Top 3 Broke Boy Activities in Chicago

Broke is a mindset. It’s also a financial status that many of us have visited. I would like to dedicate this anti-consumerist tour to those comrades who have their gas tank on E. Those high schoolers who spent their lunch money already. There are actually a decent amount of spaces in Chicago that you need no more than the clothes on your back to have an enjoyable time. 

  1. Try Not To Break A Leg at Dan Ryan Woods

Dan Ryan Woods is a top tier free space. At around 257-acres, the park is host to many family reunions, field days, and picnics – and the trail is beautiful. The walking and biking trail that skirts the park goes through several quiet, middle class black neighborhoods. It’s insulated by trees in many places, giving a very nice natural escape. The park itself is the spot for family reunions and casual picnics. Downtown is visible from the tallest hill. 

Ski jump attempts at Dan Ryan Woods in the 1920s.

A 200 foot slope, the hill in the park is ranked number 2 in the city for sledding, beat only by the hill downtown by Soldier Field (a 220 foot slope). This is for sledding fanatics and snowboarders alike. During the winter months, you will see the residents of surrounding neighborhoods dragging all types of items to sled down it – from pool inflatables to trash can tops to cardboard boxes. It’s truly a hidden gem. A note: The hill gets steeper from left to right. To the far right, if you come down it, expect a bump at the bottom. Great for getting some airtime on your boards, and even better at breaking bones. Have fun!

  1. Views from Promontory Point

This place is like those parked car conversations – but minus the car. 

Promontory Point is a spot on the Lake over near Hyde Park. The land here naturally juts out a bit into Lake Michigan. This gives the best view of the Skyline. The sunrises will make you wanna write poetry. 

There are bonfire pits here to chill around with friends. You have to rent one or get a permit technically, but honestly? I’ve never even known that until I started researching this topic. I often see groups bring firework sparklers, smores, blankets, and occasionally, a bluetooth speaker. Don’t forget to bring some wood (or ‘source’ it from fallen branches in the park). Very wholesome. Very free. 

  1. Test your strength as a swimmer (or just get whipped around a bit) in the whirlpool at The Kroc Center’s Indoor Water Park in Blue Island

Once I was driving with a friend who asked her dad when he was going to take her and me on a vacation to the islands. He looked in the rear view mirror and was like “I got islands all around you! Stony Island, Blue Island… Pick one!” 

A great addition to the blue Island neighborhood!

We stale faced his dad joke, but he’s right! Blue Island has enough gems that you won’t have to go searching outside the state at all. Have you ever been inside the Kroc Center? I say inside because if I tell you we have a community center over there on 119th, you don’t quite get the magnitude. This isn’t just a community center – it’s the largest in the state. Basketball courts, an indoor waterpark (literally), equipped with a full sized water slide and a circular pool where water is pumped into like a whirlpool. 

While the Kroc Center was built by the Salvation Army, so there’s for sure Christian missionary vibes there if that’s your cup of tea. They have a church and christmas services and all that. Besides that, there are all the educational and fitness activities offered by your average YMCA, only bigger. Check out the site, and consider being a member before you go (I do recall filling out mad forms before I wanted to go swim).  

BONUS : 6 MORE TRIED AND TRUE WEEKEND MOVES

If I were in the city a weekend, and looking for cheap or free fun, I would do the following: 

  1. Meditation at the Japanese Gardens
  2. A peaceful drive on Lake Shore Drive
  3. Visit one of the museums (top picks, in order, are the Art Institute of Chicago, the Chicago History museum, the Field Museum, then the Museum of Science and Industry)
  4. Activities with Chicago Park District (movies in the park, fireworks in the summer)
  5. Thrifting on Milwaukee Avenue
  6. Catch an architectural boat tour (one of the only touristy activities that’s fully worth it)

Now off you go! 

Relevant Links:

  1. Dan Ryan Woods
  2. Kroc Center
  3. Japanese Gardens