Wishbone is a Southern-themed restaurant in the West Loop that's been in business for years. But this year, they decided to take the plunge and set up a booth at the Taste.
"The city takes their cut, propane takes their cut, refrigeration; just the logistics and it's also somewhat complicated for the restaurant. I have to have people there too that are coordinating, bringing the food down."
That's just the beginning. Nickson is going to need to sell an awful lot of chicken etouffee and watermelon lemonade to cover his investment.
For 5-day booths, it's $3,000 up front, hundreds of dollars in equipment rentals, propane and electrical, 52 hours of labor and of course, your food. And at the end of Sunday, you give the city 18 percent of your sales, plus another 10.5 percent to the county.
"You know honestly, it's almost, I wanna break even," said Nickson.
That's why there are pop-ups. For a smaller investment, little joints like Andersonville's Jin Ju can expose their Korean bulgogi and kalbi to the masses.
"The pop-up just because we're a small restaurant, so staffing for five straight days is pretty tough so, I think one day is enough," said Kitae Kim, Jin Ju.
Last year, Kim's propane bill was about $1,300 dollars; still, he says it's good marketing.
"All that is extra, we pay out of our pockets," said Kim.
"I think it's important for the city, the city's been good to me, and I think it's an important event for the city. I think it leads to tourism in many different areas," said Nickson.
Nickson says he isn't taking any chances. He's showing off as much as he can in those five days. The etoufee and the pulled pork are, of course, on the menu, but he is also featuring Hoppin' John, made of black-eyed peas, a corn muffin, a Carolina hot dog topped with chili and Lexington 'slaw, plus a cool glass of watermelon lemonade.
In River North, there is another newcomer- Bombay Spice & Grill. The restaurant is taking a chance and hoping the crowds will enjoy Indian food that's a bit healthier than the usual fried samosas.
"People serve hot dogs, hamburgers, so we decided to take a healthy twist in Chicago," said Sunil Kumar, Bombay Spice & Grill.
That means a chicken tikka masala, made with tomatoes and coconut milk, and also a flavorful bhel puri, featuring toasted rice, lentils, vegetables and yogurt.
"If you go to India, every street corner there is bhel puri. So that's why it like really has a lot of flavors in there, crunch, and street food," said Kumar.
Even the chicken biryani is a bit different, with the addition of almonds and dried fruits.
"This is a little more Americanized; a little sweetness, because of the crunch - there are almonds in there," said Kumar.
A total of 40 restaurants are taking part in the city's biggest summer festival.