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11 Hidden Gems & Things to Do in Old Town Chicago

Although the actual location of Old Town is heavily debated, there is one thing everyone can agree on.  Old Town Chicago is filled with an abundance of community, pride, and a sense of togetherness, in a world that sometimes isn’t filled with such.

Sitting two miles north of the heart of downtown, the location of Old Town Chicago cannot be beaten. Both the original and modern-day borders are split up by North Avenue and on the west side, North Halsted Street.

Here you will find a list of things to do in Old Town and surrounding neighborhoods.  Let’s find some hidden gems for your next Chicago adventure!

Best Things to Do in Old Town, Chicago

1. Jeni’s Splendid Ice Cream

Ice Cream Cone

I’m just going to start with ice cream…because why the heck not?  I had the pleasure of tasting a scoop of their famous ice cream in a waffle cone when I was in Chicago. This was hands down one of the best ice creams I have ever tasted before. In fact, all of the people I was with said the exact same thing.

There are eight different locations in the Chicago area and more than forty locations across the United States.  Old Town was lucky enough to have the fourth location out of eight installed in 2017. And they’re still expanding locations across the Chicago area.

Be prepared to stand outside in a line anywhere between the months of March through October, it’s just that good. But the wait is well worth it.  Inside, a brightly lit compact waiting area holds the massive open freezer containing gallons of that sweet, sweet ice cream.

People who are lactose intolerant…do not fear! They have alternative options for everyone and trust me it tastes just as good. This ice cream shop is good at making sure to put a cherry on top after spending your day in Old Town.

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2. Old Town Ale House

Old Town Ale House
Old Town Ale House Facebook

Starting back in 1958, this old-timey dive bar has loads of character inside. Bruce Elliot’s art lines the walls with comedic and satirical references to United States politicians. (Not for the faint of heart!) Anthony Bourdain once called this the best dive bar in Chicago.  Ask anyone who lives in Chicago and they will most likely agree (or maybe not).

But one thing is for certain if Anthony Bourdain tells you to go somewhere, you go. This dive has not been swept up with the gentrification of the surrounding neighborhood.  The bar has a certain je ne sais quoi and is recognized for sticking to its roots. Make sure to leave the credit cards in the wallet, cash only at Old Town Ale House.

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3. Topo Gigio

Topo Gigio Interior
Topo Gigio / Facebook

This very classic Tuscan-style Italian restaurant has the charm and class you would expect from an old-style establishment in Old Town. This restaurant is located in the heart of Old Town, so getting there is an easy trek from wherever you’re staying.

This charming spot has a large indoor seating area and also has a magnificent back patio for seating in the summer.  This has been the local favorite spot for over twenty-five years! Grab a bite to start with steamed little-neck clams, raw filet mignon, or bruschetta served with rustic bread.

Specializing in pasta dishes, this quiet establishment has an extensive wine list; as well as a variety of pasta and seafood options.  Finish the night with a slice of their delicious cheesecake.

The back patio can be rented out for wedding events. With its award-winning menu options, Topo Gigio is also available for catering. Wedding parties or private events are set beneath the perfect background under the garden canopy and brick walls that surround the patio.

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4. Old Town Art Fair

Entrance Sign to Old Town Chicago Neighborhood

Who doesn’t love a good art fair?  Especially on a day when the sun is shining and everyone is in a good mood. This should definitely be on your list of things to do in Chicago for the weekend.

This annual art fair has been held for over seventy years and continues to grow with support each and every year. Held on the second weekend of June, this art fair is a must for artists and art collectors alike.

Each year people from all over the country come to attend this tradition. It sure has come a long way from the few hundred people that would be in attendance in the very beginning! Nearly 300 artists are asked to participate every year, drawing crowds of more than 30,000 people annually.

Live music, food, and drink are always in abundance.  Make sure to bring your walking shoes, because this event takes up a good chunk of the Triangle, so parking is extremely limited, even from many blocks away.

This doesn’t deter art collectors from coming, as this fair is a chance to score some very limited pieces of art that are otherwise unavailable to the public.

5. The Second City

The Second City Entrance
management / TripAdvisor

Possibly considered one of the most famous comedy clubs in the world, specifically improv, The Second City has given rise to a number of stars. This list includes but is not limited to, Stephen Colbert, Tina Fey, Larry Joe Campbell, and John Belushi.

There are many shows to choose from during any given week on a regular basis, but as we all know: check the local listings for updates regarding show times and availability.

The Second City has grown significantly throughout its lifetime, and now offers classes and even college-level courses in comedy and the art of being a comedian. This comedy club offers a lot more than just a good laugh or two.

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6. Old Town Aquarium

Old Town Aquarium Exhibit
Old Town Aquarium / Old Town Aquarium

Are you into collecting exotic fish or thinking about starting an aquarium?  Look no further, Old Town Aquarium is a one-stop shop for all your aquarium needs. The owner of the aquarium has logged hundreds of hours of dives on reefs throughout the world.

