Holidays in Chicago

Holidays in Chicago

2 travellers
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€235 - €425€425 - €616€616 - €807€807 - €997€997+ 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
7.6 Good
Near North Side
Pool
Pet friendly
Air conditioning
Denver Intl
Meals not included
3 nights + flight
€363
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
Denver Intl
Meals not included
3 nights + flight
€424
Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Lounge
Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Lounge
Residence Inn by Marriott Chicago Downtown Magnificent Mile
9.1 Wonderful
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
€408
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
2.4 Poor
Chatham
Parking
Pet friendly
Air conditioning
Denver Intl
Meals not included
3 nights + flight
€252
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
Philadelphia
Meals not included
3 nights + flight
€469
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites
8.4 Very Good
Near North Side
Pool
Pet friendly
Air conditioning
Philadelphia
Meals not included
3 nights + flight
€366
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
Denver Intl
Breakfast
3 nights + flight
€282
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
Denver Intl
Meals not included
3 nights + flight
€312
The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel - Chicago - Restaurant
The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel - Chicago - Restaurant
The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel
8.2 Very Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Denver Intl
Meals not included
3 nights + flight
€333
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
8.1 Very Good
Loop
Pool
Pet friendly
Air conditioning
Denver Intl
Meals not included
3 nights + flight
€997
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop
8.9 Very Good
Loop
Free Wi-Fi
Pet friendly
Air conditioning
Denver Intl
Meals not included
3 nights + flight
€382
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
Air conditioning
Denver Intl
Meals not included
3 nights + flight
€397
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
Denver Intl
Meals not included
3 nights + flight
€308
Marriott Chicago O'Hare - Chicago - Building
Marriott Chicago O'Hare - Chicago - Building
Marriott Chicago O'Hare
7.8 Good
O'Hare
Airport shuttle
Pool
Air conditioning
Denver Intl
Meals not included
3 nights + flight
€370
Hotel Riu Plaza Chicago - Chicago - Lounge
Hotel Riu Plaza Chicago - Chicago - Lounge
Hotel Riu Plaza Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Air conditioning
Denver Intl
Breakfast
3 nights + flight
€392
SpringHill Suites by Marriott Chicago Downtown/River North - Chicago - Building
SpringHill Suites by Marriott Chicago Downtown/River North - Chicago - Building
SpringHill Suites by Marriott Chicago Downtown/River North
8.8 Very Good
Near North Side
Free Wi-Fi
Air conditioning
Denver Intl
Breakfast
3 nights + flight
€406

Last minute holiday packages to Chicago

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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
8.1 Very Good
Near North Side
Free Wi-Fi
Pool
Air conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
€540
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.9 Very Good
Near West Side
Free Wi-Fi
Pet friendly
Air conditioning
Orlando
Breakfast
3 nights + flight
€581

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 €300; Family holiday €1,201; Romantic holiday €1,201; Luxury holiday €1,201.

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)€300
Family holiday (Flight+Hotel)€1,201
Romantic holiday (Flight+Hotel)€1,201
Luxury holiday (Flight+Hotel)€1,201