The Ultimate End of Summer Chicago Bucket List

Our days are numbered, friends.

Sure, today you might be sweating in the sunshine at your favorite neighborhood sidewalk café, but as Game of Thrones lovers & lifelong Chicagoans will tell you… winter is coming!

Whether they be Polar Vortexes, Arctic blasts or snowmageddons, they’ll be here soon enough and they’ll prevent you from enjoying some of the best things this city has to offer, so it’s time to get serious about your end of summer Chicago bucket list…

1.  Outdoor Entertainment

From free movies in neighborhood parks to concerts at Pritzker Pavilion to big name artists at Ravinia, there’s no shortage of ways to be entertained while you enjoy the last gasp of summer. Check online for free event schedules and try Craigslist for people selling last minute tickets to Ravinia concerts.

2.  Drink on a Rooftop

If you live in a city that has a breathtaking skyline like Chicago’s and you’re not drinking and hanging out on rooftops, you’re doing it wrong.  You’ve got a bevy of great options in The Loop, River North, the Gold Coast and more. For a swanky scene, try NoMI Lounge at the Park Hyatt and for something a little more laidback, head to Gene’s Sausage Shop & Delicatessen in Lincoln Square.

3.  Go See a Baseball Game

Here in Chicago, we’re lucky enough to have not one, but two great baseball teams!  Whether you’re a die-hard Cubs fan or a dyed-in-the-wool Sox supporter, you shouldn’t let a summer pass you by without spending a sunny afternoon in a ball park with a few friends, an overpriced beer and a dog (no ketchup of course).

4.  Eat al FrescoEnoteca Roma

Windy City restaurants use every square inch of outdoor space to provide us opportunities to enjoy our meals out of doors, so get out there and do it as often as possible while you still can.  Try a place like Tavern on Rush if you like a sidewalk table with a steady supply of great people watching or Ukrainian Village’s Enoteca Roma for a romantic and secluded patio.

5.  Hit the Beach

We get to live in a world-class cultural mecca and have access to beautiful freshwater beaches?  It almost makes the bad winters worth it, right?  And you’ve certainly got your pick, depending on the vibe you’re looking for.  Claim your patch of sand at Oak Street Beach if you’re after a bustling scene, outdoor dining and beach volleyball or head south to the 31st Street Beach for a great family day.  Check out this guide for more great beaches in the city.

6.  Park ItJackson Park

Did you know that 8.5% of Chicago city acreage is devoted to parks?  And you probably haven’t stepped foot in even a quarter of them!  Pack a picnic and spend the day lazing about on a blanket in one of the gorgeous parks you didn’t even know existed right here in the city.  Check out Jackson Park for their peaceful Japanese gardens or the Caldwell Lily Pool for a secret garden feel in the heart of Lincoln Park.

7.  Fest it Up

No Chicago summer is complete without at least one neighborhood street festival, which is one of our city’s great ways of allow us to soak up every ounce of warm weather we can.  And it’s not too late – there are street fests going on until the end of September. Check here for a full schedule.

8.  You’re on a Boat!

You may not be cool enough to have your very own boat, but that shouldn’t stop you from enjoying the open waters of Lake Michigan or the scenic views from the Chicago River.  Plenty of local companies offer day or evening excursions on the lake and you can always rent a kayak for an active day of fun on the river.

9.  Do the 606606

In case you hadn’t heard, there’s a very cool new elevated bike and pedestrian trail in the city called The 606 and people are loving it! This former train track in Logan Square boasts a 2.7 mile peaceful and safe path for walkers, runners and bicyclers, dog-friendly areas, and some nice views of the city.  It’s definitely worth checking out before the first freeze.

10.  Stock up at a Farmer’s Market

Why get fruits and veggies sent hundreds of miles across the country to your grocery store when you can actually shake the hands of the people who grew the stuff not far from the city?  If you’re into the sustainable and local food movement, you’re in luck because Chicago has a wealth of farmer’s markets all over the city – find the one closest to you here.

The summer isn’t over yet and we’ve still got at least a month of beautiful weather left, so instead of lamenting all the things you wish you’d done once it gets cold, get out there now and soak up all of the outdoor fun Chicago has to offer.

About the Author:  Liz Kores is the managing director of Oak Street Chicago, a business association that represents some of the finest designer boutiques, hotels, spas and restaurants in the Windy City.  She is also on the board of the Chicago Fashion Incubator and a frequent guest blogger on a variety of online style publications.  For more, visit


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