10 Reasons to Move to Chicago from a Local

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Chicago is that friend who can be painfully Midwestern at times – always throwing in a  “sorry” at the beginning and end of every sentence, yet can jaywalk like a pro. You got tired of this friend complaining that there are no decent spots for Italian beef in the college town where you met. Italian beef elitism aside, this is the friend you admire because of their worldliness, outgoing nature, and ability to adapt to whatever comes their way. 

Chicago is just that – fun, cultured, and adaptable. Besides the obvious reasons like delicious food, outdoor concerts, and public transportation that is easy to navigate, Chicago has a lot more to offer. Here are 10 reasons to move to Chicago, from a Chicago local. 

1. Chicago has excellent colleges and universities

At universities like Loyola University, DePaul University, the University of Illinois at Chicago, and the University of Chicago, you can get the best of both worlds with a college experience while still being centrally located in a big city. 

2. Chicago is an ideal city for working from home 

Chicago is perfect for remote workers especially now that more and more companies are shifting to permanently remote work. When you are looking to change your environment and get out of the house once in a while, there are dozens of public libraries, cafes, and coworking spots to make your workdays exciting. Check out Spaces in the West Loop or spend your WFH day at the spacious Marshall’s Landing in the Merchandise Mart

3. You’ll find eclectic options for food 

via Girl and the Goat

From Michelin-starred restaurants and local favorites that have been around for decades, Chicago has diverse options to satisfy your every craving. You can visit the West Loop for trendy new restaurants, or spend time on Devon Avenue and try out authentic Indian food at Nepal House

Living in Chicago means constantly having the difficult task of choosing where to get a drink. For craft beer, head to Hopleaf in Andersonville. Lost Lake is Logan Square’s tiki bar, while Scofflaw is the neighborhood’s quiet, gin-focused corner bar. Wicker Park’s neighborhood tavern Sportsman’s Club serves up spirit-forward cocktails and River North has some of the best rooftop bars in town. And don’t forget about one of Chicago’s best-kept secrets, Hoosier Mama Pie Shop.

4. Chicago has the best entertainment 

Chicago is the perfect place to be if you are looking to be wowed by entertainment. There are musicals, ballet performances, shows at the Chicago Symphony Orchestra, and outdoor concerts with a view of the skyline at Northerly Island. These are just some of the many events you can find throughout the city at any time of the year. 

There’s no shortage of live music venues with great acoustics in the Windy City. Pilsen’s historic landmark, Thalia Hall, is a spacious, yet intimate music venue. Located in Lincoln Park, Lincoln Hall offers a wide selection of musical performances in an intimate setting. Its sister venue Schubas is housed in an old Schlitz brewery in Lakeview. The intimate, low-key music venue hosts a wide range of live acts, from indie to jazz. 

Historic, legendary, and beautiful, The Chicago Theatre hosts world-class acts including Broadway shows, comedy, and legendary musicians, with stunning sound quality to boot. Built in 1926, the Aragon Ballroom is one of Chicago’s premier live entertainment venues. The ornate, Uptown spot features extraordinary architectural design and aesthetics. 

Metro has been Chicago’s independent music venue for over three decades. The intimate, cash-only venue showcases national headliners and local up-and-comers. The quintessential Chicago music venue, The Vic Theatre is an oldie, but a goodie. Located in the Central Lakeview area, the luxurious five-story vaudeville house has perfect acoustics and nice sightlines from the balcony.

5. Chicago is a cultural hub 

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Living in Chicago, you are exposed to a world of various cultural backgrounds. It’s what makes Chicago what it is, and what has contributed to its standing as a world-class city. There is a lot to learn about the history and culture of the city, and about the origins of the many unique neighborhoods. Some museums where you can do that are: 

6. Chicago has free events throughout the year

Chicago can be expensive, especially when it comes to dining and entertainment. Thankfully, the city hosts hundreds of events year-round that are free and open to the public like the Chicago Jazz Festival and movies in the park. Each neighborhood also holds events like block parties, farmers’ markets, and live entertainment. 

