20 Signs You Live in Chicago or Need to Move There

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Updated on May 4th, 2022

Reading Time: 9 minutes

We asked three Redfin real estate agents in Chicago to tell us what it’s like to live in the Chicago. Do people actually eat deep dish, have mustaches and steer every conversation toward “Da Bears”? Redfin agents Alex Haried, Stephanie Brimo and Cynthia Tobisch helped us find out. Here are 20 signs you’re a Chicagoan at heart – or that you should move to Chicago soon.

1. The Big Ten is king on Saturdays – and you wear your jersey to prove it.

Chicagoans who can’t make the drive up to Camp Randall Stadium will be sure to pack into their local Wisconsin bar. Photo credit: Stephanie Caine, Wikimedia Commons
Chicagoans who can’t make the drive up to Camp Randall Stadium will be sure to pack into their local Wisconsin bar. Photo credit: Stephanie Caine, Wikimedia Commons

“Chicago is a Big Ten town,” Haried says, “It’s the nearest large city to a lot of the traditional Big Ten schools, like Wisconsin, Iowa, Michigan, Michigan State and of course Illinois and Northwestern. On football Saturdays, birds of a feather flock together. Local bars fly flags of a particular school. For example, you’ll have an ‘Iowa bar’ packed to the gills with yellow-clad alums, next door to a Wisconsin bar, also packed with rabid fans. Particularly in Lakeview, it’s not uncommon for three or four school-themed bars to be on a block.”

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2. You have a favorite Rick Bayless restaurant.

Masa Torpedos, served at Rick Bayless’s Frontera Grill. Photo Credit: Conrad and Peter, Wikimedia Commons
Masa Torpedos, served at Rick Bayless’s Frontera Grill. Photo Credit: Conrad and Peter, Wikimedia Commons

“When people think of Chicago food, they think of hot dogs, deep dish pizza and Garrett’s popcorn. We’ve got so much more,” Brimo says. “Celebrity chef Rick Bayless lives here – he has three different restaurants in the city. Local restaurateur Grant Achatz is a national leader in molecular gastronomy. The inventive restaurants along West Randolph Street are incredible – as good as any you’ll find anywhere in the country.” Explore more foodie approved spots in our Chicago city guide.

3. You left your heart in Oak Park.

The Nathan G. Moore House, designed by Frank Lloyd Wright. Oak Park, Illinois.
The Nathan G. Moore House, designed by Frank Lloyd Wright. Oak Park, Illinois. Photo: victorgrigas, Wikimedia Commons

Oak Park has 25 Frank Lloyd Wright structures, including his home and studio, as well as Unity Temple,” Tobisch says. “Walking along a regular residential street and seeing so much amazing architecture – it can take your breath away.”

4. Navy Pier just annoys you.

Photo: David Bjorgen, Wikimedia Commons
Photo credit: David Bjorgen, Wikimedia Commons

“It’s a tourist trap,” Brimo says. “It’s crowded and there’s not really much to see. The only native Chicagoans are the people who work there. I’ve been to Navy Pier maybe twice – and that’s pretty common among locals. Unless you’re a Shakespeare buff – it’s home to the Chicago Shakespeare Theater – you’re going to stay away.”

5. Summertime: You go to a festival every. single. weekend.

Lollapalooza in 2011, Le Butcherettes performing. Photo credit: Strongmendie, Wikimedia Commons
Lollapalooza in 2011, Le Butcherettes performing. Photo credit: Strongmendie, Wikimedia Commons

“Summer is the best season in Chicago. The weather is usually fairly mild, everyone’s active and enjoying Lake Michigan, and there are tons of music and street festivals, big and small,” Haried says. “Lollapalooza is the biggest, but there’s also Mayfest, Do Division, Ribfest, Pitchfork, Taste of Chicago, the Air & Water Show and West Fest.”

6. Your kids love Casimir Pulaski Day.

Photo credit: U.S. National Archives and Records Administration, Wikimedia Commons
Photo credit: U.S. National Archives and Records Administration, Wikimedia Commons

“No one outside of Illinois knows who Casimir Pulaski is,” Brimo says, “but the first Monday in March is Casimir Pulaski Day. He was a Polish citizen who was a hero in the American Revolutionary War. It’s a state holiday. In most areas, kids get out of school and the local Polish community is honored. It’s one of those quirks unique to Chicagoland.”

7. You don’t put ketchup on your hot dog. Ever.

A Chicago-style hot dog. Photo credit: arnold inuyaki / Arnold Gatilao, Wikimedia Commons
A Chicago-style hot dog. Photo credit: arnold inuyaki / Arnold Gatilao, Wikimedia Commons

“It’s a cliché, but it’s true,” Haried says. “There are hot dog restaurants everywhere, and many of them have signs warning against ketchup. A classic Chicago dog doesn’t need it. It’s already loaded: it has a pickle, tomato, sport peppers, relish, onions, mustard and celery salt. The fact that I can rattle that off by memory just shows how popular it is.”

