Holidays in Chicago

Holidays in Chicago

2 travellers
Exact dates
Fri 6/7
Mon 6/10

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Most popular Chicago flight and hotel deals

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Thompson Chicago
8.7 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Air conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
£360
Omni Chicago Hotel
8.6 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Air conditioning
Boston Logan Intl
Meals not included
3 nights + flight
£377
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
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
£286
Downtown
Free Wi-Fi
Air conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
£353
Downtown
Pool
Pet-friendly
Air conditioning
Boston Logan Intl
Meals not included
3 nights + flight
£364
Downtown
Free Wi-Fi
Air conditioning
New York LaGuardia
Meals not included
3 nights + flight
£373
Downtown
Free Wi-Fi
Air conditioning
Charleston
Meals not included
3 nights + flight
£349
Downtown
Free Wi-Fi
Air conditioning
Boston Logan Intl
Meals not included
3 nights + flight
£207
Downtown
Free Wi-Fi
Pet-friendly
Air conditioning
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
£365
Downtown
Free Wi-Fi
Pet-friendly
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
£270
Downtown
Free Wi-Fi
Pool
Air conditioning
New York LaGuardia
Meals not included
3 nights + flight
£373
Downtown
Free Wi-Fi
Air conditioning
New York LaGuardia
Meals not included
3 nights + flight
£387
Lake View
Free Wi-Fi
Air conditioning
Minneapolis St Paul
Meals not included
3 nights + flight
£338
Downtown
Pet-friendly
Air conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
£447
Downtown
Free Wi-Fi
Pet-friendly
Air conditioning
Minneapolis St Paul
Meals not included
3 nights + flight
£398
Downtown
Free Wi-Fi
Pet-friendly
Air conditioning
Minneapolis St Paul
Meals not included
3 nights + flight
£321

Last minute holiday packages to Chicago

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The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North
8.4 Very Good
Downtown
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
£586
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
8.1 Very Good
Downtown
Pet-friendly
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
£523

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 £420; Family holiday £378; Romantic holiday £459; Luxury holiday £452; Budget holiday £307.

'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 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)£420
Family holiday (Flight+Hotel)£378
Romantic holiday (Flight+Hotel)£459
Luxury holiday (Flight+Hotel)£452
Budget holiday (Flight+Hotel)£307