Search
Best Deals
Tips
Vacation information
Holidays in Chicago

Holidays in Chicago

2 travellers
Exact dates

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

Here is why travellers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap Chicago package deals

Discover the best prices by selecting your travel dates on KAYAK.
Choose your dates

Most popular Chicago flight and hotel deals

Show all
Thompson Chicago
8.7 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Air conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
£335
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
£333
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
£225
Near North Side
Free Wi-Fi
Pet-friendly
Air conditioning
Denver Intl
Breakfast
3 nights + flight
£334
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
Philadelphia
Meals not included
3 nights + flight
£339
Near West Side
Free Wi-Fi
Pet-friendly
Air conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
£292
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
Philadelphia
Meals not included
3 nights + flight
£371
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
8.8 Very Good
Downtown
Pool
Pet-friendly
Air conditioning
Portland
Meals not included
3 nights + flight
£744
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
Baltimore/Washington
Meals not included
3 nights + flight
£362
Near North Side
Free Wi-Fi
Air conditioning
Philadelphia
Meals not included
3 nights + flight
£318
Downtown
Free Wi-Fi
Pet-friendly
Air conditioning
Dallas/Fort Worth
Breakfast
3 nights + flight
£350
Downtown
Free Wi-Fi
Pet-friendly
Air conditioning
Dallas/Fort Worth
Breakfast
3 nights + flight
£299
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
8.4 Very Good
Downtown
Pet-friendly
Air conditioning
Nashville Intl
Meals not included
3 nights + flight
£295
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Portland
Meals not included
3 nights + flight
£614
O'Hare
Airport shuttle
Free Wi-Fi
Pool
Air conditioning
Los Angeles
Meals not included
3 nights + flight
£288
Chicago Avenue Inn - Chicago - Dining room
Chicago Avenue Inn - Chicago - Dining room
Chicago Avenue Inn
7.1 Good
Humboldt Park
Parking
Free Wi-Fi
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
£213

Last minute holiday packages to Chicago

Show all
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
Minneapolis St Paul
Meals not included
3 nights + flight
£439
Near North Side
Free Wi-Fi
Pool
Air conditioning
Minneapolis St Paul
Meals not included
3 nights + flight
£312

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 £400; Family holiday £360; Romantic holiday £437; Luxury holiday £430; Budget holiday £292.

'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)£400
Family holiday (Flight+Hotel)£360
Romantic holiday (Flight+Hotel)£437
Luxury holiday (Flight+Hotel)£430
Budget holiday (Flight+Hotel)£292