8. You’d say Door County is better than Cape Cod.

Cana Island Light, Door County, Wisconsin. Photo credit: Dave from Beaver Dam, WI, Wikimedia Commons
Cana Island Light, Door County, Wisconsin. Photo credit: Dave from Beaver Dam, WI, Wikimedia Commons

“People from the coasts don’t realize that both Michigan and Wisconsin are an easy drive away. Many Chicagoans have summer cabins in one or the other,” Tobisch says. “My favorite spot is Door County, Wisconsin. Like Cape Cod, it’s a peninsula, so plenty of gorgeous views, watersports and hiking. And I’d venture to say that Door County is a bit prettier – and the people are Midwest friendly.”

9. You can stomach rotten politicians.

Former Mayor Daley and Alderman James Balcer at a Marine Week Dedication in Chicago. Photo credit: U.S. Department of Defense, Wikimedia Commons
Former Mayor Daley and Alderman James Balcer at a Marine Week dedication in Chicago. Photo credit: U.S. Department of Defense, Wikimedia Commons

“Chicago politics were pretty dirty when the city was founded,” Brimo says, “and it seems like they never got cleaned up. It makes it hard to get too interested in local politicians’ promises, since another kickback scheme or embezzlement scandal hits the papers almost every month. And it extends to state politics. Four of our last seven governors have been sent to prison. I remember with Blagojevich, there were warning signs, but people reelected him anyway.”

10. You know how much Cubs fans like to drink.

Wrigley Field. Photo credit: Nguyen, Wikimedia Commons
Wrigley Field. Photo credit: Nguyen, Wikimedia Commons

“Until you live here, it’s hard to appreciate how much partying goes on before, during and after a Cubs game,” Haried says. “There are bachelorette parties in the bleachers, Clark Street is one solid row of bars and Wrigleyville can get out of hand. Honestly, fans at the game are only paying attention about 20 percent of the time – it’s a lifestyle. And either you love it or you hate it.”

11. You’re willing to drive your car to exercise by the lake.

Along Lake Michigan, south of the Loop. Photo credit: Raidarmax, Wikimedia Commons
Along Lake Michigan, south of the Loop. Photo credit: Raidarmax, Wikimedia Commons

“The Lake Michigan waterfront has bike paths, running paths, beaches, volleyball courts – people love to exercise by the lake. And they’re also willing to drive there or take the bus, just to jog along the path – it’s that pretty,” Haried says.

12. Your friend is in an improv class – and that’s not weird.

The Chicago Improv Festival. Photo credit: Clay Robeson, Wikimedia Commons
The Chicago Improv Festival. Photo credit: Clay Robeson, Wikimedia Commons

“Improv started here – tons of people take classes, often quite seriously,” Haried says. “For years we’ve been supplying the country with comedic talent. Performers as diverse as Joan Rivers, John Belushi, Amy Poehler, Gilda Radner, Steve Carell, Chris Farley, Pete Holmes and Jack McBrayer studied or performed in Chicago institutions like iO Theater and Second City. If you love comedy, there’s a show for you. Annoyance Theater and the Playground Theater are other great spots for those in the know – and the Neo-Futurists’ show up north is not to be missed.”

13. You can’t believe former Mayor Daley sold the city’s parking meters.

Chicago’s old parking meters … we miss you! Photo credit: Adam Jones, Wikimedia Commons
Chicago’s old parking meters … we miss you! Photo credit: Adam Jones, Wikimedia Commons

“Technically, they’re leased, but still,” Brimo says. “In 2008, all our parking meters (and the revenue associated with them) were given to a private company for 75 years for an upfront payment of $1 billion. The city spent the proceeds in three years – typical. And the cost of parking has skyrocketed. It’s a total disaster.”

14. The “4 a.m. Special” is your hangover prevention plan.

The Wiener’s Circle in Lakeview, Chicago. Photo credit: Victorgrigas, Wikimedia Commons
The Wiener’s Circle in Lakeview, Chicago. Photo credit: Victorgrigas, Wikimedia Commons

“The bars in Chicago have tiered closing times. On weekends, some bars have a 2 a.m. last call, but a few have a special license that allows them a 4 a.m. last call,” Haried says. “People who stay out until the last-last call naturally get hungry. There are a few restaurants that cater to them, like Flash Taco, Wieners Circle, Jim’s Original and Express Grill.”

