Holidays in Chicago

Holidays in Chicago

2 travellers

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$290 - $478$478 - $667$667 - $855$855 - $1,044$1,044+ 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
8.9 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$429
The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
8 Very Good
Near North Side
Pool
Pet-friendly
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$339
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
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$354
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
8.3 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Las Vegas Harry Reid Intl
Breakfast
3 nights + flight
$375
Crowne Plaza Chicago West Loop By IHG - Chicago - Lobby
Crowne Plaza Chicago West Loop By IHG - Chicago - Lobby
Crowne Plaza Chicago West Loop By IHG
8.2 Very Good
Near West Side
Free Wi-Fi
Pet-friendly
New York John F Kennedy Intl
Meals not included
3 nights + flight
$426
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
Las Vegas Harry Reid Intl
Breakfast
3 nights + flight
$465
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
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$439
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites by Hilton Chicago Medical District UIC
9.3 Wonderful
Near West Side
Pool
Pet-friendly
New York John F Kennedy Intl
Breakfast
3 nights + flight
$480
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
Newark
Meals not included
3 nights + flight
$494
DoubleTree by Hilton Chicago Midway Airport - Chicago - Lobby
DoubleTree by Hilton Chicago Midway Airport - Chicago - Lobby
DoubleTree by Hilton Chicago Midway Airport
8.7 Very Good
Airport shuttle
Free Wi-Fi
Pool
New York John F Kennedy Intl
Meals not included
3 nights + flight
$514
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop
9 Wonderful
Downtown
Free Wi-Fi
Pet-friendly
Spa
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$418
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy
Near West Side
New York John F Kennedy Intl
Meals not included
3 nights + flight
$533
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
Newark
Meals not included
3 nights + flight
$400
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
Downtown
Pet-friendly
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$416
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown
9 Wonderful
South Side
Free Wi-Fi
Denver Intl
Breakfast
3 nights + flight
$482
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.6 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
$1,043

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
$1,098

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