Adventures in Chicago

Get my guided GPSMyCity Chicago article here

I must admit, I didn’t take many pictures while in Chicago. I was deeply enjoying my time spent with two of my favorite people who had recently moved to the windy city, and I didn’t think to get out my camera very often. It was an awesome weekend. The weather was sunny and hot and we took advantage of visiting interesting bars, enjoying the waterfront, and even getting a glimpse of Chinatown.

While Minneapolis has plenty of lakes in the city, the way that Chicago is situated on Lake Michigan, a body of water so large that you could easily be convinced it is the ocean, makes the city all the more impressive.

Here are some of the highlights from my quick stop in chi town

Navy Pier

I loved Navy Pier! It was so nice to walk the length of the pier, get a different view of the cityscape, listen to the waves lap the concrete of the pier and admire boats chug in and out carrying tourists. It still felt like summer, so I was a happy camper. Navy Pier is also the place to go if you want to rent a boat in Chicago.


Gilt Bar

A swanky bar located in Chicago’s River North neighborhood, this place is a great stop for cocktails. There’s a hidden speakeasy in the basement near a photo booth, just be sure to get there early because it closes around midnight. They also serve food with an emphasis on small plates on the menu.



Drink an ice cold shot out of a shot glass literally made of ice, and then get to chuck the glass at a giant bell? Sign me up! This was a super fun stop on a hot night, as it is a very open-air design with a massive patio.


Cold Storage

Oysters, crab rolls, chowder… This place had awesome seafood! We went here for dinner and drinks to start off our big night in the city. The atmosphere was great, the wait staff was super fun and it was overall a great experience.



This bar was so cool. It has a gangster feel with classic as well as specialty cocktails, bumping awesome music with a friendly and fun bartender. The drinks aren’t cheap, but their strength makes them a good value.


The Bean

No trip to Chicago is complete without a stop at the Bean, which is apparently also called “Cloud Gate.” It was a hot and sunny day, so naturally, there were huge crowds flocking about the plaza and taking photos. The reflection of the concrete jungle in the mirror of the sculpture makes it the perfect photo spot. I’d recommend going early if you want shots with minimal strange tourists in your photos.


Buckingham Fountain

We passed by this landmark while making our way walking into the city. We walked a ton while I was in Chicago, which was great not only for getting exercise but for also taking advantage of the last really hot weekend of the year (last chance for bronzed arms!) This fountain sits in Grant Park and offers a captivating view of the city.


Howl at the Moon

The first time I ever heard about a “dueling piano” bar, I am pretty sure I internally (if not visibly) rolled my eyes and made a mental note that that was something I would not be interested in. After visiting this one, however, I take back all my negativity and beg the dueling piano Gods for forgiveness. THIS PLACE WAS SO MUCH FUN! The musicians were AWESOME – absolutely killing every single song request, the crowd was dancing away and the drinks were reasonably priced, I think. This would be the perfect spot in Chicago for a bachelorette party or post-wedding nightcap.


Drinks on the Waterfront

Ok, so I guess the majority of this post is reviewing different places to drink in Chicago (ahem, Katie & Sam, what does this say about our friendship???) but the truth is, for a quick weekend visit to a city that isn’t far from “home,” passing the time with friends, enjoying cocktails and food, takes priority over rushing to every single museum and tourist attraction. Patio season was still in session, making it the perfect pastime on my weekend here. We stopped for a glass of wine at City Winery at the Chicago River Walk, across the way from Smith & Wollensky’s, and sat right on the steps at the bank of the river. It was very entertaining to watch boats go in and out, the workers of the rental agencies doing acrobatics to jump from boat to boat maneuver them into their slips at the Marina.


Chicago was so much fun, aside from the personal enjoyment I get from traveling and exploring a new city, one of the biggest joys I got out of this trip was seeing two of my best friends thriving in a new place. They loved showing me around and I could tell that the move had been such a great thing for the two of them. New adventures will be had the next time I visit, which I look forward to!

Have you been to Chicago? What bars and restaurants were the favorites that you visited? Is a visit to the Sears/Willis tower worth it? Leave a comment with your recommendation below!

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