Holidays in Chicago

Holidays in Chicago

2 travellers

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$177 - $389$389 - $601$601 - $811$811 - $1,023$1,023+ per night

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Most popular Chicago flight and hotel deals

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Thompson Chicago - Chicago - Living room
Thompson Chicago - Chicago - Living room
Thompson Chicago
8.8 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Fort Myers SW Florida Intl
Meals not included
3 nights + flight
$433
Le Méridien Essex Chicago - Chicago - Bedroom
Le Méridien Essex Chicago - Chicago - Bedroom
Le Méridien Essex Chicago
8.2 Very Good
Downtown
Fort Myers SW Florida Intl
Meals not included
3 nights + flight
$365
The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
8.1 Very Good
Near North Side
Pool
Pet-friendly
Fort Myers SW Florida Intl
Meals not included
3 nights + flight
$331
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 Myers SW Florida Intl
Breakfast
3 nights + flight
$338
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel
8 Very Good
O'Hare
Airport shuttle
Pool
New York LaGuardia
Meals not included
3 nights + flight
$417
Hotel 55 Chicago Downtown - Chicago - Restaurant
Hotel 55 Chicago Downtown - Chicago - Restaurant
Hotel 55 Chicago Downtown
8.3 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Fort Myers SW Florida Intl
Meals not included
3 nights + flight
$497
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites by Hilton Chicago Medical District UIC
9.2 Wonderful
Near West Side
Pool
Pet-friendly
Fort Myers SW Florida Intl
Breakfast
3 nights + flight
$347
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
Fort Myers SW Florida Intl
Meals not included
3 nights + flight
$375
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy
Near West Side
New York John F Kennedy Intl
Meals not included
3 nights + flight
$573
Residence Inn by Marriott Chicago Downtown/Loop - Chicago - Bar
Residence Inn by Marriott Chicago Downtown/Loop - Chicago - Bar
Residence Inn by Marriott Chicago Downtown/Loop
8.9 Very Good
Downtown
Free Wi-Fi
Pet-friendly
New York LaGuardia
Breakfast
3 nights + flight
$497
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
Fort Myers SW Florida Intl
Meals not included
3 nights + flight
$377
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
Fort Myers SW Florida Intl
Meals not included
3 nights + flight
$300
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown
9 Wonderful
South Side
Free Wi-Fi
Houston George Bush Intcntl
Meals not included
3 nights + flight
$431
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
New York LaGuardia
Breakfast
3 nights + flight
$525
Four Seasons Hotel Chicago - Chicago - Lounge
Four Seasons Hotel Chicago - Chicago - Lounge
Four Seasons Hotel Chicago
8.7 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
San Francisco
Meals not included
3 nights + flight
$976
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago
8.6 Very Good
Downtown
Free Wi-Fi
Pet-friendly
New York LaGuardia
Meals not included
3 nights + flight
$399

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
San Francisco
All-inclusive
3 nights + flight
$1,313

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