Chicago for Twentysomethings: Part 1
by Lilia Del Bosque Oakey
Editor’s note: Chicago for Twentysomethings is a three part series.
With the perfect balance of culture, clubs, bars, and free fun, Chicago is the perfect city for twentysomethings. But like most major cities, it is easy to get caught up in marquees and stay in tourist infested areas without seeing much of what the city has to offer. Even though Michigan Avenue, the Theater district, and State Street are centrally located and tourist hot spots, here are a few alternatives that will almost make you feel like a local. Almost.
Warehouse District
On the northwest outskirts of the Loop, not far from State Street, is the Warehouse District. Home of Harpo studios, and looming empty warehouses, this neighborhood is host to some of the hippest bars and best restaurants.
One of Chicago’s most popular bars, Funky Buddha Lounge is nestled at the edge the warehouse district. The epitome of a hip club bar, Funky Buddha’s leopard skin and leather clad interior is just as eclectic as the crowd. A healthy mix of local hipsters, tourists, and young professionals, the bar has a massive dance floor that is always packed on weekends of sweaty 20-somethings thumping to the sounds of hip-hop, house, reggae, electronic, Latin, jazz, or whatever happens to be up on the clubs diverse and always rotating roster of music. Don’t let the crowds fool you, this is one of the most laid back clubs you will ever visit, with plenty of spaces for small groups to gather and gossip.
Funky Buddha Lounge is located at 728 W Grand Ave
Butterfly Social Club is in the same building and owned by the same people as Funky Buddha Lounge and attracts the same crowds. One major difference between the two bars is Butterfly Social Club’s organic choices. When it first opened, Butterfly Social Club with hippie heaven, with moss covered walls and tree branch benches. Now, more modern, the bar still boasts cocktails made from fresh squeezed (literately, they squeeze it at the bar) cocktails and craft beers. Butterfly Social is usually less crowded and also features a rotating list of DJs.
Butterfly Social Club is located at 722 W Grand ave
For a bar that doesn’t try at all, head over to Richard’s Bar. This no frills bar is a bit brighter than your average dive due to glaring neon signs but cheap booze and chatty eclectic regulars, which vary from local hipsters to bruiting bearded men, give Richard’s a dive feel. Head over on weekends for a full crowd, tons of PBR, and one of the friendliest crowds you will ever meet. If you are brave, you can try one of the pickled hard boiled eggs for only 75 cents but some things might be better left in jars.
Richards Bar is located at 491 N Milwaukee Ave and is steps away from the Blue Line
Veerasway is by far not the only restaurant in the Warehouse District but the only one worth a special trip. Its fresh take on classic Indian food is enough to steer you into their doorway every night. The space is small and features long communal tables, unifying all the random guests in the restaurant. There are no wrong choices when it comes to Veerasway’s food. Labeling itself as “fresh Indian” the space hosts a healthy mix of Indian classics and Indo-American choices. The cocktails are expensive but The Bengali Tiger, which has cardamom & vanilla bean infused vodka, tamarind-date, pineapple, and red chile, is continually talked about, featured in local magazines, and might just be worth it.
Veerasway is located at 844 W. Randolph St and is easily accessible by public transportation. Please make reservations.
Alternative Theater
Chicago has big name theaters that attract touring companies, popular musicals, and loads of tourist. But Chicago’s home bred theater is a better bet and is much less expensive.
Too Much Light Makes the Baby Go Blind
As Chicago’s longest running play (a whopping 21 years) Too Much Light… is unlike any theater experience. The actors are challenged to perform 30 plays in 60 minutes. The plays are all original and continuously rotating so every show is different. If they are able to complete the challenge, they buy one pizza for the whole theater. One pizza. For all 50 or so people.
The show runs on weekends and cost $9 plus the roll of a six sided die.
More information at neofuturists.org
Goodman Theater
This theater is anything but unknown but is often forgotten by visitors. The Goodman hosts some of the best actors in the country and performs a variety of plays and musicals. Most of the plays are well known or by popular playwrights but a smaller theater is home to original and often controversial plays. Many of the playwrights are from the Chicago or at least the Midwest which gives this world renowned theater a local feel. The theaters most popular production is A Christmas Carol, which always sells out but the Goodman is always looking for volunteer ushers who are allowed to watch the show for free.
Visit goodmantheatre.org for more info
Music Venues
Because Chicago is home to so many popular acts, the music scene in Chicago is one of the best. Popular artists like Billy Corgan play at small intimate venues and national acts like Green Day often play secret shows under aliases. The local music scene in Chicago never disappoints, so choosing a random show at a great venue is usually a good weekend option. Here are three venues that are a not as well known and by far not the only small local venues worth checking out.
Metro is located in one of the most popular neighborhoods in Chicago– Wrigleyville. Located steps from Wrigley Field, Metro features popular acts such as Matt and Kim, Ludo, and local favorites Company of Thieves. Tickets are usually under $12 and big name shows rarely go over $25. Metro is a small vintage theater with detailed woodworking and carvings framing the stage but has two stories so avoiding moshing youngsters or just plain annoying concert goers isn’t a hassle. On weekend nights, Metro features popular local DJs and transforms a fun concert space into an intimate night club.
Metro is located at 3730 N Clark Stand is accessible by public transportation
Located in Wicker Park is Double Door, a bigger venue that hosts similar acts to Metro but favors rock bands over Metro’s indie acts. Tickets range from $12- $30 depending on the act and most shows have at least 3 bands playing. The crowd is older than Metro’s and most shows are 21+ so you don’t have to worry about teenagers and their parents.
Double Door is located at 1572 N Milwaukee Ave and is accessible by public transportation
The Vic Theater hosts bigger names like Built to Spill, M.I.A., Gaslight Anthem, and the Hold Steady. The venue is much larger than the other two and was originally a vaudeville theater. The theater has stayed relatively the same since it’s vaudeville days and still has marble staircases and floors, ornate sculptors, and great acoustics. When there are no concerts, the Vic transforms into “Brew and View” which screens cult and underground movies and serves beer for cheap. The crowd at “Brew and View” is one of a kind and sings, dances, and shouts out lines on cue.
The Vic Theater is located at 3145 N. Sheffield Ave and is accessible by public transportation
Chicagoans are proud of their hometown and the only way to understand their pride is to pry yourself away from tourist hot spots. Make sure you hit up favorites like Millennium Park and the Art Institute but don’t forget neighborhoods out of the loop and local favorites in order to really see the city.
Planning a trip to the Windy City? Check out our Chicago Get Going Guide for our list of hotels, restaurants, and sights you can’t miss in Chicago. Find out who made the cut, then have a blast in Chi-town
Lilia Del Bosque Oakey works in Social Media Marketing and writes memoirs and oral histories. She currently lives in Pensacola, FL.




4 Comments
I’ve been to Chi town several times, but I never seem to get past all of the deep dish pizza places and awesome hot dog stands. Thanks for the good ideas.
funky buddha is the best!
Too Much Light Makes the Baby Go Blind is the best thing I ever saw in chicago.
Metro is the place to go if you wanna hear some real music.