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Holidays in Chicago

Holidays in Chicago

2 travellers
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Most popular Chicago flight and hotel deals

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Thompson Chicago
8.7 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
£347
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
5.2 Fair
South Side
Parking
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
£133
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
£250
Near North Side
Free Wi-Fi
Pet-friendly
Air conditioning
Fort Myers SW Florida Intl
Breakfast
3 nights + flight
£327
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.4 Very Good
Near West Side
Free Wi-Fi
Pet-friendly
Air conditioning
New York LaGuardia
Meals not included
3 nights + flight
£334
O'Hare
Airport shuttle
Pool
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
£229
Viceroy Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Baltimore/Washington
Meals not included
3 nights + flight
£515
OYO Hotel Edgebrook Chicago North Shore - Chicago - Bedroom
OYO Hotel Edgebrook Chicago North Shore - Chicago - Bedroom
OYO Hotel Edgebrook Chicago North Shore
6.7 Okay
Forest Glen
Free Wi-Fi
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
£144
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
New York LaGuardia
Meals not included
3 nights + flight
£395
Near North Side
Free Wi-Fi
Pet-friendly
Air conditioning
Orlando Sanford Intl
Breakfast
3 nights + flight
£308
Downtown
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
New York LaGuardia
Meals not included
3 nights + flight
£360
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
8.3 Very Good
Downtown
Pet-friendly
Air conditioning
New York LaGuardia
Meals not included
3 nights + flight
£310
Near North Side
Pool
Pet-friendly
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
£641
Sonder The Burnham - Chicago - Living room
Sonder The Burnham - Chicago - Living room
Sonder The Burnham
8.3 Very Good
Near West Side
Free Wi-Fi
Air conditioning
Miami
Meals not included
3 nights + flight
£350
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Baltimore/Washington
Meals not included
3 nights + flight
£482
Near North Side
Pet-friendly
Air conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
£512

Last minute holiday packages to Chicago

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Near North Side
Free Wi-Fi
Air conditioning
Seattle/Tacoma Intl
Meals not included
3 nights + flight
£826

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 £401; Family holiday £361; Romantic holiday £439; Luxury holiday £432; Budget holiday £293.

'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.

<p>'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.</p><h2>Chicago holidays: The Essentials</h2><p>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.</p><h2>Highlights and attractions of a stay in Chicago</h2><p>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.</p>

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)£401
Family holiday (Flight+Hotel)£361
Romantic holiday (Flight+Hotel)£439
Luxury holiday (Flight+Hotel)£432
Budget holiday (Flight+Hotel)£293
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