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North America Travel

Seven things to see in Chicago in Winter

The Bean Millennium Park Chicago

Chicago, in Illinois, is the largest city in the Midwest and was home to the first ever skyscraper. Chicago is a city with a lot of water – from Lake Michigan to the Chicago River that runs through the city. As such, you can see how amazing it must be in spring and summer when you can go to the beach, stroll along the river and have drinks or food outside. We visited Chicago in winter and we still loved it!

It’s an amazing city with friendly people, beautiful architecture and fabulous food. If you’re visiting in winter or the colder months, there’s still lots to see and do. Just wrap up warm!

Walk along the Magnificent Mile

We were staying at the Thompson Chicago, which is just around the corner from Chicago’s famous Magnificent Mile so that was the first thing we did when we arrived. It’s a street – North Michigan Avenue – filled with department stores, such as Neiman Marcus and Saks Fifth Avenue, as well as landmarks such as the the Drake Hotel, Wrigley Building, Water Tower Place, Tribune Tower, Chicago Water Works and Pumping Station (pictured) and the John Hancock Centre, which was the first world’s tallest building, built in 1970.

Chicago Water Works and Pumping Station

During the Christmas period, businesses decorate the sidewalks all along the Magnificent Mile. It makes it so festive!

Christmas decorations along the Magnificent Mile

Stroll along the Chicago River

We were lucky when we visited Chicago that it wasn’t freezing cold so we could spend a fair amount of time outdoors. We started our walk along the Chicago River from the Trump Hotel at the top of North Michigan Avenue all the way to West Randolph Street, towards the theatre district.

Look out for (although you can’t miss it) Marina City, which was built in 1959. It’s a ‘city within a city’, with offices, apartments, shops, a theatre and event yachts moored below. It’s certainly an architectural wonder.

Marina City Chicago

Whilst we were walking along the river, we spotted lots of people fishing. We stopped to talk to some to find out what fish they were catching and they were happy to have a chat. We found Chicagoans to be really friendly.


If we’re visiting a city with a Chinatown, we always have to visit it! Chicago’s Chinatown was surprising because it’s a bit out of the way – we had to get the metro there – and it’s also fairly small. It also seems to be split into two with one part being in an outdoor shopping complex and more modern and the other, which is across the road, being older and more historic.

If you are going to visit Chinatown, then I definitely recommend having a meal there too – especially if you’re going a bit out of your way. We went to Lao Sze Chuan for lunch and really enjoyed the food!

Navy Pier

Probably best enjoyed in summer, it’s still worth visiting Navy Pier in the colder months – in fact, it’s Chicago’s biggest tourist attraction. The view, for one, is stunning – on both sides of the pier.

City view of Chicago from Navy Pier

View from Navy Pier Chicago

In the summer months you can get a water taxi or even take a trip around Michigan Lake, which I’m sure must be wonderful. As it was winter, we just got the free Trolley (which runs all year round) which goes all the way to Millennium Park. The trolley reminded me of the trams in San Francisco!

Navy Pier trolley

Oak Street Beach

I bet you’re wondering why on earth I’d recommend visiting a beach in winter! Well, purely for the views of course. Oak Street Beach is part of Chicago’s Gold Coast, which is an upscale, historic neighbourhood that was built by railroad, lumber and retail tycoons back in the 1800s. On your way to the beach, go via North Astor Street to see some of the 300 designated historic landmarks – just in that street alone!

Oak Street Beach Chicago

Millennium Park

If you’re into art, don’t miss Millennium Park which boasts a number of public art pieces. There’s Cloud Gate by Anish Kapoor which is better known as ‘The Bean’, due to its shape. It’s fun to see yourself reflected as well as the city landscape.

The Bean in Millennium Park Chicago

For architecture lovers there’s Pritzker Pavilion, which was designed by architect Frank Gehry. It’s a concert venue and there are free concerts most nights from June to August.

Pritzker Pavilion in Chicago

Crown Fountain has two 50 foot towers that project the faces of Chicagoans and it’s pretty cool. In the summer the fountains spout water for people to cool off and kids to play in.

Crown Fountain Art Chicago

Millennium park also has an outdoor ice-rink from November to March and admission is free – you just need to rent skates, if you don’t have your own.

Millennium Park ice-rink Chicago

The Art Institute of Chicago

Just across from Millennium Park is the Art Institute of Chicago. Fans of Ferris Bueller’s Day Off might recognise it as it’s where Ferris and his girlfriend kiss in front of Marc Chagall’s America Windows.

America Windows by Marc Chagall

With around 260,000 works of art you really need to dedicate a day (or at least half a day) to visit. One of my highlights was seeing Grant Wood’s 1930 American Gothic. Amazing!

American Gothic by Grant Wood

If you’re an art lover, you’ll be in for a treat as Chicago has some of the best art museums – you’ll be spoilt for choice!

Chicago is a fantastic city and we loved exploring it – even in winter! Fun fact (which I only found out when we returned): Chicago is named the Windy City not because it’s windy but because of all the ‘hot air’ from politicians!

Seven things to see in Chicago

Kirsty Marrins

Reader, writer, occasional runner, travel lover.




  • Laura

    That’s some nice stuff to do in the winter time!

    Laura ||

    • Kirsty Marrins

      There certainly is Laura! I’d love to visit again in the warmer months though 🙂

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