Moving to Chicago
Chicago is a big city with a lot going on, and figuring out where to land can feel daunting from the outside. I moved here over a decade ago, so I've been through it. This guide covers the things people ask me about most, from neighborhoods and schools to food, transit, and farmers markets. Have questions the guide doesn't answer? Call me at (312) 450-1202.
Exploring Chicagoland
Chicago proper is just one piece of a much larger picture. The broader Chicagoland area is home to more than 9 million people and stretches into parts of Illinois, Wisconsin, and Indiana. Depending on where you work and what you're looking for in a community, the suburbs might be worth a look alongside the city.
Evanston sits just north of Chicago on the lakefront and has the feel of a small city with real cultural depth. It's home to Northwestern University and a strong arts scene. Naperville is a top pick for families, with excellent schools and a walkable downtown. Oak Park is beloved for its Frank Lloyd Wright architecture and neighborhood character. Arlington Heights and Aurora offer more space with easy access to the city via Metra, which connects the broader region and serves over 80 million passengers a year.
Not sure whether to go city or suburbs? That's one of the first conversations I have with relocating buyers. Happy to help you think it through.
Chicago Schools
Chicago has a wide range of educational options, and navigating them is easier once you know what's out there.
Chicago Public Schools (CPS) is one of the largest districts in the country, with standout magnet programs and selective enrollment schools like Whitney M. Young. For families interested in private options, the University of Chicago Laboratory Schools offers a progressive curriculum, the Latin School provides a liberal arts foundation, Lycée Français de Chicago offers French immersion, and the British International School has a globally focused program.
A few resources worth bookmarking:
GreatSchools.org for ratings and reviews across public, private, and charter schools
SchoolDigger and Niche for rankings, performance data, and parent reviews
The Food Scene
Chicago takes its food seriously, and it delivers. Yes, there's deep-dish pizza and yes, ketchup on a hot dog is still a controversial topic. But the real story is the range.
Devon Avenue is a destination for South Asian cuisine. Pilsen is where you go for some of the best Mexican food in the city. The restaurant community has earned serious recognition over the years, including multiple Michelin stars and James Beard Awards. From upscale tasting menus to neighborhood taquerias to food halls worth an afternoon, there's always something new to try.
Good places to explore
r/ChicagoFood on Reddit for honest, unfiltered recommendations
Things to Do
Sports: Wrigley Field is a bucket list experience whether or not you follow baseball. The Chicago Marathon draws 45,000 runners every October. Add the Bears, Bulls, Blackhawks, Cubs, and White Sox and you've got something going on pretty much year-round.
Music Festivals: Lollapalooza takes over Grant Park every summer. The Chicago Blues Festival and Chicago Jazz Festival are both free and genuinely excellent. The city's music roots run deep.
Street Fairs and Cultural Festivals: Every neighborhood has its own calendar. The Taste of Chicago brings 80+ local restaurants together in one place. The Chicago Air and Water Show is a summer staple. The Chicago Pride Parade in June draws hundreds of thousands. The Puerto Rican Festival in Humboldt Park is a neighborhood institution. For a full list, Choose Chicago keeps a running guide.
Conferences and Expos: McCormick Place is the largest convention center in North America, and it's busy. The Chicago Auto Show, the National Restaurant Association Show, and C2E2 are just a few of the big annual draws.
Farmers Markets
Chicago's farmers market scene is genuinely great, and once you find your regular market, it becomes part of the rhythm of the week.
The Green City Market in Lincoln Park runs Wednesdays and Saturdays from April through November, then moves indoors for winter. The Logan Square Farmers Market is open Sundays year-round, with live music, food vendors, and a strong local following. The Wicker Park Farmers Market runs Sundays May through October. In Andersonville, the market runs Wednesdays May through October. Evanston's market is Saturdays, May through fall.
More Resources
Choosing the right neighborhood takes more than a quick Google search. Here are some tools I recommend to clients doing their homework.
Get a feel for the neighborhood
Choose Chicago and Chicago.gov for neighborhood overviews
Niche and AreaVibes for rankings on schools, cost of living, and amenities
Nextdoor to connect with people who actually live there
Neighborhood Facebook groups and Reddit threads for unfiltered, firsthand perspective
Figure out your commute
CTA for buses and trains within the city
Metra for suburban rail schedules and routes
Google Maps and Citymapper for route planning
And the most underrated research tool: go there. Walk around on a weekday morning and again on a Saturday afternoon. Grab coffee. See how it feels. No app replaces that.