When I was 20, my best friend Preethi had just moved to Wrigleyville, and we were in the habit of spending broke summer weekends eating the cheapest food we could find and walking around the city for hours. One 90-degree June evening, we had splurged on Flaming Lips tickets at the Aragon. We trekked the two-plus miles in the sweltering heat—it felt a lot further—and arrived at our destination sweaty, thirsty and already sleepy. After the show, we used Preethi’s U-Pass to get on the El, where we ran into several fellow concertgoers and Lenny, a drunk busker.
Lenny introduced himself to us on the platform, then boarded the train with us, where he began to play.
“Girls, this is a song I wrote. It’s about what happens when a man loves a woman, and they’re two different colors,” he said.
He proceeded to play an amazingly heartfelt rendition of Hot Chocolate’s “Brother Louie.” Of course, this was long before the song re-entered the cultural lexicon via Louis CK. We loved the song and, in our naivete, had no idea that it wasn’t original.
“That was a classic Chicago moment,” Preethi said to me as we exited the train and said goodbye to Lenny. Months later, we would discover his ruse, which would only make the exchange even more legendary to us.
This memory still stands out as one of my favorites of the city, but I’ve added many others to it over the years by visiting museums, eating and drinking in various neighborhoods and listening to live music all over the city. Inspired by my friend Mathilde’s guide to Atlanta, I wanted to write my guide to the City of Big Shoulders—an easy list to share with visiting friends and anyone else interested in exploring Chi-town.
Chicago has more tourist attractions than I could possibly list here—this is just a brief rundown of my personal favorites.
Architecture boat tour (located in the Loop/River North): This is, hands down, my favorite sightseeing pastime in the city. Ride a boat down the river for an hour or 90 minutes and learn about the origins of the Merchandise Mart, the Willis Tower, the Trump Tower and the Carbon & Carbide Building.
Millennium Park (located in the Loop): The result of the city’s 2004 downtown revitalization project. Highlights include the Pritzker Pavilion (amazing acoustics for outdoor shows) and Cloud Gate, also known as the Bean, where you can photograph a wavy reflection of the city skyline and yourself upside down. If you’re in town on a Monday, definitely check out Downtown Sound. There are other free events throughout the week as well, such as yoga on some mornings.
The Art Institute of Chicago (located in the Loop): See Grant Wood’s American Gothic, Edward Hopper’s Nighthawks, Georges Seurat’s A Sunday On La Grande Jatte and countless other iconic paintings and works of art. The 2009 addition, the Modern Wing, provides an airy, light-filled space to hang out in and a nice view of the city skyline.
Second City (located in Old Town): The comedy club that produced Tina Fey, Steve Carell, Tim Meadows, Chris Farley and Bill Murray. I’ve laughed until my face hurt every time I visited. Definitely pop in the Old Town Ale House on your way home if you go and check out the unique artwork.
Montrose Beach (located in Uptown): Our favorite beach in the city. Expansive grassy space for grilling, views of the city from the lake, usually not too crowded.
Museum of Contemporary Art (located in River North): A pretty comprehensive modern art museum. You can find lots of unusual goodies in their gift shop, too.
Chicago Cultural Center (located in the Loop): A free museum that has interesting rotating exhibits as well as a nice free hangout area and the world’s largest Tiffany stained glass dome.
Again, Chicago is a hugely musical city and contains more venues than I could possibly name here—below are the spots in which I most enjoy hearing live tunes.
The Green Mill (located in Uptown): A former speakeasy and hangout of Al Capone, this jazz club has a well-preserved ’40s feel, beautiful wood-carved walls and great musicians.
Schuba’s (located in Lakeview): A tiny bar and club that often hosts indie, alt-country and singer-songwriter acts. They have a restaurant next door called The Harmony Grill, where you can get baked mac & cheese with 17 different toppings, including black beans, mushrooms and veggie chili.
Lincoln Hall (located in Lincoln Park): A sister venue of Schuba’s that opened in 2009. It’s bigger than Schuba’s, but still intimate. The best thing about this venue is the rich, acoustically almost-perfect sound.
Food and drink by neighborhood
Chicago is famously a city of neighborhoods—no trip is complete without at least one adventure outside the bounds of the Loop. Here’s a list of my favorite hoods, and the places I love to eat and drink in them.
Visit the intersection of Milwaukee, Damen and North, also known as “The Crotch,” for your fill of hipsters, mustachioed cyclists and some of the best food and drink in the city.
Antique Taco: Delicious, somewhat reasonably priced hipster tacos! Their fish taco—smoky and deep-fried with the perfect amount of Sriracha tartar sauce and cabbage—is the best I’ve ever had.
Big Star: An iconic Chicago bar that also serves hipster tacos. Strings of lights hang over the massive outdoor patio.
The Violet Hour: Beautifully crafted cocktails likely to contain exotic ingredients such as tobacco bitters and rosewater. Swanky, fancy interior. No sign out front, and people often wait an hour to get in. But once you’re in, you’ll get your own table, and the drinks are worth the wait!
Emporium: Play ’80s and ’90s arcade games and drink craft beer. Dig Dug, Tetris, Frogger, pinball. Super fun.
Adjacent to Wicker Park, Logan Square serves as its hipster overflow zone by offering cheaper rents. Logan Square, which has Mexican grocers and cheap diners alongside its trendy bars, feels a little more authentically Chicago to me.
Revolution Brewing: One of Chicago’s best breweries. Their Anti-Hero IPA is probably my favorite local beer. Their food is delicious too.
