Chicago Holidays 2025

Why go to Chicago

Holidays in Chicago offer an authentic taste of American pie. Sitting on the banks of vast Lake Michigan in the state of Illinois, cosmopolitan Chicago is one of the largest and most popular cities in the US.

If you are looking for holidays to Chicago, use the price-comparison service on TravelSupermarket to find your ideal break...

The so-called Windy City is a sultry mix of history, intrigue and tales of Prohibition-era gangsters, combined with a modern and eclectic city buzz where excellent nightlife and a lively outdoors scene can be enjoyed.

Chicago holidays begin the moment you step off the plane at Chicago O'Hare International Airport (ORD). This busy airport gives you a flavour for the highs you're going to experience in the city.

Home of the deep-dish pizza, an array of beaches, soaring skyscrapers, swathes of parkland and baseball at Wrigley Field, Chicago is a tasty city break destination. Holidays here are also easily combined with road trips to explore more of America's midwest. You could even get your kicks on Route 66 as the famous road begins here and winds its way through the United States of America until it reaches Los Angeles.

Many of Chicago's hotels, restaurants and shops can be found along a stretch of Michigan Avenue known as the Magnificent Mile, and you might opt to pick one of the excellent accommodation options here. You'd certainly be at the heart of the action.

Alternatively, you could select a room overlooking one of Chicago's many green spaces, such as Grant Park, which features museums and galleries and was where President Obama delivered his victory speech in 2008. Grant Park is also home to Millennium Park, which is like a huge rooftop garden sitting atop a parking garage and a railway station.

Tackle the heights of one of Chicago's skyscrapers, such as the Willis Tower, formerly known as the Sears Tower, or the John Hancock Center, where a 95th-floor restaurant offers splendid views to diners. From these heights you can see the city stretch away below you and check out what's left to discover, such as: the attractions of the Loop – the city's historic commercial centre; the Chicago River Esplanade, the sculpture-dotted walk on the north bank of the Chicago River; and Soldier Field, home to NFL's Chicago Bears.

Add all of this to lots of museums and galleries, a thriving dining scene, theatres, clubs and bars, and you'll soon realise that you're never going to get bored in Chicago. And you haven't even tackled sailing or water sports on the grand Lake Michigan yet. Phew!

Start planning your break in Chicago today. You can find and compare prices of holidays by using TravelSupermarket's search tool. Book yours today.

When to go to Chicago

Summer is popular, though the sights of Chicago are a delight no matter what the weather...

Summer is hot and humid in Chicago; expect highs of up to 35C and some storms. Spring and autumn experience temperatures averaging 18C, while winter can be very cold and snowy.

Chicago is not called the Windy City for nothing. Gusts are channelled between the tall buildings and can rush through the streets at 10 miles per hour – though the nickname might have come from an age-old neighbourhood dispute, as Chicago is by no means America’s windiest city.

It’s easy to find cheap holidays to Chicago. By using the search tool on TravelSupermarket you can compare the best deals. Booking early is advisable to clinch low prices.

What to do in Chicago

The fun-loving folk of Chicago lay on plenty of annual events throughout the year...

St Patrick's Day Parade; March: Chicago is another American city with a proud Irish heritage and a thriving community. The Chicago River is dyed green to celebrate Ireland's patron saint, while the parade is a riot of green revelry.

Baseball season starts; April: The Chicago Cubs swing into action in spring and this sporting city is abuzz with baseball news and views. Book tickets early if you want to share the thrill of the ball game with the locals.

Chicago Blues Festival; June: This huge free event celebrates all that is great about the blues. It might not be the birthplace of the blues, but Chicago considers itself to be the blues capital of the world. Just try and stop your feet tapping.

Taste of Chicago; July: You can eat what you want in Chicago as eateries cater for a global palate. This is celebrated at this outdoor food fest in Grant Park. Tuck in while you watch big stars perform.

Chicago Jazz Festival; September: See all that jazz in Chicago at the annual jazz festival in autumn. Stars of the jazz world perform here every year and thousands enjoy the many and varied performances.

There’s never a dull moment in the Windy City – whatever you’re into, you’ll always find something to do...

Kids and teens: The Peggy Notebaert Nature Museum offers a fascinating insight into the insect world and it’s right in the heart of the city.

Shopping: The John Hancock Center has a sterling reputation as a superb shopping destination. As well as row upon row of shops, you’ll also find dozens of restaurants and the famous John Hancock observatory.

Nightlife: There are some weird and wonderful bars and cafes in downtown Chicago, including some of the first karaoke bars in America. The Windy City really is the ideal place to let your hair down.