It's not often one gets to brag about dumpster-diving and thrift store shopping skills in a cover letter, but when Nadia Oehlsen heard that the publishers of the Cheap Bastard
guidebooks were looking for a Chicago author, she proudly boasted, "I'm the cheapest bastard I know."
Oehlsen moved to Chicago as an adult in 1992, though her childhood is dotted with trips to the city to visit her grandfather. One of her favorite early memories of living in Chicago is an all-night, low-cost extravaganza with friends that included watching a show at the Neo-Futurarium, feasting on cheap Mexican food, heading to the Green Mill during the no-cover, late-night hours and then watching the sunrise over Lake Michigan.
With the recent release of The Cheap Bastard's Guide to Chicago still fresh in her mind, Oehlsen happily dished her top five just-about-free things to do in Chicago.
Go shopping in back alleys
I tend to use the term 'alley-scavenging' rather than 'dumpster-diving' because it's a bit more accurate and it tends to scare people away a little bit less. In Chicago there's quite a tradition of people placing things next to the dumpsters, so you can find a lot of cool stuff without ever having to get your hands dirty. In general, look for the high-rent, high-turnover neighborhoods, like Lincoln Park and Wrigleyville. If you're looking for children's toys, clothing or fitness equipment—things that you might find in an older, more stable house—Andersonville is a great place to go. October 1st and May 1st are the biggest moving days in Chicago, so the weekends nearest those dates are good (though you'll usually find stuff around the weekend nearest the turn of any month).
Take in a show without spending any dough
Volunteer ushering is fairly easy: You generally just show up a little early and hand out programs and then stay a little late and pick programs up off the floor. You can call the theater directly and ask if they need an usher or, if you usher a lot, it's worth it to join the Saints, a group that organizes ushers in the city. Most shows will allow at least one other person to usher with you because they know you don't want to go by yourself. Also, Live Bait Theater encourages people to attend their free previews. And then, if you're a night owl, I.O. Cabaret has free shows Wednesdays at 8 p.m. and Sundays at 11 p.m. Second City has free shows after every performance every night but Friday.
Enjoy a tropical vacation…indoors
Just south of the Sears Tower is the tallest concrete building in the U.S. at 311 S. Wacker Drive Inside it has a two-story winter garden that's filled with palm trees and plants and a fountain. I love indoor places that have a tropical paradise feel, and this is a great place to bring a sack lunch. A lot of people go to Pazzo's, this take-out place next to the winter garden, but no one seems to mind if you bring your cheap bastard sack lunch. Also, Garfield and Lincoln Park Conservatories have saved my sanity more than once in the winter.
Get happy (and full) at happy hours
The Celtic Crown has great, classic happy hour food like free wings from 4-7 p.m. on Tuesdays, and changing drink specials like $3 pitchers of beer. The Map Room has an international night [on Tuesdays], where they bring in food from a particular restaurant that features that [night's] ethnicity, and on Sundays they have a brunch that's not quite an all-you-can-eat buffet. Big Chicks is another favorite. It's a straight-friendly gay bar in Uptown that has a fabulous Sunday buffet and very friendly, family atmosphere. The woman who owns the bar also owns the gourmet restaurant [Tweet] next door so the food is really good.
Open your ears but not your wallet
The Chicago Cultural Center is constantly booked with free music and dance events, and there are a number of bars that always have no-cover music throughout the week. Chicago Brauhaus, a German bar and restaurant in Lincoln Square, is one of my favorites, if you want to be campy. Every single night of the week, the owners are playing music, kind of cheesy German music but a lot of fun. The Charleston Bar has no-cover music if you like jazz and Lee's Unleaded Blues on the South Side is also no cover.