The Funemployed Guide To Chicago Summer

First day of summer, first day of summer, yasssss, we made it – summer solstice! Grab the rosé, grab the inflatable swan, and grab the white jeans. Bryan Adams and Summer of 69 won’t have anything on me and Summer of 17. You’ve heard it here first. But if you are in a current stretch of funumployment like moi, or your random piles of cash simply don’t runeth over, taking advantage of everything Chicago has to offer can feel a little daunting. But since no one knows the tune about the summer I sat on the sofa watching everyone else have fun (I have sung it, it wasn’t my favorite), I am sharing with you some of my favorite dollar wise activities Chicago has to offer on even the tightest budget!

Farmer’s Markets

Who knew grocery shopping could be so fun! There are so many amazing farmer’s markets located all around the city there is a day of the week and a location for everyone. While every market has a different vibe and different flowers, produce and goodies for sale; the markets are generally a nice spot for a local snack in the city, people watching, or getting to run errands with your fur baby.


One of the very things that makes Chicago so worth it are the sandy beaches you can find all around the east edge of the city. And nothing says summer like a day by the water! Pack a cooler full of your fave fruits, salads, and sandwiches. North Avenue Beach is my personal go to not only because it’s a big beach but it has lots of rental activities too. You can take advantage of bikes, jet skis, stand up paddleboards, and bonus, during the week there are summer volleyball leagues. This beach tends to have a smorgasbord demographic – think young professional / high school / young family. Some how it all works though!

Jet ski rentals at North Avenue Beach


Pick a weekend any weekend! Chicagoans are not glutens for winter punishment just because – it’s because 100 days of summer in Chicago makes it all worthwhile! There are literally street festivals happening every weekend to help you get out and about to try, taste, or see something new. Food Truck Festival, Chicago Rose Day! Anyone, anyone? And if you are on a budget take these opportunities to try food from restaurants you’ve been wanting to try. And if you’ve been in the market for a piece of artwork at a more reasonable cost, at an art festival you will most likely get to meet the artist as well – making for an even greater experience. I got to meet and talk with artist Jason Fricke who does amazing in the moment pen and ink sketches of ballet company performances all over the world. Thank you for that Old Town Art Fair. You can spend hours at all types of festivals and enjoy the day on any type of budget!

Lobster Roll at the Pilsen Food Truck Social


Minimalist ink sketch of Jason Fricke

Movies in the Park

Ok folks, it’s not going to get much better than movies in the park! Like, this is all the way free. But because things are better when styled, do pack a lovely picnic. Charcuterie board perhaps, a couple of adult beverages, if you insist, friends, or a honey, a blanket for sitting and boom the perfect Chicago evening under the stars!

Chicago River

Giving a different perspective of the city, the Chicago river and river walk has a vibe all its own. Al fresco dining options and the popular City Winery you can be totally up close with the river. Consider cost saving by packing your own snacks and taking advantage of one of the many seating areas to watch the boats and people go by. However if activities are more your scene you can definitely take advantage of kayaking rentals or the Chicago Architectural Foundation’s amazing boat tour. And while the boat tour is a little pricier, the daytime rates is a few dollars cheaper than the twilight ones. But I can assure you, for either time of day the Chitecture views and history will be worth every penny. The extra budget friendly version – grab a Chicago architecture book and do a self-guided tour on the water taxi!


Happy Hour

It’s not called happy hour for nothing, and whatever you do – do not underestimate the power of a good happy hour! This is an opportunity to take advantage of food and drink specials all over the city! It’s also a great way to get a feel for a new place without committing to a full price, full scale dinner. Every happy hour is going to have it’s own vibe; but on a sunny Friday afternoon after a long week, Public House is always a crowd favorite. With an in house DJ, beer, liquor and food specials it never disappoints.

Leave a comment and let me know how you’re having a blast and saving $$$!

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