Holidays in Chicago

Holidays in Chicago

2 travellers
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Cheap Chicago package deals

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BreakfastHalf boardSelf cateringAll-inclusiveMeals not included

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€217 - €434€434 - €650€650 - €867€867 - €1,083€1,083+ per night

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Most popular Chicago flight and hotel deals

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The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
7.8 Good
Near North Side
Pool
Pet friendly
Air conditioning
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
€302
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Building
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Building
Intercontinental Hotels Chicago Magnificent Mile By IHG
8 Very Good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
€401
The Blackstone Autograph Collection - Chicago - Lobby
The Blackstone Autograph Collection - Chicago - Lobby
The Blackstone Autograph Collection
8.7 Very Good
Loop
Pet friendly
Air conditioning
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
€487
Admiral Motel By OYO Chicago I-94 - Chicago - Building
Admiral Motel By OYO Chicago I-94 - Chicago - Building
Admiral Motel By OYO Chicago I-94
2.6 Poor
Chatham
Parking
Pet friendly
Air conditioning
Nashville Intl
Meals not included
3 nights + flight
€186
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
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
€343
City Suites Hotel - Chicago - Bedroom
City Suites Hotel - Chicago - Bedroom
City Suites Hotel
8.2 Very Good
Lake View
Free Wi-Fi
Air conditioning
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
€341
Holiday Inn Express Chicago - Magnificent Mile By IHG - Chicago - Lobby
Holiday Inn Express Chicago - Magnificent Mile By IHG - Chicago - Lobby
Holiday Inn Express Chicago - Magnificent Mile By IHG
7.8 Good
Near North Side
Free Wi-Fi
Air conditioning
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
€300
Hotel 55 Chicago Downtown - Chicago - Restaurant
Hotel 55 Chicago Downtown - Chicago - Restaurant
Hotel 55 Chicago Downtown
8.3 Very Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
€369
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Pool
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Pool
Hampton Inn & Suites by Hilton Chicago Medical District UIC
9.3 Wonderful
Near West Side
Pool
Pet friendly
Air conditioning
Las Vegas Harry Reid Intl
Breakfast
3 nights + flight
€319
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
Air conditioning
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
€319
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
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
€339
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
9.3 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
€682
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bedroom
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bedroom
Hilton Garden Inn Chicago Downtown Riverwalk
8.4 Very Good
Loop
Free Wi-Fi
Pet friendly
Air conditioning
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
€302
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Meeting room
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Meeting room
Courtyard by Marriott Chicago Downtown/Magnificent Mile
8.1 Very Good
Near North Side
Free Wi-Fi
Pool
Air conditioning
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
€372
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Meeting room
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Meeting room
SpringHill Suites by Marriott Chicago Chinatown
9 Wonderful
Chinatown
Free Wi-Fi
Air conditioning
Las Vegas Harry Reid Intl
Breakfast
3 nights + flight
€298
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago
8.5 Very Good
Loop
Free Wi-Fi
Pet friendly
Air conditioning
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
€379

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
Seattle/Tacoma Intl
All-inclusive
3 nights + flight
€694

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
8.5 Very Good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
€929

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 €221; Family holiday €663; Romantic holiday €663; Luxury holiday €1,163.

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)€221
Family holiday (Flight+Hotel)€663
Romantic holiday (Flight+Hotel)€663
Luxury holiday (Flight+Hotel)€1,163