My “End of the Summer” in Chicago Bucket List

My “End of the Summer” in Chicago Bucket List

Technically, we only have one month and twenty three days to enjoy summer in Chicago (but who’s counting?) Instead of dwelling on the fact that it’s ‘almost over’, I plan on knocking six things off my Summer bucket list. Here I’m sharing the #savagesix things I tend to enjoy before we officially flip over to Fall.

Whether or not you are a resident of Chicago, likely you know how much us locals love Summertime Chi. The al fresco dining, street festivals, concerts, outdoor shopping markets, boats, rooftop pools…the options are quite literally endless. Of course there are the folks that are lucky enough to hop on over to Lake Michigan, but for everyone else staying in town it’s hard to be disappointed. Even during the week, a fun excursion or activity in your neighborhood can be pretty easy to come by. While some people hit the middle of summer and dread that it’s almost over, I choose to view it as we still have half of it left to enjoy. While I know most of us consider the end of the summer when their kids go back to school or simply the weekend after Labor Day Weekend, I have good news. Technically, the last day of Summer is September 22nd. With all of the amazing activities to choose from, I’m prioritizing six things to check off my bucket list before we officially head into Fall.

1. Evening on a Boat

I cannot remember the last time I’ve been out on Lake Michigan. Years ago I spent a few afternoons in my bikini sipping on beers on friend’s of friends boats out on the water, partying in the playpen. Those days don’t really appeal to me anymore, but a sunset cruise with friends, wine & appetizers sounds like a dream. If you’re lucky enough to have a friend with a boat, super! If not, there are lots of different options to choose from. Check out Chicago Boat Rentals Chicago Electric Boat Company or Chicago Sailboat Charters. My friend also suggested Captain Jack, who you can find here. You could also go the informational route and spend an afternoon learning about the city’s skyline in the BEST way possible which is via an architectural boat tour. Timeout Chicago rounded up some of the top tours here.

2. Cubs Game

This would absolutely be one of my quintessential “Chicago Summer” activities of choice. There really is nothing like being up in Wrigleyville for a beer and a hotdog. Not to mention I have yet to check out Hotel Zachary, which opened earlier this year and is right across the street from Wrigley. There are several dining options throughout the hotel, at the top of my list being Big Star for guacamole and margaritas. Or you can get there early and enjoy a beer and a hotdog the old-fashioned way.

Hotel Zachary, Image via

3. Frosé Happy Hour

Drinking frosé is fairly ubiquitous across the city, so I’m pretty confident I’ll easily be able to knock this ‘to do’ off the list. Eater Chicago published an article a couple of weeks ago on some of the top spots to enjoy frozen drinks. Since I’m on a mission for frosé, I plan to take my coworker’s recommendation and head to Benchmark for the frozen concoction one Sunday afternoon.

4. Beatnik on the River

Sadly, I did not discover this restaurant by keeping up with the hot spots in Chicago. Rather, it caught my attention as I was walking home one afternoon from Soul Cycle one evening. The decor is absolutely stunning. I’ve been to the restaurant itself for brunch a couple of times, but I love how they brought the experience to life on the River. I think I’ll have to plan on ordering some sangria and a charcuterie board with some girlfriends.


Beatnik on the River, Photo from Urban Daddy

5. Grant Park Music Festival

I have seen a couple of movies in local parks, but I have to go spend an evening in Millennium Park at Jay Pritzker Pavillion. There are concerts you can attend as well as simply listen in on a rehearsal, you can view the full schedule here.



Photo by Eric Allix

6. Lincoln Park Farmer’s Market

I don’t think there is anything I miss more about living in NYC than the Union Square Greenmarket on Saturday’s. It was only a few blocks from my apartment and I loved stocking up on fresh items for the week. Typically that included pretty flowers, a new veggie to try cooking and maybe a baked good. While there are several Farmer’s Markets in nearby neighborhoods, none are as impressive as the Green City Market in Lincoln Park. It’s situated on the grass beneath the trees in the heart of LP, right near the Lake which beats out any parking lot posting, in my honest opinion. I’m planning on making a morning of it one upcoming Saturday!

What are the things you are excited to do before the end of summer? I’ve already marked a few ideal Cubbies home games on the calendar and am researching allll of the boat options. If you have suggestions, comment or email me at anytime!




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