If you’d asked me two years ago, I would have said that I hated Chicago. I would never want to live there. I didn’t even like visiting for the day. I’d take a shopping trip to the suburbs at the drop of a hat, but you couldn’t make me go into the actual city.
This is one perk of dating a guy who lives in Chicago: Because I’ve been fortunate enough to visit him several times throughout the past year and a half, I’ve also discovered some really wonderful spots throughout the city that I never would have known existed otherwise. I love the city now, and I snatch up any opportunity I get to visit, like this past weekend over Winter Break.
Chicago is awesome for Hope students because it’s just a quick day trip away (my roommate and I left after class one Friday last year and made it back later that night). Hope’s SAC also takes a trip there every year. During that trip most people stay in the Loop (“Downtown Chicago”), but if you ever have the opportunity to explore some other neighborhoods, here are some of my favorite spots!
*Disclaimer: I am NOT a Chicago native, nor did I spend much time there for the first 19 years of my life even though I’ve always lived within two hours. This is a very incomplete list of the city’s best places and I’ve probably gotten some neighborhoods somewhat wrong, but I tried my best.
Address: 1321 W Grand Ave // 3707 N Southport Ave
Neighborhood: West Town // Lake View
Favorite thing: Lasagna pizza with whipped ricotta; CUPCAKES
I love Coalfire for many reasons, not least of which is that it is so different from a lot of the other pizza places around Chicago. Don’t get me wrong, I love deep dish as much as the next fake Chicagoan, but I’m a thin crust person at heart. Coalfire does amazing thin crust with out-of-the-norm (but not weird) toppings like whipped ricotta. Ugh. Put that on anything and it instantly gets fifteen times better. The service is also amazing. I’ve had a really great experience with the staff every time I’ve been there. And the cupcakes. Oh, the cupcakes. Even if you’re full when you leave, take one or six to go. They’re actually cheesecake cupcakes. I had a salted caramel one when I was here on Sunday and it was amazing. Just make sure not to make plans here on a Monday – they’re closed (so sad)!
*Note: I’ve been to both locations and the one on Southport is much larger, busier, and in a more attractive area, but I strongly prefer the Grand Ave location. It’s smaller, cozier, quieter, darker, and more chill, and I’ve never waited more than 10 minutes to get in (I’ve waited for much longer than that at the Southport restaurant – worth it, but tough).
Wateriders Chicago Kayak Tours
Address: 950 N Kingsbury St
Neighborhood: River North/Goose Island
Favorite thing: Tandem kayaking!
My boyfriend and I went to Wateriders in August and it was AWESOME. I want to do this every year now. We researched a lot of places to ‘yak the Chicago River, and this was the most affordable option and we had so much fun. It was a really great experience and we will be back!
Jeni’s Splendid Ice Creams
Address: 3404 N Southport Ave // 1505 N Milwaukee Ave
Neighborhood: Lake View (Southport Corridor) // Wicker Park
Favorite thing: Brown Butter Almond Brittle
Jeni’s is a nationwide (ish) chain that I first discovered on spring break in Charleston, South Carolina, last year. They have some really unique, delicious flavors. And it’s all so good.
*Note: I have only been to the location in Wicker Park, but I’m sure the Southport one is equally amazing. The Wicker Park location definitely lived up to my high expectations from experiencing it in Charleston!
**Additional note: It’s pricey, but you can order their ice cream online if you really want it but can’t make it to Chicago!
Address: 233 S Wacker Dr (Sears/Willis Tower)
Favorite thing: Night time!
It’s so cool to be able to look out over the city (day or night) from the Skydeck and see for so many miles from the 103rd floor. Supposedly you can see Indiana, Wisconsin, and Michigan from up there on a clear night, which is pretty cool. It’s a stunning view and a really awesome experience!
Plein Air Cafe
Address: 5751 S Woodlawn Ave
Neighborhood: Hyde Park
Favorite thing: Mocha
I just discovered the Plein Air Cafe this weekend and I fell in love with it. This is possibly the cutest cafe I’ve ever seen with the sweetest decor and really good coffee. If I lived in this area, I already know that I’d spend way too much time hanging out in here. And it’s connected to the Seminary Co-op (below)!
