Eating for 72 Hours in Chicago (in the winter)

For our first trip to Chicago, my list of ‘must-eat’ restaurants was a mile long. From cheeseburgers at Au Cheval to cocktails at Longman & Eagle, I had a hundred recommendations. How was I going to choose what to eat in only 72 hours in Chicago?

Trying to get reservations helped decide. The acclaimed Girl and the Goat? Booked solid. 3-Michelin star Alinea? Closed for renovations. I had to be okay with the fact I couldn’t eat everywhere. You just can’t Gabby, you just can’t. 

For us, food is such a huge part of travel it didn’t matter how cold it was in Chicago as long as we could eat. Avoiding the windy city in last February wasn’t an option, but winter travel is different; here are some tips.

How to spend 72 hours in Chicago in the winter.

Eat burgers in your bathrobe

We stayed at the Chicago Athletic Association(CAA), located on Michigan Avenue with great views of Millennium Park. The first night we arrived late and there happens to be a Shake Shack inside this hotel. Naturally, we ate burgers in bed.

72 Hours in Chicago Shake Shack

I won’t lie, we spent a lot of time in the hotel during our time in Chicago. In the summer, hotels are a place to sleep because you can spend the day exploring, but for winter travel, it’s important your hotel is somewhere you actually want to hang out.

CAA had been an athletic club (think big leather chairs and old men smoking cigars) since the 1890s until it was turned into a luxury hotel a couple years ago. It’s ridiculously cool. The hotel has several delicious restaurants and a nice lobby cafe (and a speakeasy, shh), so it didn’t feel like a waste of our trip to spend time there. In fact, we loved it.

Use hop on and hop off as transit

Typically, Adam and I don’t ever take hop-on-hop-off bus tours, but it was so freaking cold we used it as a method of informative transport.  It helped us knock off some “must sees” we only sorta cared about, and it was warm! How cold does it look in this photo? F-R-E-E-Z-I-N-G.

72 Hours in Chicago winter

Warm up with brunch at The Publican

The Publican is located in Fulton Market District where there are dozens of awesome restaurants to enjoy. This restaurant is devoted to fine pork and great beer and their brunch is just as dedicated to delicious porky fare . I devoured the fanciest steak and eggs ever featuring sirloin, grits and mojo de ajo, while Adam’s boudin noir was super tasty. Their mimosas are made with Belgian wheat beer and OJ, and their bacon is off the charts.

72 Hours in Chicago beers at The Publican

72 Hours in Chicago Brunch at the Publican

Be-an touristy and shopping

Did you know the bean in Millennium Park is actually a work of art entitled Cloud Gate inspired by liquid mercury? Me neither.

72 Hours in Chicago seeing the bean

We had no shame spending touristy time at the Bean with our new selfie stick. No. Shame.

72 Hours in Chicago selfie collage

72 Hours in Chicago millenium park

We also wandered along the Magnificent Mile to do a little shopping, but mostly to look at the architecture. The buildings in the downtown core made it worth it to be outside in frigid temperatures. From the first skyscrapers to the Neo-Classical revival, there’s a lot to look at, and you can take architecture tours of the city (on the list for next time).

72 Hours in Chicago architecture

Dinner at Boka

There are dozens of Michelin Starred restaurants in Chicago, so knocking that off the bucket list was a must. Boka was relaxed, but had an astoundingly good level of service without feeling stuffy. Along with a never ending breadbasket, Motown music and great cocktails, the food was really good. We ate chestnut ravioli, duck, and calamari just to name a few dishes. My desert of malted crème fraîche ice cream with pistachios looked as impressive as it tasted.

72 Hours in Chicago Dinner at Boka

72 Hours in Chicago Dessert at Boka

Breakfast in bed

The weekend we visited Chicago was Valentine’s day, so we treated ourselves ordered room service. Hello breakfast poutine with deep fried cheese curds.

72 Hours in Chicago Breakfast in Bed CAA

Exploring Wicker Park

This meant a stop at Stan’s Donuts, coffee at Buzz Coffee Roasters and browsing trendy local shops along Division Street. There might also have been some imaginary house-hunting — a favourite pastime of Adam and I when we visit a new city.

72 Hours in Chicago Stan's Donuts

Cocktails and boardgames at the CAA

It started to snow, like a lot, so we headed back to the hotel. The Game Room at the CAA has pool, bocce, shuffleboard and foosball, along with chess and checkers at every table. Plus there’s great cocktails and free popcorn; why wouldn’t we spend the afternoon here?

72 Hours in Chicago CAA

Visit the art gallery

On our last morning, we visited the Art Institute of Chicago. It has one of the best Impressionist collections I’ve ever seen.

72 Hours in Chicago Art Institute

72 Hours in Chicago Art Institute Gabby

There were about 100 more places I wanted to eat over the weekend; I could have spent another 72 hours in Chicago eating, but there’s always next time (maybe when it’s warmer).



1 thought on “Eating for 72 Hours in Chicago (in the winter)”

  • We have never been to Chicago, but would love to and now you’ve sparked our interest! Lots of good food, as I can see, even from the hotel, which is not always the case. We love to visit the art galleries as well, when visiting a new city, and the hop on hop off are a great suggestion. Thank you!

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