Six unique things to do in Chicago for first-timers

By Luke Chilton

You could never get bored in Chicago. The city is big and brash, but thanks to a rich history of mobsters, hip-hop and pizza, it has a unique personality of its own. Don’t be fooled into thinking this is just like any other big U.S. city, there are so many unique things to do in Chicago. Locals here like their fun, food and fresh air, and that’s a pretty good combo in our book.

I was walking across downtown Chicago in the middle of June and one such eccentric local told me why Chicago is called The Windy City. Apparently it’s thanks to its history of waffling politicians giving long-winded speeches. As a gust of wind almost blew me off a bridge shortly afterwards, I couldn’t help but have my doubts about that story. Yes Chicago is windy, whatever the season (I didn’t meet any politicians, so I can’t vouch for that) but it’s also very cool – and now I mean trendy. You’ve probably already planned to visit The Bean (etc) but these six unique things to do in Chicago for first-timers will make navigating the city a breeze…

Our pick of six unique things to do in Chicago:

Often looked over in favour of the USA’s big hitters like New York or Los Angeles, Chicago deserves a better reputation as a tourist destination. Basically you’re going to love it. It’s a massive, bustling metropolis that looks straight out of the movies (it doubled for Gotham City in the Dark Knight films). Along with all the nightlife, restaurants and museums that come with being America’s third biggest city, there are also other, brilliant and more quirky things to do in Chicago during your stay.

Go Downtown by kayak

With the rackety, elevated ‘L’ train snaking it’s way round the feet of Chicago’s many skyscrapers, Downtown never feels quiet. Look up as you walk around and you’ll see some best modern architecture in the world. But the better, cooler, way to see it is from on the Chicago River which runs through the city.

I hired a kayak from Urban Kayaks, but if you’re too lazy to paddle, there’s always the Wendella Original Architecture boat tour, complete with an expert guide who’ll talk you through 130 years of construction innovation. One of the best is the neo-gothic Chicago Tribune Tower, home to the famous newspaper that broke the Watergate scandal. More like a medieval cathedral than an office, its sadly dwarfed by the humongous Trump Hotel next door that leers over the city – a bit like the, now, President himself…

Bang in the middle of Downtown is Millennium Park, home to the famous ‘bean’ – if you don’t already know, it’s a giant baked bean-shaped sculpture that’s so shiny you can see your reflection in it. Essentially it’s an Instagram must-do and if you don’t get your picture, have you really been to Chicago at all? More interestingly, you can also see open air concerts here, hire roller skates or have a go on the rock climbing walls in the centre of the park.

LOOKING FOR MORE COOL U.S. CITIES TO GET INSPIRED? THIS IS ONE OF OUR FAVOURITES.

Head to Lakeview: the ‘Brooklyn’ of Chicago

Just north of Downtown, Lakeview is an affluent area of Chicago filled with coffee shops and independent restaurants, shops and theatres. If it’s a sunny day, it’s one of the nicest areas to take a pleasant stroll around the tree-lined residential blocks. I enjoyed popping into the family run Café Tola on Southport Avenue to try their famous empanadas. It’s a cool little ‘shutter bar’ style café that’s pretty cramped inside, but once you’ve bought your bespoke lemonade and fried snacks, you can hang outside and look at the street art spray-painted all over the outside of the building. The Southport Corridor Chicago Blog has so much good info on what to do and where to go in Lakeview. Find out more at southportcorridorchicago.blogspot.com

While in Lakeview you can also catch classic movies at the beautiful Music Box Theatre, built in 1929. Lovingly preserved, as well as showcasing the flicks, it has been used in dozens of real Hollywood films itself. They also show hours of Looney Tune cartoons in the mornings, so you can go in for a few dollars and watch a couple if you don’t have time for a whole movie but do want to experience the theatre.

If by now you’re getting a thirst on and looking for a cool place to get a drink in Chicago head to ‘Malt Row’ in the Ravenswood Corridor and pop into Dovetail Brewery and Motor Row Brewing. Home to famous mobsters like Al Capone, Chicago was once full of ‘speakeasies’ serving forbidden cocktails during Prohibition in the Twenties and Thirties. Now, the city is at the centre of the craft beer movement. Many bars have their own breweries on site, and can serve you up unique ales you won’t taste anywhere else. Ask for a taste first, as some of them (like the sour beer) are an acquired taste, plus you can get lots of free booze. Ooh, while we are on that topic, Prohibition may be long gone but Chicago is still very pernickety about underage drinking so even if you have a grey beard as long as Dumbledore, drag your ID around with you everywhere.

