48 Hours in Chicago

June 16, 2015

in Chicago, family vacation

You can download this guide over at GPSMyCity for the next time you visit Chicago!

I love short trips. They give you just enough time to get a taste of a place by forcing you to highlight what you really want to do and see in your short window of time. Short jaunts are perfect for taking advantage of long weekends so you can bank holiday and vacation time for longer, more far-flung trips.

My Memorial Day Weekends stateside have typically involved the Jersey Shore, and I thought that would be on the docket again this year. But with Brendan due in Chicago for work the Tuesday after the holiday, we decided to do something different. Landing on Friday night and leaving Monday morning gave me and Finn two full days to explore with Brendan. Here’s what we did and what you can do, too, if you only have a weekend to explore Chicago.

Day 1 


We stayed near the Convention Center so decided to eat in the South Loop at Yolk. Yolk looks like a large cafeteria full of families, but don’t bypass it for its lack of small, breakfast-nook charm. The plates are huge and the food is solid. Consider one of the specialty eggs Benedict options like the pot roast or caprese, the chicken and (bacon!) waffles with sausage gravy and maple syrup or the West Coast crepes, stuffed with avocado, mushrooms and cheese. The service is fast, so if you don’t feel like lingering, it’s a great place to dine on quality food and dash.

Plate of chicken and waffles from Yolk

Yolk is right across the street from the parkland that leads to Soldier Field, the Field Museum and Shedd Aquarium through to Lake Michigan. It was a perfect launching point for the day’s journey. We traveled through the park and decided to focus on the lake on a beautiful, mild Midwestern day, but you have your pick of things to do in the area whether or not the weather is clement. Our waterfront walk led us to Millennium Park, home of The Bean in addition to a sprawling playground through which we took Finn. There are plenty of grassy places to take a load off in addition to cafes and restaurants.

Lake Michigan in Chicago

View of The Bean from the park


After stopping to see a bit of a Memorial Day parade, we headed to River West to meet up with our friends Hannah and Michael who we knew in Sydney. We ate lunch at the French Market. You can get sandwiches, smoothies, more crepes and sweets. After a fresh-made sandwich and beer, we grabbed sweets from Lolli and Pops, a self-proclaimed “truffle bar” with options like red velvet, Bailey’s and coconut.

Gourmet truffles in Chicago


Wicker Park is a much sought-after neighborhood full of restaurants and bars, and we decided to scope it out for dinner. We found a Greek place called Taxim on Milwaukee Avenue with open outdoor seating that was recommended by a passerby. We ate small plates of food like haloumi (oh, how I missed you from Sydney), octopus and hummus and drank into the night while Finn took in the people and cars going past.

Fried haloumi on a plate

Beat salad

Day 2


Sunday morning, we bypassed the sit-down breakfast in favor of standing in line at the Doughnut Vault for fresh-made baked goods. The tiny shop makes doughnuts until they run out, hence the line. They usually serve a traditional doughnut and a special–we tried one of each. Bellies full of sweets, we walked to the John Hancock building to have a drink in the Signature Room overlooking the city. Pro tip: The best view from the John Hancock is from the women’s bathroom.

Doughnut Vault in Chicago

Chicago skyline from the John Hancock


We got sandwiches and salads on the go to make it to our 2:15 architectural boat tour. The engaging tour guide took us up and down the Chicago River pointing out some of the city’s famed constructions. My favorite was the Carbide & Carbon Building, an Art Deco done by the Burnham Brothers ,who designed the top to resemble a dark green champagne bottle with gold foil.

baby giving mom a kiss

Chicago skyline from architecture cruise

After the tour, we walked along Navy Pier and then quickly darted into the main building and jumped in a cab when it started downpouring. We headed back to our friends’ apartment, and my girlfriend and I got a massage while the boys stopped at a Mexican restaurant for chips and beers. We decided to order in deep dish from Lou Malnati’s to indulge in a quintessential Chicago culinary experience.

So there you have it–48 hours in Chicago. It was a pretty jam-packed weekend, but definitely a well-rounded, whirlwind tour of the windy city.

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