Get my guided GPSMyCity Chicago article here
I must admit, I never take many pictures when I am in Chicago. I always am enjoying my time spent with two of my favorite people who live there, and I don’t think to get out my camera very often. Chicago is a fun city to visit over and over again, thanks to the endless supply of restaurants and things to do. You can visit over and over again and never do the same things twice.
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 my Chicago highlights from over the years.
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.
Federales
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 – Dueling Piano Bar
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.
Mini Golf at The Puttery
This is a chain of mini golf, but it’s a fantastic indoor activity to enjoy if the weather is particularly hot or particularly cold. The course is super cute with fun decor and designs for each hole, and the bar is serving up some awesome cocktails. The Puttery in Chicago is worth a visit if you are looking to enjoy an activity indoors for awhile with some drinks. It’s near the famous Au Cheval restaurant, so if that is a part of your itinerary, a round of golf could fit in nicely.
Fatso’s For a Chicago Dog
When in Chicago, one must get a Chicago Dog! While there are plenty of hot dog carts scattered throughout the busier areas of the city, this establishment is well worth a visit for the classic Chicago hotdog experience. Fatso’s Last Stand has a couple locations in the city, we ventured to the Ukrainian Village location for the full deal — a dog, fries, and a drink.
The Famous Burger at Au Cheval
This legendary restaurant with its award-winning cheeseburger is a must-do at least once in Chicago, and I finally crossed it off the list in 2024. Au Cheval is a small establishment, famous for its burgers while also boasting strong cocktails and a cosy atmosphere. We got on the waitlist early but still had about two hours to kill before our time, so we opted to enjoy beers and an appetizer at Haymarket Pub across the street. It’s well worth the wait — just be mentally prepared and open to bar hopping beforehand.
Drinks on the Waterfront
Ok, so I guess the majority of this post is reviewing different places to drink in Chicago, 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 is always 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 friends thriving in a new place.
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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