Top 5 Instagrammable Places in Old Town Chicago

March 20th, 2018 by: relatedchicago

Where’s the best spot for a selfie? Where can you find a cocktail that really speaks to your followers? Which mural will make the perfect backdrop for a pic? Old Town’s an Instagrammer’s dream destination. Old world meets new in this near north side neighborhood. With historic architecture and vibrant culture, Old Town offers a multitude of Instagram-worthy photo opportunities.

1. The Old Town Signs

These beautiful iron signs (or gates) can be found at Wells/North Avenue and Wells/Division Street. Both invite tourists, shoppers and neighborhood residents to take a stroll through iconic Old Town. The signs were erected by The Old Town Merchants and Residents Association as a show of commitment to the community and its residents. If you want to show your followers that you’ve arrived, snap a selfie under one of the Old Town signs.

2. Second City

Second City is a comedy institution in Chicago. The gem of Old Town’s entertainment venues, Second City’s improv shows are unforgettable. Comedians from around the country come to hone their skills at the famed theatre and improv school. Tina Fey, Julia Louis-Dreyfus, Stephen Colbert, Cecily Strong and more of your comedy favorites got their start at Second City. The theatre itself makes for a great photo for your Instagram. But, we recommend getting a selfie with one of the performers after a show. They might be famous one day.

3. Alinea

Alinea changed the way the world thinks about food and fine dining. Chef Grant Achatz put Chicago on the map as a culinary city after opening Alinea in Old Town. The restaurant ushered in a new genre of cooking called Molecular Gastronomy. Achatz’s playful, inventive dishes are dying to be Instagrammed. The dishes at Alinea are some of the most visually exquisite in the world. A video of you eating an edible balloon would garner some likes. Is food art? Are selfies art?

4. St. Michael’s Church

Old Town’s Historic District or Old Town Triangle features some of the most stunning architecture in all of Chicago. St. Michael’s Church is a perfect example of Old Town’s historic importance and charm. After the Chicago Fire, Old Town and Chicago as a whole were almost completely destroyed. St. Michael’s Church survived the fire (although heavily damaged) and is one of the few buildings to retain its mid 19th Century design. For an Instagrammable pic, put your phone low and aim its camera upward to catch the towering spires of St. Michael’s Church.

5. The Fudge Pot

Serving the Old Town community since 1963, The Fudge Pot proves a sweet ending to a day in Old Town. Pucker up with a piece of homemade candy and share it on your Instagram. Everyone loves chocolate! This cute fudge shop tastes as sweet as it looks. If you’re looking to capture Old Town’s neighborhood vibes, look no further than The Fudge Pot.


If you’re an Insta-star already, you know that Old Town has a lot to offer. A setting for visually stunning and even breathtaking photos can be found around every corner. Brownstones overgrown with ivy, restaurants with edible art, comedians who’ll make a funny face are all waiting for you to snap their photo. Old Town is definitely one of Chicago’s most picturesque neighborhoods.

Latest News About

  • Related Realty Favorite Holiday Traditions

    We asked the Related Realty team to share some of their favorite holiday traditions during this time of the year. We hope this list inspires you to make new memories and start a few fresh family traditions that you’ll look forward to year after year. “The first family member to find the pickle hidden in the Christmas tree got an extra present.” –Lucas M. “Setting up the family Christmas tree and another mini special tree in my daughter’s room.” – Alex H. “My family and I love to bake together […]

    Related Realty Favorite Holiday Traditions
    View Detail

Looking to Buy or Rent a Chicago Property?

Let one of our professionals assist you Schedule a Call

subscribe

  • Subscribe now to get daily updates
  • * Required Fields
We are processing your message...
Please wait while we create your document