Summer Nights in Chicagoland

Long, hot summer days getting you sticky, smelly, and totally drained? Me too. That’s why I like to hibernate in the basement with the air conditioning turned to full blast, only to emerge once the sun sets. Because let me tell you, that’s when Chicagoland truly comes alive. There are endless (many free) activities to enjoy and you won’t swelter in the sun. Here are the best ways to enjoy summer nights in Chicagoland:

*Head to a drive in movie. I can’t lie, the highlight of my childhood was going to a double feature at the local drive in movie theatre and squealing with delight at “The Dancing Hot Dog” and eating my entire body weight in greasy food. I’m sad to report many drive in theatres have closed down, but McHenry Outdoor Theatre and Cascade Drive In are still around and a blast. Tip: Get there EARLY. The lines to take a step back in time are long, friends. VERY long.


*Enjoy a firework show. Clearly it’s very easy to find jaw dropping fireworks displays over the 4th of July, but what about throughout the rest of the year? That’s when you and your family should head to the newly remodeled Navy Pier and enjoy their free Wednesday and Saturday night firework shows. Try to book a nighttime boat cruise to enjoy the show away from shore, or hop on the Centennial Wheel to enjoy the show.


*Take a thrill ride at the carnival. Or simply pig out on cotton candy and funnel cake. There’s nothing like the flashing lights, loud music, and screams of joy (and terror…if you are like me!). Our favorite carnivals are Ben Fest, Frontier Days, Northbrook Days, and the Lisle Eyes to the Skies Festival.

*Cool off at some of Chicagoland’s most delicious ice cream parlors. Whether it is in a cup or a cone, it is the best way to eat the heat. And if you are able to order a flight of ice cream? HIGHLIGHT OF THE SUMMER.


*Take in some culture at one of the many park concerts across Chicagoland. Looking for the one closest to you? Simply search your town name with the phrase “park concert” and you will undoubtedly find a show within a fifteen minute drive. Our family favorite concerts at Wednesday nights at the Chicago Botanic Garden and the many concerts held through the Millennium Park Summer Music Series.


And if you are staying at home, don’t forget to bust out the grill and toast up some of these spiced up s’mores!

Happy Summer!
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  1. robin rue says

    Sounds like lots of fun to be had in the Chicago area. I need to find some Boston area happenings for my kids!

  2. Marcie W. says

    I would love to spend a few summer nights in the Chicago area! An outdoor concert and exploring different food options would both be a total must.

  3. Amanda Love says

    I think it’s awesome that there’s so much to do in Chicago! I have always liked their love for good food. It’s one of the things that I enjoy whenever I visit.

  4. Pam says

    These are some really fun options for enjoying summer in Chicago. I love drive in movies, and who doesn’t love ice cream?

  5. Louisa says

    So sad I had to cancel my trip to Chicago! We have a beautiful botanical garden where I live but based on the photos I’ve seen, I’m sure the one is Chicago is 20x better! Looks like a lot of fun activities to do.

  6. My Teen Guide says

    Sounds like Chicago is packed with fun activities! I haven’t been there in ages. I’d love to go back and sample the food again. Nothing like it anywhere!

  7. Crystal says

    I’ve never been to Chicago at night. I’m sure it’s beautiful, though. There’s always so much to see and do there that I know I’ve missed a lot the few times I’ve been.

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