Winter in Chicago

How do I even begin talking about my absolute favorite city on Earth? The city I feel more comfortable in than my own. The one I hope to one day call home. The Windy City. My favorite city. Chicago, Illinois.

When I sat down to write this, I thought it was going to be a whole lot easier to put my love for this city into words. I feel like I know so much about it and have done so many things in the city, but to be honest, it was really hard to explain what it is exactly that I do when I’m in Chicago and why I love it so much. So I’ve compiled a post of some of my favorite things to do there, realizing I like to keep it simple more than I realized.

Lifelong Affair

My mother grew up just outside of Chicago so my whole childhood included numerous trips each year to The Region. My family and I spent as many holidays as we possibly could up north. It became a ritual to spend Christmas Eve Eve in downtown Chicago before heading to my grandparents’ house for Christmas Eve and Christmas Day. Even though the trips to the city are becoming more scarce and rituals have started to fade, the love I have will never end. The five-hour drive up north became such a routine that it seemed like nothing.

I guess many people would be hesitant of the winters in a place like Chicago, yet in my opinion, there is absolutely nowhere better. I cannot imagine a better feeling than walking up and down Michigan Avenue with snowy landscaping and slick sidewalks, seeing all the hustle and bustle of shoppers getting in their last-minute shopping. The number of times I’ve slipped (and usually fallen) on the ice on the streets is unreal, and every time it’s somehow still funny. The city is so welcoming and the crowds are so friendly. I typically visit Chicago twice in December and for my last job, we would go up twice during January for the Chicago Cubs and Chicago White Sox FanFests. I know this city like the back of my hand. It truly feels like home.

Windy City Must See

One of my favorite things to do in the winter is jog down the River Walk and take in all the sites of the busy city. I love how the top of the river is frozen over, but the water underneath is usually still flowing. How pretty?! When I’m there for vacation, I usually walk about 10 miles each day, wandering around the parks, along the river and, of course, up and down Michigan Avenue. My goal each day I’m there is to see as much as I possibly can, no matter how many times I’ve seen it, all while subconsciously searching for condos to move to in the near future.

Chicago River

I usually don’t shop much, except for at one place. Eataly.

Eataly is Mario Batalli’s restaurant and market and it’s easily one of my favorite places on earth. It’s basically an Italian market with two massive floors. The first floor has gelato and Nutella shops, a place to get cappuccino, and another little place for sandwiches. You’ll also find some basic kitchen supplies and cookbooks on the first floor. The second floor is where you’ll find all of the produce, meat, cheese and seafood counters, as well as sitting places to dine and eat from various menus. They also have fresh produce and pastas, making it a complete grocery store, unlike ones we’re used to in America.

The greatest part of the whole place is the wine selection. They have the wines broken down by reds, whites, and dessert wines and in each of those categories, they’re broken up based on the area of Italy the grapes are grown in. It’s like a little liquor inside this market. Y’all already know it’s this wine loving girl’s heaven. Naturally, some of the best Prosecco I’ve ever had came from Eataly!

“Life is too short not to drink well”

Since I haven’t been yet, how does this shop compare to the streets of Italy? Is this what real Italian markets are like?

Where to Eat

Of course, winter time in Chicago isn’t complete without deep dish pizza. When I stayed downtown with my last job, we always went to Exchequer Restaurant and Pub and I can’t imagine winters without it. It is SO good, y’all. Such awesome memories and the most delicious pizza make for the best place in town. I can’t even recommend the best kind there; as long as you get deep dish, you’re going to be highly impressed. I promise!

Obviously there are tons of options for pizza throughout the city, so I definitely want to hear about your favorites and if you’re a fan of deep dish or not.

No matter what city I’m in, I like finding places that aren’t part of a chain and I really prefer hole in the wall restaurants and bars. I’ve found these are the best places to experience the culture with the locals and they always have awesome food and drinks.

We’ve been going to Jake Melnicks for years, along with Billy Goat Tavern. Billy Goat is known for their burgers and not having very good service. It’s an underground old-fashioned burger joint that has been the laughing stock of multiple SNL skits. The food is good, but it’s definitely all about the experience when going there. Jake Melnicks is more of a bar that has great wings and is the perfect place to watch the Cubbies or Da Bears. And my absolute favorite place is Sweetwater Tavern and Grille. It’s right off Michigan Avenue and everything on the menu is delicious. Burgers, salads, sandwiches, cocktails. Try them all. Please.

Game Day

Soldier Field for a Bears game is always a good idea, too! I know the Bears have been struggling the last few years, but tailgating in the bitter cold and wind and cheering like crazy for this terrible team is an experience you will not forget. Something about Chicago sports is just incredible, y’all. Please go to some kind of sports game in Chicago. Let me know how it compares to any other atmosphere you’ve experienced.

Obviously I am not able to say every single reason why I love Chicago and explain everything I do there. Chicago will be seeing me soon because writing this has helped me realize how much I miss it! What should I do when I go back up? Any cool festivals or events going on soon?

Winter in Chicago
Winter in Chicago

Your Turn!

Let’s hear all your favorite things about my favorite city, and then please share with me your own favorite city & why it means so much to you!

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