Once upon a time, I was a party chick. I lived with my girlfriends in Wrigleyville and loved dancing and flirting in the city's hottest bars and clubs. We'd start getting ready at 10 p.m. I'd put on my stirrup pants, flip my hair and tuck my driver's license and $20 somewhere into my clothing.
Today--15 years, two children and 20 pounds later--you're more likely to find me on my couch in the suburbs at 10 p.m. near a snoring husband. But every once in a while, I miss my girlfriends, and the party chick within me stirs.
Going to clubs seems a little intimidating now. But it turns out, lots of places let ladies like me party like it's 1999. Hope to see you out there. I'll be the one with the freshly flipped hair.
Let's not kid ourselves: One reason people go out is to "meet people." Plenty of friendly faces await at Gibsons. This popular North Side steak house stands in the heart of a bar-filled area nicknamed "The Viagra Triangle" because of its preponderance of older, wealthy men on the prowl.
During my first visit to this wood-paneled bar on a busy Saturday night, three men try out pickup lines. ("Don't you feel like a sardine in here?" Being out of practice, not to mention uninterested, I answer, "Yes," and keep walking.) I end up near the piano, where people are joyously singing along to Billy Joel and Neil Diamond songs.
The appetizers are huge. Gibsons is renowned for its monstrous portions, so a single trio of tender filet sandwiches or a slice of foot-high "The Meaning of Life" cake can fill you up--and even leave enough for your new friends.
Vibe Really friendly; strangers will definitely chat you up here.
Getting there 1028 N. Rush Street (312/266-8999). Parking is tough; spend $11 on valet.
The bartender swivels his hips as he mixes my tiny $8 mojito. It's hard not to dance here as salsa music pulsates through this sexy River North club. Exposed-brick walls and ceiling-to-floor burgundy drapes surround the dance floor.
It's after midnight. Wendy Thompson, 46, and Mary Hersema, 51, both of the south suburbs, sit in one of the curved booths along the wall. Their daughters brought them here for a special night out, complete with a dance lesson, dinner and lots of salsa dancing.
The loud music makes it tough to talk, but Wendy and Mary are having a great time. "You don't go here to talk," Wendy shouts over the music. Rumba is a Latin fusion supper club known for its dance floor. Around 11 p.m., the staff clears the tables away to make room for dancing. Within minutes, the area teems with women in skirts and heels and men in collared shirts. Live bands perform nightly.
Vibe High energy; great for people who want to learn to dance or watch salsa dancing.
Getting there 351 W. Hubbard Street (312/222-0770). $10 cover; $10 for valet.
"Let me hear ya say, 'All night long!' " a fedora-wearing blues guitarist shouts to the seemingly standing-room-only crowd. It's a packed room at Buddy Guy's Legends, a blues club in the South Loop owned by the 72-year-old Rock and Roll Hall of Fame guitarist.
The place doesn't feel like a juke joint, but it's definitely unpretentious. And it's not always comfortable. On crowded nights, when the general seating is full, people sit on plywood planks placed over pool tables. This place is all about the blues. So why am I feeling happy?
Maybe I'm taking a cue from Frank Alley. The Mississippian is all smiles as he dances with his wife, Ivy. "It's fun to see people from around the country who don't know the blues come and enjoy the blues," says Frank, 62.
I'm one of those people. Sure, I've heard of B.B. King. But checking out the club's memorabilia-covered walls leaves me clueless. I don't know anything about the music, but I totally enjoy jutting my neck to the live band.
Place Buddy Guy's Legends
Vibe Laid-back, bluesy live music; soul food.
Getting there 754 S. Wabash Avenue (312/427-1190). Pay meters. Cover charges vary.
Buddy Guy's Legends 
The menu at The Tasting Room in Chicago's West Loop is like a big book written in a foreign language. Even my worldly and wine-loving friend, Mary, is unfamiliar with some of the hundreds of wines available. Should we have a glass of Domaine Zind Humbrecht, Gewurztraminer or Mastroberardino Lacryma Christi del Vesuvio Bianco?