7. There’s no shortage of parks and nature 

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When living in a big city can be too overwhelming at times, there are places you can retreat to ground yourself and get your dose of nature. The Chicago Botanic Gardens is a beautiful collection of parks and gardens, featuring a calming Japanese garden. The lakefront trail is perfect if you want to stroll by Lake Michigan and watch the boats on the water, and the 606 trail in Bucktown is a converted train line that marks nearly three miles of uninterrupted walking and biking paths. 

Millennium Park has ice skating in the winter and free concerts in the summer. Maggie Daley Park, a favorite for kiddos, is just a short walk over the BP Bridge. Lake Michigan provides 26 miles of shoreline with 18.5 miles of trails and green space for hiking, biking, and recreation. Chicago’s most popular public beaches include North Avenue Beach and Montrose Beach.

We can’t get through this list without mentioning the biggest tourist trap in the city, Navy Pier, which hosts everything from festivals to fireworks. One of the best ways to see the city’s architecture is from the water on a Chicago River cruise. Lincoln Park is home to The Lincoln Park Zoo (which is always free!), running and biking trails, and farmers’ markets. You won’t have to look far to find something fun to do when you’re living in Chicago.

8. Chicago is a travel hub

Being based in Chicago gives you proximity to both airports, Midway and O’Hare, one of the busiest airports in the world. You are a quick train or car ride away from the airport, and just a few hours on a plane to major cities in the United States.

9. It’s easy to find your community in Chicago

As cliche as it might sound, one of the reasons why Chicago is so great is that you do not have to worry about fitting in. You can find your community anywhere and surround yourself with like-minded people. Maybe you want to develop an academic cohort while you attend school or try something you have never done before, like an improv class at The Second City. Whatever it is, the people in Chicago are adventurous and welcoming.

10. Summers in Chicago are elite

Despite what you may think, you can survive the winters here. Winter offers some of the best-shared experiences, the Christkindl Market, ice skating at Maggie Daley Park, and sipping espresso martinis in a heated igloo rooftop tent.  

By April (or May in some cases…sorry in advance) you will come out stronger knowing you have survived your first winter in Chicago unscathed. 

Summer is arguably one of the best things about Chicago. The city quite literally comes alive with entertainment, music, patio dining, and beautiful skyline views. You will see that the winters are worth it once you spend your first happy hour by the Chicago riverwalk

Chicago’s biggest food festival, Taste of Chicago is a five-day fest held in Grant Park in mid-July. The fest features food booths along the lakefront, rotating pop-up restaurants, local food trucks, and Celebrity Chef du Jour dining tents. Windy City Smokeout brings BBQ, bands, and beer to the city every summer. 

Pitchfork Music Festival brings three days of alt-rock, rap and hip hop, electronica, avant-garde rock, and hardcore punk to Union Park each July. And everyone is familiar with Lollapalooza, held in Grant Park at the beginning of August.

Final thoughts

Locals have heard all of the reasons why Chicago isn’t the place to be. Some choose to focus on the crime rate, which is not completely unlike any other major city in the US. Some believe the city is only livable during the summer months, which is downright untrue. 

Of course, every city has its faults, and locals here acknowledge more than anyone that improvements can be made throughout the city such as increased safety, more reliable transportation, affordable housing, and increased funding and protection for communities of color, just to name a few. Despite its flaws, there are countless advantages to living in Chicago, many of which make the city stand out. 

Chicago has long been labeled “the second city,” but in reality, all local bias aside, Chicago is second to none. How’s that for turning a negative connotation on its head? 

If you spend any time here and decide to move to Chicago, you will see that it is an ideal place to live and create new memories. 

With endless delicious dining options, shop ‘til you drop destinations, enthusiastic sports fans, and culture galore, there’s really no reason not to move to Chicago! Check out thousands of apartments for rent so you can snag a place before you even move there.


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