(Photo via Windy City Paws)

Visiting Chicago? If you’ve already been to the Bean, museums and Navy Pier, try something new and step off the beaten path and into one of the city’s 77 unique neighborhoods.

Each has one-of-a-kind places to shop, eat and explore. Need a little guidance? No problem.

This weeks spotlight: Old Town


Old Town Map

(Map via Joe Mills Illustrations)

Summary: The Near North Side community — located just north of the Loop and just west of Lake Michigan — has grown from its 19th century German Catholic roots into a neighborhood known nightlife, Wells Street restaurants and, of course, the famous Second City comedy club.






Pomp and Circumstance | 1400 N. Wells St.

It offers farm-to-table dishes, a long drink menu and a speakeasy vibe. Start with the brussel sprouts and try the “When the Smoke Clears” from the drink menu.

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Eva’s Cafe | 1447 N. Sedgwick St.

This brick-faced cafe is completely homey – equipped with a real fireplace, unique mugs and plenty of outlet options. Stop it for a quick coffee or grab a bite, say awhile and get cozy.

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Topo Gigio | 1516 N. Wells St.

Looking for some Italian food so good that will taste like it is fresh from Grandma’s kitchen? Enjoy hearty portions of classic dishes that are perfect for a family-style dinner.  



Happy Camper | 1209 N. Wells St.

Tire swings, air stream trailers with tables inside and neon everywhere. But, the pizza here is the star of the show. Come for a meal and camp out for the evening.

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Woodie’s Flat | 1535 N. Wells St.

Enjoy comfort food, music videos from the 90s and $5 jug beers. Order anything with mac-and-cheese — the famous Mac Attack Burger, the Mac and Cheese Stuffed Fried Chicken, or just a classic bowl of mac.

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Mama Milano’s Pizza Bar | 1421 N. Wells St.

This quaint Italian restaurant is famous for its spinach bread, but also serves classics such as lasagna, chicken parm, sausage and peppers and, of course, Italian-style pizza.

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Buzz Bait Taqueria | 1529 N. Wells St.

Pair a famous fish taco (or bowl) with a fruity margaritas to make a perfect night.

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The Vig | 1527 N. Wells St.

Enjoy an elevated brunch, dinner or the entire evening in this warm,elegant contemporary parlor. The deviled eggs, chicken and waffles and turkey burger are among the standouts.

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(Food photo’s via Tavi J.)





Fudge Pot | 1532 N. Wells St

Fudge pot has been crafting creations since 1963. From fudge, truffles, toffee, caramel apples, chocolate- covered apples, marshmallows, strawberries… they have it all!

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La Fournette | 1547 N. Wells St.

Start the morning here with Intelligentsia coffee and fresh French pastries. The menu includes baguettes and croissants, in addition to casual breakfast or lunch offerings. If you’re in the mood for something sweet, the macarons are magnific.

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Old Town Ale House | 219 W. North Ave.

With a jukebox full of smooth jazz, interesting… semi-inappropriate artwork, and draft beers on tap, this dive bar is a Chicago original. Stop in before or after a show at Second City, and if you’re there late, you might even get to grab a bag of hot tamales from the city’s Tamale Guy, who makes late-night stops at bars selling snacks.

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Suite Lounge | 1446 N. Wells St.

This intimate basement lounge specializes in strong martinis. Highlights from the extensive martini menu are the Blackberry Smash, the 007, and the Pop Rock (complete with real Pop Rocks candy!).

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(Photo via Tasha K.)

Benchmark | 1510 N. Wells St.

The freshest place to catch the game and grab a cocktail and a burger with friends. There’s always a weekday deal and on weekends brunch includes a build-your-own bloody Mary bar.

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(Photo via Jacqueline R.)


The House of Glunz | 1206 N. Wells St.

This refurbished space from 1888 is a five-generation old fine wine and spirit shop. Come in and enjoy brunch, chose your own drink, or get tips from the staff about spirits..

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Second City | 1616 N. Wells St.

Since its opening in 1959, Second City has produced some of the greatest names in comedy… Tina Fey, Amy Poehler and Stephen Colbert, just to name a few. With live shows every night on a variety of stages, have a laugh and see some of the comedy world’s up-and-coming faces.

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Chicago History Museum | 1601 N. Clark St.

The museum offers insights on what makes Chicago tick. You can be in and out in about an hour with a better understanding of Chicago’s past, and where it’s going.

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Old Town Oil | 1520 N. Wells St.
A shop full of unique olive oils and balsamic vinegars for cooking, dipping or even salad dressings. The staff can help you narrow down your choices before you purchase.

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(Photo via Keith G.)


The Spice House | 1512 N. Wells St.  

The spice specialist. Stop in just to enjoy the aromas, or to take home some seasonings and rubs for cooking.

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(Photos via Diana R. and Doug V.)

* All photos credited to company websites expect when noted.