The Insiders' Guide to Chicago

Traveling to Chicago? Learn more about visiting the Windy City on the shores of Lake Michigan

Being a metropolis in the Midwest gives Chicago the best of both worlds: friendly folks and an urban lifestyle. It's the type of place where if you stand on a corner with an open map, more than one passerby will stop to ask if you need help—really. The city’s reputation as a gentler, cleaner option than our East Coast cousin is what brings people here—and keeps them here, too.

While New York may be the “city that never sleeps,” Chicago is, as the famous song says, “my kind of town” where “people smile at you.” L.A. may have its posh Hollywood hills and fancy red carpets, but Chicago has soaring skyscrapers and beachfront paths. Sure, the winters last too long, but Chicagoans tough it out and patiently explain to visitors and newcomers, “You just need to dress for it.” Then, as soon as the thermometer inches over 60, Chicagoans dash outside to play until winter starts again. With its easy public transportation system, top-notch cultural institutions, shopping meccas and stunning architecture, it’s no wonder that Chicago has grown from its days as a swampy, stinky place in the middle of nowhere to a world-class city, boasting a booming economy and a bustling tourism industry that attracts more than 45 million people each year.

Each fall, the Chicago Marathon brings nearly 34,000 runners to Windy City streets, making it the second largest marathon in the country, behind New York and ahead of Boston with about 10,000 more participants. Why the extraordinary turnout? Well, for one thing, novice marathoners appreciate that the course has just one slight incline. And that’s Chicago for you: flat. But that merely describes its topography, because there’s absolutely nothing monotonous about any other aspect of the city.

Thanks to the city government's concerted effort to bring people into the heart of the city over the past two-plus decades, Chicago’s downtown area has blossomed into a desirable place not just to work, but also to live and to explore. Loop offices and crowded lunchtime hangs may go dark during non-business hours, but that’s when downtown comes alive with a different feel—with theatergoers off to see everything from original dramas to brilliant Broadway musicals; with hordes of people making a beeline for the city’s ever-expanding shopping options; and with couples, families, groups of friends and visitors flocking to year-round activities at Millennium and Grant parks. The best part is that multiple buses and trains, plus a range of downtown hotels, offer convenient access to all of it.

And the locals know that these things are not just for tourists. They make the most of their city, too. They head to the museums for indoor entertainment; they hit the beaches and city pools whenever weather permits; they meet at festivals throughout the city and throughout the year; they try the more than 7,300 eateries, from four-star restaurants to ethnic dives; they root for their home sports teams; and they live in more than 175 distinct neighborhoods that make up the multihued, multifaceted fabric of Chicago.

With so many neighborhoods, Chicago takes on fascinatingly distinct identities. It could be the quiet, suburb-like quality of Hyde Park or the posh digs of the Gold Coast, the vibrant atmosphere near Lincoln Park’s DePaul University, or the revitalized, artsy feel of Bucktown. Residents frequently relocate within the city, choosing locations depending on what they can afford and what they need. Families search for homes in school districts they prefer; young and single crowds tend to congregate in places that are walkable to shopping, bars and restaurants; and those with strong religious affiliations select their church or synagogue first, then find nearby housing.

Though city promoters don’t like to admit it, in a city with a population of more than 2.7 million, there are inevitable degrees of crime and poverty, but they certainly don’t define this city whose alternative motto to “City in a Garden” is “I Will.” As Chicago’s first new mayor in more than two decades (taking office in 2011, following Daley’s 22-year tenure), Mayor Rahm Emanuel may have some economic and social challenges ahead. But Chicago’s “I Will” attitude continues to motivate and inspire, providing the backbone for many of this determined city’s civic projects and civic pride.

To plan your visit: See our Chicago city guide to restaurants, attractions, landmarks, nightlife, shopping and more, plus information on when to visit Chicago.

This information originally appeared in the "Insiders' Guide to Chicago" and is ©2012, Morris Book Publishing/Globe Pequot Press.