Holidays in Chicago

Holidays in Chicago

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€138 - €317€317 - €497€497 - €676€676 - €856€856+ per night

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Most popular Chicago flight and hotel deals

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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
9.1 Wonderful
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Dallas/Fort Worth
Breakfast
3 nights + flight
€313
Omni Chicago Hotel - Chicago - Building
Omni Chicago Hotel - Chicago - Building
Omni Chicago Hotel
8.7 Very Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Orlando
Meals not included
3 nights + flight
€333
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
8.1 Very Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Orlando
Breakfast
3 nights + flight
€204
Hotel Chicago Downtown, Autograph Collection - Chicago - Building
Hotel Chicago Downtown, Autograph Collection - Chicago - Building
Hotel Chicago Downtown, Autograph Collection
8.4 Very Good
Near North Side
Air conditioning
Philadelphia
Meals not included
3 nights + flight
€281
L7 Chicago by LOTTE - Chicago - Lounge
L7 Chicago by LOTTE - Chicago - Lounge
L7 Chicago by LOTTE
9.1 Wonderful
Downtown
Free Wi-Fi
Pet friendly
Air conditioning
Orlando
Meals not included
3 nights + flight
€311
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
8.8 Very Good
Downtown
Pool
Pet friendly
Air conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
€909
Homewood Suites by Hilton - Chicago Downtown South Loop - Chicago - Living room
Homewood Suites by Hilton - Chicago Downtown South Loop - Chicago - Living room
Homewood Suites by Hilton - Chicago Downtown South Loop
8.1 Very Good
Downtown
Free Wi-Fi
Pool
Air conditioning
Orlando
Breakfast
3 nights + flight
€202
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
8.3 Very Good
Downtown
Pet friendly
Air conditioning
Santa Ana J. Wayne/Orange Cnty
Meals not included
3 nights + flight
€252
Hotel Felix Chicago - Chicago - Lobby
Hotel Felix Chicago - Chicago - Lobby
Hotel Felix Chicago
7.5 Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Orlando
Meals not included
3 nights + flight
€225
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
Dallas/Fort Worth
Meals not included
3 nights + flight
€538
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown
8.9 Very Good
South Side
Free Wi-Fi
Air conditioning
New York LaGuardia
Breakfast
3 nights + flight
€259
The Westin Michigan Avenue Chicago - Chicago - Living room
The Westin Michigan Avenue Chicago - Chicago - Living room
The Westin Michigan Avenue Chicago
8.3 Very Good
Near North Side
Pet friendly
Air conditioning
Santa Ana J. Wayne/Orange Cnty
Meals not included
3 nights + flight
€314
Homewood Suites by Hilton Chicago Downtown/Magnificent Mile - Chicago - Lounge
Homewood Suites by Hilton Chicago Downtown/Magnificent Mile - Chicago - Lounge
Homewood Suites by Hilton Chicago Downtown/Magnificent Mile
7.9 Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Orlando
Breakfast
3 nights + flight
€249
Virgin Hotels Chicago - Chicago - Building
Virgin Hotels Chicago - Chicago - Building
Virgin Hotels Chicago
8.6 Very Good
Downtown
Free Wi-Fi
Pet friendly
Air conditioning
Orlando
Meals not included
3 nights + flight
€324
Hampton Inn Chicago Downtown/Magnificent Mile - Chicago - Living room
Hampton Inn Chicago Downtown/Magnificent Mile - Chicago - Living room
Hampton Inn Chicago Downtown/Magnificent Mile
7.6 Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Orlando
Breakfast
3 nights + flight
€262
Club Quarters Hotel Central Loop, Chicago - Chicago - Lobby
Club Quarters Hotel Central Loop, Chicago - Chicago - Lobby
Club Quarters Hotel Central Loop, Chicago
8.1 Very Good
Downtown
Free Wi-Fi
Pet friendly
Air conditioning
Orlando
Meals not included
3 nights + flight
€210

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
Orlando
All-inclusive
3 nights + flight
€828

Last minute holiday packages to Chicago

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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
Norfolk
Meals not included
3 nights + flight
€553
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
8.4 Very Good
Near North Side
Free Wi-Fi
Pool
Air conditioning
Norfolk
Meals not included
3 nights + flight
€520
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
Norfolk
Breakfast
3 nights + flight
€468

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 €1,163; Romantic holiday €1,223; 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)€1,163
Romantic holiday (Flight+Hotel)€1,223
Luxury holiday (Flight+Hotel)€1,233
Budget holiday (Flight+Hotel)€1,003

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