Dollar Deals in Chicago

Get the best bang for your buck with dollar deals in Chicago. Yep, we scoured Chicago--dining, drinking and even bowling our way around the city--to find out just how far we could stretch a single greenback. Sure, you can almost always track down a $1 PBR or burger deal, but we found specials that are a bit more, well, special. Without further adieu, we present to you, fellow penny pincher, our favorite dollar deals in Chicago.

Updated: July 12, 2010

Dollar Restaurant Deals in Chicago

Simone's Bar

960 W 18th St, Chicago, IL 60608

With its innovative bar food and downright zany decor, this Pilsen fave always draws a crowd. But frugal foodies know that Sunday and Monday nights are where it's at. That's when, from 10:30pm till close, a single George Washington will score you a made-from-scratch, thin crust cheese, sausage or pepperoni pizza.


3101 N Sheffield Ave, Chicago, IL 60657

Lots of bars have Taco Tuesday deals, but you?d be hard-pressed to find a dollar taco as tasty as the tilapia version this low-key Lakeview joint dishes up. The boneless filet-- sauteed in white wine with onions and jalapenos and blanketed by a soft flour tortilla--would still be a steal at five times the cost.


2023 N Damen Ave, Chicago, IL 60647

On Friday afternoons, this compact Bucktown BYOB teems with thrifty noshers reveling in the too-good-to-be-true 99-cent falafel sandwich special. After downing the goods--ground chickpea nuggets with tomato, cucumbers and tahini, all wrapped in a pita--you'll walk away with a full belly and a penny to spare.

Five Star Bar & Grill

1424 W Chicago Ave, Chicago, IL 60642

Every Thursday, this biker-themed West Town watering hole slings its juicy Vienna beef corn dogs on the cheap. OK, so this one will run you $1.50, but when you sink your teeth into the delectably crunchy fried goodness on a stick, we think you'll agree a fifty-cent "splurge is warranted.


3339 N Halsted St, Chicago, IL 60657

Sadle up to this glitzy Boystown haunt for the crowd-pleasing Monday night bruschetta bargain. Mix and match your carb-filled feast with innovative combos like prosciutto, figs and brie with mint, or smoked salmon, capers, shaved red onion and crema. They cost (you guessed it) $1 a piece.

Dollar Drink Deals in Chicago

Taqueria El Ranchito

2829 N Milwaukee, Chicago, IL 60618

Bargain hunters descend on this authentic, far-from-fancy Logan Square taqueria every Thursday to get their hands on the 99-cent margaritas. They're not the strongest `ritas around, and they're not super-sized like some of the meals here, but they wash down those huaraches and salty tortilla chips quite nicely.

Big Star

1531 N Damen Ave, Chicago, IL 60622

Nothing compliments pork belly tacos like cheap suds, which is why we're crazy about the $1 Schlitz drafts at this immensely popular Wicker Park spot. And the best part? This screamin? deal is on every day of the week. As if we needed any more reason to drop in ?

Fun Dollar Deal in Chicago

Diversey River Bowl

2211 W Diversey Pkwy, Chicago, IL 60647

Weeknights at this 36-lane bowling alley bring in denizens of uniformed league bowlers, and weekends attract an energetic young crowd with a combo of thumping beats and flashy pyrotechnics. But you can't top Mondays from 12pm-5pm, when games cost a mere dollar per person, and shoes run you just a buck more.