The Chicago Summer Bucket List.

Let me start with saying that the Chicago Summers ARE THE BEST.

I am fortunate enough to have already experienced two summers here and I’m very excited about this upcoming one. Having struggled (for real) through the long cold Chicago winter, here is my Chicago Summer Bucket list:

  1. Rent a boat or do the architecture tour.


2. Go to the music and street festivals;

  • Lollapalooza
  • Mamby on the beach
  • Pitch Fork
  • Taste of Randolph
  • Wicker Park Fest
  • West Town Fest

Lollapalooza, Pitchfork and Mamby on The Beach to name but a few. I would be lying if I said I didn’t plan on going to the majority again this year. The street festivals such as Taste of Randolph and Wicker Park fest which generally only have a small admission fee are definitely worth a potter around also.

3. Head to the Rooftops

Top Picks:

The Cabana Club at the Robey

Gibson’s Italia


Cindy’s Rooftop

Raised at The Renaissance Hotel


Bernie’s Lunch & Supper


The J.Parker


4. Go to a Chicago Cubs baseball game at Wrigley Field

5. Bike ride along the lakefront

Rent a Divvy bike and ride along the lakefront from Belmont Harbor to the Shedd Aquarium and take in the views of the skyline.


6. Join a volleyball league

Join a team and play down at North Avenue Beach – Summer league begins in May – Autumn league begins in August.

7. Air and Water Show 

Happens mid August every year

8. Take a Stand up paddle boarding (SUP) class with Chicago Paddle Co.

These classes are based on Ohio Street Beach and you can combine yoga with SUP boarding.

9. Castaways Bar

Located in the building shaped like a ship on North Avenue beach – take in the skyline views and the beach or to wind down after a volleyball game.

10. Register for a 5 K, 10 K or Half Marathon

This is a great way to motivate yourself to get out and train for a run on the 606 or lakefront.

Some races to sign up to:

  • The Color Run
  • The Rock & Roll Half Marathon


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