Summer may be winding down but the good weather will be hanging around a little longer and there is plenty of time to squeeze in some good old fashioned summertime Chi fun. Whether you grew up here, are a transplant, or maybe you are just spending a long weekend here – there are a couple key things you must do in Chicago before summer ends and the real cold weather arrives. 

One of the great things about Chicago is that people really understand that we may only have a couple of months of this perfectly amazing summer weather so it’s important to soak up every single moment of it that you can. Be outside as much as possible, go out as many nights as you can handle, hit the beach as often as possible and somehow, keep working during it all. Find a local bar with a great patio, take in the skyline at a rooftop party or cool off in the lake. Bike the lakefront path, cruise on a paddle board with a magnificent view of the skyline or catch some late night blues. There are so many ways to enjoy this city and it’s so fun to do when it’s warm out.

Without further ado, here are five things that you must do in Chicago before summer is officially over. In no particular order, here we go. 

Stand Up Paddle Boarding in Lake Michigan

Stand Up Paddle Boarding in Chicago by Jess BellStand Up Paddle Boarding in Chicago by Jess BellStand Up Paddle Boarding in Chicago by Jess Bell

If you have yet to enjoy the lake this summer, I have to ask – what on earth are you waiting for? Big, beautiful Lake Michigan is just steps away and even if you have never stepped foot on a paddle board before – we can guarantee you will enjoy yourself. Depending on where you live, there is a rental place nearby ready to help get you out on the water. Take in the views of our beautiful city skyline, relax, soak up the sun and get a workout without really noticing that you are actually working out. Checkout a list of our favorite chicago sup rental spots

Take A Ride (on something with two wheels..)

Chicago Bikes by Jess Bell

Sometimes, life, and the beautiful sights of our city can pass us right by. In my opinion, the best way to avoid this is a good old fashioned bike ride. Pedaling thru the neighborhoods, taking in all the scenery is a great way to remind yourself that we live in an amazing city. Take the scenic route, stay off the major streets, take a few wrong turns, explore your city and you might happen upon your new favorite bar, shop or future ‘hood to reside in. Don’t have wheels of your own? The recent arrival of baby blue bikes that we know as Divvy Bikes have arrived in Chicago. Located all over the city, these bikes are available for just $7 for a 24-hour period so you can ride and return at your leisure. Memberships are available as well if you like the ride. So grab your whip (or rent one) and hit the road! 

Neighborhood Bar Crawl

Chicago Bars by Jess Bell

Can you do this in any city? Yeah, sure. But I’d like to think that here in Chicago, we just do it a little better. The bar and nightlife scene in the city is second to none (yeah NYC, I said it) and each neighborhood has something completely different to offer. No matter what kind of scene you are looking for, the city has it – you just have to find it. On this mission, we recommend picking a neighborhood, hopping a cab, and start bar hopping. This is exactly how you end up finding those random dive bar gems, secret hilarious karaoke spot or favorite new wine bar. It would take a decade to hit every bar in the city so make sure to spice things up and try different ‘hoods. Summer is the perfect time to do this since the weather is walk friendly. So grab a taxi and adventure somewhere in the city that you’ve always wanted to go. 

Late Night Blues Mission

Chicago Blues by Jess BellChicago Blues by Jess BellChicago Blues by Jess Bell

If there is one thing Chicago does better than a lot of cities, it’s music, and specifically, Blues. Tracking all the way back to the 1920’s, Chicago’s blues history is rich and the music is still alive as ever. Sure, you can hear the blues year round, but there’s something really soothing about strolling in to your favorite blues bar at 1am on a warm, late summer night. Depending on where you live in the city, there is a blues joint nearby ready to rock you to the wee hours of the morning. Here is a list of some of the best blues clubs

Street Fest

Chicago Street Festivals by Jess BellChicago Street Festivals by Jess BellChicago Street Festivals by Jess Bell

From May all the way thru October, every weekend, somewhere in the city, there is a street fest happening. Where the food is plentiful, you are surrounded by friends, and the beer flows like wine. Whether you go for the music, the shopping, the food or the people watching – entertainment awaits you, just down the street. If you’ve been slacking all summer, the good news is, September is full of fests all over the city. Find a list of Chicago street fests, round up some friends, rally your appetite and so support your favorite local neighborhood. 

We hope you enjoyed this little reminder of how much awesomeness is out there to enjoy in this beautiful city of ours. Now go make the most of whats left of the good weather. Enjoy!