Moving to Chicago? Not only is the Midwestern metropolis rated one of America’s 50 best cities to live; it’s also an extremely hot real estate market with home values up 7.5 percent year-over-year. But in order to become a true Chicagoan, you must make a few crucial decisions. Will you root for the Cubs or the Sox? Will you refrain from putting ketchup on your hot dog? Will you live in the city or the burbs?

To get you in a Chicago state of mind, we asked locals 15 questions about living in the Windy City. Here’s what they had to say:

1. Cubs or Sox?

Cubs! North Sider all the way. — Colette Conway

Sox. — Kaitlyn

Cubs and many years of misery. — Peter Block

2. Windy City, Second City, Chi-town, Chicagoland or City of Broad Shoulders?

East Wacker Drive at night. The docked boats are mostly for architecture tours and there's a pedestrian walkway known as the Chicago Riverwalk. Source: Jonathan via Flickr Creative Commons

Tour boats and the Chicago Riverwalk. Source: Jonathan via Flickr Creative Commons

Hmm, I’d have to go with Chi-town. — Marisa M.

Chicago is the only city I’ve ever heard of that tags the word “land” to the end of it, and I’ve always thought that was the coolest thing ever. It makes Chicago even more unique than it already is and adds an air of mystery to the city. — Melissa Blake

We are the WINDY CITY! — Jen Evers

3. What’s the problem with ketchup on a Chicago Dog?

Chicago_Kris_Cain-9_Chicago Dog

Source: Kris Cain

It’s just not supposed to be there. You need a hint of tang, which is why mustard is a most excellent complement. — Johanna Grange

It’s nasty. I prefer a hot dog PLAIN, but I know that makes me unusual. — Jen Evers

Because this is just not the way we roll. — Lena Burkut

4. Tricks to survive the brutal winters?

Your scarf has to go on the outside of your coat and around your face to keep the wind from blowing your hood down. You’re welcome. — Marisa M.

You know, we are tough and still go out in the winter. Snowshoeing is fun if we have enough snow. We also keep track of fun winter events and have found that there are things to look forward to each year. Love, love, love the Chocolate Expo in February at the Morton Arboretum. Winter is also a great time to take in a play or visit one of the magnificent museums in Chicago. Besides keeping busy, it is important to prepare before winter starts and make sure you are stocked up on winter supplies. We also carry a container full of emergency items in the car just in case — blankets, snacks, a shovel, flashlight, first aid kit, etc. — Melissa Schwartz

A knee-length parka, three pairs of socks and a lot of stamina. — Debra Lipson

5. Favorite music festival? 

Taste of Chicago. Source: Kris Cain

Taste of Chicago music festival. Source: Kris Cain

Lollapalooza is a great attraction for the natives and tourists. — Lena Burkut

Market Days is always a blast and not as crowded as Lolla. Plus it’s free! — Debra Lipson

Ravinia, the summer long music festival, is amazing and has been a favorite of mine for years. — Colette Conway

6. City or the burbs?


Downtown Chicago skyline. Source: Kris Cain

Having lived in both, I gotta say, although being able to hop in my car is unbelievably convenient, the city is SO much cooler. And the trains aren’t that bad, anyways! — Jessica Rosati

Live in the burbs and play/dine downtown. — Peter Block

7. Best place to get a deep-dish pizza?

Serving a slice of Lou Malnati's deep-dish pizza. Source: Larry via Flickr Creative Commons

Serving a slice of Lou Malnati’s deep-dish pizza. Source: Larry via Flickr Creative Commons

Gotta go with Lou Malnati’s! “The Lou” may be in my top-10 favorite meals of all time. — Jessica Rosati

I’d say it’s a tie between Lou Malnati’s and Ginos East, but I may be a bad Chicagoan because I LOVE thin pizza 😉 — Lisa

8. Best neighborhood for 20-30 somethings?

This Lake View house is walking distance to Tango Sur and Wrigley Field. It's currently listed for $2,000 a month.

Looking for a Lake View rental? This 2-bedroom house is walking distance to Tango Sur and Wrigley Field. It’s currently listed for $2,000 a month.