The beauty of The Tasting Room is that you can order little tastes of any of them. I tell the waitress I like Pinot Noir, so she steers me toward the popular flight called "The Birds." A flight includes three wineglasses filled one-third each. It arrives on a sheet of paper labeling each glass. We couple that with cheese fondue, served with potatoes, chicken, red peppers, bread and apples. All the food groups are represented. Could this be healthy?
Upstairs, smooth jazz washes over the brick-walled room with big windows and skyline views. We stay away from the cozy couches and chairs (too tempting to doze off) but settle in at a table and spend hours chatting, sipping, dipping into chocolate fondue and reminiscing.
Place The Tasting Room
Vibe Upscale, quiet, perfect for catching up.
Getting there 1415 W. Randolph Street (312/942-1313). Street parking.
The Tasting Room 
You know you've found a good place when the band has a white-haired man jamming on a bass. Live jazz music makes this 101-year-old club one of Chicago's gems, even though it's in the sometimes-shady Uptown neighborhood. I feel safe coming with my friends, though, and we order a round of beers and vodka martinis.
The only thing that rivals the music in this place is the decor. It's a Prohibition-era styled club. Murals hang on the walls. Curved velvet booths line the dark, banjo-shape room.
At one time, the Green Mill was a hangout of mobsters and celebrities, including Al Capone and Frank Sinatra. Today, the club attracts a mix of young hipsters and older jazz lovers. Green Mill tends to get crowded, so get there early if you want a seat or a view of the stage. And be aware: Panhandlers often stand near the bar's front door. But, hey, that's all part of the ambience.
Place The Green Mill
Vibe A mix of young hipsters and older jazz lovers. A 1940s feel.
Getting there 4802 N. Broadway (773/878-5552). Free parking. Cover charges vary.
The Green Mill 
In between sips of our martinis and conversations about guys we used to date, my girlfriend and I suddenly stop talking and croon along with the piano player. "Isn't she luhhh-vely? Isn't she won-derful?"
Our behavior isn't unusual at Redhead Piano Bar, a downtown fixture. If you go hoping to sing karaoke, you'll be disappointed. No on-stage patron singing is allowed. But customers are welcome to--and often do--sing along with the piano player and the professional singer, whose by-request repertoire includes John Denver tunes and the theme from Lost.
I could consider drinking a whole vat of the "Jimmy's Got a Pear" martinis, made with Grey Goose vodka, La Poire Disaronno and a splash of sweet and sour. I also love the bar's specialty drink, the Redhead, a sweet martini with orange vodka, Licor 43 and pineapple and cranberry juices.
Most weekends, expect lines and limited seating options. But good singers always stand up.
Place Redhead Piano Bar
Vibe Fun and classy. Dress code--no gym shoes, flip-flops or sweatshirts. No food.
Getting there 16 W. Ontario (312/640-1000). $15 valet; no cover.
Redhead Piano Bar 
Back in the day, I used to love finding unknown bands, becoming a fan and then bragging when they hit it big. If I still had time to do that now, I'd hang out at FitzGerald's, a roadhouse-style, live-music mecca in Berwyn, just a few blocks west of Chicago.
We sit around a tiny table, drink bottled domestic beers and listen to a rockin' band called Mr. Rudy Day. Unlike its city rivals, FitzGerald's manages to avoid the frat-boy feel. People come here to listen to the music, which ranges from rock to big band. "I'm 55, and I'm booking the place, so that helps a little," says co-owner Bill FitzGerald, whose family has owned the night spot for 28 years. "We're all over the place, age-wise and music-wise."
FitzGerald's is actually a homey, U-shape campus with several places to hang out: a big bar with a dance floor, a little bar, a courtyard and a Southern restaurant called Wishbone. It's all designed for a night of dinner, drinks, dancing--and almost-famous music.
Vibe Roadhouse. Bar scene in A League of Their Own filmed here.
Getting there 6615 W. Roosevelt Road, Berwyn (708/788-2118). Covers vary.
(A version of this story appeared in Midwest Living® March/April 2009.)