24 Hours In Chicago, Illinois

I have a few places in the world…

Places where my heart feels like it thrives. They don’t necessarily have that home feeling, but there’s something different. My first one was Vegas. Every single time I visited, my heart just went insane. I felt so full, which is weird, being Vegas is a place where people go because they’re so empty. I’ve always loved being there. The second was Disney World. I realized that I don’t have a Disney obsession, but yet I have an obsession with the feeling of magic being a part of my life. Disney is the only place I’ve found that actually feels magical. My third place, is Chicago. It’s weird, because I’d only been here once before we started going for St Patrick’s Day, and while most of the St. Pat’s weekends, I don’t remember, I just love it here. 

It could be because the city reminds me of a bigger Minneapolis. It could be because everywhere feels like something new. It definitely could be because there’s people there who really do mean something to me. Or, it could just be because I’ve never gone there and not had the time of my life. Regardless, from an outsider’s, totally not a local’s perspective- here’s some things to do in Chicago, to make 24 hours feel for you, how it does for me.

#1. Walk

This place is nothing short of an Instagrammer’s paradise, mixed with a bunch of stores you can afford, and then even more you can’t. We walked about four miles the last time we were there, in -17 degree weather, just because it’s what you do. Even as a frozen tundra, the Chicago River is beautiful, and there’s a Starbucks on every corner to warm you up.

Luckily, if you’re a newbie to the area- Uber is a huuuuuge part of getting around, so if you’re going from the Bean to the John Hancock building, there’s nothing stopping you from getting there quickly. I’m just saying, there’s so much to see (and so many stores like Chanel, Gucci, etc), and so much to do along the way, that if the weather is not -17, you should walk it.

#2. Do

I’m not a local, so the tourist traps have literally trapped me, every single time I’ve gone. I’m sure there’s a bunch of hole in the wall locations that offer a real Chicago experience, but unfortunately I’m basic and want to go places that serve my Instagram aesthetic. Here are a few of my favorites:

The Bean: Cloud Gate, Chicago, IL 60601 

Think of a big, giant, reflective bean, that every single person needs to take a picture with. It’s located in Millenium Park, and is right on the edge of Chicago. This place would be gorgeous to walk around in the summer, unfortunately, we always miss it when it’s warmer out.

The John Hancock Building: 875 N Michigan Ave, Chicago, IL 60611

Going up! This building shows you Chicago from every angle. You can see the lake, you can see the buildings, neighborhoods, and everything in between. They also have something called “The Tilt”, where you get tilted out of the building and face the street below. I’m not sure which white people decided this was a good way to make money, but they got my $7.00, and my hands shook from adrenaline for the rest of the day.

Navy Pier: 600 E Grand Ave, Chicago, IL 60611

Near the North Side of Chicago, Navy Pier is exactly it’s name. It’s a giant pier where you can shop, buy things that say “Chicago” on it, ride a Ferris Wheel, and spend your money. It’s pretty much a glorified tourist trap on the water, but honestly, it’s something to do when you’re in the city. I’d recommend going once, and probably only once.

Magnificent Mile: This is located at North Michigan ave in Chicago, and it’s an entire mile of shopping. (That’s why it’s magnificent). The range of shopping goes from Macy’s to Chanel. There’s a Tiffany’s, Gucci, Dylan’s Candy Bar and everythingggggg in between. This is why I say to “walk the city”, because there’s just too much to see that isn’t normal in all our little suburbs that we live in.

They also have a pretty great aquarium, I’ve heard, but I’ve never gone. Along with that, Chicago has the Willis Tower which is the John Hancock building with a glass floor! 

#3. Eat

This is where all the haters are going to come in. “Jen, you’re totally not a local because x, y, z is the real Chicago Style Pizza and because a, b, or c is totally better and more authentic for their burgers” You’re right, I don’t live here, but when I come, there’s two places that we always eat at, and the third on my list is only there because Dylan forces me to go.

Ditka’s Steakhouse: 100 E Chestnut St, Chicago, IL 60611

One time Millman forced (gently suggested) we ate here, and since Dylan is a (fake) Chicago Bears fan, we visit the steakhouse every single time we’re in the city. It’s covered in old news articles about the Bears, a bunch of team pictures, and a whole lot of Mike Ditka (who is apparently called coach)… The menu is reasonably priced with steakhouse prices, and it’s something to see if you’re a Bears fan. (This is where I tried squid!) I’d say overall, this gives you a good “Chicago feel”, for a nicer dinner, but not too fancy. 

Portillo’s: Google it, they’re everywhere

Portillo’s is this giant “I love Chicago” restaurant which specializes in hot beef, hot dogs, and their quick service. Here’s three reasons why I love it here: 1. I stopped eating hot dogs because I’m not a fan of beaks and stomachs, but when I’m at Portillo’s, I just do it. They’re so good, and the buns are the best part of the whole meal. 2. It’s got this fast food, family vibe, and it’s basically Chik Fil A service, so there’s that. Like when they announce your meal they’re say “Order number 1-2-0 you are our HERO!” They’re cute. 3. They have this cheese sauce that totally delicious. It’s pretty much a basic orange cheese sauce, but I’m a french fries and cheese kind of girl so this place passed my test. Side note, they also have this chocolate cake that is to. die. for. (Portillo’s is in Indy now, so if you want to try it, come visit me!) (Also, Minnesotans… make the trip to Maple Grove to try your Portillo’s. Worth it)

Chicago Style Pizza at Pizzaria Due: 619 N Wabash Ave, Chicago, IL 60611

Here they come. The haters. Everyone says that Giordano’s is the best pizza place in Chicago if you’re looking for the “real Chicago Style pizza”, but I disagree. The meal at G’s was good, but the whole experience at Pizzaria Due was better. I liked their pizza better, I liked the little pizza atmosphere better, and I liked not being a sell out and raving about “Chicago Style Pizza from Giordano’s” because that’s the popular thing to do. I suggest you shop around though, because pizza is a thing of the city, and you can get a good slice from a lot of places.

*Please note, when I say forced by Millman to go to Ditka’s, it was more like two towers of Green Beer let us know that Ditka’s was the best life decision we could ever make.

I can’t wait until St. Patrick’s Day year three! Bring on the towers of beer and the traffic cones, but don’t bring a jacket because it could get lost! #HomeAwayFromHome 

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