The Windy City, the Second City, Chi-Town, whatever you call it, the third biggest city in the U.S. is possibly one of the best cities in the country (at least in my books). The whole vibe of the city was a lot more relaxed and easygoing than anywhere in New England or New York City: we were waiting for brunch outside of a restaurant on our last day and a woman who said she was in a rush stopped to talk to us for ten minutes, recommending other places we could try even though we hadn’t asked her for advice. I’m definitely a fan of Chicago and all it has to offer, so here are some of the things I enjoyed while I was there.

1.) Coffee—Chicago has a lot of great coffee shops, and these are good options for lighter and cheaper meals if you’re not looking for a sit-down breakfast. My favorite was The Wormhole. This Wicker Park coffee shop is decorated with toys and posters from old video games and movies, and their drinks are named after some old school favorites, so how could I resist trying a Peanut Butter Koopa Troopa latte? Great vibe inside and my favorite coffee.

We also visited Intelligentsia Coffee. This chain has some locations throughout Chicago as well as New York and LA, but the coffee here was great, they had tasty baked goods, and there was a good, relaxed feel inside (which is what I got from the city overall, so I’ll have to stop saying that). Another spot we tried was Overflow Coffee. This shop was located in a weird spot and inside of a strange building that seemed sort of empty and sparse, but the coffee was good. It’s similar to Wormhole in that they play soundtrack music from Inception and Jurassic Park in the background. I recommend either the Nutella Mocha Latte or the Overflow.

2.) Lou Malnati’s–Now for the real food. Chicago is known for deep dish pizza and its Chicago Dogs, and for good reason. For some incredible deep dish pizza, head to Lou Malnati’s. They have locations throughout the city, and their pizza is unreal (if you’re ever looking for a birthday present idea, Lou’s ships across the country…). With thick buttery crust and a flavorful tomato sauce, their pizza tasted so good, and what I thought Chicago would taste like if it were a food. We all split a medium cheese and a small Lou’s Classic (which was sausage on it as well), and it was a little much, but not too much to conquer after a day of walking all over the city (Chicago is also massive). If you’re used to New York pizza, keep in mind that this is a lot heavier.

3.) Art Institute of ChicagoOne of the best art museums I’ve been to, hands down. We spent a good amount of time here, and there were so many interesting things to see that it was hard to get bored. They have a huge range of famous names: Picasso, Matisse, Rodin, Renoir, Warhol, O’Keeffe, Rivera…the list goes on and on. They also have a number of iconic paintings and works, like American Gothic (Wood), The Old Guitarist (Picasso), and some Chagall windows. On their lower floor, they have an exhibit of Thorne’s Miniature Rooms which was something cool and unique to see. Ferris Bueller goes here on his famous day off, and there are a number of places to see in this museum that he and his friends visit, like A Sunday Afternoon on the island of La Grande Jette. I particularly liked the impressionist collections, and we spent a good amount of time in that gallery. Bring your student ID for reduced admission ($17 with ID, $23 adults). 

4.) Second CityIf Tina Fey, Amy Poehler, and Steve Carell all come from the same place, you know that place has to be doing something right. Second City’s a comedy club (not too far from a Lou’s!) and school where young actors go to practice and learn improv and comedy. They put on a number of shows, and we went to their Second City E.T.C. stage revue. With a cast of six actors, they put on a hilarious show, which I can never do justice to in writing about it. There were a lot of quotable moments, as well as some that resembled the Kabarett (like when they played on the audience’s lack of knowledge about U.S. history), and we barely stopped laughing the whole time we were there. I absolutely would go back and definitely recommend going to a show if you’re in Chicago. Platform tickets are around $23.

IMG_28035.) Chicago Architecture Foundation Boat TourChicago has a lot of famous architecture: from the Sears Tower (now Willis Tower) which was the tallest building in the world for 24 years to the new, controversial Trump Tower. Chicago’s skyline is impressive, so it’s only natural to learn more about it. We hopped on a boat tour through the Chicago Architecture Foundation and were guided along the Chicago River by our incredible volunteer docent Rebecca, who told us all about the different prominent architecture styles in the city (art deco, converted warehouses, modern, contemporary), the buildings’ architects, and some Chicago history. Make sure to go on a nice day, because fog swept through the city frequently over the weekend (I think from Lake Michigan) and hid some of the taller buildings in the clouds.

