Holidays in Chicago

Holidays in Chicago

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€76 - €221€221 - €366€366 - €512€512 - €657€657+ per night

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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 Very Good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
€266
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
Air conditioning
Philadelphia
Breakfast
3 nights + flight
€241
Admiral Motel By OYO Chicago I-94 - Chicago - Balcony
Admiral Motel By OYO Chicago I-94 - Chicago - Balcony
Admiral Motel By OYO Chicago I-94
3.3 Poor
South Side
Parking
Pet friendly
Air conditioning
Miami
Meals not included
3 nights + flight
€174
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
Pet friendly
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
€180
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
7.7 Good
Near North Side
Free Wi-Fi
Air conditioning
Philadelphia
Breakfast
3 nights + flight
€201
Chicago Marriott Downtown Magnificent Mile - Chicago - Bedroom
Chicago Marriott Downtown Magnificent Mile - Chicago - Bedroom
Chicago Marriott Downtown Magnificent Mile
8.3 Very Good
Near North Side
Air conditioning
Philadelphia
Meals not included
3 nights + flight
€276
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
Air conditioning
Philadelphia
Breakfast
3 nights + flight
€193
Hotel 55 Chicago Downtown - Chicago - Restaurant
Hotel 55 Chicago Downtown - Chicago - Restaurant
Hotel 55 Chicago Downtown
8.2 Very Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Philadelphia
Meals not included
3 nights + flight
€260
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
9.2 Wonderful
Near West Side
Pool
Pet friendly
Air conditioning
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
€184
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
Miami
Meals not included
3 nights + flight
€188
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop
9 Wonderful
Downtown
Free Wi-Fi
Pet friendly
Air conditioning
Philadelphia
Meals not included
3 nights + flight
€232
Eurostars Magnificent Mile - Chicago - Living room
Eurostars Magnificent Mile - Chicago - Living room
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
€180
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
Air conditioning
Philadelphia
Meals not included
3 nights + flight
€212
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
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
€576
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
Air conditioning
Philadelphia
Breakfast
3 nights + flight
€199
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Air conditioning
Miami
Breakfast
3 nights + flight
€234

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
Philadelphia
All-inclusive
3 nights + flight
€815

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 €1,155; Romantic holiday €1,215; Luxury holiday €1,225; Budget holiday €996.

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)€1,155
Romantic holiday (Flight+Hotel)€1,215
Luxury holiday (Flight+Hotel)€1,225
Budget holiday (Flight+Hotel)€996