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
Los Angeles
Meals not included
3 nights + flight
$613
Admiral Motel By OYO Chicago I-94 - Chicago - Bedroom![Admiral Motel By OYO Chicago I-94 - Chicago - Bedroom]()
Admiral Motel By OYO Chicago I-94
South Side
Parking
Pet-friendly
Los Angeles
Meals not included
3 nights + flight
$349
Near North Side
Free Wi-Fi
Pet-friendly
Los Angeles
Breakfast
3 nights + flight
$533
Downtown
Pet-friendly
Los Angeles
Breakfast
3 nights + flight
$490
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Burbank Bob Hope
Meals not included
3 nights + flight
$823
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
Fort Lauderdale
Breakfast
3 nights + flight
$695
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
Los Angeles
Meals not included
3 nights + flight
$548
The St. Regis Chicago - Chicago - Restaurant![The St. Regis Chicago - Chicago - Restaurant]()
The St. Regis Chicago
Downtown
Pool
Pet-friendly
Spa
Fort Lauderdale
Meals not included
3 nights + flight
$1,715
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
Burbank Bob Hope
Meals not included
3 nights + flight
$516
Downtown
Free Wi-Fi
Pet-friendly
Philadelphia
Breakfast
3 nights + flight
$647
Near North Side
Free Wi-Fi
Pool
Los Angeles
Meals not included
3 nights + flight
$413
Downtown
Pet-friendly
Spa
San Francisco
Meals not included
3 nights + flight
$702
Downtown
Free Wi-Fi
Pet-friendly
San Francisco
Meals not included
3 nights + flight
$660
Downtown
Free Wi-Fi
Pet-friendly
Los Angeles
Meals not included
3 nights + flight
$491
Downtown
Free Wi-Fi
Pet-friendly
Los Angeles
Meals not included
3 nights + flight
$762
Last minute holiday packages to Chicago
Show allThe Neighborhood Hotel Little Italy - Chicago - Living room![The Neighborhood Hotel Little Italy - Chicago - Living room]()
The Neighborhood Hotel Little Italy
Near West Side
Dallas/Fort Worth
Meals not included
3 nights + flight
$1,136
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
Dallas/Fort Worth
Breakfast
3 nights + flight
$736
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.