Holidays in Chicago
2 travellers
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Most popular Chicago flight and hotel deals
Show allLe Méridien Essex Chicago - Chicago - Bedroom![Le Méridien Essex Chicago - Chicago - Bedroom]()
Le Méridien Essex Chicago
Downtown
Nashville Intl
Meals not included
3 nights + flight
$488
Sonder Onterie - Chicago - Living room![Sonder Onterie - Chicago - Living room]()
Sonder Onterie
Near North Side
Free Wi-Fi
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$794
Near North Side
Free Wi-Fi
Pet-friendly
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
$667
Near North Side
Free Wi-Fi
Nashville Intl
Meals not included
3 nights + flight
$541
Near West Side
Free Wi-Fi
Pet-friendly
Nashville Intl
Meals not included
3 nights + flight
$518
Near North Side
Free Wi-Fi
Pet-friendly
Nashville Intl
Meals not included
3 nights + flight
$567
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
Near West Side
Pool
Pet-friendly
Nashville Intl
Breakfast
3 nights + flight
$720
The Royal Sonesta Chicago River North - Chicago - Lounge![The Royal Sonesta Chicago River North - Chicago - Lounge]()
The Royal Sonesta Chicago River North
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$713
Airport shuttle
Free Wi-Fi
Pool
Nashville Intl
Meals not included
3 nights + flight
$617
The St. Regis Chicago - Chicago - Restaurant![The St. Regis Chicago - Chicago - Restaurant]()
The St. Regis Chicago
Downtown
Pool
Pet-friendly
Spa
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$1,453
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
$713
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
Downtown
Pet-friendly
Nashville Intl
Meals not included
3 nights + flight
$529
Sonder The Burnham - Chicago - Living room![Sonder The Burnham - Chicago - Living room]()
Sonder The Burnham
Near West Side
Free Wi-Fi
Nashville Intl
Meals not included
3 nights + flight
$646
Chicago Avenue Inn - Chicago - Dining room![Chicago Avenue Inn - Chicago - Dining room]()
Chicago Avenue Inn
Humboldt Park
Parking
Free Wi-Fi
Newark
Meals not included
3 nights + flight
$362
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby![SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby]()
SpringHill Suites by Marriott Chicago Chinatown
South Side
Free Wi-Fi
New Orleans Louis Armstrong
Breakfast
3 nights + flight
$759
Last minute holiday packages to Chicago
Show allNear North Side
Free Wi-Fi
Pool
London Heathrow
Meals not included
3 nights + flight
$1,600
Hyatt House Chicago Medical/University District - Chicago - Building![Hyatt House Chicago Medical/University District - Chicago - Building]()
Hyatt House Chicago Medical/University District
Near West Side
Free Wi-Fi
Pet-friendly
London Heathrow
Breakfast
3 nights + flight
$1,479
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.