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Holidays in Chicago

Holidays in Chicago

2 travellers

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Cheap Chicago package deals

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Most popular Chicago flight and hotel deals

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Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites
8.3 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$339
Holiday Inn Express Chicago - Magnificent Mile - Chicago - Lobby
Holiday Inn Express Chicago - Magnificent Mile - Chicago - Lobby
Holiday Inn Express Chicago - Magnificent Mile
7.7 Good
Near North Side
Free Wi-Fi
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
$349
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
7.8 Good
Near North Side
Free Wi-Fi
Pet-friendly
Los Angeles
Breakfast
3 nights + flight
$386
Hyatt House Chicago Medical/University District - Chicago - Bedroom
Hyatt House Chicago Medical/University District - Chicago - Bedroom
Hyatt House Chicago Medical/University District
8.4 Very Good
Near West Side
Free Wi-Fi
Pet-friendly
Tampa
Meals not included
3 nights + flight
$369
21c Museum Hotel Chicago - Chicago - Restaurant
21c Museum Hotel Chicago - Chicago - Restaurant
21c Museum Hotel Chicago
8.4 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$419
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North
8.4 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
New York LaGuardia
Meals not included
3 nights + flight
$431
Palmer House a Hilton Hotel - Chicago - Lobby
Palmer House a Hilton Hotel - Chicago - Lobby
Palmer House a Hilton Hotel
7.7 Good
Downtown
Free Wi-Fi
Pool
Pet-friendly
Spa
New York LaGuardia
Meals not included
3 nights + flight
$500
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop
8.8 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Spa
New York LaGuardia
Meals not included
3 nights + flight
$430
The Neighborhood Hotel Little Italy - Chicago - Living room
The Neighborhood Hotel Little Italy - Chicago - Living room
The Neighborhood Hotel Little Italy
Near West Side
New York LaGuardia
Meals not included
3 nights + flight
$431
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
8.1 Very Good
Downtown
Pet-friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$411
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
Tampa
Meals not included
3 nights + flight
$766
Courtyard Chicago Downtown/Magnificent Mile - Chicago - Lounge
Courtyard Chicago Downtown/Magnificent Mile - Chicago - Lounge
Courtyard Chicago Downtown/Magnificent Mile
8.3 Very Good
Near North Side
Free Wi-Fi
Pool
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$422
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown
9.1 Wonderful
South Side
Free Wi-Fi
New York LaGuardia
Breakfast
3 nights + flight
$396
SpringHill Suites by Marriott Chicago Downtown/River North - Chicago - Lounge
SpringHill Suites by Marriott Chicago Downtown/River North - Chicago - Lounge
SpringHill Suites by Marriott Chicago Downtown/River North
8.6 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Los Angeles
Breakfast
3 nights + flight
$454
Radisson Blu Aqua Hotel, Chicago, IL - Chicago - Bedroom
Radisson Blu Aqua Hotel, Chicago, IL - Chicago - Bedroom
Radisson Blu Aqua Hotel, Chicago, IL
8.1 Very Good
Downtown
Free Wi-Fi
Pool
Pet-friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$503
Club Quarters Hotel Central Loop - Chicago - Lobby
Club Quarters Hotel Central Loop - Chicago - Lobby
Club Quarters Hotel Central Loop
8 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Tampa
Meals not included
3 nights + flight
$382

Last minute holiday packages to Chicago

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Sonder The Burnham - Chicago - Living room
Sonder The Burnham - Chicago - Living room
Sonder The Burnham
8.3 Very Good
Near West Side
Free Wi-Fi
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
$571
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$274 - $460$460 - $647$647 - $834$834 - $1,020$1,020+ per night

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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.