If you were dropped anywhere in Chicago, you could probably find a good Chicago-style hotdog within a half-mile radius. The competition for who does it best is stacked, and everyone has an opinion on the matter.
In Humboldt Park, Lola’s Coney Island has found a way to stand out. While they do a pretty mean Chicago-style hotdog, Lola’s is special because they’re one of the only places in the city that specializes in the Detroit-style Coney Island dog.
Like many hotdog stands in the city, Lola’s is housed in a small building on a corner lot. On warmer days, there is outdoor bar seating and a few tables on their sidewalk patio. There is also limited seating inside when the weather isn’t cooperating. 
Here’s the Detroit-style Coney Island dog in all its magnificence. It’s a beef and pork sausage smothered in a bean-less chili and topped with onions and yellow mustard. As good as this is, its origins are mired in even more delicious hotdog drama. The story starts as a tale of immigrant success, but it soon becomes embroiled in sibling rivalry, ruthless business tactics, and competing claims of superiority. It’s like the show Succession but for hotdogs.
Before we move on to the next place, if you want to conduct your own personal taste test, they also do a Chicago-style dog, a New York-style dog, and a classic Polish. Get a sampling of all four and chalk it up to a very necessary research project.
After hotdogs, you’ll walk a few blocks to Space Oddities, a bookstore, and an oddball shop. They specialize in rare books and literature about the occult, mythology, and the paranormal. So if you ever find yourself in an exorcism-type situation, this is the shop you visit to do your research.
For being a store with a collection of generally weird stuff, their staff was super friendly and eager to show us around.
Browse around, ask questions, and get a tarot reading if the owner is there. If you have time to do some extra planning, try to time your visit with one of the many events they regularly host, like tarot readings, artists’ exhibitions, and live music acts.
After shopping at Space Oddities, head across the street for some pie at Spinning J Bakery.
This place looks like your classic American diner from the past. A couple of small booths run along the wall, and stools line the counter.
If you’re rolling solo and not pressed for time, go all-in on this retro experience, grab a local newspaper, and pull up a seat on the stool at the bar.
If you want to expand beyond their pie options, they have a nice brunch spread with things like chicken pot pie and sausage egg and cheese sandwiches.
Your neighborhood walkabout continues on the same block. A few doors down is Humboldt House, a feminist home goods and gift shop that’s been a neighborhood mainstay since 2013.
It’s the type of shop you go to when you don’t have anything specific in mind, but you go hoping to stumble upon that perfect thing you didn’t know you needed.
Owner Claire Tibbs opened Humboldt House as an embodiment of feminist values and a reflection of her queer artist background. You see that in the products and art on display, which are largely made up of pieces from makers in the LGBTQ+ community. 
The day’s last stop is to The Hi-Lo, a neighborhood cocktail bar that opened up in the middle of the pandemic but has been in the works since 2017.
As you walk through the door, you’ll first make your way through a 20-seat indoor bar. The atmosphere is casual, but the space is designed with an upscale European cafe feel with a touch of Southwest desert vibes.
When we spoke with owner Issac Liberman, he said those design decisions were intentional. He wanted The Hi-Lo to be a place where you have an early afternoon spritz while reading a book but also a place to crank it up later in the evening when the situation calls for it.
Head towards the back of the bar and make your way outside to their patio. Their outdoor patio and veranda are more than double the indoor space’s size. It’s a four-season space, so even in the dead of winter, you can hang outside under the covered portion of the patio and cozy up next to their outdoor fireplace.
