Holidays in Chicago

Holidays in Chicago

2 travellers
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€194 - €343€343 - €493€493 - €642€642 - €791€791+ per night

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Most popular Chicago flight and hotel deals

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Thompson Chicago - Chicago - Lobby
Thompson Chicago - Chicago - Lobby
Thompson Chicago
8.9 Very Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Miami
Meals not included
3 nights + flight
€348
The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
7.9 Good
Near North Side
Pool
Pet friendly
Air conditioning
Miami
Meals not included
3 nights + flight
€301
The Blackstone Autograph Collection - Chicago - Lobby
The Blackstone Autograph Collection - Chicago - Lobby
The Blackstone Autograph Collection
8.5 Very Good
Loop
Pet friendly
Air conditioning
Miami
Meals not included
3 nights + flight
€513
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
Pool
Pet friendly
Air conditioning
Miami
Meals not included
3 nights + flight
€343
Hilton Chicago - Chicago - Living room
Hilton Chicago - Chicago - Living room
Hilton Chicago
7.9 Good
Loop
Pool
Pet friendly
Air conditioning
Miami
Meals not included
3 nights + flight
€338
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel
8.2 Very Good
O'Hare - International
Airport shuttle
Pool
Air conditioning
Nashville 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
8.3 Very Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Miami
Meals not included
3 nights + flight
€341
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
Miami
Meals not included
3 nights + flight
€790
Residence Inn by Marriott Chicago Downtown/Loop - Chicago - Bar
Residence Inn by Marriott Chicago Downtown/Loop - Chicago - Bar
Residence Inn by Marriott Chicago Downtown/Loop
8.6 Very Good
Loop
Free Wi-Fi
Pet friendly
Air conditioning
Miami
Breakfast
3 nights + flight
€358
Waldorf Astoria Chicago - Chicago - Bar
Waldorf Astoria Chicago - Chicago - Bar
Waldorf Astoria Chicago
9.2 Wonderful
Near North Side
Pool
Pet friendly
Air conditioning
Miami
Meals not included
3 nights + flight
€607
Hotel Felix - Chicago - Lobby
Hotel Felix - Chicago - Lobby
Hotel Felix
7.6 Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
€298
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
Los Angeles
Meals not included
3 nights + flight
€556
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
Miami
Breakfast
3 nights + flight
€348
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
Miami
Breakfast
3 nights + flight
€346
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.8 Very Good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Miami
Meals not included
3 nights + flight
€721
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
Houston George Bush Intcntl
Meals not included
3 nights + flight
€394

Last minute holiday packages to Chicago

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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
€622
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
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
€640
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
Las Vegas Harry Reid Intl
Breakfast
3 nights + flight
€637
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
€745

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 €228; Family holiday €685; Romantic holiday €685; Luxury holiday €1,202.

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)€228
Family holiday (Flight+Hotel)€685
Romantic holiday (Flight+Hotel)€685
Luxury holiday (Flight+Hotel)€1,202