Holidays in Chicago

Holidays in Chicago

2 travellers

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$284 - $645$645 - $1,004$1,004 - $1,364$1,364 - $1,723$1,723+ 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
Dallas/Fort Worth
Meals not included
3 nights + flight
$465
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
Miami
Meals not included
3 nights + flight
$504
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
7.7 Good
Near North Side
Free Wi-Fi
Newark
Breakfast
3 nights + flight
$421
Ruby Room - Chicago - Living room
Ruby Room - Chicago - Living room
Ruby Room
8.6 Very Good
Free Wi-Fi
Newark
Meals not included
3 nights + flight
$566
Crowne Plaza Chicago West Loop By IHG - Chicago - Lobby
Crowne Plaza Chicago West Loop By IHG - Chicago - Lobby
Crowne Plaza Chicago West Loop By IHG
8.2 Very Good
Near West Side
Free Wi-Fi
Pet-friendly
Miami
Meals not included
3 nights + flight
$420
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
Newark
Meals not included
3 nights + flight
$430
The Wicker Park Inn - Chicago - Bedroom
The Wicker Park Inn - Chicago - Bedroom
The Wicker Park Inn
8.7 Very Good
Free Wi-Fi
Newark
Breakfast
3 nights + flight
$625
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
Miami
Meals not included
3 nights + flight
$505
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop
9 Wonderful
Downtown
Free Wi-Fi
Pet-friendly
Spa
Newark
Meals not included
3 nights + flight
$493
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
8.1 Very Good
Downtown
Pool
Pet-friendly
Spa
Los Angeles
Meals not included
3 nights + flight
$1,123
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy
Near West Side
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$630
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
Newark
Meals not included
3 nights + flight
$422
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
$328
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Newark
Breakfast
3 nights + flight
$509
SpringHill Suites by Marriott Chicago Downtown/River North - Chicago - Lounge
SpringHill Suites by Marriott Chicago Downtown/River North - Chicago - Lounge
SpringHill Suites by Marriott Chicago Downtown/River North
8.8 Very Good
Near North Side
Free Wi-Fi
Newark
Breakfast
3 nights + flight
$362
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.6 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
Orlando
Meals not included
3 nights + flight
$1,049

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
Las Vegas Harry Reid Intl
All-inclusive
3 nights + flight
$1,299

Last minute holiday packages to Chicago

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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
London Heathrow
Meals not included
3 nights + flight
$1,390
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
London Heathrow
Breakfast
3 nights + flight
$1,493
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
London Heathrow
Breakfast
3 nights + flight
$1,429

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