Here are some of my other picks:


  1.  Piece Brewery & Pizzeria (Bucktown)–They make their own beers, and the pizza is made in the New Haven style.
  2. Scooter’s Frozen Custard (Lakeview)– Their flavors are so good (like Chocoloreo, Coconut Cream, Caramel Fudge Nut Brownie Chip) and the frozen custard was perfect after all that walking. It’s heavier than soft serve, and a small serving is plenty.
  3. Gold Coast Dogs–We’d looked up some places to check out for the best Chicago dogs, but we were all starving after trekking around the Art Institute and this was the closest place for lunch. I always get hot dogs completely plain, so I was a little tenuous about trying one of these, loaded with tomatoes, peppers, onions, relish, and pickles, but they were really good: the peppers in particular added a nice punch.
  4. Longman and Eagle–a place we’d thought about going for brunch but it was a little out of the way
  5. Wildberry Pancakes and Cafe–another popular brunch spot, but we couldn’t get in
  6. Eggy’s Diner–brunch spot, the service was quick and their breakfast food was great.
  7. Artists Cafe–We came here after landing late at night, and they have great fries and good sandwiches.


  1. Wrigley FieldThe second most loved ballpark in America (after Fenway of course), Wrigley’s another beautiful ballpark filled with energetic fans. Frozen vodka lemonade also comes recommended.
  2. Grant and Millennium Parks–These two parks make for a great place to run through on a crisp morning. Grant Park has a huge fountain and is close to Lake Michigan and the running paths that go parallel to the water, but it’s also not too far from the famous Millennium Park. Millennium Park is filled with lots of modern, public art, like the famous Cloud Gate, a stainless steel sculpture in the shape of a bean. It gets quite crowded as people like to take their pictures reflected in the sculpture, but when we went running through the park at around 8:30 AM, it was practically empty and a lot more enjoyable (and a good way to get a first glimpse of this sculpture). It’s cool to see the skyline reflected in it, but it’s tough to discern on a foggy day.
  3. Chicago River Walk–Chicago has mandated that development along the Chicago River provide public access and walkways so that the space becomes more usable. There are some restaurants and a couple of nice, small parks along the river, so it’s a cool place to walk around.
  4. Lincoln Park–When we planned on going to Lincoln Park for a walk, we had no idea that they have a completely free zoo. There are a bunch of apes and chimps which were very animated, between eating lunch, climbing around, and peeing on a log in front of everyone. Other favorites of ours were the otters, beaver (which is really interesting to watch swim because it curls its arms up into its chest), and sea lions.
  5. Lake Michigan–Not too far from Lincoln Park is a beach with great access to Lake Michigan and an incredible view of Chicago’s skyline. For the view alone, it’s definitely worth it, but dipping your feet in the water is a nice way to cool off and unwind after a lot of walking. There are running/biking paths between the beach and the road which a lot of joggers and cyclists used, and plenty of people also went in the water, which was clear but also very cold.
  6. Wicker Park & Bucktown–Finally, we took the L (their subway) into a trendy section of the city  with a Portland-esque vibe. These neighborhoods are filled with bookstores, record shops (try Reckless Records), restaurants, vintage clothing stores, you name it. We visited two bookstores: Quimby’s, which I thought was remarkable for the number of zines they sell, and Myopic Books, which is a really great shop with tall bookshelves and that classic used bookstore feel. Rudy’s Roundup is a general store similar to Pinecone & Chickadee in Portland, selling weird tchotchkes.

Getting around: Walking is a good way to see a lot of Chicago and its impressive architecture, but what I learned in my short time there is that Chicago is a massive city. The L (Chicago’s subway system) is really navigable, and a day pass is only $10, so it’s worth it if you plan to hop around a lot. It’s also mostly above ground, so it’s not quite as dreary as being stuck in an underground tunnel.