11 things to do in Chicago

Tamara Hinson

Tamara Hinson

Chicago is one of America's most popular cities, and with its brilliant shopping, gorgeous architecture and fantastic food scene, it's easy to see why. Here are 11 things to do in the Windy City.

Things to do in Chicago, USA
Things to do in Chicago, USA © City of Chicago

Getting to Chicago: book your flights to America's third-largest city with Virgin Atlantic and you'll fly to one of the major hubs, such as New York, Boston or Atlanta, and transfer to a connecting flight with its partner Delta Air Lines. Check out the latest Virgin Atlantic sale* for great value fares to Chicago.

Pay homage to pizza

For Chicagoans, pizza is pretty much regarded as one of their five-a-day. The Chicago-style deep-dish was invented here in 1943 (the restaurant responsible, Pizza Uno, celebrated its 75th anniversary in 2018), and there's even a museum dedicated to the doughy delight.

The US Pizza Museum is one of Chicago's top attractions - head here to learn about the city's pizza-related history and to admire the collection of weird and wonderful exhibits, ranging from rare, pizza-faced Garbage Pail Kids cards and crocheted pizzas, to a DVD featuring images of pizza and "the soothing sound of sizzling".

Watch a ball game

Chicagoans might well love pizza, but sport - baseball in particular - comes a close second. And you don't have to be a sports fan to appreciate the atmosphere when the Chicago Cubs play a home game.

Take in a ball game at the home of the Chicago Cubs
Take in a ball game at the home of the Chicago Cubs © City of Chicago

To give you an idea of locals' passion for the team, consider this: when the Cubs won the World Series in 2016 (their first World Series victory since 1908), five million people attended the homecoming parade, making it one of the world's largest gatherings in history.

Bagged a ticket for a game at their home stadium, Wrigley Field? Don't forget to order a hot dog from the Hot Doug food stand, where sauces are named after players. And nab a seat in the upper deck if possible - it's the section with the best views.

Explore Obama's 'hood

It's a myth that Chicago's South Side - where Obama still owns a property - is a no-go zone. Avoid it and you'll miss out on some of Chicago's top attractions. Take Hyde Park, where architectural gems include Frank Lloyd Wright's Robie House - now open to the public once more, following a major restoration - and the wonderfully gothic University of Chicago.

Hyde Park also has some of Chicago's best museums: the Museum of Science and Industry offers something for kids of all ages, while the DuSable Museum of African American History is regarded as one of the top cultural institutions in America.

Beverly is another affluent South Side neighbourhood with plenty of architectural eye candy including the Given's House - a turreted castle built in 1886 - and dozens of Frank Lloyd Wright-designed homes.

Pound the pavements

Chicago may be huge but it's easy to get between its main attractions on foot, and by doing so you'll gain a whole new insight into the Windy City. If your navigational skills are lacking, consider signing up for a walking tour - Free Tours By Foot are (surprisingly) free to join, and there's a wide range of tours on offer.

Visit the Cloud Gate sculpture in Millennium Park, Chicago
Visit the Cloud Gate sculpture in Millennium Park, Chicago © City of Chicago

A great starting place for a self-guided walk is the Navy Pier - just look for the enormous Ferris wheel. From there, head towards the Magnificent Mile, before heading south towards Millennium Park, where you'll find Anish Kapoor's famous coffee bean-shaped Cloud Gate sculpture.

Get an art fix

Chicago's jam-packed with brilliant galleries and museums, whether it's the Art Institute of Chicago, which has the largest collection of impressionist and post-impressionist art outside the Louvre, the Hyde Park Art Center, set up to make contemporary art more accessible, or the Museum of Contemporary Art, one of the world's largest modern art venues.

If you're visiting the latter, aim for Tuesdays, when there's no admission fee. There are some fantastic independent galleries too, such as Monique Meloche Gallery, named after its founder. Meloche has stints at the Museum of Contemporary Art under her belt, and her gallery is known for its striking installation art.

Looking for a city break? You could save by booking your Chicago flights and hotel together with Virgin Holidays*.

Watch a comedy show

The Second City in Chicago's beautiful Old Town is a comedy club with some seriously impressive alumni - Tina Fey, Bill Murray, Steve Carrell, Mike Myers and John Candy all cut their teeth here.