15. You can’t wait to take visitors on the riverboat architecture tour.

Architectural tour along the Chicago River. Photo credit: John Picken, Wikimedia Commons
Architectural tour along the Chicago River. Photo credit: John Picken, Wikimedia Commons

“Like most cities, if you live here, you don’t spend too much time doing the tourist stuff. The one exception is the riverboat architecture tour,” Brimo says. “When a friend visits from out of town, I can’t wait to ride along the Chicago River and look at all the great architecture. It really is amazing – and Chicago’s reputation as an architectural hotbed is well-deserved.”

16. As far as you’re concerned, Mike Ditka is still “Da Man.”

People in Chicago love the Bears … and that still means Ditka! Photo credit: Trostle, Wikimedia Commons
People in Chicago love the Bears … and that still means Ditka! Photo credit: Trostle, Wikimedia Commons

“Even though the Bears last won the Super Bowl in 1985, and Ditka was fired in 1992, Ditka does a great job of staying in the limelight,” Haried says. “He’s a spokesman for everything, like Al’s Beef (a local fast food chain), State Farm, Overstock.com. You see him everywhere, so he stays top of mind.”

17. The North Shore is your never-ending John Hughes movie.

The house featured in Photo credit: anarchosyn, Wikimedia Commons
The house featured in “Home Alone,” in Winnetka, Illinois. Photo credit: anarchosyn, Wikimedia Commons

“Chicago’s North Shore suburbs have a village-like, gracious feel to them,” Tobisch says. “In the summer they’re leafy green and their beaches are much less crowded than those in the city. They can easily embody an idealized American experience, which is why many of John Hughes’ movies were filmed on the Shore. Cameron’s house from “Ferris Bueller’s Day Off” is in Highland Park, and the “Home Alone” house is in Winnetka, for example.

18. You’re used to a green river.

The Chicago River dyed green for Saint Patrick’s Day. Photo credit: J. Crocker, Wikimedia Commons
The Chicago River dyed green for Saint Patrick’s Day. Photo credit: J. Crocker, Wikimedia Commons

“On St. Patrick’s Day, the Chicago River is dyed bright green and people start drinking as soon as they wake up,” Haried says. “It’s a serious celebration – held in different spots throughout the city. One prime spot is the South Side Irish Parade, which was one of the largest outside of Dublin. It had 15,000 marchers and 250,000 spectators at its height, but it became a sprawling, drunken mess. It was shut down after the 2009 edition, and then reinstated in 2012 with a more family-friendly focus.”

19. Deep down, you’re a thespian.

A still from a performance of Carmen. Photo credit: Cebula, Wikimedia Commons
A still from a performance of Carmen. Photo credit: Cebula, Wikimedia Commons

“Chicagoans love theater; the groundbreaking Steppenwolf is here, as well as the Goodman,” Tobisch says. “The quality of acting is incredible – and not just in the major theaters. Locals also go to storefront theaters, which can be found all across the city. One of my favorites is The Hypocrites Company, which often perform at the Chopin Theater in Ukrainian Village.”

20. Your neighborhood is who you are.

A view of Wicker Park, a popular Chicago neighborhood, from the El. Photo credit: Daniel Schewn, Wikimedia Commons
A view of Wicker Park, a popular Chicago neighborhood, from the El. Photo credit: Daniel Schewn, Wikimedia Commons

“There are over 200 neighborhoods in Chicago,” Brimo says. “More so than most cities, people use their neighborhood to define who they are and what they do. If you live in Bridgeport, for example, you might go to 20 White Sox games a year, jog through Palmisano Park, have dinner at Nana and catch an art exhibit at Co-Prosperity Sphere after. And that’s just one neighborhood! The variety and choice of neighborhoods is amazing – once you choose one to your liking, it can be hard to leave.”

If you’re thinking of buying or selling a home in Chicago or the surrounding area, be sure to get in touch with our local Redfin real estate agents, or check out what’s on the market on Redfin.com.

If you are represented by an agent, this is not a solicitation of your business. This article is for informational purposes only, and is not a substitute for professional advice from a medical provider, licensed attorney, financial advisor, or tax professional. Consumers should independently verify any agency or service mentioned will meet their needs. Learn more about our Editorial Guidelines here.
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Alex Starace

Alex provides journalists with the information they need for their stories. Prior to joining Redfin, he was a freelance writer who wrote extensively on the ins and outs of condo purchasing. He also covered luxury goods, with a minor in book reviews. He lives in Chicago and is lucky enough to be able to walk to work. Redfin is a full-service real estate brokerage that uses modern technology to make clients smarter and faster. For more information about working with a Redfin real estate agent to buy or sell a home, visit our “Why Redfin?,” page.

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