Best Chicago Spots From A Born & Bred Wisconsinite

When you have lived in Wisconsin your entire life, you always hear how much Illinois is inferior to your cheese state. Most Wisconsinites, when you mention you traveled over the border to the southern state, will say disgustedly: “ugh.” However, then, I started dating a Chicago guy, and discovered the beauty of the city. There are so many things to do and see. You can have fun, even if you’re from Wisconsin.

Ice Cream Museum: Streeter Ville/River North

One of my favorite Museums in the whole city offers a sweet treat. You will definitely cool down once you discover and taste the history of Ice cream. It is the perfect summer activity.

You start the tour by picking your “Ice Cream name.” For example, you could use “Sundae Sally” or “Chad Mint Chip.” I personally used “Candy Katy.” Then you walk through a little pink train, (just like the “L”) and you arrive at the first part of the museum: the bar. It looks like a pink 50s diner. We ordered a Candy Martini. Now, this was $15, but oh my goodness was it strong. 10/10 recommended it was delicious and my boyfriend and I were both buzzed.

There were about 6 rooms total to go through and each room you got a sweet treat. We got gelato in the Jelly Belly room (A room filled with Jelly belly artwork and history), shaved ice in the next, but the absolute weirdest thing I tried was in the next room. There was a donut/sundae theme room that included 3 rounds of mini golf. The treat? Hotdog flavored ice cream. It was served on a pink bun with mustard and relish. I’m not going to lie, it was unpleasant, but did indeed taste like a hotdog.

All rooms were filled with activities and fun facts. I learned Germany has an ice cream called “spaghettis” which is ice cream that looks like spaghetti, topped with “marinara” or strawberry sauce. We also played whack a “ice cream cone” instead of whack a mole. To end your ice cream journey, you jump in a huge sprinkle pool, but be careful when you do. My boyfriend lost his phone amongst the sprinkles.

JoJo’s Milkshake Bar: River North

Now this is a popular spot in River North, but not everyone knows about JoJo’s Milkshake Bar. To me, it is my absolute favorite restaurant to this date. Obviously, they are known for their milkshakes, which are spectacular. You can top your vanilla/blueberry/chocolate/etc. Milkshake with cookies, cotton candy, doughnuts, lollipops, and so much more. It is delicious, but they have so much more to offer. First of all, the drinks are so delicious. The bloody marys are topped with a Chicago hot dog. I’ve had the chai-tini and the champagne sangria and they don’t even taste like alcohol. Don't want alcohol? Try the blueberry lavender milk, it is to die for. They also have a variety of shots to take. I tried the Fruity Pebbles shot and it was served in a shot glass made of Fruity Pebbles.

The food is also worth noting. I’ve had chicken pot pie, fruit salad, and tomato soup. Each dish left me groaning with every bite. It was so delicious and creamy. Loaded tater tots are also a good option, especially as an appetizer. Who would have thought a place with milkshake in the name would have had delicious food?

Replay Arcade Bar: Lincoln Park

If you’re looking to get drunk and play your favorite vintage video games, look no further than Replay. Aesthetically, it is one of the coolest places I’ve seen in Chicago. There’s spray painted artwork around the building. There’s old school collectables and colorful lights all over the inside of the place. The games are totally worth it. There’s several pinball machines with themes ranging from The Beatles, to Jurassic Park, to Batman, to the Simpsons. You can go old school with Pacman, Tetris, and Space Invaders. There’s hunting and sports games as well. My two personal favorites are The retro Simpsons Game and Burger Time.

When you go up the stairs, you’re in for a treat. When my boyfriend and I went there, they were hosting a murder mystery game inspired by Clue. The bartender gives you a card for clues and you follow the hidden qr codes and solve the murder. To say the least, I got competitive, but we did solve the case! We celebrated by getting a vodka lemonade, but for beer drinkers they have a variety of local beers to choose from.

Second City: Old Town

Everyone knows Chris Farley, Steve Carrel, Amy Poehler, Mike Myers, Tina Fey, but what do these celebrities have in common? They all have been students of Second City, a comedy club located in Old Town, Chicago. The people who perform in the second city have the best training and make their audiences laugh for hours. I had the pleasure to go there for a Valentine’s Day celebration and the price of the tickets are worth it. If you go to a late night show, you can get tickets for $40-$60.

I walked in and the ceiling was covered with chairs. It makes you want to sit upside down. There’s a few bars to get a quick drink before you sit at your table. The walls are covered with black & white pictures of past comedy students, including a huge picture of Steve Carrell.

We sat near the front of the stage, but be worn, they will interact with you if you sit near the front. There’s a group of young performers who perform short funny skits, kind of like SNL. These skits are hilarious. The topics range from robbing a museum for a family heirloom, to a dad meeting his daughter’s prom date, to an insane family road trip. They have such an ability to talk about all different topics in such a funny, uplifting way.

We got wrapped into a scene when it was two of the performers dressed up as old ladies trying to find their seats at the venue. They interacted with several seated people acting like they knew them. For example, they talked to “Bob” from down the street and his new fence. They thought we were the neighborhood hoodlums who spray painted words on the tennis court. We were asked what word we spray painted. For the first time in my life, I was at a loss for words, so I said the juvenile equivalent of a male genitalia. Despite the second hand embarrassment, the show was one of the funniest shows I have ever seen.

These are just a few of the best places I’ve been to in Chicago and there is so much more to see. The sites to see, activities to do, and food to eat is all amazing if you know where to go. I’m glad I have someone who lives there to show me where things are. In the past, when I thought of Chicago, I just thought of the West Loop and the river. Chicago is a huge city and I am not done exploring it.