Explore the Windy City (But Watch for Falling Ice) - An Insider's Guide to Renting in Chicago

From Lake Shore Drive to the O’Hare Airport, the city of Chicago is a study in diversity, resilience, and culture. If you’re making the move to Chicago, or already live here and want to get to know it better, I’m your local expert who can assist. Here’s what I want you to know about the Windy City.

Current Rental Pricing for Apartments in Chicago

Current Rental Pricing for Homes for Rent in Chicago

A City with a Fiery History

To truly know a city, you need to know its history. The mob, a cow-inspired fire, a bitter rivalry with St. Louis, and even reversing the flow of a river are all part of the history of Chicago, and some of it’s quite fascinating.

The lake, river, and railroad are what put Chicago on the map, which doesn’t surprise me because they’re still vital to our city. The city itself was officially incorporated in 1837, but prior to that, it had already been growing as a vital transportation hub. The city grew steadily, and buildings were thrown up rapidly, until the fateful Chicago Fire. Legend has it that Mrs. O’Leary’s cow kicked over a can to start the fire, but natives know that’s just a fable. Still, it makes for a great story out of a devastating event that destroyed most of the city.

The Great Chicago Fire showed one thing about Chicagoans – we’re resilient. With 100,000 people left homeless, the city was forced to rebuild quickly (but with better fire safety in mind, of course). News spread around the globe, and we ended up getting a donation from the United Kingdom. Today, you can visit the Chicago Public Library to see how we put the money to good use.

Another interesting tidbit from Chicago’s history is the time we decided it would be a good idea to change the flow of the Chicago River. In 1887, sewage and pollution were making the drinking water in the mouth of the Chicago River toxic. So, instead of cleaning it up, we just moved it. Engineers reversed the flow, and our dirty water started pouring into St. Louis via the Mississippi. Have you ever wondered why the Cubs and Cardinals have such a bitter rivalry? It all started with making our dirty water their problem.

Sports are a major part of life here, too, and part of our history. We’re one of only a few cities to have two major league baseball teams, the White Sox and the Cubs. The Cubs are one of the eight original baseball teams and got their start in 1889. A visit to historic Wrigley Field is a must for any sports person or history buff in the city. Of course, maybe you prefer the White Sox, and if you do, I’ll forgive you, but my love for the Cubbies runs deep.

Our history wouldn’t be complete without a nod to the mob. Al Capone made his home here, and he continues to live on in infamy through museums, restaurants, and shops dedicated to his history. The 1920s during his reign were a bit rough, but like we always do, Chicago’s resilience got us through.

Getting Around While Staying Sane in Chicago

Chicago’s traffic is legendary, but getting around the city isn’t too bad if you ditch the car. Our robust transportation system, complete with commuter rail and the L-train, as well as multiple bus lines, will get you anywhere you need to go in the city and its suburbs. Most Chicago neighborhoods have multiple bus stations and L-train stops.

So how can you navigate like a native? First, now your colors. The L has eight colored lines, the Red, Blue, Brown, Green, Orange, Pink, Purple, and Yellow lines. Each has a specific area of the city it serves. For instance, the Green Line is a rapid train that runs between the suburbs of Forest Park and Oak Park to the South Side, then through downtown and the Loop. Once you get to the main neighborhood you want to visit on the L, you’ll use the bus for shorter drives within that area. While it’s hard to learn all of the lines, you’ll find that you catch on pretty quickly to the routes that take you to your favorite spots.

If you need to drive and wish to avoid rush hour, stay off the main roads between 6 and 10 AM and again between 3 and 7 PM. Expressways are usually faster routes, but you’re not going to avoid traffic at these times, no matter which road you choose.

The Lakeside Life

Chicago’s location on the shores of Lake Michigan is what made it grow into the powerhouse that it is today. Those who call Chicago home know the impact of the lakefront. There’s nowhere more beautiful for wedding, prom, and family photos, yet those lake-effect snowstorms are no joke. It’s the center of tourism, industry, and history for the city.

So, how best do you experience the lakefront? If you’re not fighting weather brought on by the lake, you may want to enjoy the views with a bike ride or run on the Lakefront Trail. Do you have a special dinner? Any of the restaurants along the lakefront provides upscale dining options. I’m particularly fond of the food and views at Waterveiw, which is on the 15th floor of Wolf Point Plaza. For a quick bite while watching the boats on the water, the seasonal Waterfront Café in Edgewater is a great choice that’s open seasonally and has a large outdoor terrace.

It’s Showtime!

Ah, the theater! The local Broadway scene in Chicago is to die for! While it’s not New York City, Chicago’s theater scene is pretty close. A theater buff myself, I love to visit the Cadillac Palace Theater or the James M. Nederlander Theater for a live performance. Even if I don’t have tickets, strolling through the theater district after dark, when the marquees light up, triggers feelings of joy.

One of the perks of living here is the chance to score discounted tickets to plays (and avoid those online charges). Many of the theaters will also offer rush tickets, which are day-of tickets at a discounted price. If you have flexibility in your schedule, you can save quite a bit by taking advantage of these offers, but line up early to have a chance to snag a rush ticket, especially when Hamilton or Hadestown come to pay a visit.