Tickets are cheap (you'll pay around £10 for some shows) and a bar service allows you to get drinks delivered to your seat. Steer clear of the popular improv shows if you're a shy and retiring type - you might just find yourself being interrogated by one of the performers.

Shop 'til you drop

The Magnificent Mile is exactly that - a mile-long, 13-block avenue jam-packed with over 460 stores, 275 restaurants and 60 hotels. It's undoubtedly the best spot for shopping in Chicago.

An insider tip? Consider kicking off your shopping spree at Water Tower Place, The Shops at North Bridge or 900 North Michigan Shops - three of the Magnificent Mile's biggest shopping centres.

Start of the Magnificent Mile at DuSable Bridge, Chicago
Start of the Magnificent Mile at DuSable Bridge, Chicago © City of Chicago

Why? All three will deliver your shopping to your hotel on the same day, freeing up your arms for more of the same. Another tip: if you're hitting the shops in Water Tower Place on a Friday afternoon, break up your spree with a guided tour of this historic Chicago landmark.

Get a caffeine fix

Chicago has some of America's best coffee shops. Not convinced? Head to the funky Wicker Park neighbourhood for coffee at the Wormhole Café, where the menu resembles the score screen of a retro video game, and where décor includes a DeLorean - the car from Back to the Future.

Or to Bucktown's Ipsento 606 - a warehouse-esque coffee shop which transforms into a cocktail bar after sunset. If you're exploring Hyde Park, squeeze in a visit to Plein Air Café, where you can chase rare blends with French tartines and pastries.

Take a spin on Navy Pier's Ferris wheel

Chicago's Ferris wheel is a 59-metre tall icon with 42 air-conditioned gondolas. It's a world apart from the world's first Ferris wheel, which was designed by George Washington Gale Ferris Jr and erected in Chicago in 1893 for the World's Columbian Exposition.

Take a spin on Navy Pier's ferris wheel
Take a spin on Navy Pier's ferris wheel © Ranvestel Photographic - photo courtesy of Choose Chicago

More than 1.4 million people paid the 50-cent fee to ride it, but financial problems led to it being blown apart by dynamite and sold as scrap metal in 1906. That's one way to take the "out with the old, in with the new" mantra to extremes...

Admire the architecture

We've already touched on Chicago's fantastic architecture, but there's so much more to the city than Frank Lloyd Wright's (admittedly beautiful) creations and the gothic grandeur of the University of Chicago's Hyde Park Campus.

Some of Chicago's most stunning works are in the heart of the city. If you're splashing the cash on the Magnificent Mile, keep an eye out for the Water Tower - a castle-like building in the shadow of the city's tallest skyscrapers. This gothic revival masterpiece was built to house a standpipe system which allows water to be pumped from Lake Michigan.

Other gems to look out for include Washington Street's Chicago Cultural Centre, with its lobby mosaics of gold and mother of pearl, and the Tribune Tower, which incorporates fragments of Beijing's Winter Palace, Westminster Abbey and Athens' Parthenon.

Take a wander around Wicker Park

An achingly-hip (but not pretentiously so) neighbourhood close to the city centre, Wicker Park is known for its coffee shops, vintage boutiques, innovative restaurants and ice cream parlours.

Start with a preservative-free sugar fix at Jeni's Splendid Ice Creams - go for the pistachio and honey. After some shopping (our favourites include Moon Voyage for jewellery and Goorin Bros for funky hats), toast Chicago at one Wicker Park's cocktail bars.

The Violet Hour is a beautiful, prohibition-style night spot - start with the Sins of the Father, made with Wild Turkey bourbon, Hellfire bitters and tobacco. Cheers!

Weather in Chicago

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The weather in Chicago is typically seasonal with long, warm days with plenty of sunshine in summer and cold, short and dark days in winter. Don't forget to check out when we think is the very best time to go to enjoy all of the above attractions and activities.

Ready to book your flights to Chicago? Don't miss the latest offers from Virgin Atlantic to help you save on fares and get you to the largest city in Illinois in no time at all.

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Tamara Hinson

Tamara Hinson

Tamara Hinson is a freelance travel writer who loves getting off the beaten path. Specialising in adventure travel, she often covers outdoor activities such as snowboarding, mountain biking and scuba diving. Tamara's work features regularly in newspapers such as The Telegraph and The Independent along with numerous travel websites.

Posted on Thursday 19th December 2019 in: City Culture North America Summer

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