Taking a Trip to Chicago

efore I encountered her sprawling, gleaming lakefront and her diverse neighborhoods, I met her on my TV screen.

She was the gritty stomping ground in which the knuckleheaded teenagers in Cooley High broke all the rules, the backdrop for which my favorite Good Times characters fought for the American Dream.

It’s where Harry met Sally, and where Darius met Nina.

Yes, I’m talking about Chicago, also known as The Windy City, home to more than 2.5 million residents.

As an adult, I have come to know and appreciate Chi-Town in all her contemporary glory, and with the summer season in full effect, you can, too.


Like many metropolitan areas, the Second City–as it is also called—has deep African-American roots. According to historians, Jean Baptiste Point du Sable, a free Black man of Haitian ancestry, became the city’s first non-indigenous, permanent resident in the late 1770s.

About 140 years later, Black southerners began migrating to the city, transforming Chicago forever.  What resulted included a gumbo of thriving subcultures, including “Chicago Step” and a soulful house scene that emerged in the 1970s. Of course, it also became the birthplace of an in-studio dancing show, which the late Don Cornelius transformed into what we all know as “Soul Train.”

Getting to the city for a weekend getaway should be a breeze for metro Detroiters, who upon arrival will sense the city’s familiar, laid back and unassuming, Midwestern vibe. The Megabus will zip budget travelers from Detroit to the Windy City in about five hours for prices as low as $1, if riders purchase tickets in advance.

Amtrak and major airlines such as Southwest regularly offer special deals that drop visitors off at Chicago Midway and Chicago O’Hare, the   two major airports. Both connect to Chicago Transit Authority’s subway system.

Visitors also will be relieved to find that the city offers cheap, efficient ways to get around ranging from cabs and water taxis to unlimited CTA passes. The Chicago Trolley & Double Decker Co.’s Signature Tour also offers a viable alternative to public transportation if visitors want to explore the city’s key attractions with a tour guide’s help.

With its free events, easy traveling options and cultural mainstays, Chicago has something for everyone. 



The 26 miles of lakefront property owned by the Chicago Park District is a tourist attraction that is not to be missed. The free beaches along Lake Michigan, including the popular Oak Street and Ohio Street locations, offer a 18-mile trail for runners and cyclists and picturesque, cool relief from the summer heat.


If you end up gorging on the city’s famed deep-dish pizza, Garrett’s popcorn and Harold’s Chicken Shack, try Karyn’s Cooked to redeem yourself and replenish your health. Located on the Near North Side, this highly rated vegan restaurant serves delectable entrees that do the body and the taste buds good. 738 N. Wells St.


A popular spot for the 20- and 30-something crowd, this music venue and bar offers a mix of old school and contemporary hip-hop, R&B/soul, Afro-Beat, Chicago House, reggae and dancehall music. Former performers include Kindred The Family Soul, Questlove of The Roots and Les Nubians. 2109 S. Wabash Ave.


Located in the opposite direction of the luxury, chain retailers of The Magnificent Mile, this street market offers quirky, hard-to-find goods from around the world. Held on the last weekend of every month through the end of September, this West Loop attraction boasts antiques, jewelry, a global food bazaar, vinyl records, indie fashion and original artwork representing the city’s many ethnic enclaves. Tickets can be purchased online at discounted rates, and kids under 12 are always free. 1340 W. Washington. 


Often referred to as the front yard of the city, this family-friendly park houses monuments, museums, gardens and playgrounds within its 319-acre perimeter. During the warm weather months, it’s known for hosting movies and some of the year’s most popular music and food festivals including the Chicago Jazz Festival and the Taste of Chicago. Located between Michigan Avenue and Lake Michigan, it’s also home to Millennium Park where Cloud Gate, the massive stainless steel figure also called “The Bean,” will likely mesmerize children.

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