After living in Chicago since 1989, I’ve built up a long list of places I keep coming back to.
Some are restaurants I’ve loved for years. Others are parks, trails or shopping streets that I still recommend to clients and friends when they ask what makes Chicago feel like home.
I also share many of these neighborhood favorites on Cindi and the City, where I highlight the restaurants, amenities and local spots I actually enjoy throughout Chicago.
For Pizza
Pequod’s
There’s plenty to debate when it comes to Chicago pizza, but Pequod’s is still one I recommend.
I lived nearby for 10 years, and we used to go there before it became nearly as busy as it is today. I still recommend it when someone wants a pizza experience that feels distinctly Chicago. The sauce is one of my favorite parts, and I haven’t found anything quite like it elsewhere.
For an Old School Chicago Dinner
La Scarola
La Scarola is one of those restaurants that still feels like Chicago to me, and the food also reminds me of what I grew up eating in Ohio.
I’ve been going there for years and love the menu, especially the greens and beans. To me, seeing something like that on the menu is always a sign that you’re in a truly old school Italian restaurant. It’s the kind of place I send clients when they want something classic rather than trendy.
For Bucktown
Club Lucky
Club Lucky has been one of my longtime Bucktown favorites.
I love the atmosphere, location, food and service. Their homemade pasta and ravioli are always worth ordering, and the bar has such a charming vintage feel. It’s the kind of place that has kept its personality over the years.
For a Special Dinner
Le Colonial
When I want somewhere that feels a little more special, Le Colonial is still one of my favorites.
I usually recommend it for the seafood, but the atmosphere is a big part of why I love it. The specialty cocktails are another favorite, and it’s one of those longtime Chicago restaurants that still feels beautiful every time you go.
For Walking Chicago
The Chicago Riverwalk and The 606
Some of my favorite Chicago recommendations have nothing to do with food.
The downtown Chicago Riverwalk, which runs along the Chicago River toward the lakefront, is one of those places that reminds you how beautiful the city can be, especially in warmer weather. I love the views, the people watching and the fact that you can stop for food or a drink along the way.
The 606 is completely different. It gives you a great way to walk or bike while seeing another side of the city through Bucktown, Logan Square and Humboldt Park.
When clients are new to Chicago, I like recommending both because they show two very different sides of the city.
For Parks I Keep Coming Back To
Lincoln Park Zoo and Horner Park
Lincoln Park Zoo is one of those Chicago places I enjoy in both summer and winter. ZooLights is still one of my favorite Chicago traditions.
Horner Park is another favorite and one I’ve spent countless hours at over the years. We were there for basketball, Lane Tech football games, baseball, softball, sledding and plenty of time on the playground.
The park has also become even better connected to the Chicago River. Its natural area runs along the North Branch and includes trails and river access, so you can often watch canoes and kayaks passing by.
These days, my dog Archie is a particularly big fan of Horner Park.
For Shopping and Wandering
Southport and Armitage
I still love both Southport and Armitage when I want to shop, grab something to eat or just walk around.
Armitage is especially nostalgic for me because it was one of my old stomping grounds when I lived in Lincoln Park. I still stop at Art Effect for gifts, and Southport is another favorite because you can shop and then easily grab dinner somewhere like Coda di Volpe or Ella Elli.
Why I Share These Places With Clients
One of the things I enjoy most about real estate is helping people understand what it actually feels like to live in a neighborhood.
A house matters, but so does where you grab dinner, where you walk on a Saturday morning, which park you use and which neighborhood streets you keep coming back to.
These places have made Chicago feel like home to me for decades, and they are still the places I find myself recommending today.
For more of my neighborhood favorites, I also share local restaurants, shops and things to do on Cindi and the City.
