An UPchicago Summer Bucket List

chicago lakefront
Photo Credit

There are some things you just have to do during a Chicago summer. Then, there are a lot of things you should do. Lastly, there are all those things you plan to do and never seem to get around to. This year, we’re making them happen. All of them. And you should too; after all, a Chicago summer only lasts so long. Here are our picks for the ultimate Chicago summer bucket list.

  • Visit the Lincoln Park Zoo or Brookfield Zoo.
  • Spend a day at North Avenue Beach (bonus points if you play sand volleyball!)
  • Find somebody with access to a boat on Lake Michigan and spend the day tubing, water skiing, or simply basking in the sun.
  • Go to a Cubs or Sox game.
  • See a show at Ravinia. Don’t forget to pack a picnic dinner and some vino!
  • Attend a music festival (like Lollapalooza, Pitchfork, North Coast…)
  • Plan a weekend getaway (try Lake Geneva, Door County, or Michigan City, IN)
  • Make a picnic and attend a Movie in the Park.
  • Grab a bottle (or two) of wine and enjoy a Free Music Monday at Millennium Park.
  • Bike the lakefront (try to do the whole thing! Start at Hollywood and bike to 67th Street)
  • Eat and drink inside as little as possible — check out our patio guides for inspiration.
  • Join a summer league (kickball, softball, dodgeball, etc — the possibilities are endless!)
  • Kayak down the Chicago River. It’s a view of the city unlike any other.
  • Jump in on a pickup game of basketball at your local park.
  • Check out the city’s local craft breweries, then bring home a six pack from each one for an at-home beer fest.
  • Visit Promontory Point Park — it really has one of the best views of the city.
  • Want to work up a sweat? Check out one of the Yoga in the Park classes, every Saturday morning at Millennium Park. Pilates and Zumba are also offered.
  • Attend one of Chicago’s monthly arts events (usually free! Bonus points for enjoying a night on the Museum of Contemporary Art terrace)
  • Get a group of friends together for a bar crawl in your neighborhood of choice. There’s nothing like bar hopping when you don’t have to wear a down coat.
  • Catch as many street fests as possible (chances are there is at least one in your neighborhood)
  • BBQ! (in a friend’s backyard, a park, anywhere will do! Bonus if you get meat from Paulina meat market or the Vienna Beef Factory)
  • Buy tickets to a production at Theater on the Lake .
  • Play 18 holes at Marovitz Golf Course or any other Chicagoland golf course.
  • Buy tonight’s dinner at a Chicago Farmer’s Market.
  • Join a group run! There are tons of running groups around the city, and it’s a great way to exercise and meet new people. Check out Fleet Feet’s Wednesday Night Fun Runs.
  • Watch the airplanes soar at the Chicago Air & Water Show.
  • Catch the Navy Pier Fireworks on a Wednesday or Saturday.
  • Grab some Italian Ice on a hot day (it’s more of a Chicago staple than ice cream! — try Mario’s in Little Italy)
  • Get up and dance! Head to Grant Park for one of the city’s SummerDance nights. Enjoy a one-hour dance lesson, then watch the masters do their thing. Try everything from Salsa to Swing.
  • Attend a Chicago Fire game.
  • Head to the lakefront to view the start of the longest freshwater sailing race in the world — the Race to Mackinac Island.
  • Party at the Gay Pride Parade.
  • Let out your inner child. Head to Six Flags Great America and Hurricane Harbor for a day of roller-coasters, water-slides, and blatant immaturity. Sounds like fun, doesn’t it?!
  • Take your dog (or borrow a neighbor’s, a friend’s, your mom’s) and watch him enjoy a Chicago dog park or the dog beach.
  • Visit the Chicago Botanic Garden.
  • Go on a city tour, even if you were born and raised in Chicago we guarantee you’ll learn something (for a more unique tour try the Chicago Pedway Tour. Bonus Points if you look like a dork and go on a Segway Tour)
  • Head to Oak Park and visit Frank Lloyd Wright‘s many buildings as well as the Ernest Hemingway Museum.
  • Make the trip to Springfield in August for the annual Illinois State Fair. Because who doesn’t love eating food off a stick?

So, who’s in? Let’s start making this one of the best summers yet.

Think you’ve got something to add to this list? Leave us a note in the comments section! Want to embark on the journey of completing this list? We’d love to feature you on UPchicago!


Click here to download a printable version of the list, then start checking things off!

About UPchicago Team

Urban Philosophy is a way of thinking that you develop when you’re a true city person. Whether you’ve spent your whole life living in Manhattan, or you just moved from small-town Iowa to the city of Chicago, the longer you stay, the more you come to understand what it means to live in a city. Our Urban Philosophy is that no matter who you are, where you are from, and what your likes and dislikes may be, there’s something for everyone in city life.

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