Holidays in Chicago

Holidays in Chicago

2 travellers
Exact dates
Sat 5/11
Tue 5/14

Search hundreds of travel sites at once for holiday package deals in Chicago

...and more

Let KAYAK do the searching

Save on your next holiday

Search and compare hundred of travel sites at once for holiday packages in Chicago, Illinois

We’re completely free to use - No hidden charges or fees

Filter by free cancellation, free breakfast and more

ATOL Protected: All packages are ATOL protected

Cheap Chicago package deals

Most popular Chicago flight and hotel deals

Show all
Thompson Chicago
8.6 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Air conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
£278
Downtown
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Minneapolis St Paul
Meals not included
3 nights + flight
£283
Downtown
Free Wi-Fi
Pet-friendly
Air conditioning
Denver Intl
Meals not included
3 nights + flight
£200
Downtown
Free Wi-Fi
Air conditioning
Denver Intl
Meals not included
3 nights + flight
£250
Downtown
Pool
Pet-friendly
Air conditioning
Denver Intl
Meals not included
3 nights + flight
£220
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
Denver Intl
Meals not included
3 nights + flight
£290
Downtown
Free Wi-Fi
Pet-friendly
Air conditioning
Denver Intl
Meals not included
3 nights + flight
£240
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
Denver Intl
Meals not included
3 nights + flight
£216
Downtown
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
New Orleans Louis Armstrong
Meals not included
3 nights + flight
£468
O'Hare
Airport shuttle
Free Wi-Fi
Pool
Air conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
£251
Downtown
Air conditioning
Denver Intl
Meals not included
3 nights + flight
£381
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown
9.1 Wonderful
Downtown
Free Wi-Fi
Air conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
£281
Downtown
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Dallas/Fort Worth
Breakfast
3 nights + flight
£277
Kinzie Hotel
8.4 Very Good
Downtown
Pet-friendly
Air conditioning
Denver Intl
Meals not included
3 nights + flight
£280
Downtown
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
£552
Downtown
Free Wi-Fi
Pet-friendly
Air conditioning
Minneapolis St Paul
Meals not included
3 nights + flight
£214

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 £427; Family holiday £384; Romantic holiday £467; Luxury holiday £460; Budget holiday £312.

'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)£427
Family holiday (Flight+Hotel)£384
Romantic holiday (Flight+Hotel)£467
Luxury holiday (Flight+Hotel)£460
Budget holiday (Flight+Hotel)£312