My favorite Things to do in Chicago

Posted on January 4, 2016 by in Things to Do (City Guides)

Things to do in Chicago – Understand

Chicago has thankfully avoided the fate of many American cities that seem to endlessly drift apart towards high-end and low-end neighborhoods. Batman’s Gotham City theme is Chicago but the real life Chicago is anything but Gotham City. Chicago Downtown and the surrounding areas are highly urban, clean, safe and surprisingly walkable. The city is flat and sidewalks aren’t crowded (unlike San Francisco or New York City). The Downtown attractions around Magnificent Mile, Riverwalk and Millennium Park are a true city highlight and neither run down nor overly touristy.

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Chicago feels much more European and the city has made great strides to rejuvenate itself.

Things to do in Chicago – Things to See

Millennium Park (Chicago Bean and Sculptures, Cloud Gate)

Millennium Park is the center of new downtown Chicago. It was famously delayed – Millennium Park was scheduled for the year 2000 but was actually opened only in 2004. The park did cost a stunning $475 million. But boy the city got one of the best green spaces in the world for it. Isn’t that better than just another officer tower?

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The park is compact but also big enough to have the crowds disperse a bit. It features several contemporary art works but it does not feel like a museum. The Chicago Bean is stunning because of its format and reflective glass.

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During my time the weather wasn’t great with constant rain and cloud cover but it was still a fantastic sight.

While this is touristy this is a must do for every Chicago visitor and local every once so often.

Chicago Cultural Center

Right next door is the Chicago Cultural Center – the former building of the Chicago library that now houses various changing exhibitions in a very well restored historic building. There is no admission and it is a great way to warm up after Millenium Park excursion.

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Chicago Riverwalk

This is a good as it gets for rejuvenating an older river front – go here at night and be stunned!

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Art Institute of Chicago

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This bastion of art has been named the worlds best museum by TripAdvisor in 2014! I had my grand share of old masters when I lived in Europe (for a time I tried to see them all in every city) so I skipped this opportunity. It’s located just across from the Millennium Park. Admission is $25.

Museum of Contemporary Art

A bit further north (the area is called River North) is the Museum of Contemporary Art – there isn’t that much to see (plan for 45-60 minutes) but it does not have big crowds and a number of exhibitions that will make you think (and others rightfully just wonder).

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Admission is $12 but there i an ongoing TravelZoo deal for $9.

Things to do in Chicago – Things to Eat and Drink

You may (or may not be) surprised but Chicago is much more than pizza and hot dog. The city (like many other big American cities) has adopted fresh, creative and tasty food from many origins. From what I found Mexican, Italian and ‘New American’ were the dominant cuisines.

Chicago has a few neighborhoods that you should make the destination of your trip. They are all a quick Uber ride away from Downtown.

Deep Dish Pizza, Pequod’s Pizzeria

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Before we start – of course you all want a deep dish pizza when in Chicago – there are a few places but the locals I asked swore by Pequod’s Pizzeria and I found the pizza and the whole little restaurant to be fantastic. It’s low key but focuses on quality with a friendly vibe without the crazy crowds that most places get (or every decent food place in San Francisco now).

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Things to Eat and Drink in Chicago – Downtown

Do-Rite Donuts & Stan’s Donuts

Right next to each other, close to the Hyatt Chicago, are these two temples of temptation. Both have fantastic donuts (not like SF’s Mr. Holmes). Do-Rite wins in the authentic and rustic department while Stan’s wins you over with nice seating out of the wind (i.e. indoors).

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This is actually a Chicago born chain of third-wave coffee that was set up in 1995> I love their places in New York City and Los Angeles. The coffee is fresh, has a very balanced flavor and the baristas have less attitude (coming from SF that is at least). Intelligentsia has moved into more ‘high traffic’ areas and the Downtown Intelligentsia is just footsteps from Millennium Park. There is no reason to go there now.


Dollop is another chain with great coffee – its less hipster-ish and the coffee is still excellent. There are a number of locations across the city.

