Weekend in Chicago: 8 Must-Visit Hot Spots

I’ve been to Chicago dozens of times, mainly for a day at a time for work-related reasons, but decided it was high time I visit purely as a tourist, and a three-day weekend was the perfect time to make it happen! Here are 8 great spots I was able to visit during this latest trip:

Millenium Park

I feel like Millenium Park is the place everyone goes, even if they only have time for this to be the only place they visit, yet I hadn’t made it there until this week! Go figure. I took a picture in front of the Bean, which I found out is named “Cloud Gate” when I tried to check-in on Yelp. After seeing sooo many people take pictures in front of this thing, it was finally my turn!

And, with a perfect backdrop of light snowfall, a visit to the ice skating rink at the park was a must. I hadn’t been ice skating since I was a kid and I was terrible at it then. Turns out I’m still terrible at it now!

Meli Cafe

I had never heard of this place before this last visit, but am now a fan after having brunch here! Love the modern cafe decor, and the portion sizes of the food are generous. As a girl that loves her brunch and is always on the lookout for grits at any brunch spot, I was happy to find cheddar grits on the menu for the weekend, though it’s not a regular occurrence here. And the banana french toast was to die for!

I didn’t partake in any of the juice blends or smoothies on the menu but made a mental note to come back and try one next time.

The Chicago Theatre

On a previous trip, I was in the area of the theater during the day and have been wanting to come back to see it at night since then, and I was happy to get a chance to snap a pic at night this time!  It’s a super-touristy thing to do and I loved every minute of it!

Howl at the Moon

We’ve got this same dueling piano bar in Indy, but it has been a long time since I’ve been to the Indy location, so it was fun to pop in here in Chicago. I wouldn’t say the piano players were the best, but it was a fun spot to hang for a while.

ROOF on theWit


This place is swanky! It’s definitely on the pricey side for ordering a full meal, but a fantastic place to stop for a drink & app and enjoy a gorgeous view of the downtown Chicago skyline. It would also be a gorgeous place to host a private event, though I can’t imagine how expensive that would be here.

B.L.U.E.S on Halstead

If you’re from Indy and have been to the Chatterbox, B.L.U.E.S. has a similar vibe — intimate, well-worn and divey, but in a good way. The music here was great and the service was fantastic. And, even though they don’t serve food, they do allow you to bring in food from outside. This place has a limited drink menu, but that’s expected given the overall vibe.

Bub City

Bub City’s a Nashville bar in Chicago’s River North area that has good live country music, delish drinks (get the Back Porch Tea — you’ll thank me later), a fun atmosphere, and a brisket mac & cheese that I kept thinking about for a long time afterward. Based on the looks of food I saw other people order here, you can’t go wrong with anything on the menu.

Kingston Mines

This was hands-down my favorite spot of this trip! I’m always focused so much on food when I visit Chicago, I’d never really looked into the music scene, and I regret not finding out about this place sooner. Phenomenal live music at Kingston Mines and they had bands alternating on each of the two stages, so you were able to hear different groups throughout the night. I didn’t try the food here, but the drinks were good.

Though I was able to check out a lot of hot spots during this trip, there are still plenty of items on my Chicago bucket list for upcoming trips! I’m hoping to catch a Cubs game, visit the Skydeck and take an architectural river tour when it gets warmer, along with finding more fun places to eat of course! What’s your favorite thing to do, eat or see in Chicago? Leave a comment!

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