This cafe has been a welcomed part of Bridgeport for close to 10 years. That’s, in part, because there isn’t the same density of coffee shops here as compared to other neighborhoods, but its also because you won’t need to spend $5 for an iced coffee either.
We did the research. A 16 oz iced coffee goes for $2.75 at Jackalope, while the average 16oz iced coffee in the city can go anywhere between $4-5. 
You’ll find Jackalope Coffee just off Halstead Street, one of the the main roads that run through Bridgeport. While there’s a lot of traffic along Halstead, the coffee shop itself is located at the end of a cul-de-sac that insulates their sidewalk patio from all the traffic nearby.
Walk into the entrance and you’ll find a bright color palette splashed on the walls and an eclectic assortment of art hanging from the ceilings. It’s got a new age, 1970’s hippy vibe going for it, which is a nice change of pace from the more standard coffee shops around.
If you’re in the mood for something sweet to kick start your neighborhood exploration, behind that glass case are an assortment of donuts and other pastries. All of those goodies are from Bridgeport Bakery, another institution located at the other end of the neighborhood. Grab a donut here and you’re basically knocking out two neighborhood gems in one visit.
Take a left at the counter and go through this passageway to get to the dining area where you can post up and hang out for awhile. 
Coffee shops are a place to relax and unwind. This giant picture they have of Dolly Parton holding a kitten lets you know that everything will be okay.
Our next stop is a just a few blocks away. We’re at Co-Prosperity Sphere, which is an arts center that has a rotating mix of exhibitions, and in pre-covid times, would have a different event happening nearly every weekend.
If you wanted a picture that sums up Bridgeport, then here you go. Co-Prosperity Sphere is located in the building with the massive art mural on its wall. In the background is an historic Polish Cathedral Style church that towers over the neighborhood. It’s a reminder of the community’s Polish roots, but as time has gone by, it’s become a thriving artistic community with folks from all different backgrounds calling this neighborhood home.
Here’s an interesting fact. The past 20 years has introduced a wave first and second generation Mexican-Americans and Chinese-Americans. According to the last census, nearly 40% of the residents identify as Asian, 23% Hispanic, and 33% White. There was a DePaul University study conducted in 2008 that listed Bridgeport as one of the most diverse neighborhoods in Chicago, describing the neighborhood’s demographic as “extreme diversity.” The only type of extremism we can get behind. 
With the pandemic putting a hamper on Co-Prosperity Sphere’s normal schedule of events, they’ve focused their efforts on putting together window exhibits for the time being. 
In normal times, you might find the the place hosting a punk rock show, a local artist exhibit, or a game night. There’s no singular theme, other than, “let’s curate interesting events.”
Here is a throwback from a time we caught an improvised comedy show hosted by the founder and writers of Cards Against Humanity. Someday soon, this is the type of stuff you can expect on your visit.
From Co-Prosperity Sphere, we’ve got two options for food depending on the mood. Our first option is Martinez Supermercado, which has been around since 1977. It got it’s start as a corner grocery store, but over the years they added in a small kitchen that grew and grew. Today it’s become more restaurant than market. 
The long-time family owners gave the store an update a few years back that gave this space a new life. Gone are the packed grocery aisles. Most products are on shelves behind the register that reach up to the ceiling. It’s sort of a throwback to the general stores you’d see in old Western movies where customers would give a list of items to a clerk who’d pull the items for you. 
You can find the kitchen in the back of the store. Order at the counter, and they’ll give you a ticket that you’ll take to the register up front. As a reminder, our last stop of the day is to a park so if you want to grab any other provisions, you can do that now and pay for it all up front. There are fridges along the wall with drinks, fresh produce, and other snacks.
The specialty here are their burritos. They’re called baby burritos on the menu, but it’s not because they’re small — it’s because they are the size of a baby. These are 3lbs of meat, onions, cilantro, beans, tomatoes, and cheese in a massive tortilla. Pictured above is their steak burrito, and if your closest benchmark to a good burrito is a Chipotle burrito, then be prepared to have your expectations raised.
Our last stop is just a short walk away. This is perhaps the crown jewel of the neighborhood. It’s 27 acre park that was established in 2009, which at the time, was a well overdue addition to Bridgeport that was in need of some major green space. Before being a park, this space was a landfill — before that it was a rock quarry — and before that it was the site of an ancient coral reef dating back 400 million years ago. 
On a warm day, this park is bustling with picnic-goers, people fishing, and anybody that just needs some wide open green space that’s easily accessible. When you enter the park, you’ll find three different sections to explore. There’s (1) the giant lawn, (2) a rock quarry pond, and finally (3) the hilltop.
The first is this giant lawn on the West side of the park. There’s a gravel walking trail that circles the lawn, and at the North end of it, you can look down into the rock quarry and get a birds-eye view of the rest of the park.
Here’s the view from the North end of the giant lawn.
Criss-crossing the park are trails and metal walkways that lead you down to the rock quarry pond. That’s where we’re headed next.
Today, the quarry is filled with water and serves as a small fishing pond open to visitors. The metal walkways take you all the way down to water level. To give you an idea of where we were before, on the top left of the picture is a fence on the cliff’s edge. That’s the North end of the giant lawn and you can walk right up to it and look down on the water.
Keep following the metal walkways, and you’ll eventually come across a stone stepping path that will lead you up a hill overlooking the city. Follow this up. 
Here’s the big payoff at the top of the hill. It’s a big space with a lot of room to stretch out. and with the extra elevation, it doubles as a premium spot for kite flyers.
To end the guide, here’s one last look from our day in Bridgeport. We’ve touched on just one small segment of the neighborhood, but that just means more trips to this wonderful community in the future.