Lake View! TONS of fun restaurants (my favorite is Tango Sur!), parks, and it boasts a young crowd. — Jessica Rosati

Even when I was a kid, I loved Lincoln Park. The Children’s Hospital is there, and the houses along the tree-lined streets were gorgeous! If I won the lottery, Lincoln Park would be on my short list of Dream Places To Live. — Melissa Blake

I’m sure some would name the Near North Side. But having never lived up that way I can’t speak on it personally. However, I did work in Hyde Park for several years. And having just recently visited I have to say that I love the changes. It is definitely different and thriving. It seems like a great place to live. It is a great, diverse neighborhood. — Kris Cain

9. Best place to raise a family?

After a $10,000 price cut, this Arlington Heights home is just over the area's median home value. It's ideal for a family with top-rated schools nearby.

After a $10,000 price cut, this Arlington Heights home is just over the area’s median home value. With 3 bedrooms and top-rated schools nearby, it’s ideal for a family.

Gotta shout out the ‘burbs, baby. I teach in Arlington Heights and it is an AMAZING school district! — Jessica Rosati

Naperville. — Lena Burkut

If you want a more quiet, suburban life with great public schools, I’m partial to the North Shore, as that is where I grew up.  If you want to be a city dweller with a family, Lincoln Park is fantastic. — Colette Conway

10. Which ‘L’ line do you ride and which do you avoid?

The Chicago El. Source: K Hardy via Flickr Creative Commons

The Chicago ‘L’. Source: K Hardy via Flickr Creative Commons

Brown all the way and the red line at night makes me squeamish. — Johanna Grange

I avoid the ‘L’ entirely. — Melissa Schwartz

Frequent red line passenger and I don’t have qualms with it. The brown line is scenic but it takes longer. — Debra Lipson

11. Is Frank Lloyd Wright architecture a big deal or old news?

The William Winslow House   is the first house Frank Lloyd Wright built as an independently commission architect. Located 20 minutes from downtown Chicago, the home is currently on the market for $1.85 million.

The William Winslow House is the first home Frank Lloyd Wright built as an independently commissioned architect. Located in the River Forest suburb, the home is currently on the market for $1.85 million.

Old news, but still a big deal. For years I worked right across the street from the Robie House on the campus of the University of Chicago. I still love his designs. — Kris Cain

Definitely still a big deal. — Melissa Schwartz

12. Best park in Chicago?

Chicago_Kris_Cain-2_Cloud Gate at Millennium Park

“The Bean” at Millennium Park. Source: Kris Cain

Millennium Park is my fav. — Lena Burkut

Lincoln Park. On any given day there might be a farmers market, event at the zoo, trapeze class, and the beautiful boats all in one jog!  — Marisa M.

13. Favorite way to get your local morning news?

The WGN Weather Center. Source: Monika Thorpe via Flickr Creative Commons

The WGN Weather Center. Source: Monika Thorpe via Flickr Creative Commons

I watch WGN Morning News. The folks on that show are nuts and I love it. — Kris Cain

I usually read the Chicago Tribune online or check out ABC 7 Chicago online. — Melissa Schwartz

Old school — on the television (WGN). — Jen Evers

14. Willis or Sears Tower?


Willis (formerly Sears) Tower spans 110 stories in the heart of downtown Chicago. Source: Robert Blackie via Flickr Creative Commons

Definitely the Willis Tower. I went there a couple years ago and had lunch on one of the top floors — talk about eating in high style. The city’s horizon was breathtaking. — Melissa Blake

Willis still makes me angry. — Johanna Grange

Sears Tower for sure! No real Chicagoan will ever call it the Willis Tower. — Colette Conway

15. Chicago’s best-kept secret?

The Chir

The Chicago River is dyed green every year in celebration of St. Patrick’s Day. Source: Ian Freimuth via Flickr Creative Commons

Its people. Chicago has its cast of characters, that’s for sure, but I’ve never seen so much pride in one group of people. They’re genuinely proud to be from the Windy City and take it very seriously. I mean, what other city would dye its river green? — Melissa Blake

Skip the big apartment buildings and try to rent from a condo owner. You can usually get a better unit for the price and the amenities of a condo building without the assessment fee! — Marisa M.

Chinatown. I always direct tourists that way. Get off the beaten path aka Michigan Avenue! — Johanna Grange


Catherine Sherman, a real estate writer for Zillow Blog, covers real estate news, industry trends and home design. Read more of her work here.

About the Author

Catherine Sherman, a real estate writer for Zillow Blog, covers real estate news, industry trends and home design.

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