Holidays in Chicago

Holidays in Chicago

2 travellers

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$211 - $410$410 - $611$611 - $809$809 - $1,008$1,008+ per night

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Most popular Chicago flight and hotel deals

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The Blackstone Autograph Collection - Chicago - Lobby
The Blackstone Autograph Collection - Chicago - Lobby
The Blackstone Autograph Collection
8.5 Very Good
Downtown
Pet-friendly
Spa
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$434
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
Baltimore/Washington
Meals not included
3 nights + flight
$599
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
8.2 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Baltimore/Washington
Breakfast
3 nights + flight
$442
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
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$365
Hampton Inn Majestic Chicago Theatre District - Chicago - Building
Hampton Inn Majestic Chicago Theatre District - Chicago - Building
Hampton Inn Majestic Chicago Theatre District
8.3 Very Good
Downtown
Pet-friendly
Dallas/Fort Worth
Breakfast
3 nights + flight
$471
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
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$418
The Royal Sonesta Chicago Downtown - Chicago - Building
The Royal Sonesta Chicago Downtown - Chicago - Building
The Royal Sonesta Chicago Downtown
8.7 Very Good
Downtown
Pet-friendly
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$453
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
8.9 Very Good
Downtown
Pool
Pet-friendly
Spa
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$1,008
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop
9 Wonderful
Downtown
Free Wi-Fi
Pet-friendly
Spa
Dallas/Fort Worth
Meals not included
3 nights + flight
$483
Hyatt Regency Chicago - Chicago - Living room
Hyatt Regency Chicago - Chicago - Living room
Hyatt Regency Chicago
8.7 Very Good
Downtown
Free Wi-Fi
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$477
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
8.3 Very Good
Downtown
Pet-friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
$406
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
8.3 Very Good
Near North Side
Free Wi-Fi
Pool
Tampa
Meals not included
3 nights + flight
$349
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
Las Vegas Harry Reid Intl
Breakfast
3 nights + flight
$380
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Las Vegas Harry Reid Intl
Breakfast
3 nights + flight
$421
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
Tampa
Breakfast
3 nights + flight
$377
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection
8.5 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$502

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
Birmingham
All-inclusive
3 nights + flight
$1,727

Last minute holiday packages to Chicago

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The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy
Near West Side
Fort Lauderdale
Meals not included
3 nights + flight
$937
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.6 Very Good
Near West Side
Free Wi-Fi
Pet-friendly
Fort Lauderdale
Breakfast
3 nights + flight
$772

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