Holidays in Chicago

Holidays in Chicago

2 travellers

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$346 - $591$591 - $836$836 - $1,082$1,082 - $1,327$1,327+ 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
8.7 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Minneapolis St Paul
Meals not included
3 nights + flight
$623
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
4.8 Mediocre
South Side
Parking
Pet-friendly
Los Angeles
Meals not included
3 nights + flight
$346
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
Free Wi-Fi
Pool
Pet-friendly
Los Angeles
Meals not included
3 nights + flight
$446
Holiday Inn Express Chicago - Magnificent Mile - Chicago - Lobby
Holiday Inn Express Chicago - Magnificent Mile - Chicago - Lobby
Holiday Inn Express Chicago - Magnificent Mile
7.6 Good
Near North Side
Free Wi-Fi
Newark
Breakfast
3 nights + flight
$578
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
7.9 Good
Near North Side
Pool
Pet-friendly
Los Angeles
Breakfast
3 nights + flight
$626
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
Orlando
Meals not included
3 nights + flight
$575
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North
8.6 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Orlando
Meals not included
3 nights + flight
$591
Millennium Knickerbocker Chicago - Chicago - Lobby
Millennium Knickerbocker Chicago - Chicago - Lobby
Millennium Knickerbocker Chicago
7.8 Good
Near North Side
Orlando
Meals not included
3 nights + flight
$428
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop
8.9 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Spa
New York LaGuardia
Meals not included
3 nights + flight
$620
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
8.4 Very Good
Downtown
Pet-friendly
Orlando
Meals not included
3 nights + flight
$563
Waldorf Astoria Chicago - Chicago - Balcony
Waldorf Astoria Chicago - Chicago - Balcony
Waldorf Astoria Chicago
8.9 Very Good
Near North Side
Pool
Pet-friendly
Spa
Los Angeles
Meals not included
3 nights + flight
$1,039
SpringHill Suites by Marriott Chicago O'Hare - Chicago - Patio
SpringHill Suites by Marriott Chicago O'Hare - Chicago - Patio
SpringHill Suites by Marriott Chicago O'Hare
8.1 Very Good
Airport shuttle
Free Wi-Fi
Pool
Pet-friendly
Orlando
Breakfast
3 nights + flight
$401
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel
8.8 Very Good
Downtown
Pet-friendly
Spa
Orlando
Meals not included
3 nights + flight
$542
Virgin Hotels Chicago - Chicago - Building
Virgin Hotels Chicago - Chicago - Building
Virgin Hotels Chicago
8.6 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Orlando
Meals not included
3 nights + flight
$638
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
Sacramento Intl
Meals not included
3 nights + flight
$1,363
The Talbott, Autograph Collection - Chicago - Bar
The Talbott, Autograph Collection - Chicago - Bar
The Talbott, Autograph Collection
8.6 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Los Angeles
Meals not included
3 nights + flight
$640

Last minute holiday packages to Chicago

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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
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$766
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.4 Very Good
Near West Side
Free Wi-Fi
Pet-friendly
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$913

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.

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