At 219 acres, there’s a lot of park to explore. So to make it easy, we’re going to start our fishing expedition at Humboldt Park’s boathouse, which is a nice central location and with plenty of free parking spaces in their lot if you’re driving in.
The boathouse overlooks the historic lagoons, which is where we’ll be doing some urban fishing.
Before we go on, here’s a fun fact about the boat house. In the picture below,those six square openings at the bottom of the boathouse actually were once warming rooms for ice skaters in the winter. Unfortunately, they are no longer in use.
Back the guide. Starting from the boathouse, there are trails that take you all around the lagoon. On a nice day you’ll see plenty of people with fishing rods sitting in fold-able camping chairs right by the water’s edge. Grab a spot anywhere you like.
We were lucky enough to come on a day where Chicago park staff were out providing fishing demonstrations and offering a few tips to first time fishers. Here are some helpful notes.
– The lagoon is stocked with Blue Gill, Channel Catfish, Carp, Yellow Bullhead, and Large Mouth Bass. And apparently a crocodile.
– You can catch fish using almost anything. Try corn or hot dogs. Live bait like night crawlers or minnows might give you a better chance. There’s a bait shop by Montrose Harbor if you’re looking for live bait.
– Most folks catch and release, but you’re welcome to take home and eat the fish you catch.
– Fishing in Humboldt Park has become popular over the past few years, which started with long-time resident, Larry Green, who founded the Humboldt Park Fishing Society. It’s a FB group of locals who share tips and stories about fishing in Humboldt Park.
While we’re focused on fishing with this guide, from time to time the park will host events throughout the year where they’ll bring in boats for people to use for free to explore the park’s waterways. Starting this summer, there are swan shaped boats you can rent and cruise along the lagoon.
After you’re successful fishing expedition, we head south through the park and out to the surrounding neighborhood. This is where you’ll find the center of the Puerto Rican community in Chicago, and we’re going to take advantage of that and grab some eats at Diana’s Restaurant. This is a casual mom and pop Puerto Rican diner where you order at the counter.
If you haven’t had Puerto Rican food, it’s a mix of Spanish, Carribean, African and US cuisine all mixed together. I’m not Puerto Rican food experts, so I can’t comment on the authenticity, but it was mighty fine meal which I’ll be visiting again if nearby. What am I kidding, I would go way out of my way for this meal again. 
Below are some shots of our food. On the left is roast pork with Spanish rice. On the right are two different appetizers. The brown colored appetizer is called Alcapurrias. It’s a deep fried plantain stuffed with ground beef. The orange colored appetizer is the Relleno de Papa, which is a deep fried potato ball stuffed with ground beef.
All of this was just $15 and was enough food for two people.
At the table was a house made Puerto Rican hot sauce which we used on everything. It’s made from hot peppers and vinegar, which gave our meal a nice little kick in each bite. 
That’s Diana and her husband in the picture above. Just a very warm and lovely couple who stopped by our table a few times to make sure we were enjoying our food. Kind of like the way your parents or grandparents would stop by and make sure you’re eating enough and liking everything they cooked.