1. Taking selfies at “The Bean” before selfies were a thing.
The beauty of growing in Chicago meant visiting the “Bean,” a world-famous art installation called Cloud Gate. Before selfies were even invented, my best friends and I would stand in the front of the Bean, snapping pictures with the stunning Chicago skyline in the background. Because the bean is made of mirror, the Bean helped us take the world’s first selfies. Yeah, we’ll claim that.
2. Taking the Orange Line to White Sox games.
There weren’t more die-hard White Sox fans than us. We’d jump on the Orange Line El from the south side and head to Comiskey Park, aka U.S. Cellular Field, aka Guaranteed Rate Field (the commercialization is palpable) decked out in our black- because good guys always wore black. Cherished memories include the Crosstown Classic where the south side White Sox would square off against the north side Chicago Cubs. We’d spend hours talking shit to Cubs fans before entering our domain for an eventual win.
3. Hanging out at swanky piano bars.
Somewhere between turning 21 and being tired of frequenting dodgy house parties at UIC and Little Village, our friends developed a love for frequenting high-class piano bars. A particular favorite was the Red Head Piano Bar on Ontario Street. We got to know our Piano Man pretty well, learning that he hated playing Billy Joel’s “Piano Man.” When we asked him to play his favorite song, he performed the most heartwarming rendition of “Walking in Memphis” we’d ever heard.
4. Sunbathing at Oak Street Beach
Oak Street Beach in the summer is Chicago at its finest. It didn’t matter that my best friends were predominately of Eastern European heritage with red hair. We spent summers lying out next to ice cold, but oh-so-beautiful Lake Michigan. Dinner was always at Cheesecake Factory at the John Hancock Center.
5. Shopping on Michigan Avenue.
They don’t call it Magnificent Mile for nothing. Hello, Saks, Bloomingdale’s, and about a million other stores none of us could afford. That never stopped us from jumping in and out of luxury stores, feeling as fabulous as Carrie Bradshaw and her friends in Sex in the City.
6. Taking advantage of free places like Lincoln Park Zoo and Grant Park.
Like most young girls, we always took advantage of hanging out at the free haunts around the city. Favorites include Lincoln Park Zoo and its awesome Conservatory (indoor tropical garden in the dead of winter was always a life-saver), and Grant Park, the site of many events, concerts, Buckingham Fountain and more.
7. Hunting for the weirdest alternative shops we could find.
Though we were south siders at heart, nothing beat the north side when it came to shops specializing in the weird, funky, and downright wrong. Therein we discovered places like The Alley, a place where you can buy wigs and leather, and Frenchy’s – a place for, well, lovers’ things.
8. Eating frozen bananas from the Mexican pushcart.
Was there anything more satisfying than dreaming away the afternoon at North Avenue Beach, when, as if on cue, the jingling bell from the ice cream man sounded from the distance? Like Pavlovian dogs salivating for a treat, us girls would enjoy one of life’s most simple pleasures: a frozen chocolate-covered banana from the ice cream man’s pushcart. He also served a variety of other goodies, usually of the Mexican variety, like chicharones.
9. Having senior prom at the Field Museum.
Maybe we didn’t realize it at the time, but we had just about the sweetest prom venue ever. Where most people’s schools rent out a room at a local banquet hall, we were partying amongst the largest, most well-preserved T-Rex in history, SUE. Couple that with the museum’s on-point catering and awesome acoustics, we lived through the prom of a lifetime together.
10. Smoking Hookah.
My best friends and I routinely smoked hookah, and a favorite was a place called Samah Lounge. You walked in and were surrounded by private suites all separated by intoxicating hookah smoke and sexy sheer linens. You gathered around the table, seated on the floor, ate delicious Middle Eastern food and smoked yourself into oblivion.
11. Partying in Boystown.
Boystown, aka Chicago’s “gayborhood,” became our party playground. With several gay friends in our crew, we were the kings and queens of places like Roscoe’s Tavern and Taverna, a swanky tapas restaurant.
12. Chilling at Rock-N-Roll McDonalds.
Back in its heyday, this McDonald’s was the best in the world, as it paid homage to music’s most legendary artists like Elvis Presley and The Beatles. TVs looped popular music videos, and music memorabilia adorned all the walls. Seating was for 300, so it was a popular hangout for groups of friends. Some might remember the song “Rock-N-Roll McDonald’s” by Wesley Willis, a hilarious underground musician: “People flock here to get down to the music.”
13. Going to free concerts at the Taste of Chicago.
I can’t even count on one hand all of the first-rate acts I’ve seen perform for free at the annual Taste of Chicago festival. Highlights include Erykah Badu (before she became a “DJ”), LeAnn Rimes, Counting Crows, and John Mayer.
14. Taking field trips to Navy Pier.
Whether we were watching Fantasia 2000 on the giant floor-to-ceiling IMAX screen or taking a ride on the Spirit of Chicago, Navy Pier was the sight of many-a-memory for me and my besties.