Chicago

I'm testing out a new format where I consolidate all my pickup basketball activities within a city onto a single page. I got tired of creating separate pages for each time I played (Singapore I, Singapore II, Singapore III, and...soon Singapore IV…), so I thought it would be easier to bundle all my pickup basketball experiences in a city onto one page. To view my 2020 post on Chicago, scroll down to the Chicago, Illinois (IndoorHoops.com) January 2020 section. 

Chicago, Illinois (Seward Willams Park) July 2024

Last time I traveled to Chicago in 2020, I accomplished three goals:

• Ate deep dish pizza

• Took a picture with the Bean

• Played basketball

Four years later, I returned to Chicago with three more goals in mind:

• Eat deep dish pizza

• Take a picture with the Bean

• Play basketball

This time, however, I had the privilege of trying out deep dish pizza from three different places over three consecutive days, making sure each had meat. To avoid ruffling any feathers among fellow Chicagoans, here are my rankings

1. Giordano's

2. Pizano

3. Lou Malnati's

I'll leave it at that before starting a pizza war on my pickup basketball blog.

Next, I attempted to take a picture at the Bean but was thwarted by construction. Nevertheless, I wasn't too disappointed as I never fully understood the significance of the Bean anyway.

Unlike my last visit when I played at Indoor Hoops, this time I wanted to explore outdoor courts around the city to see if I could spot the next Michael Jordan.

Similar to Austin and Denver, I rented a Divvy Bike and explored the city to find where the local ballers played pickup.

Durso Basketball Courts

My first stop was at the Durso Basketball Courts. To my surprise, I may have spotted my first celebrity sighting. On the courts, I'm pretty sure I saw Instagram, TikToker, and YouTube personality Tristan Jass filming his next video. I wasn't entirely sure what was happening, but it was cool to see behind the scenes. I'm still waiting for the video to come out; if you happen to see it first, let me know!

While it would have been amazing to play against him, they spent the entire time filming so no chance of pickup basketball here.

Lincoln Park Basketball Court

Hoping to create some great pickup memories on a court next to a beach like in Vancouver, I biked to the Lincoln Park Basketball Court near the water. The court was impressive, but unfortunately, no one was playing.

Seward Williams Park

This seemed to be the place for basketball enthusiasts in the heart of Chicago. With four basketball courts, you could almost always find a group to play with, unless the pickleball craze from Hawaii took over. One full court was already taken over by pickleball, but the other three were open for basketball. Some courts were half court, while others had people just shooting around. But as you know, I had to play a full-court game.

After waiting a bit to get my turn, I finally joined a full-court run. Games were competitive, played to 15 points (twos and threes...good), and the teams were surprisingly solid for pickup basketball. The courts were well-marked, with clear boundaries and three-point lines. The backboards and rims were in excellent condition for a pickup game. 

Conclusion

While my visit to the Bean was a letdown, Seward Williams Park is definitely the place to be for basketball enthusiasts. With four full courts, you'll have plenty of opportunities to shoot around or join various pickup games. After playing, treat yourself to some Chicago deep dish pizza!

Travel Tip from Chicago Airports to central Chicago

The cheapest way to travel from either Chicago airport into the city is by taking the Chicago Transit Authority (CTA). 

• From Chicago Midway Airport (MDW), board the Orange Line heading towards the city. 

• From Chicago O'Hare Airport (ORD), take the Blue Line towards the city. 

For both lines, you can't go wrong by boarding in the wrong direction, as the airports are the final stops and all trains will bring you into the city!

Chicago, Illinois (IndoorHoops.com) January 2020

I arrived in the Windy City with 3 goals in mind:

• Eat deep dish pizza

• Take a picture with the Bean

• Play basketball

Eating deep dish pizza was easy but I will say I was a tad disappointed because all my colleagues out-voted me on what type of deep-dish pizza and settled on cheese only...who gets pizza without meat?!?! Getting a picture of the Bean was also easy as I convinced a colleague to wake up early, Uber to the Bean, take a couple photos and then depart to the airport all in 10 minutes time. And then there was playing basketball in Chicago. Well, that was the easiest. Just like in New York City (NYC) and what I almost used in San Francisco (SF), indoorhoops.com had a presence in Chicago and it made playing basketball almost too easy.

While Indoor Hoops' availability of gyms and games in Chicago weren't as plentiful as NYC, it did have a lot more options than SF. I won't go into too much detail on how Indoor Hoops works because you can read about it HERE. In short, they rent out gyms and the first 15 people to sign up will get to play.

I knew I only had one night to play basketball in Chicago, so I reserved my spot early Tuesday for a Wednesday run. Though there were 4 slots available when I signed up a day before, the run was full by Wednesday.

Last time in NYC the only knock I had on Indoor Hoops was for not sending a confirmation email after signing up to play. This time, I did receive a confirmation email.

Also, if you take a look at the "Total:" you may notice that I received a discount. That's because my cheap ass remembered that their marketing emails sent me a 50% off code a year ago from my New York experience to play again. For those of you who wonder how I get to travel so much, it's partially because I save money in instances like this (Sorry Indoor Hoops, I really should be supporting you as much as I can).

The Gym

The game was held at the Salvation Army at 1 N. Ogden Avenue Chicago, IL 60607. The court itself was relatively small and most likely used as a multipurpose room as well. There was so little room that on one side the out of bounds almost touched the wall, and the other side, you could barely fit a row of chairs. Regardless, it was still a cozy court to get a good run in for the evening. Standard court lines, backboards, rims and nets.

The Players

All players were pretty good but you could tell there were two just better than the rest. It's been a while since I've played in games where big men dominated but this was the case here. One big played like a guard who could shoot 3's, while the other one posted up, constantly scoring inside at will. The rest of us were pretty much guards or forwards who ran around the perimeter. Heights were evenly distributed between 5'5 to 6'5 and ages were 28 to 40. 

This particular group did not have as many 3 point shooters as I'm accustomed to but there were still a good amount of 3 point shots.

The Game

On the website, Indoor Hoops states that games are to 7 all by 1's. I assume they put that because some gyms may not have 3 point lines. But because we had a 3 point line, our games were 1's and 2's to 9. This may be different depending on the players who play that day.

Standard check rules, check the ball at the top of the key at all dead balls and call your own fouls.

Because the court was relatively small, there weren't that many opportunities for fast breaks so maybe that's why the big men dominated more in this pickup. Another casualty of the small court was the corner 3 point shots. There were at least 2 instances when the shooter in the corner thought they had a good shot, only to be standing out of bounds.

Conclusion

I have really nothing but positives to say about Indoor Hoops. My only wish would be that they were able to extend their reach into other cities around the world. It was extremely easy for a nonlocal to sign up on their website and start playing basketball. One thing I did notice was that there was not a person to check you in this time, so I wonder what would have happened if someone showed up without paying or if there were more than 15 players.