They scrimped, they pinched, and for four weeks, they stretched their $25 budgets as far as they could go. In the end, three teams of Deal Breakers, including fan faves Jackie and John and Allison and Colette, withstood our Guinness-soaked and Mardi Gras-laced challenges to make it to the final round.
The final challenge: Delve into one of three “parks” — Rogers Park, Hyde Park and Humboldt Park — and score the best deals in food, drinks and entertainment.
Matt Reilly and Colin Hogan
Status: Roommates
Assigned ‘hood: Hyde Park
Number of wins: 1
Entertainment: In a scholarly spirit (we were in University of Chicago territory, after all), we visited the famed Oriental Institute (1155 E. 58th St. 773-702-9520), which boasts priceless Near Eastern artifacts. The museum, open 10 a.m.-6 p.m. Tuesday-Sunday, is always free of charge. Total spent: $0
Food: Next, we indulged in a hefty meal at The Medici on 57th (1327 E. 57th St. 773-667-7394). This Hyde Park eatery is usually swarmed with students, but it’s always a great place to grab a large pizza. Total spent: $13, including tip
Drinks: When in Hyde Park, you have to stop by Jimmy’s Woodlawn Tap (1172 E. 55th St. 773-643-5516). This low-key bar attracts a unique blend of clientele, from local South Siders and U. of C. students to Nobel Prize-winning professors. We grabbed a pitcher of beer and enjoyed the laid-back atmosphere. Total spent: $12, including tip
Best deal of the day: Oriental Institute’s free admission
Total time elapsed: 4 hours
Grand total spent: $25
Jackie and John McCloskey
Status: Newlyweds
Assigned ‘hood: Humboldt Park
Number of wins: 1
Dinner: Our night started at Latin American Restaurant and Lounge (2743 W. Division St. 773-235-7290), where you can find a variety of authentic Puerto Rican appetizers for less than $3. We chose empanadas, dipped codfish and Puerto Rican beans. Total spent: $8.50, including tip
Drinks: After dinner, we stopped at a cozy bar we thought was named Zimne Piwo, which means “cold beer” in Polish. Turns out, it’s called Mel’s Place (4359 W. Division St. 773-292-2380), and lucky for us, Mel likes to sell his Old Style cans for $1.75. Next up was Stella’s Tap (935 N. Western Ave. 773-384-0077) for a couple of $2.50 PBR pints, offered daily. Total spent: $9.75, including tip
Entertainment: Our last stop was Empty Bottle (1035 N. Western Ave. 773-276-3600), known for live music, not to mention $5 beer-shot combos. We arrived early to hear the band’s sound check for free before the sold-out show and sipped $3 Bell’s drafts. Total spent: $6.75, including tip
Best deal of the night: Empty Bottle, which combines great specials, rockin’ entertainment and an attentive staff all week long.
Total time elapsed: 4 hours
Grand total spent: $25
Allison Yates and Colette Syputa
Status: Roommates
Assigned ‘hood: Rogers Park
Number of wins: 2
Dinner: To truly experience the neighborhood, we decided to have a Red Line rendezvous near the Morse stop. Faced with lots of diverse restaurants, we chose Mexican BYOB La Cazuela (6922 N. Clark St. 773-338-5425), where we munched on chips and salsa, ordered up chicken tacos and rice ($7.25) and washed it all down with a shared 40-ounce Corona ($2.25). Total spent: $11.25, including tip
Drinks: After dinner, we headed to Red Line Tap (7006 N. Glenwood Ave. 773-274-5463), a worn-in, friendly neighborhood bar that serves $2.50 Honker’s Ale & 312 drafts. We played a couple rounds of Ms. Pac-Man (50 cents total), then chilled at the bar listening to a two-man rock band. Total spent: $6.50, including tip
Entertainment: Trendy nightspot Morseland (1218 W. Morse Ave. 773-764-8900) was next, and we slipped in early to avoid paying cover (free before 10 p.m.). After ordering $3 domestic bottles (Miller Lite and Old Style), we took in the musical stylings of local folk band the Heat Birds. We finished the night listening to alternative tunes from Bloomington, Ill., rockers Ohtis. Total spent: $7, including tip
Best deal of the night: Red Line Tap and Morseland, where we found three free bands in one night
Total time elapsed: 4.5 hours
Grand total spent: $24.75
Ultimate Deal Breakers
Jackie and John! Great beer deals and authentic Humboldt Park eats, plus a sweet strategy to get in on a little sold-out concert action (even if it was a bit outside of Humboldt Park’s borders) wins this thrifty duo top cheapskate honors.