The Boiler Room: Delicious pizza, cheap drinks, old movies with the sound off, usually ’90s rock on the speakers, booths to sit in … what more could you want?
Longman & Eagle: Epic brunch. Fancy drinks & expertly made omelets. Expect the wait to be long, but worth it.
A neighborhood near and dear to me, as I lived there for two and a half years (I just moved to Albany Park/Ravenswood … more on my new hood in a future post!). Neighborhood residents are a mix of hip kids and Ukrainian immigrants that came over in waves from the 1870s to the 1990s, after the fall of the Soviet Union. Home to a number of beautiful Ukrainian churches; you’ll see several if you walk down Oakley Street from Division Street to Huron Street.
Fatso’s Last Stand: Classic Chicago greasy spoon fare. Think Chicago hotdogs, gut-busting burgers and crispy fries. They also serve the elusive vegetarian Chicago-style hotdog, which I haven’t tried yet, but it’s on my list.
Happy Village: Probably the best outdoor drinking area in the neighborhood. Ping pong tables indoors. Cheap drinks.
Bite Cafe: A cozy little BYOB spot with a nice brunch. They serve breakfast bebimbap, which is my favorite.
The Lockdown: A prison-themed heavy metal bar that serves unbelievable burgers. Expect to have your ears blasted by Slayer while you foodgasm from the culinary delights. Half-priced burgers on Tuesdays.
To be honest, Lincoln Park technically isn’t one of my favorite neighborhoods, but a few of my favorite restaurants live there, and it’s a convenient hood for out-of-towners to visit, as it’s near the Loop and it houses the Lincoln Park Zoo.
Pequod’s: Chicago-style pizza at its best. I’m honestly not a huge fan of the deep dish, but I love taking out-of-towners here. The pies are spot on and I love the homey, chill atmosphere as well.
Franks ‘n’ Dawgs: Super-fancy artisan hotdogs and sausages served on Texas toast.
Encompasses Wrigleyville and Belmont & Clark, a mecca of thrift stores and specialty stores selling goth and punk apparel. I loved this area when I was in high school and early college. Think mid-20s baseball fans from the suburbs, rebellious teenagers and young professionals. Nowadays I prefer hanging out on the city’s West side, but again, a few of my favorite eateries are here.
House of Sushi & Noodles and Wasabi Cafe: Why eat sushi in the Midwest? Because all you can eat. These sister restaurants know how to do it. Wasabi Cafe is a few dollars more, but also is BYOB and has a bigger dining room. It’s better for groups.
Headquarters: If you love old arcade games, this is the place for you. Much bigger than Emporium, and the games are all free. In return, you pay more for drinks, but they serve a lot of good craft brews.
Crisp: Korean-style fried chicken. If you haven’t had it, it’s lighter, juicier and more spice-infused than American fried chicken. Crisp was highlighted in Travel & Leisure’s “America’s Best Fried Chicken” back in 2010. Take that, the South!
Soupbox: Nothing but lots and lots of heavenly soups. I practically fainted when I had the lobster bisque—the perfect amount of cream and lobster, with just a touch of mint. Swoon.
A Mexican neighborhood on the city’s West Side. Famous for good Mexican food, art galleries and thrift stores.
The Skylark: This was my favorite hangout in the city when I was 22. It’s a classic Chicago dive with booths, dim lighting, cheap drinks and amazing tunes on the jukebox. But what elevates it above the other Chicago dives? Soul food! In particular, tater tots with three dipping sauces. PBR + tots = Every college kid’s dream.
A fun South Side hood. Encompasses U.S. Cellular Field, and is thus a good neighborhood to check out after a Sox game.
Maria’s Packaged Goods & Community Bar: A super-chill bar that serves craft beer and fancy cocktails. Out of the way for most, but worth the trek. It has two epic outdoor seating areas.
The Polo Cafe: I haven’t tried it yet, but it’s on my list. Has a ’50s atmosphere and is the No. 14 restaurant in Chicago on TripAdvisor. Standard American fare. Surf and Turf.
Nana: A cute little vegan-friendly eatery. Heavy on the local, organic and sustainable fronts. I had the chickpea fries and they rocked my world.
A historically Swedish neighborhood famous for brunch, bakeries and antiques.
Hopleaf: A Belgian-style bar inspired by the Cadieux Cafe, my favorite establishment in Detroit. Bounty of Belgian brews on tap, double-fried French fries, light and airy dining room.
Simon’s: An old Swedish-themed bar that feels like stepping back into the ’70s. Has live jazz on occasion and a fantastic jukebox. (Full disclosure: I haven’t actually been here, but Travis loves this place and provided this review.)
Also on the South Side, near Bridgeport. A fun place to walk around, especially if you are in the area. Definitely make the trek to Chinatown Square, an outdoor-mall-like strip that really feels like Asia (says the girl who lived there for two years!).
Hing Kee: Soups and stews with homemade noodles. Reasonably priced and delicious.
Aji Ichiban: The Chicago branch of a chain candy store based in Hong Kong. Worth visiting just to see the plethora of random Asian candy they have on offer as well as the dried squid.
Out of bounds
Here are a few places I love that didn’t fit in any of the neighborhoods on my list.
The Signature Lounge (located in River North): A must for visitors lucky enough to catch the city on a clear day. It’s a bar on the 96th floor of the John Hancock building. Enjoy the city from above while drinking an $8 Budweiser.
Lincoln Square Lanes (located in Lincoln Square): An old-school bowling alley complete with an Abe Lincoln mural, pool tables, shuffleboard and a rowdy clientele.