Explore Lake Michigan

Most tourists in Chicago head straight there, but NEWSFLASH, there are other places to see Lake Michigan from Chicago that are not Navy Pier. (Although I have a soft spot for the Winter Wonderland Christmas Tree exhibition held here every year in December, shh). If you have a car, go for a cruise on Lake Shore Drive, heading north. With the lake on one side and the city on the other, you get a real look at what a beautiful city Chicago is, whatever the season.

The lakefront path in Chicago is 18-miles long – don’t forget to pack your FitBit! Any part of the route is worth a visit for a little wander, or if you have the whole day, rent a bike and go for a spin with the wind in your hair. We headed to Bobby’s Bike Hike, a fab bike rental Chicago lakefront trail start location. Along the lakefront you will find beaches, parks and lovely spots for a picnic or a cheeky swim (in summer). If you’re visiting Chicago in winter, beware that this place gets cold! The lake has been known to freeze over in parts and you may even see snow on the pier and beaches. Quite a change from summer where people freely jump into the lake from rocks or the jetty, or spend the day fishing on the shore.

Go to Amy Poehler’s comedy club

Okay, it’s not technically Amy’s club… but Chicago is home to one of the world’s best comedy clubs, ‘The Second City’, where Amy, Tina Fey and Bill Murray all got their big break. For 55 years, comedy students from around the country have studied their craft here, and there are shows most nights of the week. One of the most popular is the late-night Improv hour, where you might see the next Steve Carrell, (but watch out, sit near the front and you could end up becoming the star of the show yourself!). With table service cocktails and food, it feels uniquely American, and nothing like your average Comedy Store in Leicester Square…

On the subject of belly laughs, if you are a fan of Amy, Tina and the SNL gang, the Museum of Broadcast Communications has a Saturday Night Live Experience. Sit on the famous couch, tour sets, props and costumes from the groundbreaking show and see how an episode is put together. The attraction has been incredibly popular but the SNL exhibition is due to close on December 31st 2018 so get in there quick. Another interesting place to go when it rains in Chicago (the weather can be changeable) is the very unique Video Game Art Gallery. It’s pretty interesting but you probably do already need to be a video game fan to fully embrace it.

It’s all about the Base-ball

No trip to Chicago is complete without a visit to either of their beloved baseball clubs, the Cubs or the White Sox. Coming from the UK, you might not understand what on earth is going on, but the actual sport almost comes second to crowd banter, scoffing hot dogs and soaking up the atmosphere. Almost every bar and shop in Chicago will be emblazoned with one of the club’s logos in their window, as well as having a massive TV showing the game, so you might pick up a few pointers along the way. If in doubt, just stand up and cheer when everyone else does. Buy the souvenir cap and you’ll fit right in.

Where to find the best deep dish pizza in Chicago

Chicago isn’t just famous for wind and baseball – it’s also the birthplace of Deep Dish Pizza. In case you don’t know, this seems to be a cross between a pie and a pizza and nothing like your average Dominos takeaway. Don’t go crazy with the ordering, often one slice is enough. Even though it is literally a shortcrust-style pastry filled with tomato sauce and melted cheese, there is some strong competition around who serves the best pie. Locals argue over where to get the best deep dish pizza in chicago, but most agree it’s between Lou Malanti’s, who’ve been serving up slices since the 1940s, and Pequod’s, known for their caramelized “halo” of crispy cheese. I mean, who are we to decide – best you try them both.

Still hungry, another place we loved was the cute retro hot dog joint Superdawg, which I think we all agree is the most American name ever. Superdawg opened in 1948 and not much has changed – the whole place is like a scene from Grease. I’m not really sure what constitutes a ‘Chicago’ hot dog as such, but I can confirm they are delicious.

Finally, go for desert (or breakfast and coffee, lunch, afternoon snack, pre-dinner palate cleanser…) at Do Rite Doughnuts, another Chicago institution and this time with sprinkles on.

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Where we stayed: pick from a range of cool hotels in Chicago

I stayed at Hotel Zachery, which is one of the newest and swankiest hotels in Chicago. It’s situated right across the road from the legendary Wrigley Baseball Stadium – home of the Chicago Cubs. The hotel’s premium suites have huge windows overlooking the historic grounds, (you can’t QUITE see over the stadium walls to glimpse the game, sadly). If your budget doesn’t stretch to a stay here, the bar has a balcony where you can watch the crowds gather on game day which is perfect for people watching. The hotel is also minutes from Lake Michigan. Rooms start from £180 for a double room.

Luke visited Chicago as a guest of choosechicago.com and flew with Norwegian Air on their direct service from London Gatwick. This is not a sponsored post, nor were we paid to run this post on the most unique places to do in Chicago for first timers.

Cover image: Quinn Dombrowski