Holidays in Chicago

Holidays in Chicago

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€144 - €370€370 - €596€596 - €822€822 - €1,049€1,049+ 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
8.8 Very Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
New York John F Kennedy Intl
Meals not included
3 nights + flight
€381
Hyatt Regency Mccormick Place - Chicago - Patio
Hyatt Regency Mccormick Place - Chicago - Patio
Hyatt Regency Mccormick Place
8.5 Very Good
Near South Side
Free Wi-Fi
Pool
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
€453
Intercontinental Chicago Magnificent Mile By IHG - Chicago - Meeting room
Intercontinental Chicago Magnificent Mile By IHG - Chicago - Meeting room
Intercontinental Chicago Magnificent Mile By IHG
8.1 Very Good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
€435
Admiral Motel By OYO Chicago I-94 - Chicago - Bedroom
Admiral Motel By OYO Chicago I-94 - Chicago - Bedroom
Admiral Motel By OYO Chicago I-94
4 Mediocre
South Side
Parking
Pet friendly
Air conditioning
Nashville Intl
Meals not included
3 nights + flight
€175
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
Nashville Intl
Meals not included
3 nights + flight
€265
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.5 Very Good
Near West Side
Free Wi-Fi
Pet friendly
Air conditioning
Charlotte Douglas
Breakfast
3 nights + flight
€336
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Jacksonville
Meals not included
3 nights + flight
€818
Hampton Inn & Suites Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites Chicago Medical District UIC
9.1 Wonderful
Near West Side
Pool
Pet friendly
Air conditioning
Orlando
Breakfast
3 nights + flight
€372
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
Nashville Intl
Meals not included
3 nights + flight
€347
Courtyard by Marriott Chicago at Medical District/UIC - Chicago - Patio
Courtyard by Marriott Chicago at Medical District/UIC - Chicago - Patio
Courtyard by Marriott Chicago at Medical District/UIC
8.4 Very Good
Near West Side
Free Wi-Fi
Air conditioning
Charlotte Douglas
Meals not included
3 nights + flight
€322
Eurostars Magnificent Mile - Chicago - Lounge
Eurostars Magnificent Mile - Chicago - Lounge
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
€411
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
8.4 Very Good
Downtown
Pet friendly
Air conditioning
Nashville Intl
Meals not included
3 nights + flight
€317
Waldorf Astoria Chicago - Chicago - Balcony
Waldorf Astoria Chicago - Chicago - Balcony
Waldorf Astoria Chicago
8.9 Very Good
Near North Side
Pool
Pet friendly
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€854
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
Air conditioning
Charlotte Douglas
Meals not included
3 nights + flight
€599
Marriott Chicago O'Hare - Chicago - Building
Marriott Chicago O'Hare - Chicago - Building
Marriott Chicago O'Hare
7.4 Good
O'Hare
Airport shuttle
Free Wi-Fi
Pool
Air conditioning
Charlotte Douglas
Meals not included
3 nights + flight
€256
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel
8.7 Very Good
Downtown
Pet friendly
Air conditioning
Nashville Intl
Meals not included
3 nights + flight
€326

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
Pet friendly
Air conditioning
Los Angeles
All-inclusive
3 nights + flight
€849

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: Family holiday €1,164; Romantic holiday €1,224; Luxury holiday €1,233; Budget holiday €1,003.

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

Family holiday (Flight+Hotel)€1,164
Romantic holiday (Flight+Hotel)€1,224
Luxury holiday (Flight+Hotel)€1,233
Budget holiday (Flight+Hotel)€1,003

Chicago holiday: Search Chicago holiday packages on KAYAK. KAYAK is a travel tool that searches Chicago trips on hundreds of travel sites to help you find the Chicago package that suits you best. Discover Chicago deals now and book your Chicago flight and hotel today.

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