Holidays in Chicago

Holidays in Chicago

2 travellers

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$218 - $529$529 - $840$840 - $1,151$1,151 - $1,464$1,464+ per night

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Most popular Chicago flight and hotel deals

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Thompson Chicago - Chicago - Living room
Thompson Chicago - Chicago - Living room
Thompson Chicago
8.8 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Denver Intl
Meals not included
3 nights + flight
$549
Intercontinental Chicago Magnificent Mile By IHG - Chicago - Meeting room
Intercontinental Chicago Magnificent Mile By IHG - Chicago - Meeting room
Intercontinental Chicago Magnificent Mile By IHG
8.1 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Denver Intl
Meals not included
3 nights + flight
$613
Warwick Allerton Chicago - Chicago - Bedroom
Warwick Allerton Chicago - Chicago - Bedroom
Warwick Allerton Chicago
8 Very Good
Near North Side
Free Wi-Fi
Denver Intl
Meals not included
3 nights + flight
$408
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
Denver Intl
Meals not included
3 nights + flight
$670
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
Houston George Bush Intcntl
Meals not included
3 nights + flight
$314
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
Nashville Intl
Breakfast
3 nights + flight
$448
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
Miami
Meals not included
3 nights + flight
$841
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
Denver Intl
Meals not included
3 nights + flight
$424
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
Denver Intl
Meals not included
3 nights + flight
$572
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
Denver Intl
Breakfast
3 nights + flight
$570
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
Denver Intl
Meals not included
3 nights + flight
$577
The Neighborhood Hotel Little Italy - Chicago - Living room
The Neighborhood Hotel Little Italy - Chicago - Living room
The Neighborhood Hotel Little Italy
Near West Side
Nashville Intl
Meals not included
3 nights + flight
$658
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
Nashville Intl
Meals not included
3 nights + flight
$544
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
Spa
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$912
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
Nashville Intl
Meals not included
3 nights + flight
$660
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
Spa
Denver Intl
Meals not included
3 nights + flight
$1,491

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
Las Vegas Harry Reid Intl
All-inclusive
3 nights + flight
$1,213

Last minute holiday packages to Chicago

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The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
8.8 Very Good
Downtown
Pool
Pet-friendly
Spa
Rochester Greater Rochester Intl
Meals not included
3 nights + flight
$2,289

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.

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 vacation: 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.

Not what you’re looking for? Find thousands of other hotels, flights, car hires and package deals with KAYAK.