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Xoco is a Mexican/ Fusion eatery downtown. The same owners also run a full service restaurant next door. Confusingly you can’t get Tacos but delicious sandwiches at Xoco.

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This Speakeasy bar has a huge underground space with live music on the weekends.


Celeste is a smaller, more classy bar in downtown with great music and a less loud sound setting than normal.

Three Dots and a Dash

This ‘underground’ bar does not want to be found – literally. The entrance is an unmarked entrance in a back alley where most of the delivery trucks park. Nonetheless it gets crowded on weekends for its fantastic cocktails.

Things to Eat and Drink in Chicago – Logan Square

Gaslight Coffee Roasters

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Gaslight Coffee Roasters occupies a small corner store around Logan Square. Few tables though so I guess they are not happy with too many laptop people. I could not try their coffee as I was already past my 4th shot that day.

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Longman & Eagle

If you are looking for draft beers on tap – this is the place to be. You won’t be disappointed.

Fat Rice

This Asian/ Fusion restaurant comes highly rated but I did not get an opportunity to try it.

Revolution Brewing

This cool neighborhood bar has a number of beers on tap as well.

Things to Eat and Drink in Chicago – Wicker Park


Another Intelligentsia – across from the Walgreen and a Bank of America – you guessed this location does not have the greatest atmosphere.

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Bangers & Lace

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This fantastic places has two dozen craft beers on tap and has friendly staff telling you all about it.

Coalfire Pizza

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Coalfire Pizza stays true to its name and makes incredibly looking (Italian style) pizzas.

Wormhole Coffee

This is certainly the most hipster/ alternative coffee shop in town. I waited 30 minutes for my Gibraltar on a not so busy day. Quality trumps quantity here.

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Things to Eat and Drink in Chicago – West Town/ Fulton Market

Au Cheval

Au Cheval makes Chicago’s best burgers – it’s a must do on your trip. I loved the atmosphere and the look of my food though my burger was just ok taste-wise. Expect long waits or consider dropping by the Little Au Cheval which has the same ingredients but more space and the same great taste.

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La Colombe Torrefaction

I really liked La Colombe Torrefaction in New York but the one at Fulton Market in Chicago lacks atmosphere and design. Also just a few people came by on a Saturday afternoon.

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Sawada Coffee

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Sawada is the front part of of an indoor Texas (read German) style beer garden. Get coffee first – move on to beer and briskets later.

If you have more time go explore Little Goat, Momotaro, Ramen Takeya and Sushi Dokku in the same neighborhood.

Things to Eat and Drink in Chicago – Lincoln Park

Chicago Pizza and Oven Grinder

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Long lines and another Chicago pizza favorites that are made in a cast. Come prepared for an hour wait here.

Happy Camper

This sports bar serves surprisingly good thick crust pizza (not deep dish).

Velvet Taco

Velvet Taco comes highly rated but it was closed over the holidays when I visited Chicago. I would totally try it on my next visit.

Things to do in Chicago – Views

Chicago offers a ton of options for views. They range from cool rooftop bars to rather touristy (and expensive) viewing platforms. When I visited visibility was so bad I did not actually venture up.


This one gets crowded and it’s expensive – so beware.

ROOF on theWit

This is a great looking roof-top bar – perfect for a summer sunset view.

The J. Parker

This rooftop bar is a bit outside the city which makes for great views of downtown.

North Avenue Beach

This is likely the best view for a sunset in summer – don’t even think about going here on a windy winter day – it’s too cold.

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360 Chicago

Yes it is at the 94th floor and you will pay for the pleasure!

Sears Tower

I haven’t been able to confirm that you can go up – but I believe so.

Enjoy your trip to Chicago!

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About the author: Torsten is a serial entrepreneur who started almost a dozen ventures on four continents. Torsten's love for travel has brought him to 130+ countries and travel with most of the world's airlines. You can reach Torsten at [email protected]

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