Seminary Co-op Bookstore
Address: 5751 S Woodlawn Ave
Neighborhood: Hyde Park
Favorite thing: Clearance tables. $6 religion books.
I looked up the Seminary Co-op after leaving it this weekend, and apparently it’s kind of a big deal. I guess it’s hailed as one of Chicago’s really great bookshops, and I can see why. It was quiet and felt studious, but it was also colorful and geometrically winding, filled with shelves marked with genres I’d never even heard of with so many interesting-sounding books that almost seemed to leap off the shelves just with the environment of the store. I loved this place, and I will be back.
Address: 1960 N Western // 1813 W Montrose
Neighborhood: Logan Square // North Center
Favorite thing: Moose Tracks. Moose Tracks. Moose Tracks.
Margie’s is your classic ice cream parlor. It reminds me of places I imagine my grandparents going on dates all those years ago. Both locations are pretty cramped inside, so be prepared for that, but it’s an awesome standby pick for really good ice cream and a really nostalgic atmosphere.
*Note: I’ve been to both locations and I prefer the North Center one. They’re both pretty cramped (it’s a super busy place!), but Margie’s in North Center was a little less overwhelming to me.
Art Institute of Chicago
Address: 111 S Michigan Ave
Favorite thing: “Blue and Green Music” by Georgia O’Keeffe
The Art Institute is one of the world’s best art museums. This place is home to my favorite painting of all time, and a lot of other really wonderful (and confusing) pieces of art. Make sure to stop here – you could explore it forever and still not get through it, but it’s definitely worth a trip and the entrance fee!
Museum of Science and Industry
Address: 5700 S Lake Shore Dr
Neighborhood: East Hyde Park
Favorite thing: Weather zone – Learn about how tsunamis, tornadoes, avalanches, and more work!
I love the Museum of Science and Industry. It’s a classic Illinois-kid field trip spot. I actually took a science club field trip here in high school. I wasn’t even in science club (shhh). I went back this weekend and I will never cease to be amazed by this place. There is so much to do and I’m sure I could spend days there and still feel like I hadn’t seen it all, but it is an incredible place in which to spend any amount of time. So, so cool.
*Boyfriend on the avalanche exhibit (before we figured out that it was supposed to simulate an avalanche): “I’m not sure what I’m learning, but I like it.”
Bryn Mawr Breakfast Club
Address: 3401 W Bryn Mawr Ave
Neighborhood: North Park
Favorite thing: Cinnamon pancakes
The Bryn Mawr Breakfast Club has arguably the best breakfast I’ve ever had. NEIU is taking over the building and putting in a dorm, so be sure to get here while it’s still in existence in this location! I’m sure they’re just moving somewhere, but the spot they’re in now is so cute and put-together. It’s the perfect place for a sweet or savory breakfast.
- Portillo’s (The chopped salad, the cheeseburgers, the chocolate cake shakes, the cheese fries… Oy.)
- Tre Kronor
- Joy Yee (I’ve only been to the ones in the suburbs, but there are four locations in the city and I’m sure they’re just as great!)
- The Sweden Shop
- Chicago Bagel Authority (I’ve just been to the one on Belmont!)
- Field Museum
- Sprinkles Cupcakes (Cupcake ATM! Cupcake ATM!)
- Giordano’s (the bruschetta!)
- Ann Sather (only for the cinnamon rolls – otherwise it’s not my favorite, but the cinnamon rolls are AMAZING)
Places I still want to go:
- La Colombe (I always drive by the one in Andersonville and think it looks so nice!)
- Chicago Brauhaus
- The Allis // Chicken Shop (at Soho House)
What’s your favorite place in Chicago? Leave a comment, tweet at me (@hopekathryn17), or send me an email at email@example.com! Also, be sure to check out my Etsy shop (LakesPointCollective) and donate to Dance Marathon! Thanks for reading!
The LORD passed in front of Moses, calling out, “Yahweh! The LORD! The God of compassion and mercy! I am slow to anger and filled with unfailing love and faithfulness.”