How to Make Your Summer Trip to Chicago Perfect


Everyone knows about The Bean, the Skydeck, and Navy Pier; being a local I of course avoid these places like the plague. Chicago has endless opportunity for fun, and if you spend all your time hitting major tourist attractions you are honestly missing out on what this city has to offer. Let’s get started

Where to Eat

Yo…other cities…I’ma let you finish, but Chicago has some of the best food I’ve ever had. Skip Giordono’s and Garrett’s Popcorn, hit these places instead!

  • Chicago Pizza and Oven Grinder– This is hands down my favorite restaurant in the whole city. Tucked away in Lincoln Park is this small and locally owned pizza place that has been around since the 50’s. The restaurant specializes in two things: pizza pot pies and and oven grinders. A pizza pot pie is exactly what you are thinking and that’s the only way I know how to describe it. The oven grinder’s are these HUGE and yummy sandwiches. I typically do the full 3 courses and get a chef salad, with Mediterranean bread, and a cheese only pizza pot pie (you can add meat or mushrooms if you want.) I MUST warn you though, this place does not take reservations and it gets busy FAST especially on the weekend. I would highly recommend going around 5:00PM to avoid a long wait.
  • The Athenian Room- Not only a favorite of mine but also a favorite of the beloved Tina Fey as well. I love this place because it doesn’t break the bank, but it has some of the most amazing Greek food I’ve ever consumed. Like Tina Fey, my favorite meal would also have to be the Chicken Kalamata and crack fries. It’s kinda simple, but the flavors will blow you away.
  • Clarke’s on Belmont– Looking for the perfect hangover food, or maybe a good place for some comfort food? Clarke’s is the exact place. This diner, which is a Chicago native serves some of the homiest food you can find in the whole city. They honestly have something for everyone, whether you want Salmon Eggs Benedict, the perfect waffle, or just a classic breakfast sandwich their menu covers it all.

What to Do

  • Museum of Contemporary Art- Don’t get me wrong, the Art Institute is absolutely beautiful. The MCA has such a different vibe to it though. At the MCA you are going to see more culturally relevant pieces that really make you think and feel something which I don’t find as easy in some of the pieces at the Art Institute. The displays are constantly rotating and they always have really neat exhibits up. On top of that they also have a beautiful outdoor cafe for you to sit at after you take in all the art inside. PLUS, students and Illinois residents always get a discount. This is also perfect walking distance if you are staying on the Magnificent Mile.
  • WhirlyBall- This isn’t kid friendly, but god it makes you feel like a kid. WhirlyBall is a business located in Lincoln Park that pretty much specializes in a good time. They have a bar, bumper cars, games, and bowling. Plus this place is open until 3:00 AM, come on you know you all want to get a little tipsy and then play bumper cars.
  • Lincoln Park Conservatory- Lincoln Park Conservatory is one of Chicago’s only glimpses of nature in the whole city. Although I prefer Garfield Park Conservatory much more, for the sake of visitors though LP is just a much more centralized location. This beautiful conservatory features beautiful plants from all types of environments. This is perfect for families and children as well. Make a whole day out of it and after you finish up at the conservatory, walk across the street to Fullerton beach, grab an ice cream cone from one of the many vendors, and relax with the picturesque skyline behind you.
  • Shop in Wicker Park and Logan Square- These two neighborhoods are by far my favorite places in the whole city. There’s tons of food, bars, street art, and shopping along the street. You can get everything from a Ramen Burger, to classic comfort food. The walk between Wicker Park and Logan Square is about 2.1 miles, but if you enjoy walking and window shopping it’s not bad at all. For me personally, I love shopping at Ragstock, Buffalo Exchange, Village Discount, Kokorokoko, and Crossroads Trading Post. There’s honestly something for everyone in each of these shops.

Where to Drink 

Chicago is not only boujee, but boozy! Check out these fun bars below

  • Cindy’s Rooftop- Located downtown, across the street from Millennium Park is the stunning Cindy’s Rooftop. Cindy’s has a home-y but still modern vibe, and the drinks are the same way. In addition to the fun and crafty cocktails, there’s also an absolutely STUNNING rooftop overlooking Lake Michigan and Millennium Park. A must for first-timers in my opinion.
  • Emporium- Located in Wicker Park, this bar takes you back in time. Complete with hundreds of arcade games like Pacman and Pinball and a vintage 70’s setting, this bar is sure to have you feeling like you are in a different decade. For my crafty beer drinkers, this place is made for you! Emporium has DOZENS of beers for you to choose from as well as hand-crafted cocktails.
  • Three Dots and a Dash- Head straight to the island with Three Dots and a Dash. Located in West Loop, this Polynesian bar will give you all the beach vibes. Not only is the whole place decorated in Polynesian attire, but the drinks are as well. All of their juices are cold pressed daily, and paired with fresh seasonal fruit to ensure some of the freshest drinks you can find. Nearly every drink comes in a cute tiki themed cup. Put your watch on island time, and dance the night away.
  • The Green Mill- This one is a bit different, but it’s too great for me not to mention it. The Green Mill, located in uptown is a bar that has been around since Prohibition times. Velvet booths line the stage with a giant stage in the front for local musicians or speakeasy poetry on Sunday evenings. Behind the bar you can find a tunnel in the floor that was used to hide alcohol in the 1920’s. My favorite part about this place though is that it was also Al Capone’s favorite, and he even has a booth dedicated to where he would sit and enjoy his cocktails when he would take a short break from being a mob boss

That’s it everyone! I’d be more than happy to answer any questions you all might have so shoot me a message if so. Have a great 🙂

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