Holidays in Chicago

Holidays in Chicago

2 travellers

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$338 - $534$534 - $730$730 - $924$924 - $1,119$1,119+ per night

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Most popular Chicago flight and hotel deals

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The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
8.1 Very Good
Near North Side
Pool
Pet-friendly
Newark
Meals not included
3 nights + flight
$436
Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Lobby
Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Lobby
Residence Inn by Marriott Chicago Downtown Magnificent Mile
9 Wonderful
Near North Side
Free Wi-Fi
Pet-friendly
Orlando
Meals not included
3 nights + flight
$520
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical - Chicago - Lounge
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical - Chicago - Lounge
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
8.3 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Raleigh-Durham
Breakfast
3 nights + flight
$449
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
$418
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
7.9 Good
Near North Side
Pool
Pet-friendly
Orlando
Breakfast
3 nights + flight
$523
Hampton Inn Majestic Chicago Theatre District - Chicago - Building
Hampton Inn Majestic Chicago Theatre District - Chicago - Building
Hampton Inn Majestic Chicago Theatre District
8.5 Very Good
Downtown
Pet-friendly
Orlando
Breakfast
3 nights + flight
$469
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
Orlando
Meals not included
3 nights + flight
$496
Staypineapple, An Iconic Hotel, The Loop - Chicago - Lobby
Staypineapple, An Iconic Hotel, The Loop - Chicago - Lobby
Staypineapple, An Iconic Hotel, The Loop
9 Wonderful
Downtown
Free Wi-Fi
Pet-friendly
Spa
Raleigh-Durham
Meals not included
3 nights + flight
$504
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
8.2 Very Good
Downtown
Pool
Pet-friendly
Spa
Raleigh-Durham
Meals not included
3 nights + flight
$1,143
Moxy Chicago Downtown - Chicago - Lounge
Moxy Chicago Downtown - Chicago - Lounge
Moxy Chicago Downtown
9.1 Wonderful
Near North Side
Free Wi-Fi
Pet-friendly
Raleigh-Durham
Meals not included
3 nights + flight
$434
Hotel Lincoln - Chicago - Balcony
Hotel Lincoln - Chicago - Balcony
Hotel Lincoln
6.9 Okay
Lincoln Park
Free Wi-Fi
Pet-friendly
Orlando
Meals not included
3 nights + flight
$468
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy
Near West Side
Orlando
Meals not included
3 nights + flight
$711
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
8.4 Very Good
Downtown
Pet-friendly
Newark
Meals not included
3 nights + flight
$425
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
8.2 Very Good
Near North Side
Free Wi-Fi
Pool
Newark
Meals not included
3 nights + flight
$400
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
Newark
Breakfast
3 nights + flight
$429
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$541

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
Houston George Bush Intcntl
All-inclusive
3 nights + flight
$1,820

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