I get a lot of messages from Couchsurfers who are coming to Chicago and want suggestions on things to see or do during their stay. The following is a list of favorite activities/sights/restaurants that I highly recommend (links included!). Of course, it's not comprehensive -- it's based mostly on personal taste (and budget) -- but feel free to leave any of your own recommendations in the comments section. If I agree with you, I'll add it in the original post! (NOTE: Please avoid the hating. I want you to post your own favorites, not lambaste mine.)
[Last Updated: August 2014]
Windy City Checklist:
First off, pick up a current copy of the CHICAGO READER when you get into town. It's the alternative paper and features tons of listings for music, movies, theater and whatever else you seek in Chicago.
Late Night Karaoke @ Alice's Lounge: Alice's Lounge is a dive bar that arguably features the best Karaoke in Chicago. (Actually, it's been voted Best Karaoke for two years running -- 2011 & 2012 -- in the Chicago Reader!) This is all thanks to emcee Fred Wood and his mind-boggingly comprehensive songbook of Karaoke favorites new and old. (Not to mention plenty of obscure stuff you wouldn't even imagine was available for belting out drunkenly to an unsuspecting crowd!) If that weren't enough, Fred also possesses a legendary bag of props to liven up the performances. (Trust me, it's way cooler than it sounds!) This is my favorite haunt in all of Chicago, so chances are good that you will find me here, especially on Thursday nights after the Chicago Weekly Meeting.
Alice's Lounge -- 3556 West Belmont @ Central Park (Avondale). Wednesdays, Thursdays and Fridays, 11 p.m.-3:30 a.m.; Saturdays, 11:00 p.m.-4:30 a.m. No cover, but you are expected to buy/nurse a drink. 21+
Too Much Light Makes The Baby Go Blind: Sketch theater at its finest. The premise is 30 plays in 60 minutes, and the ever-revolving cast deliver some of the most hilarious, absurd, shocking, provocative and inspiring sketches I have ever witnessed. The actors are fearless when it comes to baring everything -- heart, soul and skin -- for the sake of entertaining, confronting and connecting with the audience. Simply, I am floored by the level of talent on display at this show, and that's why I look forward to both attending -- no, being part of it! -- every week.
The Neo-Futurarium -- 5153 North Ashland @ Foster (Andersonville). Fridays & Saturdays, 11:30 p.m. Sundays, 7:00 p.m. (Get in line early, especially on Fri. & Sat.!) Tickets $9 + roll of a six-sided die (=$10-$15). CASH ONLY. All ages.
That's Weird, Grandma: After teaching creative writing workshops in Chicago public schools, the cast of the Barrel of Monkeys theater troupe sift through thousands of stories, poems and plays written by children and adapt them into a series of entertaining sketches. Kids enjoy the show for its silliness; adults love the sheer inventiveness of the adaptations. Whether it's a cheer-off that leads to disastrous results (A Bad Day) or the most sensational Indian musical in the world (The Dance of Yousail), BOM will leave you giddy and giggling long after you have left the theater. (I will personally testify to reciting such gems as "Oh, no, it's JoJo, the owner of the barrel!" and "I'm taking the whale for a ride! I'm taking the whale for a ride!" for months after first hearing them here!)
The Neo-Futurarium -- 5153 North Ashland @ Foster (Andersonville). Mondays, 8:00 p.m. Tickets: $12 for adults | $6 for kids. CASH ONLY. All ages.
Baby Wants Candy: I've mentioned my favorite sketch shows in the city, but if you prefer your comedy to be completely made up on the spot, you'd be hard-pressed to find a better improv group than Baby Wants Candy. The premise is simple: The audience shouts out a title of a musical that has never been performed before. Accompanied by a full band(!), the first title that BWC hears becomes the title and theme for that evening's completely improvised 60 minute musical that they create then and there. (Or as they say just before showtime, "And now the opening and closing night of ____________.") Improv comedy alone is difficult to pull off successfully; now imagine how much skill it takes to get your audience to literally howl with laughter while fleshing out a cohesive storyline complete with musical numbers. Baby Wants Candy does exactly that, and you'd be at a loss to miss this show.
Apollo Theater -- 2540 North Lincoln Avenue (Lincoln Park). Fridays, 10:30 p.m. Tickets: $20 | $10 with student discount. All ages.
Music Box: A wonderful old-time movie theater that showcases the best in independent, classic and foreign films. Better yet, they have midnight showings of cult films during the weekend. The squeaky, thin-cushioned seats are nothing to rave about, so I wouldn't recommend anything over two hours, but you will nevertheless be impressed by the design of the place. The main theater even has an organ, which comes in quite handy during the annual showings of Nosferatu, Sing-Along Sound of Music and others.
