The fabulous Heather, a longtime friend of Dwellsy and an apartment dweller in Chicago, was generous with her time and got on a Zoom with our team recently.  With pleasure, here’s Heather’s list of seven things to love about Chicago from the South Side to the North Side.

1. Street festivals

The first thing on Heather’s list is the legendary street festivals of Chicago, and we at Dwellsy can attest to how incredible these are.  Across Chicago, in virtually every neighborhood, a different street fest is held each year. A street is shut down for a few blocks and neighbors come out of their apartments to celebrate summer in epic fashion.  

These fests, they come in every theme you can possibly imagine: food fests, wine fests, craft fests, book fests, beer fests, flower fests, art fests, renaissance fests and more.  Whichever you choose, make sure you wear sunscreen (yes – that’s from Chicago too), bring a hat, and prepare to meet friends and make merry.  

Heather’s recommendations?  The 57th Street Art Fair is a wonderful and eclectic fair that features amazing art in a historic neighborhood and the Printer’s Row Lit Fest is the best book celebration going.   

chicago street fair

2. Lakefront 

It’s not called the Third Coast for nothing…Chicago’s Lake Michigan frontage is a true treasure.  First time visitors to town are often shocked by the color of the water – an exceptional aqua that seems more appropriate to the Carribean than to the Midwest.  Along this amazing coastline, Chicago has built parks, trails and other amenities that, frankly, blow the mind.  

For an amazing day on the Lakefront, Heather recommends that you start at the southern-most end of the city where you can enjoy a round of golf by the water, ride horses or host an event at the South Shore Cultural Center (where Presidents have gotten married!).  From there, you can wind a full 18.5 miles north by bike or on foot, seeing marina, wildflowers, public art, more golf, restaurants, bars and stunning beaches.  So many things to do and enjoy!

3. Riverwalks 

It’s been a long time since Mayor Daley (the second one) decreed that all buildings built along the river had to provide public access to the river, but it turns out to be one of the smartest long term urban planning decisions ever made.  From its sad, decrepit state a few decades ago, the riverfront, and the riverwalks along them, have turned into one of the gems of the city.  

Heather is particularly fond of the Riverwalk along Wacker Drive in the heart of the city, from Merchandise Mart to Navy Pier.  Along this stretch, there is a winery that hosts concerts, you can rent kayaks to take out on the river, there are Belgian Fries, and even an Irish Pub.  And, on long summer evenings, they even project public art on the Merchandise Mart for all to see.  

chicago riverwalk

4. Historic neighborhoods

Chicago has a rich history full of colorful characters and firsts for the U.S., and one of the best ways to experience that history is to explore its many neighborhoods.  Heather treasures the cultural heritage and evolution of Chicago neighborhoods in particular.  

For example, she filled us in on the fact that Pilsen, which today is known for its many hispanic residents, actually got its name from being a Czech enclave.  Heather recommends that as you look around Chicago for your next home or apartment to rent, you do some research to understand how each neighborhood got its name and how it ended up making sense that you find Polish-Korean fusion restaurants in Bridgeport, for example.

5. The food 

Heather is not shy in describing Chicago as the best food city in the nation, and indeed as several Dwellsy team members have lived there, we can vouch for her justifiable pride in the food scene.  First, the variety is amazing – you can get nearly any cuisine you’d like, from nearly anywhere in the world. Chicago’s cultural enclaves have imported food from everywhere.

And, it’s not just that you can get anything you want – when you find it, the quality is incredible.  The chefs are like gods, tracked by many Chicagoans like sports stars get tracked in other cities. This is a place that truly cares about good food, so if you do too, then maybe you’re meant to live in Chicago.  

Lastly, on the food…Heather is very clear that ketchup on hotdogs is an abomination and deep dish pizza is the finest pizza.   If you’re moving to Chicago, you should get used to that perspective – Heather’s got lots of company on those two perspectives.

6. Weather

Yes, Heather is citing the weather as one of the best things about Chicago – a controversial point of view, perhaps?!?

Don’t worry about Heather one bit – she’s got the goods to back it up.  

She’s a huge fan of all four seasons in Chicago.  The delight of watching the city bloom in the spring, the way Chicagoans explode out of their apartments and homes in the summer, the long, luxurious fall (perfect weather!), and the plethora of things to do in the winter – even when the cold really howls in across the lake.  

When it’s cold out, Heather recommends finding an igloo along the riverwalk with a loved one, a visit to one of the winter markets or a trip to one of the many skating rinks.  Maggie Daley park even has an ice skating trail!

7. People 

There’s nothing quite like good old midwestern nice, and Heather felt it was appropriate to end with this, because in Chicago, the people really do make the city.  

In Heather’s view, regardless of whether you’re meeting people on a fun-filled summer afternoon or during tough times – Chicagoans are genuine, kindhearted people who are all in it together.  They rally around each other, take pride in their city, and even give directions to lost tourists on the street. Can you imagine a nicer group?

That’s it.  We’re moving.

Chicago sounds too good to be true.  Time to look for a place!

Fond of Chicago but not sure if it’s the place for you? Check out our other local guides here. Here at Dwellsy we are determined to help you find the right rental for you.