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A Guide to Chicago’s Old Town

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I have lived in Old Town for nearly two years, so I think it is time that I tell you a bit about the neighborhood. I have gathered up information on all my favorite things to do in Old Town, including where to eat, where to work out, and where to shop.

Restaurants: Honestly, Old Town could use some more restaurants. There are lots of bars/restaurants, but we need some nicer places. For the record, I am only listing restaurants that I would recommend. 


Kanela Breakfast Club: This is probably the most popular brunch spot in Old Town, get there early on weekends, or be prepared to wait a little while. The menu has a nice mix of breakfast and lunch, and sweet and savory. I tend to order one of the benedicts.

Old Town Social Brunch

Old Town Social: If you want brunch without having a wait for a table, go to Old Town Social. This large bar/restaurant on North Avenue has a fun menu with everything from Chilaquiles to Poutine and Chicken & Waffles. During the day it’s a calm and quiet restaurant, and at night Old Town Social is a lively bar (and one of the better ones in the area). Note: Don’t confuse Old Town Social with Old Town Pour House (which is a large bar without much personality), or my favorite dive bar Old Town Ale House (a cash only place with a nude portrait of Sarah Palin).


Kamehachi: I have come to realize that if you want dinner in Old Town, Kamehachi is one of the best options. Charle likes the sushi and I look forward to their stir frys. It’s popular, but still easy to get a reservation, and it is one of the only eateries in Old Town that doesn’t function mainly as a bar. Their bento box lunch special (pictured above) is a really good deal.


Buzz Bait Taqueria: A fun fast casual taco joint with fresh fish sourced by Kamehachi next door. I love the fried avocado tacos, while Charles likes the mahi mahi.


Le Pain Quotidien: This is our go-to place to buy fresh loaves of bread, and we love their more European approach to breakfast. Usually tables are easy to get for weekend brunch, and I love their goat cheese and mushroom omelet.

Happy Camper Chicago

Happy Camper: A large pizza place/bar and sister restaurant to Homeslice right on Wells Street.

La Fournette

La Fournette: A French bakery/cafe with wonderful breads, pastries, coffees, and colorful macarons.


Woodies’s Flat: When we moved to Old Town, we went to every bar to decide which bar would become our hang out. We liked Woodies because the staff is so nice, and it isn’t as much of a pick up scene as the other places in Old Town.


Benchmark: If you ate at Benchmark a long time ago, let me tell you that they totally revamped the menu and it’s great! The brunch menu could be a bit bigger, but this is a fun place to grab a bite on a weeknight or to watch sports. On Friday and Saturday nights expect a line of people trying to get in, since this is a popular destination for people going out for the night.


Doodles Doughnuts: Old Town finally got a doughnut shop! The concept is that you can buy frosting and literally doodle on your doughnut, but the doughnuts are good, and they have a selection of crispy bacon with different seasonings.

Twin Anchors: A BBQ Joint off the beaten path on Sedgwick just north of North Avenue that is famous for being one of Frank Sinatra’s hangouts. It’s the only BBQ place in Old Town, but it happens to serve up solid food. The only drawback is that they don’t take reservations.

Mama Milano

Momma Milano: A small pizza place hidden just off of Wells Street. (This a photo of a slice of leftover pizza from Mama Milano that I turned into breakfast).

Eva's Cafe

Eva’s Cafe: A cute independently owned coffeehouse, and popular hangout for college kids studying. I often stop in for hot Chai Lattes.


Real Good Juice Co.: This juice cafe serves fresh cold pressed juices and smoothies with clever names (this is the Wendy Peffercorn). It the place I go when I want to squeeze extra fruit into my diet.


Cocoa + Co.: A chocolate shop and cafe that serves chocolates and hot chocolate. It’s a great place to get a gift for a chocolate lover.

Salpicon: A restaurant that serves contemporary Mexican food, and one of the better restaurants in the neighborhood. You have the option to order a la carte, or to enjoy a 7-course tasting menu for $75.


Nookies: A diner just north of North Avenue on Wells Street, it’s in our brunch rotation. I like the hues rancheros and Charles likes the omelets.

Workouts: I tell everyone in Old Town to join Classpass since there are so many gyms in the area.

Pure Barre: I am a regular at this barre studio. I love it because the classes work your entire body, and especially your abs, butt, and thighs, without turning you into a sweaty mess. You can go to a class and then just go on with your day.

Sproing: No joke, I burned 430 calories in 45 minutes, and I know because they strapped a heart rate monitor on me.

Flywheel: A high intensity spin class with the option to have your performance ranked against others.

GoCycle: They offer a less competitive spin environment, and a much more affordable price. A monthly pass is $170, compared to $270 at Flywheel.

Shopping: I love that there are no big box stores in Old Town (other than Walgreens). Here are some of my favorite locally owned boutiques.

Greer: A stationary and gift shop and a perfect place to pick out a unique gift.

Judy Maxwell: This quirky little shop is owned by Joan Cusack. Expect to find things like clever kitchen tools, pool floats, and Chicago themed onesies.

String a Strand: A jewelry shop where you can make your own jewelry.

Luxury Garage Sale: The place to find second hand luxury fashion including designer handbags, coats, clothing, and shoes.

Village Cycle Center: A massive bike shop that also sells all the bike accessories you might need, including helmets.


Movies in the Park at the Chicago History Museum: The schedule for 2016 isn’t available yet, but I love the movies in the park, which are shown on the Chicago History Museum’s terrace.

Old Town Art Fair: A street fest/art fair that takes place the second weekend in June. There is art, food, and live music.

The Air and Water Show: I absolutely hate this, but it’s one of the biggest events in Chicago so it gets a mention. I think it is loud and obnoxious and who really cares about some jets buzzing around? Let me tell you, the sound of half a dozen jets flying low in the sky over your home is mildly terrifying. This year it is taking place on August 20-21, I am already plotting my escape from Chicago that weekend.

Comedy: Old Town is home to two amazing comedy clubs including the historic Second City.

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Second City: This is the place to see improv. My parents were lukewarm about the idea of going when they were visiting last fall, but they loved Second City. Every show is different, and I make a point to go at least once a year.

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Zanies: While Second City shows consist of teams of performers doing improv, Zanies is the place to see stand up comedy, and they get major acts including SNL stars.

Did I miss anything? What are you favorite things to do in Old Town?

Kira @ The Imperfectionist

Friday 1st of April 2016

Love Old Town and omg that donut looks amazing!

Kira |

Kit Graham

Monday 18th of April 2016

Thanks Kira! I love living in Old Town :)

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