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A Day of Dining for $10 in Chicago

One Hamilton only goes so far.

Suthipong Tantivanichkij/Shutterstock

As part of Eater's first Cheap Eats Week, colleagues across the Eater Universe took on a challenge to spend a day dining in their respective cities—and spend no more than $10. Here now, a day of dining for $10 in Chicago.

8:30 a.m., Wicker Park: The day started at Stan's Donuts next to the Damen Blue Line stop. Often bustling with commuters in the morning, the shop was surprisingly quiet on this day, and after waiting for a 20-something gentleman and elderly man to pick out a dozen, a glazed doughnut was purchased for the regular price of $1.75. A tasty, circular sugar buzz of fried dough was the first meal of the challenge. Cash remaining: $8.25.

Stan's Donut

11:00 a.m., University Village: Jim's Original, home of the "Original Maxwell Street Polish Sausage Sandwich," was up next on the cheap eating docket. Originally there for a hot dog, Jim's revealed upon arrival that the price of a dog had risen to $3.80. But a minor miracle occurred—Jim's was selling Polishes for $2 as an anniversary special (76 years!). The large, plump, charbroiled, iconic sausage on a bun, slathered with yellow mustard, topped with a mound caramelized onions, with two hot peppers on the side, would be the most fulfilling meal of the day—and for very cheap. No need to even worry about tipping, as the "we do not expect tips" sign is prominently featured next to the order window. The Polish was eaten on the counter while the lunchtime crowd waited in line and ate from paper bags while perched on the dashboards of their cars. Cash remaining: $6.25.

Jim's Original Polish

1:30 p.m., Pilsen: A short excursion southwest to Pilsen would be next, home of perhaps the most options for cheap Mexican food in Chicago. La Casa Del Pueblo, a cafeteria-style Mexican eatery across an alley from a Mexican grocery of the same name, has many sorts of cheap and tasty deals in steam tables for the budget-conscious, but a tamale held the bullseye. Five flavors (pork, chicken, cheese, beans, and a dessert tamale) are available for just $1 each.

La Casa Del Pueblo

"Solo uno tamale?" the owner said, a cockeyed look on his face, after hearing the order for just one pork tamale.

A staffer, who handed over the tamale in a paper bag, looked just as bewildered as the owner after noticing the cheapest of orders. "Solo uno tamale??"

The one tamale, as it turned out, was of good size compared to the miniscule price tag, although three or so would be needed to construct a decent meal. Greasy, tasty and wrapped in a corn husk, there's lots of meat flecked with red pepper and encased in masa. Cash remaining: $5.25.

2:30 p.m., Pilsen: Another minor Cheap Eats Week miracle occurred moments later, just a few blocks away. Seeking something sweet—for cheap, obviously—a Mexican ice cream cart appeared seemingly out of thin air. Nieves Naturales, one of the few push carts selling frozen treats in the area, was nearly tripped over on the corner of 18th and Ashland.

Nieves Naturales


"Uno dolar."

"Uno fresa, por favor."

And just like that, sweet sweet strawberry ice cream was scooped from the cart and stuffed into a small paper cone on this summer day—for $1. Cash remaining: $4.25.

Nieves Naturales

5:00 p.m., Avondale: After a break, the north side was next on the docket—specifically Joong Boo Market in Avondale. The Korean grocery store next to the expressway and two blocks from the Belmont Blue Line stop is chock full of interesting Asian grocery items. It also has a small full-service cafe in the back, but that was too rich for this cheap eating adventure. The tiny dumpling stand next to the store entrance, Joong Boo Wang Mandoo, was the target.

Joong Boo

There's three flavors of dumplings for sale—pork, pork and kimchee, and black bean—for just $2 each. Plus, they're more bao than dumpling, and much larger than most. A large teardrop-shaped pork and kimchee was purchased, which is the size of a mini-football and served in a styrofoam box.

Joong Boo Dumpling

It was consumed from on top of a pile of large bags of flour that are stacked next to the stand. And it was delicious and filling, with minimal dough used for casing, and jammed with bits of pork and pieces of spicy red cabbage. There may not be a better cheap eats option in Chicago. Cash remaining: $2.25.

Joong Boo Dumpling

9:00 p.m., River West: It's nightcap time, and City Pool Hall and Sports Bar, a neighborhood spot on Hubbard and Des Plaines with nine pool tables, cheap food and cheap drinks, was stumbled upon. And then its menu, which features a slider for just $1.50, was noticed, and one of said sliders was ordered. Despite the low low price, it was a juicy patty that was large for a slider, and it was consumed between games of 9-ball.

City Pool Hall slider

Cash remaining: $0.75.

Stan's Donuts & Coffee

1560 North Damen Avenue, , IL 60622 (773) 360-7386 Visit Website

Jim's Original Hot Dog

1250 S Union Ave, Chicago, IL 60607 (312) 733-7820 Visit Website

La Casa Del Pueblo

1834 S Blue Island Ave, Chicago, IL 60608 (312) 421-4664 Visit Website

City Pool Hall

640 W Hubbard St, Chicago, IL 60654 (312) 491-9690 Visit Website

Joong Boo Market

3333 North Kimball Avenue, , IL 60618 (773) 478-5566 Visit Website