Venturing The Windy City

Jona Kay
Oct 11, 2024
2 min read

I grew up two hours south of Chicago, and somehow have only been three times for very short weekends to explore. The third was this past June where we REALLY packed in the sights. With a lot of research, and planning ahead with reservations, I can confirm that I've finally crafted a truly remarkable must-see itinerary.

We'll start with food because... duh. These beautiful gourmet donuts are brought to you by Stan's, with locations all around the Chicago area. We got a taste of it in the suburbs, but they're also located on Michigan Avenue. They've also got coffee ready to fuel your day.

Our lunch reservation was at Beatnik On The River. I had seen this place over and over on TikTok for months, and knew that we had to get in. Luckily, we scored a reservation and the perfect seat against the window. This place has a menu just as unique as its ambiance, but be prepared to pay a pretty penny because this place was probably the most expensive place that we went to. It's also a popular hangout for celebs. We walked past Addison Rae on the way out. You can arrange reservations online.

Dinner was at Ciccio Mio, a place on my bucket list for years... and it was so well worth it. I'm an absolute sl*t for Italian food in River North. Their mozzarella sticks and pasta were some of the best we had ever had; while the reservation was one of the hardest we've ever had to get. We refreshed the window on the exact day we were eligible to reserve, and took the last slot available only one minute in. This place is an absolute must... and don't forget to dress up. You can arrange reservations online.

Moving onto the sights...

The Bean

Navy Pier

Shopping on Michigan Avenue

The Skydeck's of Willis Tower & John Hancock

(John Hancock is preferable, but both prices were similar)

Swimming in Lake Michigan

An MLB game at Wrigley Field

...or even simply taking a walk on the river. There is truly SO much to do! Chicago is a very spread out city. It's difficult to walk to everything, even with a plan because of the distance. As always, the bus tour comes in handy to have so that you can have somebody drive you to everything, and get on and off as much as you want during operating hours. Don't try to do Chicago in 24-hours... even with a long weekend, you'll still miss some things. Do some research and prioritize your must-sees.