Chicago Summer

My first Chicago summer as a resident has ended. It came and went as fast as a speeding train and there I was left standing at the platform. I guess things do change when you actually live in the city and not just visiting as a “tourist”. But between jobs and responsibilities, I managed to sneak in a few summer escapades in the Windy City. The best thing about Chicago summer is that you can finally enjoy walking along the beautiful Riverwalk or hangout at one of the outdoor waterfront establishments in the city.


When some of my friends from Connecticut came for a few days, we did the infamous architecture tour. It is a Chicago MUST!



We also grabbed brunch at Bridge House Tavern, a polished waterfront restaurant with a docking space. You know, so you can park your boat.


Earlier in the summer, I went to my first Lollapalooza Music Festival. This year, it took place for three days (July 28 to 31). I only went on the last day, which was enough for me. Some of the more popular acts I saw were Ellie Goulding, Third Eye Blind, LCD Soundsystem & Haim.



lolla4 lolla

Chicago is also a city of music festivals. Friends I made opened this whole new world of festival life. Most of them go to every single festival AND would do its entire run. They love music and they love to party!

Here are some of the popular summer music festivals:


Chicago Blues Festival

Spring Awakening Music Festival

LakeShake Festival

Green Music Fest

Pitchfork Music Festival

Wicker Park Fest

Chicago Jazz Festival

Riot Fest

I wish I was able to enjoy more of the summer festivities, but adult life always get in the way especially now that I’m a resident and not just visiting Chicago. On the other hand, since I NOW reside in this beautiful city, I now have the luxury of taking my time exploring. Still, time flies by when you’re having fun and so I found myself already bundling up for fall. Hopefully, I get to enjoy fall as well before I see snow on the ground!


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Jen is a Chicago-based traveler and a full-time Director of Development for an arts & culture organization. Originally from Connecticut, she created JetsettingJen as a place to share her travel stories and photos with friends and family. Now, it is a place for adventurers, explorers and dreamers. Its purpose is to inspire and encourage people to see the world and achieve a better work-life balance.