Holidays in Chicago

Holidays in Chicago

2 travellers
exact duration

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Cheap Chicago package deals

These are the best prices for 14-17 Jun.
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BreakfastHalf boardSelf cateringAll-inclusiveMeals not included

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195 € - 377 €377 € - 559 €559 € - 742 €742 € - 923 €923 €+ per night

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Free breakfastFree internetFree airport shuttleFree parking

Most popular Chicago flight and hotel deals

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The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
7.9 Good
Near North Side
Pool
Pet-friendly
Air Conditioning
Portland
Meals not included
3 nights + flight
499 €
Kimpton Gray Hotel - Chicago - Lobby
Kimpton Gray Hotel - Chicago - Lobby
Kimpton Gray Hotel
8.9 Very Good
Downtown
Pet-friendly
Air Conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
564 €
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel
8.1 Very Good
O'Hare
Airport shuttle
Pool
Air Conditioning
Nashville Intl
Meals not included
3 nights + flight
363 €
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
455 €
The Royal Sonesta Chicago Downtown - Chicago - Building
The Royal Sonesta Chicago Downtown - Chicago - Building
The Royal Sonesta Chicago Downtown
8.8 Very Good
Downtown
Pet-friendly
Air Conditioning
Portland
Meals not included
3 nights + flight
489 €
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
Air Conditioning
Columbus
Meals not included
3 nights + flight
448 €
Waldorf Astoria Chicago - Chicago - Restaurant
Waldorf Astoria Chicago - Chicago - Restaurant
Waldorf Astoria Chicago
9.2 Wonderful
Near North Side
Pool
Pet-friendly
Air Conditioning
Washington, D.C. Dulles Intl
Meals not included
3 nights + flight
575 €
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
Downtown
Free Wi-Fi
Pet-friendly
Air Conditioning
Portland
Breakfast
3 nights + flight
447 €
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
Newark
Meals not included
3 nights + flight
717 €
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Lobby
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
509 €
Best Motel By OYO Chicago I-90 - Chicago - Bedroom
Best Motel By OYO Chicago I-90 - Chicago - Bedroom
Best Motel By OYO Chicago I-90
2.2 Poor
South Side
Parking
Pet-friendly
Air Conditioning
Nashville Intl
Meals not included
3 nights + flight
194 €
Chicago Marriott Ohare - Chicago - Building
Chicago Marriott Ohare - Chicago - Building
Chicago Marriott Ohare
7.6 Good
O'Hare
Airport shuttle
Free Wi-Fi
Pool
Air Conditioning
Columbus
Meals not included
3 nights + flight
369 €
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel
8.6 Very Good
Downtown
Pet-friendly
Air Conditioning
Newark
Meals not included
3 nights + flight
556 €
The Westin Michigan Avenue Chicago - Chicago - Front desk
The Westin Michigan Avenue Chicago - Chicago - Front desk
The Westin Michigan Avenue Chicago
8.2 Very Good
Near North Side
Pet-friendly
Air Conditioning
Columbus
Meals not included
3 nights + flight
432 €
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.7 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Air Conditioning
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
787 €
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago
8.6 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Air Conditioning
Newark
Meals not included
3 nights + flight
539 €

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
Phoenix Sky Harbor Intl
All-inclusive
3 nights + flight
776 €

Last minute holiday packages to Chicago

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The Neighborhood Hotel Little Italy - Chicago - Living room
The Neighborhood Hotel Little Italy - Chicago - Living room
The Neighborhood Hotel Little Italy
Near West Side
Air Conditioning
Orlando
Meals not included
3 nights + flight
681 €
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.7 Very Good
Near West Side
Free Wi-Fi
Pet-friendly
Air Conditioning
Orlando
Meals not included
3 nights + flight
792 €

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 cheap holiday packages Chicago

  • 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 29 €; Family holiday 118 €; Romantic holiday 118 €; Luxury holiday 667 €; Budget holiday 179 €.

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)29 €
Family holiday (Flight+Hotel)118 €
Romantic holiday (Flight+Hotel)118 €
Luxury holiday (Flight+Hotel)667 €
Budget holiday (Flight+Hotel)179 €