
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$512
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
$1,361
Homewood Suites by Hilton - Chicago Downtown South Loop - Chicago - Living room
Homewood Suites by Hilton - Chicago Downtown South Loop - Chicago - Living room
Homewood Suites by Hilton - Chicago Downtown South Loop
8.1 Very Good
Downtown
Free Wi-Fi
Pool
Houston George Bush Intcntl
Breakfast
3 nights + flight
$401
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
Orlando
Meals not included
3 nights + flight
$457
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
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$800
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
Houston George Bush Intcntl
Meals not included
3 nights + flight
$369
Central Loop Hotel - Chicago - Front desk
Central Loop Hotel - Chicago - Front desk
Central Loop Hotel
8 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$453

Last minute holiday packages to Chicago

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The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy
Near West Side
Nashville Intl
Meals not included
3 nights + flight
$936

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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