This gives him insight as to how to handle these exotic fish, and how what their behavior is like in their natural habitat.  Many of these fish can be found in the Old Town Aquarium.

This aquarium is special due to the fact that the owner has been around the world, and has studied the impact it has on the habitats of these exotic fish. Old Town Aquarium takes pride in responsibly sourcing exotic species.

The owner and his employees are dedicated to helping both the novice and the expert in building their perfect aquarium.  They also make sure to keep up with the ever-changing aquarium maintenance, and science of collecting, participating in education, and annual marine aquarium conferences.

Check out the fully-stocked aquarium today for all your salt and freshwater aquarium needs, or just stop by to view all of the beautiful species of fish, you won’t be disappointed.

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7. St. Michael in Old Town

St. Michael Church

This church was originally built for German immigrants that were outcasts in the original Old Town, and the town’s main church St. Joseph’s was overcrowded. When completed in 1869, it was the tallest building in Chicago before the Chicago Board of Trade Building was completed in 1885.

The building was one of the seven buildings to remain standing after the Great Chicago Fire of 1871 roared through Old Town.

Serving nearly 700 households in the Chicago area, St. Michael’s is a nationally and internationally recognized church due to its large catholic influence around the world.

Even if you aren’t a religious person, the architecture alone is worth seeing, as the building still has remnants of its past history when it was first built. It is said to be true by locals: “If you can hear the church bell of St. Michael, you’re in Old Town.”

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8. Chicago History Museum

Chicago History Museum Building
Thomas Barrat /

If you are a history buff, this section is for you.  This is another family-friendly option on the things to do in Old Town Chicago, in one of Chicago’s safer neighborhoods.

Relying on Chicago’s rich history and culture, the museum offers in-depth looks at how Chicago was formed, and reformed after the Great Chicago Fire.

Explore what it was like to live in Chicago during the 1800 and 1900s.  There are some very interesting historical facts and figures that are important to be remembered. To see what online exhibitions are showing now click here.

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9. Hotel Lincoln

Hotel Lincoln Building
Hotel Lincoln /

Depending on who you ask some will tell you Hotel Lincoln is in the Lincoln Park district, and some will tell you it is still located in Old Town. I’m not here to pick sides! Whether you are staying in Lincoln Park or Old Town you always have the option to stay at Hotel Lincoln.

Centralized enough that Wrigley Field is only located two and a half miles away, Hotel Lincoln is the perfect place to rest your head during your adventure throughout Chicago.

Within walking distance lies a variety of different shopping, dining, and family-friendly activities. There is art by local artists that hang on most walls throughout the hotel.  The boutique feel gives a perfect mix between “vintage and contemporary vibes” not to mention the view of the city on the higher floors.

Lincoln Hotel is the perfect place to rest after a long day of exploring the concrete jungle and planning your next step on the list of things to do in Chicago.

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10. The Sono Chicago

The Sono Living Room
The Sono Chicago

This newly built high-end boutique bed-and-breakfast offers everything you would expect from a bed-and-breakfast. Located in the heart of Old Town, The Sono is located on a tree-lined street in a friendly, charming neighborhood.

This three-story newly built house is a perfect getaway from the downtown hustle and bustle. The rooftop patio offers views of the city, accompanied by a built-in firepit.  Continental breakfast is the obvious choice before your day in Old Town starts.

The newly designed kitchen and three-story house make you feel as if you have stepped onto the scene of a movie. The picturesque open-island kitchen with long hallways and steep stairs leading up and down makes your visit quite luxurious.

This highly recommended bed-and-breakfast is sure to make your experience in Old Town Chicago a pleasant memory for years to come.

11. Floating World Gallery

Floating World Gallery painting
Floating World Gallery

Bill and Roberta Stein have created something very special. Starting off in the spare bedroom of their home, then expanding to an 8,000-square-foot gallery with office space, they turned their love for Japanese art into something truly amazing.

Something that started as an innocent collection over thirty years ago, has grown into something significantly larger.  They received their first woodblock prints as a wedding present, and from then on their love for Japanese art and the artists who create these pieces grew.

Promoting works of contemporary masters of Japanese art, their collection grew to where they could open gallery space.  Now, this is one of the largest galleries of fine Japanese art in the entire world.

With an extensive number of contacts in the art world, Floating World Gallery takes pride in working with the artists, their families, and estates in order to source these fine pieces of artwork to the United States.

They actually supply a number of art dealers around the country. Their extensive online catalog is always available.  And if there is something you cannot find, the gallery is more than willing to use its vast network to help with your quest to find the most exclusive, and exquisite Japanese art on the market today.

Whether it be exploring food, the city, or all of the above, I can’t recommend Old Town enough.  There is a quaint charm that is unescapable and will entice you time and time again. Go and find the hidden gems that lie in the heart of Old Town Chicago!

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