Holidays in Chicago

Holidays in Chicago

2 travellers

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Most popular Chicago flight and hotel deals

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Le Méridien Essex Chicago - Chicago - Bedroom
Le Méridien Essex Chicago - Chicago - Bedroom
Le Méridien Essex Chicago
8.2 Very Good
Downtown
New York John F Kennedy Intl
Meals not included
3 nights + flight
$349
The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
8.1 Very Good
Near North Side
Pool
Pet-friendly
New York John F Kennedy Intl
Meals not included
3 nights + flight
$310
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Lobby
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Lobby
Intercontinental Hotels Chicago Magnificent Mile By IHG
8 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
New York John F Kennedy Intl
Meals not included
3 nights + flight
$485
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
Pet-friendly
Charlotte Douglas
Meals not included
3 nights + flight
$295
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.7 Very Good
Near West Side
Free Wi-Fi
Pet-friendly
Orlando
Breakfast
3 nights + flight
$331
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
Newark
Meals not included
3 nights + flight
$304
The Wicker Park Inn - Chicago - Bedroom
The Wicker Park Inn - Chicago - Bedroom
The Wicker Park Inn
8.8 Very Good
Free Wi-Fi
Newark
Breakfast
3 nights + flight
$548
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
Charlotte Douglas
Meals not included
3 nights + flight
$375
Palmer House a Hilton Hotel - Chicago - Lounge
Palmer House a Hilton Hotel - Chicago - Lounge
Palmer House a Hilton Hotel
7.8 Good
Downtown
Free Wi-Fi
Pool
Pet-friendly
Spa
Los Angeles
Meals not included
3 nights + flight
$426
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 John F Kennedy Intl
Meals not included
3 nights + flight
$400
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
8 Very Good
Downtown
Pool
Pet-friendly
Spa
Los Angeles
Meals not included
3 nights + flight
$990
Hyatt Place Chicago Downtown/The Loop - Chicago - Bedroom
Hyatt Place Chicago Downtown/The Loop - Chicago - Bedroom
Hyatt Place Chicago Downtown/The Loop
8.3 Very Good
Downtown
Free Wi-Fi
Pool
Pet-friendly
Newark
Meals not included
3 nights + flight
$379
Travelodge by Wyndham Downtown Chicago - Chicago - Lounge
Travelodge by Wyndham Downtown Chicago - Chicago - Lounge
Travelodge by Wyndham Downtown Chicago
7.2 Good
Downtown
Free Wi-Fi
Charlotte Douglas
Meals not included
3 nights + flight
$256
Hotel Chicago West Loop, SureStay Collection by Best Western - Chicago - Living room
Hotel Chicago West Loop, SureStay Collection by Best Western - Chicago - Living room
Hotel Chicago West Loop, SureStay Collection by Best Western
7.5 Good
Near West Side
Free Wi-Fi
Pet-friendly
New York John F Kennedy Intl
Meals not included
3 nights + flight
$327
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
Charlotte Douglas
Meals not included
3 nights + flight
$274
The Westin Michigan Avenue Chicago - Chicago - Front desk
The Westin Michigan Avenue Chicago - Chicago - Front desk
The Westin Michigan Avenue Chicago
8.3 Very Good
Near North Side
Pet-friendly
Spa
Newark
Meals not included
3 nights + flight
$484

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
Los Angeles
All-inclusive
3 nights + flight
$1,100

Last minute holiday packages to Chicago

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Cabin 105 by 747 Lofts - Chicago - Building
Cabin 105 by 747 Lofts - Chicago - Building
Cabin 105 by 747 Lofts
6.3 Okay
West Town
Free Wi-Fi
New York John F Kennedy Intl
Meals not included
3 nights + flight
$439
River West, Third Floor Chicago by 747 Lofts - Chicago - Building
River West, Third Floor Chicago by 747 Lofts - Chicago - Building
River West, Third Floor Chicago by 747 Lofts
8.4 Very Good
West Town
Free Wi-Fi
New York John F Kennedy Intl
Meals not included
3 nights + flight
$449
Virgin Hotels Chicago - Chicago - Building
Virgin Hotels Chicago - Chicago - Building
Virgin Hotels Chicago
8.6 Very Good
Downtown
Free Wi-Fi
Pet-friendly
New York John F Kennedy Intl
Meals not included
3 nights + flight
$434

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