Holidays in Chicago
2 travellers
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Most popular Chicago flight and hotel deals
Show allNear North Side
Free Wi-Fi
Pet-friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
$700
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
$470
Near North Side
Free Wi-Fi
Pet-friendly
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
$640
Near West Side
Free Wi-Fi
Pet-friendly
Nashville Intl
Breakfast
3 nights + flight
$560
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
Philadelphia
Meals not included
3 nights + flight
$707
Downtown
Pet-friendly
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
$605
Near North Side
Free Wi-Fi
Pet-friendly
Nashville Intl
Meals not included
3 nights + flight
$675
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
Nashville Intl
Meals not included
3 nights + flight
$620
Downtown
Free Wi-Fi
Pet-friendly
Spa
Dallas/Fort Worth
Meals not included
3 nights + flight
$559
The Neighborhood Hotel Little Italy - Chicago - Living room![The Neighborhood Hotel Little Italy - Chicago - Living room]()
The Neighborhood Hotel Little Italy
Near West Side
Baltimore/Washington
Meals not included
3 nights + flight
$755
Near North Side
Free Wi-Fi
Nashville Intl
Meals not included
3 nights + flight
$747
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
Los Angeles
Meals not included
3 nights + flight
$1,148
Near North Side
Free Wi-Fi
Pool
Nashville Intl
Meals not included
3 nights + flight
$532
O'Hare
Airport shuttle
Free Wi-Fi
Pool
Los Angeles
Meals not included
3 nights + flight
$600
Chicago Avenue Inn - Chicago - Dining room![Chicago Avenue Inn - Chicago - Dining room]()
Chicago Avenue Inn
Humboldt Park
Parking
Free Wi-Fi
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$445
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
Charlotte Douglas
Meals not included
3 nights + flight
$1,501
Last minute holiday packages to Chicago
Show allSonder The Burnham - Chicago - Living room![Sonder The Burnham - Chicago - Living room]()
Sonder The Burnham
Near West Side
Free Wi-Fi
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$791
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.