Deal Breakers!

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Who doesn’t love a deal? These days, no one. But not everyone has a natural knack for finding bargains. That’s why we’re seeking out the biggest cheapskates we can find and turning them loose to dig up deals for the rest of you.

Here’s how it works: Each team gets $25 to spend on food, drinks, entertainment and, if they really want to impress, a little something extra. We evaluate their finds based on creativity and value to decide who advances to the next round, when we'll bring in challengers to try to topple them.

We put out our first call for Deal Breakers a few weeks ago, and four fierce competitors rose to the challenge.

Their first challenge: In a single night, show us the best of what your neighborhood has to offer.

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Allison Yates and Colette Syputa
Status: Roommates
Neighborhood: Lakeview

Allison and Colette go way back—all the way to first grade, when they were in the same Girl Scout Brownie troupe in suburban Bloomingdale. They went their separate ways for college but reunited in Boystown, where they’re now roommates. Every weekend’s an adventure for these two single ladies, but they were in rare form when they set out for some pre-Valentine’s fun on Friday the 13th.

Dinner: We decided to first try our luck with munchies at Fizz Bar & Grill, which offers half-price appetizers until 8 p.m. on Fridays. We arrived in just the nick of time, ordering a crostini plate and quesadillas, which were brimming with whole leaf spinach and red peppers—extraordinarily better than your basic pub variety. It was all a whopping $7.25. Total spent, including tip: $9.

Drinks: With full bellies, our minds turned to drinks, so we headed over to Houndstooth Saloon. In a neighborhood known for partying hardy, this spot is a nice change of pace. We ordered $3 domestics—a Miller Light and Old Style. Total spent, including tip: $7.

Entertainment: After drinks, we trekked up Clark to the midnight Improv Jam at iO, a weekly event where audience members are invited to play alongside iO vets. Though the tickets only cost $3 a pop, we got more than our money’s worth in laughs. Total spent: $6.

The deal that’ll break ’em: Rolling out of the comedy club after 1 a.m., we decided to curse Valentine’s Day with $1 Jell-O shots at Big City Tap. Though we didn’t meet our valentines, we had a deal breakin’ good night!

Total time elapsed: 5.5 hours

Total spent: $25

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Oren Matteson and Sarah Ross
Status: Dating
Neighborhood: Lincoln Park

Who says you’ll never meet someone special at a bar? Oren and Sarah met at Gaslight Bar & Grille about a year ago, and they’ve been dating ever since. They’re moving in together in Wicker Park in April, so last weekend’s Valentine’s Day adventure in Lincoln Park was their swan song for Oren’s neighborhood, where they’ve spent countless hours getting to know one another.

Dinner: We started at Binny’s Ivanhoe Castle, where we told the wine manager we were looking for a rockin’ red for less than $10. He steered us toward an ’06 Castano Monastrell. It was $7.99, but we shaved off a dollar by signing up for a free Binny’s card. Then we headed to Sultan’s Market for two falafel sandwiches ($4.14 each). Sultan’s is a counter-service operation, which eliminated the need for tipping. So when a homeless veteran selling love poems approached us outside the restaurant, we even had some change to help his cause. Total spent: $16.

Entertainment: On full stomachs, we hit Stay Smooth, a free DJ show at Schubas’ upstairs lounge, where DJs Bald Eagle and STV SLV offered a mix of ’80s slow jams and one-hit wonders.

Drinks: A night of dancing to old favorites wouldn’t be complete without cocktails. A $3 PBR bottle and a $4 vodka and tonic helped bring out the party animals in both of us. Total spent: $7.

The deal that’ll break ’em: Wallets bursting with two remaining dollars, there was only one place left to go: Rose’s Lounge. Rose, the 75-plus-year-old bartender, runs this cozy hole-in-the-wall with a 50 cent-per-game pool table. We ordered two Old Style drafts for a buck each and threw in a $1 tip. Total spent: $3.

Total time elapsed: 4 hours

Total spent: $26

WEEK 1 WINNERS: Allison and Colette. This frugal duo wowed us with a full night of creative choices, while staying in their ’hood and under budget.