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.

Search
Best Deals
Tips
Vacation information

Cheap Chicago package deals

Most popular Chicago flight and hotel deals

Show all
The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
7.9 Good
Near North Side
Pool
Pet-friendly
Air conditioning
Fort Lauderdale
Meals not included
3 nights + flight
£324
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Fort Lauderdale
Meals not included
3 nights + flight
£427
Omni Chicago Hotel
8.9 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Air conditioning
Los Angeles
Meals not included
3 nights + flight
£416
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
San Francisco
Meals not included
3 nights + flight
£340
Near North Side
Air conditioning
Los Angeles
Meals not included
3 nights + flight
£426
Near West Side
Free Wi-Fi
Pet-friendly
Air conditioning
Fort Lauderdale
Meals not included
3 nights + flight
£344
Near North Side
Free Wi-Fi
Pet-friendly
Air conditioning
Fort Lauderdale
Meals not included
3 nights + flight
£359
Loop
Free Wi-Fi
Air conditioning
Fort Lauderdale
Meals not included
3 nights + flight
£385
Near North Side
Free Wi-Fi
Air conditioning
San Francisco
Meals not included
3 nights + flight
£322
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
Loop
Pet-friendly
Air conditioning
San Francisco
Meals not included
3 nights + flight
£342
Loop
Free Wi-Fi
Pet-friendly
Air conditioning
Fort Lauderdale
Breakfast
3 nights + flight
£343
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
San Francisco
Meals not included
3 nights + flight
£561
Near North Side
Free Wi-Fi
Pool
Air conditioning
Fort Lauderdale
Meals not included
3 nights + flight
£341
O'Hare
Airport shuttle
Free Wi-Fi
Pool
Air conditioning
Ontario
Meals not included
3 nights + flight
£294
Loop
Pet-friendly
Air conditioning
Los Angeles
Meals not included
3 nights + flight
£466
Loop
Free Wi-Fi
Air conditioning
Los Angeles
Meals not included
3 nights + flight
£422

All inclusive holiday packages to Chicago

Show all
The Wheeler Mansion
9.8 Wonderful
Near South Side
Free Wi-Fi
Air conditioning
Ontario
All-inclusive
3 nights + flight
£602

Last minute holiday packages to Chicago

Show all
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North
8.6 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
New York LaGuardia
Meals not included
3 nights + flight
£864
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.8 Very Good
Near West Side
Free Wi-Fi
Pet-friendly
Air conditioning
New York LaGuardia
Breakfast
3 nights + flight
£653

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 £79; Family holiday £191; Romantic holiday £277; Luxury holiday £166; Budget holiday £188.

'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)£79
Family holiday (Flight+Hotel)£191
Romantic holiday (Flight+Hotel)£277
Luxury holiday (Flight+Hotel)£166
Budget holiday (Flight+Hotel)£188