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Neighborhoods, schools, food, getting around, and the local know-how that helps a new city feel like home.

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Deborah Libby smiling in sunglasses and a fur-lined winter hood on a Chicago street

Welcome to Chicago

Chicago is a big city with a lot going on.

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.

Stop 1

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

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

Naperville is a top pick for families, with excellent schools and a walkable downtown.

Oak Park

Oak Park is beloved for its Frank Lloyd Wright architecture and neighborhood character.

Arlington Heights + Aurora

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.

Let's talk it through

Stop 2

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 school districts in the country, with magnet and selective enrollment schools like Whitney M. Young.

Children working on a project in a classroom

For families interested in private options

University of Chicago Laboratory Schools offers a progressive curriculum.

The Latin School provides a liberal arts foundation.

Lycée Français de Chicago offers French immersion.

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

Stop 3

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

Eater Chicago TimeOut Chicago Choose Chicago r/ChicagoFood on Reddit for honest, unfiltered recommendations

Stop 4

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 + 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 + 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.

Stop 5