* BEST DEALS
Cocktails at NV Penthouse
The best part about the drinks at this swank bar’s free Wednesday-night reception? The view. Pick a cocktail and then take a seat on the canopied benches that line the seventh-floor bar’s outdoor deck. If you’d rather soak up NV’s soft green lighting (for eNVy, get it?), grab a seat at the reserved tables.
Hidden cost You’ll likely be subjected to some marketing campaign (the night I went was sponsored by antihangover pills) and asked for a $10 to $15 donation. I didn’t pay it, and I still got free booze. Wednesdays 9–10pm. 116 W Hubbard St (312-329-9960).—Jacob Nelson
Friday Night Happy Hour at More
The only thing better than free booze is free booze in the form of a cupcake. Stop into this tiny, sleek bakeshop after work on Fridays, and you’ll be greeted by trays of free cocktail-inspired mini cupcakes. The flavors change frequently, but recent selections included Cuba Libre (chiffon cake with rum-infused frosting) and Lemon Drop (limoncello cake frosted with vodka-tinged buttercream).
Hidden cost The friendly women behind the counter don’t pressure you to make a purchase, but those bigger cupcakes behind the glass look so beautiful and tempting and delicious…and they’ll cost you. Fridays 5–7pm. 1 E Delaware Pl (312-951-0001).—Julia Kramer
Green Room Sessions at Uncommon Ground Devon
Free food is easy to find. Organic, locally grown free food is pretty rare. Chef Brian Millman’s appetizers make the rounds at this speaker series and networking event at the environmentally focused Edgewater restaurant.
Hidden cost Rambling, insufferable liberals and the pressure to mingle with them and listen to what they have to say. Second Thursday of the month, 6–8pm. 1401 W Devon Ave (773-465-9801).—JK
* Late-night buffet at Sedgwick’s Bar & Grill
When it comes to midnight bar buffets, if it’s free and not reheated from Costco, it’s hard to argue. Still, the mac and cheese, veggies with dip and pizza here are decent enough that not even neighborhood yuppies bat an eye before piling dozens of wings onto appetizer-size plates.
Hidden cost Those post-frat guys, the ones yelling things like, “Suck it, Krugman!” as some line of economics debate…yeah, they’ll be there. But not as many of them as you might fear. Fridays at 11pm, Saturdays at midnight. 1935 N Sedgwick St (312-337-7900).—JK
Cooking classes at Whole Foods Market
“Chef Susan” of Cardamom Kitchen regularly leads free cooking classes at WFM. This month’s “Gluten-Free Baking: Cookies!” will teach you how to bake chocolate-chip and sugar cookies. Or rather, how to eat them.
Hidden cost Gluten-free cookies: Sorry, having a hard time seeing the joy in that. Sat 19 at 1pm. Whole Foods Market, 3640 N Halsted St (773-472-0400).—JK
* Buffet at Big Chicks
Uptown’s ebullient queer saloon has been serving up a year-round Sabbath supper for two decades. Folks love it for the all-you-can-shove smorgasbord of carny- and veggie-friendly dishes like burgers and tofu dogs with fruit salad in the summer and heartier fare like lasagna and mixed greens during the winter.
Hidden cost Arrive by 4pm in the summertime or suffer unbearable queues. It’s understood you’ll buy some booze so try the reasonably priced, head-spinning vodka lemonades. Sundays 4–6:30pm. 5024 N Sheridan Rd (773-728-5511).—Jason A. Heidemann
Friday-night wine tastings at Fion Wine Bar
The word about Fion’s Friday wine tastings may not have spread, but that’s the reason to go: The light attendance spells attentive service and a relaxed, frat-free atmosphere for kick-starting the weekend with a mini flight. The cozy wine bar offers ample, if not generous, rotating samples of two whites and two reds. You’re likely to make at least one new discovery—it was the Zuccardi Malbec Serie A for me.
