Chicago Summer Bucket List: A Guide to Eternal Awesomeness

Chicago Summer Bucket List: A Guide to Eternal Awesomeness
courtesy of Kelsie Rae Photography

Between unseasonal heavy downpours, temps barely reaching a respectable 75, and cloudy skies galore, it can be hard to believe Chicago is smack dab in the swing of summer. Regardless of your proposed length of solstice, there's only so much dizzying, mind-melding, gut-busting, summer lovin' you can fit in just a few short weeks. That's when you bring in 4-Star Explorer's Summer Bucket List. Not just any list, but one dedicated to sites and sounds surrounding Chi-town. Read the details of my Summer Bucket List below for witty commentary as well as links and deals to some of the most compelling spots and events in the city. Start your own list or share YOUR amazing fetes of summer in the Comments Section!

The 4-Star Explorer's Summer Bucket List

1. Ride (mechanical) bull

There's a reason it's become one of the most overused metaphors for getting off your butt and taking action. The feeling of flailing about on a pressurized metal death trap is exhilarating...or so I'm told.

2. Movie in the park

Grass. Movies. Blanket. The equation. God bless one of the only city agencies to still get things done, Chicago Park District. Visit their website for the movie listings near you.

3. Walk around city until morning

Easily one of my favorite 90s era shows,The Adventures of Pete and Pete, this episode sparked an early sense of adventure. It was then that my dream of the perfect all night summer excursion arose. The song, Summerbaby, by indie rock group Polaris is also a hands-down choice for essential summer soundtrack music.

4. Get into a major Chicago event/Slip into random event
5. Attend a roof party
6. Leave notes in books around the city

Because I like PostSecrets and I'm weird.

7. Go on a random one day trip

I's so Eat.Prey.Love. but unlike the main character in that story I can neither afford to get rid of everything I own nor backpack in Bali. A random flight to Seattle may have to suffice.

8. Take a cooking class

Because asking does microwaving HotPockets count as cooking is no longer cute to the male species.

9. Go wine tasting

Well technically, I go wine tasting quite often, but tasting while in my bummy sweatpants and watching Golden Girls isn't quite the regal experience I'm searching for.

10. Go berry picking or farmers market
11. Eat Burt’s Place pizza
12. Write to a random famous person
13. Photologging/See how many people I can take pics with in 1 day
14. Explore Chinatown

This movie. Need I say more?

15. Go to a baseball game

Whether Sox or Cubs, we can all agree that drinking beer at noon in the cheapest seats in the park makes for the best experiences.

16. Go on a date that doesn’t suck
17. Have an old school game night

18. Anime marathon night

Because I'm counting down 'til Anime Midwest next week. And also because I am a closeted nerd

19. Read at least 2 books
20. Write either a short story or 5 new poems

Does blogging count?

21. Go to Trivia Night event
22. Hit a jazz night

Maybe finally I can make it out to a Rio Bamba performance?!

23. Do karaoke

Bob San

...I'm coming to join ya!
24. Volunteer
Once again, does blogging count?

25. Bike ride around the city

Bike and Roll is an excellent source for bike rentals if you're not so blessed to already have one (I still have visions of the day my Huffy was stolen) or you just don't feel like lugging the thing downtown. And well...*looks around* I'm just gonna live this coupon here. Thank me later.
26. Enter contest
27. Attend Chicken and Porn Night

I can't count the number of conversations where it was appropriate to bring up the topic of chicken and porn. Apparently, there's a lot of these events that have sprawled up at various clubs and bars around the city. Wicker Park's EVIL OLIVE sports one of the most frequented events of the variety, recently winning Chicago Reader's Best Dance Party of 2013. But it all looks very 28 Days Later to me...

Make sure to share your outrageous challenges before summer kicks the bucket in the Comments Section! And contruct your own Summer Bucket List. Because your ideas are just as gnarly as mine. Maybe even more so.



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  • The ballparks in Chicago are nice, but for a great summer trip you should travel up about 90 miles north to one of to what has become my favorite ballpark in the region if not the country.
    (And it looks like somebody else agrees.)

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