Holidays in Chicago

Holidays in Chicago

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Cheap Chicago package deals

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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
Air conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
£233
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
Air conditioning
Miami
Meals not included
3 nights + flight
£252
Near North Side
Free Wi-Fi
Air conditioning
Newark
Breakfast
3 nights + flight
£211
Ruby Room
8.6 Very Good
Free Wi-Fi
Air conditioning
Newark
Meals not included
3 nights + flight
£284
Near West Side
Free Wi-Fi
Pet-friendly
Air conditioning
Miami
Meals not included
3 nights + flight
£211
Near North Side
Free Wi-Fi
Pet-friendly
Air conditioning
Newark
Meals not included
3 nights + flight
£216
The Wicker Park Inn
8.7 Very Good
Free Wi-Fi
Air conditioning
Newark
Breakfast
3 nights + flight
£313
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
Air conditioning
Miami
Meals not included
3 nights + flight
£253
Downtown
Free Wi-Fi
Pet-friendly
Air conditioning
Newark
Meals not included
3 nights + flight
£247
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
8.1 Very Good
Downtown
Pool
Pet-friendly
Air conditioning
Los Angeles
Meals not included
3 nights + flight
£563
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy
Near West Side
Air conditioning
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
£316
Near North Side
Free Wi-Fi
Air conditioning
Newark
Meals not included
3 nights + flight
£212
Near North Side
Free Wi-Fi
Pool
Air conditioning
Newark
Meals not included
3 nights + flight
£164
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Air conditioning
Newark
Breakfast
3 nights + flight
£255
Near North Side
Free Wi-Fi
Air conditioning
Newark
Breakfast
3 nights + flight
£181
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Orlando
Meals not included
3 nights + flight
£526

All inclusive holiday packages to Chicago

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The Wheeler Mansion
9.8 Wonderful
Near South Side
Free Wi-Fi
Air conditioning
Las Vegas Harry Reid Intl
All-inclusive
3 nights + flight
£651

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
Air conditioning
London Heathrow
Meals not included
3 nights + flight
£697
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
Air conditioning
London Heathrow
Breakfast
3 nights + flight
£748
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
Air conditioning
London Heathrow
Breakfast
3 nights + flight
£716

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.

Tips for finding cheap holiday packages Chicago

  • There are loads of types of holidays in Chicago and the cost will depend on what type of trip you’re taking and for how long you’d like to stay. Here are the latest prices for a 3 night trip for 2 travellers: Top holiday £397; Family holiday £358; Romantic holiday £434; Luxury holiday £428; Budget holiday £290.

'The Windy City' is the third largest city in the United States and occupies a sprawling metropolitan area. Chicago is also known as the Second City, as the first one almost entirely burned down in 1871. After Los Angeles and New York, Chicago ranks as the third largest film producer in America.

Chicago

Chicago holidays: The Essentials

Chicago holidays are best planned in June to September, when warm weather prevales. During these months, average temperatures can vary from 23 - 28 degrees Celsius. The winter months are cold, with snow, sleet and wind dominating the weather from December through to March. Chicago is located in the Central Time Zone (UTC - 06:00). Chicago is served by the O'Hare International Airport (ORD) and the Midway International Airport (MDW), however taxis from the airports can be expensive, so it is best to book with a hotel that offers free shuttle services. The city is also accessible by bus, train, rental car and has an extensive and affordable public transportation network.

Highlights and attractions of a stay in Chicago

The 'magnificent mile', home of numerous upscale stores, is also the site of the Water Tower, and a great place to begin a tour of the city. A long standing relic that survived the fire of 1871, the Water Tower is something of a local icon. Chicago's Chinatown is one of the most active in the world and, along with Little Italy, Greektown and Indian Village, it provides testimony to the city's multicultural identity. In the summertime, Lake Michigan's beach tempts visitors away from the city. Local culinary delights, without which Chicago holidays would be complete, include the deep dish pizza, created, perfected and highly regarded in the city and the Chicago hot dog, an all beef frankfurter in a poppy seed bun.

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.

Chicago holiday information

Top holiday (Flight+Hotel)£397
Family holiday (Flight+Hotel)£358
Romantic holiday (Flight+Hotel)£434
Luxury holiday (Flight+Hotel)£428
Budget holiday (Flight+Hotel)£290