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Old Town Neighborhood Guide

Chicago’s Old Town neighborhood is squeezed between the edges of Lincoln Park, Goose Island, and the Gold Coast, about a mile north of The Loop.

This cozy neighborhood of tree-lined streets and old victorian-era buildings oozes an old Chicago feel, from it’s well-heeled restaurants and taverns to its thriving theatre and performance scene. This affluent, historic neighborhood is notably home to one of only seven churches that survived the Great Chicago Fire, St. Michael’s Church.

The neighborhood is great for strolling around, one of the most dense and walkable in the city.

The Old Town Art Fair is one of Chicago’s most popular street festivals. Each June more than 250 artists display work of all mediums at the fair, which also hosts live music, a garden walk, and tours of the historic neighborhood.

Old Town is also home to a wide array of small independent boutiques, though you’ll also find familiar names and restaurants within its boundaries.

All of this adds up to what named the most coveted naeighborhood in the country in 2013, as measured by internet searches by zip code.  

Bars & Restaurants

Twin Anchors:  One of our absolute favorites tucked into a residential street in Old Town, where the ribs are so good that Frank Sinatra made it a regular stop.

Old Town Ale House:  One of the best bars in Chicago, frequented by the stars of Second City and loved by generations. If you’re going to stay in Old Town you have to stop in at least once!

Butch McGuire’s:  Technically not Old Town, but just outside the boundaries. This is a must-stop during the holidays, as you’ll be hard-pressed to find a bar that gets decked out for the season anything close to Butch’s. A staple for decades, it’s always packed in the evenings but is a great place for an afternoon soak as well.

Benchmark Tavern:  Huge garage doors open to the street at this lively social spot great for watching games or grabbing food.

Old Town Social:  A “sophisticated sports parlour, Old Town Social features a large bar and casual dining area. Since it opened to rave reviews in 2009, this bar has been high on the list of Chicago’s food and bar lovers.

The Fireplace Inn:  Famed for its BBQ and a solid burger menu, The Fireplace has been a neighborhood staple since 1969.

Intelligentsia Coffee:  A Chicago coffee roaster, Intelligentsia might just hook you in one stop. Try pour-over brews in a beautiful coffee house great for meeting friends or working away a morning.


Second City:  One of the best deals in the city. Hilarious improv and sketch comedy at the small theater where Saturday Night Live finds so much of its talent.

Up Comedy Club:  Stand-up, improv, sketch comedy seven nights a week from the Second City’s sister stage.

Chicago History Museum:  Become a true insider. Learn about the events and people that made Chicago what it is, and explore outstanding exhibits on photography, eras, and people.

Lincoln Park:  Just north of Old Town, Lincoln Park is one of the gems of Chicago. A vast park that is home to the Lincoln Park Zoo, the Peggy Notebaert Nature Museum, Green City Market, Alfred Caldwell Lily Pool, and the Lincoln Park Nature Boardwalk.


Public transit in Chicago is excellent, and although the systems are easy to use, using the CTA website ( or Google Maps for trip planning is always a good idea. Google Maps is very accurate for Chicago Public Transit - it’s what we use.  

A one-way train or bus fare is $2.25 per person. If you intend to use public transit multiple times throughout your trip, consider an unlimited 3 day or 7 day pass.  These are available at any CVS Pharmacy or Walgreens.

On the CTA Red Line Get off at (transfer to the Brown Line at Belmont or Fullerton):

  • Chicago: The Gold Coast, Water Tower Place, Hancock, and the Magnificent Mile.
  • Grand:  Navy Pier, Magnificent Mile,Riverwalk, Chicago Riverboat Architecture Tours
  • Monroe, Jackson:  Art Institute of Chicago and Grant Park
  • Harrison, Jackson, Roosevelt:  Grant Park
  • Roosevelt: Museum Campus, including the Shedd Aquarium, Field Museum, Adler Planetarium, Soldier Field
  • Monroe:  Millenium Park, The Bean, Pritzker Pavillion
  • Cermak/ Chinatown:  Chinatown
  • Fullerton:  Lincoln Park, DePaul, Transfer to Brown Line
  • Sox/ 35th:  U.S. Cellular Field

CTA Busses

Busses can be used to access a multitude of the Chicagoland area’s attractions, including Michigan Avenue. Google Maps has accurate directions for using the bus system.


You can usually flag down a cab quickly, but we also love Uber, a simple mobile app you can use to have a cab come right to your door. The app has clear pricing and allows you to split your fare with other riders.


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