Music Box Theatre -- 3733 North Southport @ Grace (Lakeview). Check site for showtimes. Tickets: $9.25 $7.25 for matinee showings.
Concerts: Chicago has a great music scene simply because it's a crossroads. If you're a band on tour, especially in the Midwest, it is in your best interest to play a show in the Windy City. If you want to experience live music in Chicago, find out when your favorite band might be coming through town and then make plans to visit the city. That way you'll have bragging rights on how far you'll go to see a favorite artist. (My record: A 2700 mile road trip from Washington, DC to Seattle, WA for Bernard Fanning, lead singer of Powderfinger. Awesome interview, too!)
Favorite Venues: Schubas, Beat Kitchen, Uncommon Ground, Lincoln Hall, S.P.A.C.E., Park West, Double Door, Riviera Theatre (aka The Riv), Metro, Subterranean, Empty Bottle, Reggie's Live, The Hideout
SHAMELESS PLUG: Stop by BFN NETWORKS -- my podcast network -- to see what upcoming concerts are at the top of my list. While you're there, I highly encourage you to check out a long list of insightful and uninhibited band interviews on The Sound Of You & Me! Subscribe to this podcast and others (links at the top of the sidebar) and download a treasure trove of incredible live in-studio performances!
Theater: For better or worse, Chicago is a theater town. I once had a small-time online theater critic for a roommate, and thanks to his extensive knowledge of the arts and access to free seats for productions big and small, I received a once-in-a-lifetime opportunity to witness all the best (and worst) the Windy City had to offer. Rest assured, it was an invaluable education that I will forever be grateful for. When you come to Chicago, do your best to attend any kind of theater. Whether it be sketch comedy, improv, musical or drama; a Broadway hit or a little-known one-act; a beloved classic or a world premiere, find something that sounds appealing to you and just go for it. Life's about taking risks. Even if it's a terrible show -- and, oh boy, have I had my fair share of awful plays in this city! -- at least you tried to get some culture among all the hours spent exploring downtown and bar-hopping.
Recommended Theater/Companies: The House Theatre of Chicago (Seriously, Do. NOT. Miss!), The Strange Tree Group (A MOST weird & whimsical SUPER <3), The Neo-Futurists, Dream Theatre Company, Barrel Of Monkeys, Baby Wants Candy, WildClaw Theatre, Route 66 Theatre Company, Seanachai Theatre Company, Chopin Theatre, Goodman Theatre, Vaudezilla . . . and so much more!
Also, I HIGHLY recommend Chicago Theater Beat for their reviews of current shows in town. I am pleasantly surprised by how often I agree with their reviews, which more often than not save me a lot of time, money and grief when it comes to choosing a show that I know nothing about.
And if you'd like to find discounts on a wide range of productions in town/nationwide, I suggest that you sign up for Goldstar.com.
View Velander's Guide to Downtown Chicago in a larger map
If you like to eat and drink, Chicago is your kind of town. Here's a list of my favorite places to get a meal or enjoy a drink with friends. Of course, there are definitely a million other restaurants in this sprawling city, all likely worthy of your time, money and palette, but this is what I recommend during your visit.
Brown Sack (3581 W Belden Avenue) - A hidden gem tucked away in the southwest corner of Logan Square, this cozy and hip Mom & Pop "soup, sandwich and shake shack" should be a required stop during your tour of the city. The sandwiches look like they should be framed and put on a wall and taste even better. People generally hail the Corned Beef Reuben, but my heart belongs to the BLT with avocado and shrimp. My mouth waters just thinking of the all the wonderful flavors in that sandwich. (The Cajun Po'boy is nothing to scoff at either. In fact, everything is good here!) Also, both the Peanut Butter Shake and the Mocha Shake are nothing short of mind-blowing. They're reason enough why Brown Sack has become my favorite restaurant in Chicago, and I personally know several people who have gone out of their way to stop by and order one more for the road.
Kuma's Corner (2900 West Belmont) - If you're in search of the best burgers in the WORLD, you'd be hard-pressed to find a better place than Kuma's Corner. Even with the atmosphere (and attitude) of a neighborhood (albeit more upscale) biker bar, I've seen all walks of lifes make the trek and wait anywhere from thirty minutes to three hours(!!!) just to get their hands on one of these divine patties served on a soft pretzel bun. To match the devil's music that blasts continuously from the speakers -- thankfully loud enough to appreciate yet not enough to drown out conversation -- the burgers are named after heavy metal groups and, of course, are prepared in such a way to pay tribute to the band's music. The more intense the metal, the more intense the burger. (The Plague Bringer is hot, but the Metallica will make you want to scream, especially when you're foolish enough to order it with extra buffalo sauce. Which I recommend.) Moreover, the bar has one of the best selections of local/regional beers in the city due to their efforts to support local and/or independent breweries. Last but not least they serve whiskey on tap, which I think is fucking awesome (and I don't even drink!).
