How I Would Spend One Perfect Day in Chicago

From sun up to sundown, here’s how to take advantage of the Windy City

Photo by Benjamin Rascoe on Unsplash

While attending grad school in Chicago, I occupied a tiny little apartment on the corner of Belmont and Broadway in the Lakeview neighborhood. The cozy community charm there was perfect for me to return to after hectic school days in the South Loop. It felt like the rest of the city unfolded to me in no time after that — so many neighborhood pockets with their own adventures and gems to discover. After graduating, I’ve since moved away. But as a non-native Chicagoan who is lucky enough to come back and visit often, here is how I would take advantage of 24 perfect hours in Chicago.

1. Breakfast at Meli Cafe

Let’s imagine these 24 hours start with a morning flight that lands at Midway. I’m going to hop on the orange line train and head straight into the South Loop for breakfast at Meli Cafe. Their Printer’s Row location is an easy walk from the orange line, and perfect for a hearty brunch. My recommendation is the chicken and waffles — drizzle on some of that maple bacon maramalade and it’s heaven. The menu also features classic breakfast staples as well house-made crepes and a vegan + gluten-free menu. And if you’re feeling boozy, Meli’s has multiple mimosa concoctions for you to choose from.

2. The Art Institute of Chicago

Photo by Kristin Beal

Just a few blocks away from Meli’s in the South Loop, you’ll find one of the nation’s oldest and best art museums. The Art Institute of Chicago is so expansive that you could probably make a trip here last your entire day in Chicago and still have a fantastic time. Inside its halls you will find art from cultures and countries across the globe, as well as pieces from iconic artists like Picasso, Pollock, and O’Keeffe. Be sure to check out their special exhibits, too! It costs a few dollars extra than the price of general admission, but with past showcase spotlights on artists like Monet, Warhol, and Van Gogh, it’s well worth it.

3. Bourgeois Pig Cafe

Next stop — caffeine. With so many incredible local coffee shops to choose from in Chicago, you really can’t go wrong. But take the red line train up to the Fullerton stop, and you’ll find my favorite spot to unwind with a cup of coffee: The Bourgeois Pig Cafe. Not only do they have everything your hot and iced coffee dreams are made of, they also have a fantastic cafe food menu (including all day breakfast). I personally like to take my iced latte up to the second story and settle into one of their cozy study nooks.

4. Belmont Harbor/Lake Michigan

Photo by Dylan LaPierre on Unsplash

I can’t imagine a trip to Chicago without a visit to Lake Michigan. There are so many great access ways to the lake — Navy Pier or Oak Street Beach to name a few. But since I used to live off of Belmont and Broadway, my favorite way to get there is via the Belmont Harbor entrance. It’s a little quieter than places like Navy Pier, but still full of views. I love to pack a blanket and lay out on the lawn to watch all the boats coming in and out of the lake. The perfect way to absorb the lakeside sunshine and the Chicago skyline.

5. Crisp

Just down the street from the Belmont Harbor is one of my absolute favorite hidden gems in Chicago. Crisp is a hole-in-the-wall fast food Korean restaurant with menu items that will blow your taste buds. They have delicious Buddha bowls and Korean burritos, but the star of the show is their Korean fried chicken. My favorite is the boneless (although bone-in wings are an option) with the the sweet Seoul sassy sauce. Try it and thank me later.

7. Roscoe’s Tavern and Sidetrack

photo by Sidetrack

Once the day gives way to the night, my favorite place to spend time in Chicago is in Boystown. Boystown is one of the oldest LGBTQ+ neighborhoods in America, and has an overwhelmingly positive and vibrant vibe. The clubs and bars in this part of town are all worth visiting, but if I’m in town for just one night, I’m definitely going to be spending time between Roscoe’s and Sidetrack. These two LGBTQ+ bars light up at night with incredible cocktails, dance floors, and drag shows. The Chicago drag scene is like no other in the country. I would highly recommend going on a night where you can catch a show! Also, both clubs also are currently requiring proof of full covid-vaccination before entering, so you can safely party all night.

8. Cheesie’s

I’ll be honest, Cheesie’s is delicious any time of day. But it hits just a little bit different after a fun night of drinking and partying in Boystown. Just underneath the Belmont train stop, Cheesie’s is your go-to for something fried and delicious to soak up all that alcohol. Their menu is a grilled cheese-lover’s heaven: from the OG (American and cheddar on texas toast) to the Tenderizer (cheddar, mozzarella, bacon, and chicken tenders on texas toast), this menu has you covered. My personal favorite is the Caprese with a side of tots. In all honesty, it’s hard to go wrong at Cheesie’s.

9. Stan’s Donuts

Photo by Kristin Beal

As my 24 perfect hours come to a close in Chicago, my last stop before leaving the city is always going to be Stan’s Donuts. The Chicago donut debate is a heated one, but I’m a Stan’s loyalist. And with donuts like the Chocolate Pocket with Nutella and Banana, or their Buttercream Bismark (think a little Debbie chocolate cupcake but bigger), Stan’s always comes through. They even have vegan donuts and a full coffee bar! My order is one Cinnamon Sugar donut, one Toffee Cake donut, and an iced oatmilk vanilla latte. Sweet tooth, satisfied. I’ll happily board my flight home in a Stan’s sugar coma anytime.

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Dynamic young freelance writer, content strategist, and filmmaker. She/Her.

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Kristin Beal

Dynamic young freelance writer, content strategist, and filmmaker. She/Her.