Chicago Skyline With Blue Clear Sky; Shutterstock ID 189356366 l

Chicago is a great city to live in and explore — by land or by water.


Considering a move? Here’s what Chicago real estate experts love most about their city.

The Windy City, Chi-Town, Chicagoland; the beautiful, chilly, Midwestern city known for its incredible views of Lake Michigan, quaint brick bungalows, and a citizenry averse to hot dogs with ketchup.

Considering a move to the Midwest? Moving to Chicago is extremely affordable for a metropolitan area, with an average home sale price of $248,500. In addition to low home prices, Chicago’s many diverse neighborhoods offer great amenities even for the most particular house hunter. Near West Side and Roscoe Village are just two areas that boast safe, easy access to great schools, restaurants, nightlife, and the city’s excellent 24-hour public transportation system, the “L.”

Whether you are visiting for the weekend or planning to relocate, Chicago offers plenty to explore, but don’t just take our word for it! Check out what some local real estate experts had to say about the best areas and things to do in Chicago.

Speaking of neighborhoods, what is the best place to raise a family in Chicago?

“Ravenswood is a great neighborhood for families. It’s a bit off the beaten path, so you can get some quiet when you want it. But you’re also close to everything that makes Chicago special.” — Dan Rafter, editor of Midwest Real Estate News

“As a kid who lived in Old Irving Park, this is the best place to raise a family, because the homes have huge, sprawling yards. It’s easy for kids to make friends when they can see the next-door neighbor’s kid playing outside. Not to mention that the location has tons of city amenities like popular restaurants, convenient retail, easy access to downtown, playgrounds, and is just minutes away from a forest preserve.” — Alice Jordan of The MG Group

“Roscoe Village. Like a village within the city, this quaint community is very popular with young families. Parents are often seen pushing strollers past the shops with colorful awnings, small restaurants, and trees that line Roscoe Street, the neighborhood’s main thoroughfare. Vintage brick walk-ups and well-maintained frame houses with front porches help maintain the atmosphere of this family-oriented community.” — Ron Goldstein, vice president of sales, Jameson Sotheby’s International Realty

Although Chicago is most well-known for its Chi-dogs and deep-dish pizza, what would you say is Chicago’s most delicious specialty cuisine?

“I’ve always loved deep-dish pizza, especially Lou Malnati’s. But if I’m looking for something healthier — and almost anything is — I’d go with any of the great sushi restaurants in Chicago.” — Dan Rafter, editor of Midwest Real Estate News

“The Berghoff is an iconic Chicago restaurant that is a time capsule for the bygone Victorian era. As a fifth-generation Chicagoan, my family has been going here for over a century.” — Alice Jordan of The MG Group

“Jerk: Modern Jamaican Grill. Hip, modern, and the best jerk this side of Bob Marley. Live music and amazing craft beer selection.” — Ron Goldstein, vice president of sales, Jameson Sotheby’s International Realty

Where can you find the best cup of coffee in Chicago?

“OK, I never drink coffee. My wife, though, likes Uncommon Ground on Clark Street. That’s where we had our first date.” — Dan Rafter, editor of Midwest Real Estate News

“Metropolis on Granville. They pride themselves in their state-of-the-art espresso machine — I was told that it is the ‘Porsche of espresso machines.’” — Alice Jordan of The MG Group

“Intelligentsia. They actually develop the beans while working alongside the farmers.” — Ron Goldstein, vice president of sales, Jameson Sotheby’s International Realty

We have to ask: Cubs, Sox, or Bears?

“I’ve always been a Sox fan. That wasn’t easy this year. I’m the kind of Sox fan who actually wants the Cubs to lose, so this year was pretty painful for me.” — Dan Rafter, editor of Midwest Real Estate News

“Bears. They had me at the ‘Shuffle.’” — Alice Jordan of The MG Group

“Sox all the way!” — Ron Goldstein, vice president of sales, Jameson Sotheby’s International Realty

What is the best neighborhood for millennials looking to rent or buy in Chicago, and why?

“Lincoln Square is a great place for millennials to hang out. I like the old Bavarian-style restaurants there combined with the newer, hipper restaurants.” — Dan Rafter, editor of Midwest Real Estate News

“Logan Square is a blend of Old World Chicago (access to the Loop, part of the 1909 Burnham Plan, greystones, and the actual square) and the Chicago of today (farmers markets, creative retail, cutting-edge restaurants, startups, and environmentally friendly companies.” — Alice Jordan of The MG Group

“Wicker Park. A great deal of downtown workers have moved to this area. In this neighborhood northwest of the Loop, there are stores, restaurants, and bars catering to young professionals.” — Ron Goldstein, vice president of sales, Jameson Sotheby’s International Realty

What is the best nontouristy thing to do in Chicago?

“Ride a Divvy in downtown Chicago. I don’t know if many tourists are brave enough to hop on a Divvy bike when commuters are whizzing by in their cars — it makes me nervous too — but seeing downtown Chicago on a Divvy bike is actually a real treat.” — Dan Rafter, editor of Midwest Real Estate News

“Storefront theaters, from improv to stage productions! Often, our small theaters are the start of future Broadway shows and Hollywood stars.” — Alice Jordan of The MG Group

“Garfield Park Conservatory. Travel through the conservatory and experience the lush flora and tropical temperatures in their magnificent facility.” — Ron Goldstein, vice president of sales, Jameson Sotheby’s International Realty

Where is the best place to take in the city skyline?

“It’s a thrill to go up into the John Hancock building. I think it’s a better view than the one offered by the Willis Tower.” — Dan Rafter, editor of Midwest Real Estate News

“The front steps of the Adler Planetarium offer the best unobstructed skyline view of the entire city.” — Alice Jordan of The MG Group

“From behind the Adler Planetarium.” — Ron Goldstein, vice president of sales, Jameson Sotheby’s International Realty

What is Chicago’s best-kept secret?

“I still think a lot of people don’t know about the newly revamped Chicago Riverwalk. It’s a great way to take in some great Chicago scenery.” — Dan Rafter, editor of Midwest Real Estate News

“Very few know that you can kayak in the Chicago River.” — Alice Jordan of The MG Group

“Jazz Showcase. Since 1947, the true greats (Charlie, Dizzy, Miles) have always found a way to get here. So have lovers of pure jazz.” — Ron Goldstein, vice president of sales, Jameson Sotheby’s International Realty

What is the best way to take in a Lake Michigan sunrise or sunset?

“It’s been a while, but I don’t think that you can beat watching the sunrise from the museum campus. It’s pretty inspiring with all those magnificent museum buildings surrounding you.” — Dan Rafter, editor of Midwest Real Estate News

“Boating off of North Ave. Beach is the best way to watch the sun set and rise.” — Alice Jordan of The MG Group

“On the Windy sailboat from Navy Pier.” — Ron Goldstein, vice president of sales, Jameson Sotheby’s International Realty

Have any additional insider knowledge about Chicago? Are you a local writer with insider tips? Shoot an email to hgoodman@trulia.com so we can work together!