However, all is not perfect in the world of Kuma's. Like I mentioned, the bar has become notorious for its ridiculously long waiting times. I myself am not one to hang around for longer than an hour, so if you want to avoid a packed house, heed this advice: Skip the weekend altogether 'cause no matter the time there is always a crowd. Instead go early in the evening on a weekday (anytime between 3-6 p.m. is ideal) and go with no more than four people. (The less people in your party, the easier it will be to get a table.) Also, if there are seats available at the bar, don't be afraid to sit down and order there. That's how I got to eat right away during my first visit.
Kin Sushi & Thai Cuisine (1132 North Milwaukee) - Chicago has a lot of Thai restaurants, but the problem is that most of them specialize in only one or two dishes, leaving the remainder of the menu something to be desired. That's certainly not the case with Kin, where I've always had a stellar meal no matter what I've ordered.
Fat Willy's Rib Shack (2416 West Schubert @ Western) - My favorite place for BBQ in Chicago. The ribs melt right off the bone, the cornbread (served with honey butter) is sensational and the hot brownie sundae (if you have room for it) brings decadence to a whole new level.
Mi Tierra (1039 West Belmont) - The interior looks gaudy, but they have excellent Mexican food. Stellar chimichangas, and I've yet to meet anyone who didn't enjoy the margaritas.
Mr. Greek Gyros (234 South Halsted) - Located in the heart of Greektown on the West Loop, Mr. Greek will fulfill all your Chicago-centric gastronomic needs. Probably one of the best deals on Italian Beef in the city, and the chicken burrito -- big enough for two people -- is to die for. Best of all, it's open 24 hours. (One of my first Chicago haunts!)
Potbelly Sandwich Works (Multiple locations) - Although it's now a regional chain, Potbelly first began as Chicago's answer to Subway and Quizno's. I don't know how they do it, but their subs blow the competition out of the water. Great milkshakes, too.
Giordano's (Multiple locations) - Chicago-style deep dish pizza is a must during your visit simply because that's what the city is famous for. Stop by any Giordano's and order up a Deep Dish Spinach & Cheese to see what the fuss is all about.
NOTE: These pizzas can take anywhere from 30-60 minutes to cook, so if you want to save the wait, call ahead and make your order on the way over.
Luke's (215 West Jackson) - If you want to aim for the local favorites, stop by this popular lunch spot downtown (a stone's throw from the Sears Tower) and order up a Chicago dog or Italian Beef. (Skip the pizza; it's garbage.) DO NOT forget the fries!
Taqueria Los Comales 11 (2148 North Milwaukee) - I don't know if this place is open 24 hours or what, but it's a great spot to get cheap Mexican food at 2 a.m. The specials are delicious, the tortas are massive and the horchata (rice water) is incredibly sweet.
Athena (212 South Halsted) - Stop by this restaurant to fulfill all your authentic Greek needs. The saganaki is superb, and I've always been a fan of their Mediterranean Pasta.
Mario's Italian Lemonade (1068 West Taylor) - This is a tiny stand in University Village (near UIC) that specializes in refreshing Italian ices -- think of a fruit-flavored slushee -- that are perfect during the unbearable Chicago summers. Only open early May-September 15.
Scooter's Frozen Custard (1658 West Belmont) - The best frozen custard you'll find without having to make a trip to Milwaukee.
Map Room (1949 North Hoyne) - This popular Bucktown hotspot has an extensive selection of beers from all over the world. This place has a great vibe, so it's no surprise that there's oftentimes a line out the door.
Quencher's Saloon (2401 North Western @ Fullerton) - Like Map Room, this bar has a great selection of beers from all over the world, only this place appeals more to the alternative crowd. If you like loud rock music, piercings and roller derby girls, Quenchers will win your heart.
Sabatino's (4441 West Irving Park) - Last but certainly not least, Sabatino's is fine dining at its best. If you're willing to splurge a little bit on yourself during your visit -- a three-course meal with a glass of wine will likely run you to the $30-$40 range -- you simply cannot go wrong with this classy Italian restaurant located just half a mile from the Irving Park Blue Line stop. You don't have to be dressed to the nines to eat here, but do try to look presentable. Trust me, you won't regret it.