It's Time to Get an Education

Life in Chicago’s not all just fun and games (go Cubs!). There’s also a rich educational history here. The museums in Chicago are legendary, with collections that people travel from all over the globe to explore. The Field Museum, with its iconic T. rex display, is one of the best, but I’m particularly fond of the architecture and displays, especially the holiday display, at the Museum of Science and Industry.

You can’t forget the Adler Planetarium, the Peggy Notebaert Nature Museum, and the Shedd Aquarium when planning out an educational day in Chicago. I’ve found that you can spend a full day at each of these, but my favorite way to spend an afternoon is with a visit to the nature museum at 2 in the afternoon, when they release the butterflies.

Higher education also has a major presence in Chi-town. The city has 28 public and private universities, including well-known names like Northern Illinois University, Northeastern Illinois University, and Illinois Institute of Technology. You’ll find programs and degrees in any field imaginable are available close to home in Chicago.

Watch out for Falling Ice (for Real)

One of my earliest memories of Chicago is from before I lived in the area. I was visiting with some friends on a high school trip in the early spring. Everywhere we looked, signs said, “Watch for falling ice.” We were in the process of making fun of these signs, when a falling chunk of ice smacked me in the head.

Let me just say, I was seeing stars.

In the winter, Chicago’s skyscrapers and the lake-effect temperatures can create hazardous conditions. When those signs come out, take them seriously! A chunk falling from 40 stories up will make an uncomfortable impact on your head.

This somewhat embarrassing story points out another fact about life in Chicago. The weather can be unpredictable. The city’s earned its nickname of “Windy City” for a reason. You’ll find the winds coming off the lake to be quite intense, and they just kind of swirl around in the midst of our skyscrapers. In fact, if you take one of the riverboat architectural tours, you’ll learn about the lengths the architects had to go to ensure these skyscrapers wouldn’t blow completely over. Did you know one of our buildings actually has a completely empty floor? The 83rd story of the St. Regis Chicago is fully open and allows the winds to pass through so the building can stand tall without swaying.

Those winds can also bring in sudden lake-effect snowstorms and unexpected rain, so always be prepared for a shift in the weather.

Where to Go if You’re Not a Tourist

Chicago’s full of attractions, but which ones are the ones locals really love? While a trip to the Art Institute of Chicago (say hi to the lions outside) is definitely worthwhile at least once, you might find that the antics of the animals at the Lincoln Park Zoo are more entertaining. This particular Chicago icon’s also free, so you can come and go as you like.

In my opinion, you can skip “The Bean,” AKA Cloud Gate. It’s always surrounded by tourists. However, right next to the iconically strange sculpture is the Pritzker Pavilion. This outdoor venue hosts music festivals, concerts, and cultural performances throughout the year. Even if you don’t stop, you can walk by to hear live performances while you explore other offerings of the city.

What about shopping? You’ll find upscale shops along the Magnificent Mile and the Gold Coast, but I prefer the deals at Chicago Fashion Outlets. You’ll also find boutiques scattered throughout the city for unique shopping options.

Chicago’s a busy and noisy city. Sometimes, I just want a quiet place. Of its many gardens, the Garden of the Phoenix, a Japanese garden in Jackson Park, is one of my favorites. It’s also historic, dating back to 1893. But I just like to stroll and take in the beautiful displays as a way to be quiet and take a break from the vibrant city life.

Dine Around the World Without Leaving Home

Ah, food. This city has it all. You’ll find most cultures represented in the culinary scene. Do you want Asian? Head to Chinatown. Is Mexican what you’re craving? Taco stands and authentic restaurants are everywhere. My favorite flavorful option is Mercadito in River North, but Little Village also has multiple options, as well as colorful Mexican shops.

Maybe you want something a little more exotic? In West Ridge, you’ll find Indian and Pakistani restaurants. In fact, Devon Avenue has been named “Little India” because of the culinary options here.

If your exploration of the city takes you to the West Loop, be sure to stop at Greektown. This small area of the neighborhood has many traditional Greek eateries, bakeries, and bars.

Finally, don’t forget a visit to Little Italy to sample authentic Italian dishes! Of course, you’ll want to stay away from Italian-style pizza because you can’t really enjoy pizza in Chicago unless it’s Chicago-style deep dish. Like everything else we do here in Chicago, we do pizza a little differently. The sauce sits on top of a pile of cheese, rather than underneath it, in this dish. My favorite local spot for these flavorful pies is Giordano's. Yes, I know it’s technically a chain, but they’re the best in my opinion.

If you can’t decide what type of food you’re in the mood for, then the Chicago French Market has you covered. While it’s not gourmet, this international food court is quite authentic. You’ll find most flavors represented here. I know I prefer this more casual setting.

Sure, Chicago’s traffic is a bear, and our weather can change on a dime, but the rich cultural heritage, vibrant performing arts options, competitive sports teams, and interesting history make this city one I love to call home. The longer you live here, the more it becomes part of who you are.