Holidays in Chicago

Holidays in Chicago

2 travellers
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€123 - €283€283 - €444€444 - €605€605 - €765€765+ per night

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Most popular Chicago flight and hotel deals

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Intercontinental Chicago Magnificent Mile By IHG - Chicago - Meeting room
Intercontinental Chicago Magnificent Mile By IHG - Chicago - Meeting room
Intercontinental Chicago Magnificent Mile By IHG
8 Very Good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Philadelphia
Meals not included
3 nights + flight
€323
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
Las Vegas Harry Reid Intl
Breakfast
3 nights + flight
€303
Kimpton Gray Hotel - Chicago - Lobby
Kimpton Gray Hotel - Chicago - Lobby
Kimpton Gray Hotel
8.9 Very Good
Downtown
Pet friendly
Air conditioning
Nashville Intl
Meals not included
3 nights + flight
€390
21c Museum Hotel Chicago - Chicago - Restaurant
21c Museum Hotel Chicago - Chicago - Restaurant
21c Museum Hotel Chicago
8.4 Very Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Philadelphia
Meals not included
3 nights + flight
€266
Hampton Inn & Suites Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites Chicago Medical District UIC
9.1 Wonderful
Near West Side
Pool
Pet friendly
Air conditioning
Philadelphia
Breakfast
3 nights + flight
€244
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton
8.9 Very Good
Downtown
Free Wi-Fi
Air conditioning
Philadelphia
Meals not included
3 nights + flight
€296
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
Nashville Intl
Meals not included
3 nights + flight
€380
Hotel Emc2, Autograph Collection - Chicago - Restaurant
Hotel Emc2, Autograph Collection - Chicago - Restaurant
Hotel Emc2, Autograph Collection
8.9 Very Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Nashville Intl
Meals not included
3 nights + flight
€345
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
Nashville Intl
Breakfast
3 nights + flight
€218
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
Nashville Intl
Meals not included
3 nights + flight
€308
Sheraton Grand Chicago Riverwalk - Chicago - Living room
Sheraton Grand Chicago Riverwalk - Chicago - Living room
Sheraton Grand Chicago Riverwalk
8.1 Very Good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Nashville Intl
Meals not included
3 nights + flight
€297
Courtyard Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard Chicago Downtown/Magnificent Mile
8.4 Very Good
Near North Side
Free Wi-Fi
Pool
Air conditioning
Philadelphia
Meals not included
3 nights + flight
€210
Sofitel Chicago Magnificent Mile - Chicago - Patio
Sofitel Chicago Magnificent Mile - Chicago - Patio
Sofitel Chicago Magnificent Mile
8.9 Very Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Nashville Intl
Meals not included
3 nights + flight
€295
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
Denver Intl
Meals not included
3 nights + flight
€844
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
Philadelphia
Breakfast
3 nights + flight
€235
Club Quarters Hotel Wacker at Michigan - Chicago - Building
Club Quarters Hotel Wacker at Michigan - Chicago - Building
Club Quarters Hotel Wacker at Michigan
8.3 Very Good
Downtown
Free Wi-Fi
Pet friendly
Air conditioning
Miami
Meals not included
3 nights + flight
€304

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
€695

Last minute holiday packages to Chicago

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The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
8.1 Very Good
Near North Side
Pool
Pet friendly
Air conditioning
Rochester Greater Rochester Intl
Meals not included
3 nights + flight
€697
Admiral Motel By OYO Chicago I-94 - Chicago - Bedroom
Admiral Motel By OYO Chicago I-94 - Chicago - Bedroom
Admiral Motel By OYO Chicago I-94
3.7 Poor
South Side
Parking
Pet friendly
Air conditioning
Rochester Greater Rochester Intl
Meals not included
3 nights + flight
€265

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 €1,224; 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)€1,224
Budget holiday (Flight+Hotel)€996

Chicago holiday: Search Chicago holiday packages on KAYAK. KAYAK is a travel tool that searches Chicago trips on hundreds of travel sites to help you find the Chicago package that suits you best. Discover Chicago deals now and book your Chicago flight and hotel today.

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