Holidays in Chicago

Holidays in Chicago

2 travellers
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Cheap Chicago package deals

These are the best prices for 29 Jul - 1 Aug.
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€167 - €406€406 - €644€644 - €882€882 - €1,121€1,121+ 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
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€375
Omni Chicago Hotel - Chicago - Building
Omni Chicago Hotel - Chicago - Building
Omni Chicago Hotel
8.9 Very Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Houston George Bush Intcntl
Meals not included
3 nights + flight
€422
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
Pool
Pet friendly
Air conditioning
Houston George Bush Intcntl
Meals not included
3 nights + flight
€348
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
Air conditioning
Los Angeles
Breakfast
3 nights + flight
€395
River Hotel - Chicago - Property amenity
River Hotel - Chicago - Property amenity
River Hotel
8.4 Very Good
Loop
Free Wi-Fi
Pet friendly
Air conditioning
Houston George Bush Intcntl
Meals not included
3 nights + flight
€352
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 Very Good
Near West Side
Free Wi-Fi
Pet friendly
Air conditioning
Los Angeles
Breakfast
3 nights + flight
€375
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton
8.9 Very Good
Loop
Free Wi-Fi
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€493
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€369
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
8.4 Very Good
Loop
Pet friendly
Air conditioning
Houston George Bush Intcntl
Meals not included
3 nights + flight
€377
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
8 Very Good
Loop
Free Wi-Fi
Pet friendly
Air conditioning
Los Angeles
Breakfast
3 nights + flight
€416
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bedroom
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bedroom
Hilton Garden Inn Chicago Downtown Riverwalk
8.6 Very Good
Loop
Free Wi-Fi
Pet friendly
Air conditioning
Houston George Bush Intcntl
Meals not included
3 nights + flight
€335
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago
8.4 Very Good
Loop
Free Wi-Fi
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€420
Club Quarters Hotel Wacker at Michigan, Chicago - Chicago - Building
Club Quarters Hotel Wacker at Michigan, Chicago - Chicago - Building
Club Quarters Hotel Wacker at Michigan, Chicago
8.3 Very Good
Loop
Free Wi-Fi
Pet friendly
Air conditioning
Houston George Bush Intcntl
Meals not included
3 nights + flight
€333
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.9 Very Good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€845
Sofitel Chicago Magnificent Mile - Chicago - Lobby
Sofitel Chicago Magnificent Mile - Chicago - Lobby
Sofitel Chicago Magnificent Mile
8.8 Very Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€541
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection
8.5 Very Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€443

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
Air conditioning
Los Angeles
All-inclusive
3 nights + flight
€763

Last minute holiday packages to Chicago

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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
Air conditioning
Columbus
Meals not included
3 nights + flight
€726
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Building
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Building
Courtyard by Marriott Chicago Downtown/Magnificent Mile
8.2 Very Good
Near North Side
Free Wi-Fi
Pool
Air conditioning
Columbus
Meals not included
3 nights + flight
€747
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.8 Very Good
Near West Side
Free Wi-Fi
Pet friendly
Air conditioning
Columbus
Breakfast
3 nights + flight
€798

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 €224; Family holiday €671; Romantic holiday €671.

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)€224
Family holiday (Flight+Hotel)€671
Romantic holiday (Flight+Hotel)€671