Hidden cost Fion’s intimate aura gets jarred if you use the restrooms, situated in the rather less luxurious BelAir hotel. And it’s dangerously easy to slide from the tasting into full-fledged drinks and dinner. Fridays 6:30–8:30pm. 426 W Diversey Pkwy (773-549-5400).—John Beer
Monday Rehab and Wednesday No Tell Motel at Debonair Social Club
While free drinks and no cover might lure Wicker Park barflies to Debonair Social Club for these nights, the real fun comes from a campy vibe that’s often scarce on weeknights. DJs spin at Rehab parties (R.S.V.P. to going.com), whereas local burlesque artists take the stage for No Tell Motel (no R.S.V.P. required).
Hidden cost Complimentary beverages are limited to Champagne and PBR at Rehab (with three drink tickets) and Champagne at No Tell Motel. The free drinks last only from 9–10pm, meaning the 15-minute wait to get in can be a buzzkill. 1575 N Milwaukee Ave (773-227-7990).—Margaret Rhodes
* Pizza and wings at Faith & Whiskey
Faith & Whiskey hasn’t been around for long, but it has already reconcepted (it’s now the “new” Faith & Whiskey). The best part of the revamped rock bar is Faith Fridays, where a table near the door is piled with veggie and sausage pizzas and wings.
Hidden cost Little to none, really. The bartenders were almost eerily happy to point out the grub, which by 7:30pm had barely been touched—but had gone pretty cold. Fridays 5–8pm. 1365 W Fullerton Ave (773-248-9119).—David Tamarkin
* Barbecue buffet at Map Room
Bartenders at Bucktown’s reigning beer bar know nothing goes better with barbecue than a nice cold one. So they lead the horses to water by setting out a spread of ’cue from Leon’s each weekend day around noon. The fried chicken and hot links are actually tastier than the ribs, but these aren’t bad bones—especially when they’re free.
Hidden cost These beer guzzlers can eat—the buffet typically gets devoured in a little under two hours. And while no one keeps track of whether you’re dropping dough on pricey craft beers while partaking, the least you could do is not look like a cheapskate and grab a round. Saturdays and Sundays 12:15–3pm. 1949 N Hoyne Ave (773-252-7636).—Heather Shouse
Wine tastings at wine shops
Any wine shop worth its corks will have at least a few free tastings a month. These stores understand that the best way to get customers to buy a bottle is to let them taste it (not just gawk at the pretty label). The tastings are often hosted by a winemaker or distributor (a.k.a. somebody heavily invested in promoting their brand). Expect to try small pours of three to six wines.
Hidden cost If the tasting is at a prime time (Saturday afternoons or Friday nights), expect large crowds. If it’s at a slower time, expect to listen to a spiel about the wines from whoever is pouring. And no matter what time it is, expect to get just tipsy enough that buying a case of $45 cabernet seems like a great deal. Saturdays 2–4pm at Just Grapes (560 W Washington Blvd, 312-627-9463); Mondays and Fridays 6–7:30pm at Taste Food & Wine (1506 W Jarvis Ave, 773-761-3663); Tuesdays 6–8pm at ThePoisonCup (1128 W Armitage Ave, 773-935-1325).—DT
Buffet at Cityscape Bar
There’s a lot to be impressed by at the 15th-floor hotel bar of this Holiday Inn. Take the gorgeous views of the city and the Chicago River, for one, or the incredibly affordable wine list, which includes a good number of generously poured glasses for $5 and up. To sweeten the deal, the bar has a little complimentary buffet (all brought in from the adjacent Italian-Asian fusion restaurant Italiasia).
Hidden cost We do love the wine and views so the buffet is something of a disappointment with its soggy, tempura-battered broccoli and zucchini, and cheesy spinach gratin and crackers with dip that manage to simultaneously taste like nothing and burn with heat. That aside, if you’re looking to turn this into a meal (or at least a generous snack), you’ll need a seat at the bar or at one of the tables, which means you’ll need to order a drink to not look like a total jerk. But since the cheap wine’s a better deal than the free food, this is more like a hidden gain. Wednesdays 5–7pm. Holiday Inn Chicago Mart Plaza, 350 W Mart Center Dr, 15th floor (312-836-5000).—JK