Holidays in Chicago

Holidays in Chicago

2 travellers

KAYAK searches hundreds of travel sites at once for holiday package deals in Chicago

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Cheap Chicago package deals

Discover the best prices by selecting your travel dates on KAYAK.

Most popular Chicago flight and hotel deals

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The Wade
8.1 Very Good
Near North Side
Pool
Pet-friendly
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$368
Downtown
Pet-friendly
Spa
Fort Myers SW Florida Intl
Meals not included
3 nights + flight
$457
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
8.9 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Orlando
Breakfast
3 nights + flight
$456
Omni Chicago Hotel
8.8 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Fort Myers SW Florida Intl
Meals not included
3 nights + flight
$570
Near North Side
Free Wi-Fi
Pet-friendly
Fort Myers SW Florida Intl
Meals not included
3 nights + flight
$313
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
Orlando
Breakfast
3 nights + flight
$325
Park Hyatt Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$840
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
Fort Myers SW Florida Intl
Breakfast
3 nights + flight
$366
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
Orlando
Meals not included
3 nights + flight
$324
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy
Near West Side
Orlando
Meals not included
3 nights + flight
$650
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
8.3 Very Good
Downtown
Pet-friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$405
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
Orlando
Meals not included
3 nights + flight
$664
The Drake
8.2 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$385
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
$407
Downtown
Free Wi-Fi
Houston George Bush Intcntl
Meals not included
3 nights + flight
$348

All inclusive holiday packages to Chicago

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The Wheeler Mansion
9.8 Wonderful
Near South Side
Free Wi-Fi
San Francisco
All-inclusive
3 nights + flight
$1,321

Last minute holiday packages to Chicago

Show all
Near North Side
Free Wi-Fi
Pool
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$607

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.