Holidays to Chicago

United States
Chicago's blend of office-laden skyscrapers and rail and steel industries lend it a cosmopolitan feel with blue-collar sensibility. Tourists are drawn to The Loop with its high-rise hotels and iconic attractions like the Willis (formerly Sears) Tower , the world-renowned Art Institute of Chicago , the Museum of Contemporary Photography …

Photos from other travellers

How to get to Chicago

Here's what you need to know about getting to Chicago. You can see the cheapest month to fly and a snapshot of flight prices for the following month. Also, don't forget to factor in your travelling time - the typical flight from London Heathrow to Chicago takes 7 hours, 25 minutes.

When to go to Chicago

Typical Holiday Price

£3188 per person

The average price of hotels and apartments in Chicago varies according to the time of year. To help you plan when to go, we've looked at the hotels available on our site, then worked out the average price per night for the quietest and the busiest months.

Cheapest Month to Visit


Based on a typical 1 week holiday - adding together the cost of flights and accommodation - September is the cheapest month to go to Chicago.

Where to stay in Chicago

Whatever your travelling style, we can help find you the perfect place to stay. From luxurious hotels to practical apartments, these are our most popular places in Chicago, according to other travellers.

Things to see and do in Chicago

Shaine C | Trip by SkyscannerMillennium Park
Millennium Park
Mark Zuckerman | Trip by SkyscannerArt Institute of Chicago
Art Institute of Chicago
Yvonne Brett | Trip by SkyscannerWillis Tower
Willis Tower
Ahboon Net | Trip by SkyscannerWrigley Field
Wrigley Field
Echo | Trip by SkyscannerFamily Pavilion At Navy Pier
Family Pavilion At Navy Pier
--Mike-- | FlickrCloud Gate
Cloud Gate
Vaida S | Trip by SkyscannerShedd Aquarium
Shedd Aquarium
rucha patwardhan | Trip by SkyscannerJohn Hancock Center
John Hancock Center
pelican | FlickrLincoln Park Zoo
Lincoln Park Zoo
Daniel Romano Moussali | Trip by SkyscannerThe Field Museum
The Field Museum

Reviews of Chicago

Violene D
Violene D

I had a really great time in Chicago! Would recommend visiting the Chicago Loop, lots of fun things to do there!

John Wright
John Wright

So much to do in my favourite city. Navy pier makes a lovely family day. The untouchables tour was so funny, very educational, see where the tin man got valentines and Dillinger sites. Night cruise was mind blowing. Totally unforgettable!

Ryan A
Ryan A

Chicago is my favorite city to visit. The food, culture, and music scene there is outstanding.

Ayo Oweke
Ayo Oweke

Chicago night life is awesome I really enjoyed the beach the high park area amazing

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