Just One More Day: 6 Things I Wish I’d Done in Chicago

Yesterday I shared all the fun my sister and I had during our three days in Chicago (part one, part two) … but there’s so much more we could have done! I hadn’t even left the city before I was already scheming about everything I would love to do next time I visit Chicago.

1. Take a Chicago Crime Tour

My interest in organized crime and the twisty politics in Chicago was first sparked when we binge watched Kelsey Grammer’s terrific-but-short-lived show Boss a few years ago. And of course Chicago has a rich and storied history of criminals, mobsters, and gangsters. Chicago Crime Tours merges crime and history to show you famous landmarks showcasing criminals from Al Capone to H. H. Holmes.


Chicago Crime Tours | Our Streamlined Life

2. Kayak on the Chicago River

I absolutely love the idea of urban kayaking, and paddling down the Chicago River through the heart of the city sounds like an awesome way to see the city! Wateriders offers everything from history tours to fireworks paddles — you can even combine crime and kayaking. Pretty sure it doesn’t get more fun than that.

Kayak on the Chicago River | Our Streamlined Life

3. Take a Chicago Architecture River Cruise

Another way to see the river and the city is with a Chicago Architecture Foundation River Cruise. We went back and forth between doing this and a Lake Michigan boat excursion; we ultimately opted for the lake cruise because it seemed a bit more kid-friendly, but next time I’d love to take in Chicago’s tremendous architecture from the river.

Chicago Architecture Foundation River Cruise | Our Streamlined Life

4. Visit a Distillery (or Two!)

We had an awesome experience at CH Distillery, and that just whetted my appetite for Chicago’s distillery scene. Koval has a dry gin I’d love to try, and a full calendar of special events; Rhine Hall specializes in fruit brandies and offers tours, tastings, and brandy cocktails. And both spaces look awesome, which is definitely a plus.

Rhine Hall | Our Streamlined Life

5. Enjoy a Chicago Brunch

Just about every article I read about Chicago practically screamed, “YOU MUST EAT BRUNCH WHILE YOU ARE THERE.” We didn’t end up brunching, but I’d love to check out a few mouthwatering places next time I’m in town. The Hampton Social offers a relaxed nautical ambiance and fresh coastal menu. Fig & Olive offers a — wait for it — fig & olive salad, which looks tremendous … and hello, blood orange mimosas. And Waffles Cafe has waffle flavors you never knew you needed to try. (Mexican Chocolate Waffle, please and thank you.)

Fig & Olive | Our Streamlined Life

6. Run or Ride the 606

I’m kind of obsessed with rail trails, and The 606 is the best kind: a combination elevated rail line and park. Running through the Logan Square, Humboldt Park, Bucktown, and Wicker Park neighborhoods, it reminds me of the High Line, one of my favorite features in New York City. Read more about The 606 here.

The 606 Humboldt Blvd Lookout | Our Streamlined Life

Have you been to Chicago? What’s on your must-do list?

For more ideas on things to do in Chicago, check out our Chicago Pinterest board.

Just One More Day: 6 Things I Wish I'd Done in Chicago | Our Streamlined Life

I'm the oldest of 12 crazy kids and two pretty awesome parents. My love of travel developed during my early years traveling the globe as an Air Force brat. I'm a runner, a writer, and a reader, and I love cooking up good food and cozying up our camper.

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