Beyond the bean: Chicago in 72 hours

Chicago in the summer just hits different. It’s buzzy, breezy, and packed with things to do—but never feels overwhelming. And while it’s tempting to take a million selfies with the Bean (I mean, who can resist?), don’t forget to explore a bit beyond it. With Sun Country flying to O’Hare up to four times a week (Sunday, Monday, Thursday, Friday), it’s super easy to squeeze in a long weekend. I went out on a Thursday and came back Sunday night—just enough time to get a full dose of the city without feeling rushed. 

I stayed right on the Chicago River, between Streeterville and River North, and I’d book that area again in a heartbeat. It’s super walkable—think quick strolls to Navy Pier, riverfront dining, and easy access to Oak Street Beach, where you can hang out by Lake Michigan or take a dip in the water. The area is perfect for soaking in the sun and people-watching or just taking a break from the busy city vibe. 

One of my favorite parts of the trip was spending time along the Riverwalk. It stretches a little over a mile and is packed with places to eat, drink, and just enjoy the view. You’ll see kayakers, architecture boat tours, and happy hour crowds all in one place. 

If you’re a shopper, you’ll want to hit the Magnificent Mile. It’s basically Chicago’s version of retail heaven, running about 13 blocks and filled with everything from Nordstrom and Bloomingdale’s to local boutiques and quick bites. Even if you’re just browsing, it’s worth the walk. 

Coffee lovers, this one’s a must: the Starbucks Reserve Roastery on Michigan Avenue. There are only six of these in the world, and Chicago’s version is five stories tall. The coffee is incredible, but what really sealed the deal was heading to the top floor for a cocktail. Yes, they do espresso martinis. Yes, it’s worth it. 

Chicago also has an incredible arts and culture scene. If you get the chance, definitely check out a show at the historic Chicago Theatre. The architecture, the history, the energy—it all feels special. You can also explore the Art Institute, catch live music in Millennium Park (yes, the Bean is located here), or check out the Museum of Contemporary Art if you’re in the mood for some creativity. 

And if you're visiting in the summer, don’t leave without going to a Cubs game at Wrigley Field. The stadium is a true piece of history, with ivy-covered walls and a vibe that feels like it hasn’t changed in decades. It’s a must-see even if you’re not a huge baseball fan. Pro tip: grab a Chicago Dog (it’s a true local treat) and take in the atmosphere. 

Chicago makes it easy to say yes to a last-minute weekend away. It’s just a short flight from MSP, so you can land with plenty of time to explore—no time wasted, just straight into the action. Great food, tons of things to do, and a city that actually feels good to walk in? Sign me up every summer.

Pack a pair of sneakers, your sense of adventure, and book your flight today. Get To Going. 

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