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The Ultimate Chicago Summer Bucket List!

One thing you’ll be all too familiar with hearing if you’re a Chicago resident is comments about how crazy you must be to put up with our winters. Truth be told, I really think people are really overdramatic about that, but to each her own! Either way, you can be sure that most Chicagoans responses to that statement resemble something about how the incredible summer lifestyle here makes it more than worth the frigid months that follow. 

I’m coming up on my THIRD summer living here (which is crazy to think about!) and I’m still finding a never-ending list of activities I love along with those I can’t wait to try. I’ve crossed some pretty amazing ones off of my bucket list already, and most of those will be repeat activities for many years to come.



Here are some of the big bucket list items for us to try (or do again) as soon as the weather starts to warm up and stay warm! I've done my best to break them up into categories for easier searching, too - that way you can save it on Pinterest and come back to it when you're looking for fun plans! 


When You're Feeling Touristy...

  • Try out a boat tour along the river. My advice? Pick one around sunset. It gave me views of the city I'd never experienced before! 
  • Walk around Millenium Park and be sure to stop by the Bean and Buckingham Fountain
  • Explore Navy Pier and Ride the Ferris Wheel - I recommend going at night!

When You're Hungry (Or It's Happy Hour)...

  • Scout out food truck locations and have an impromptu picnic outside
  • Cool down with ice cream (my favorite spot is Oberweiss in Lakeview) and walk around the neighborhoods after dinner
  • Try out Chicago's best rooftops - J.Parker and Cindy's are two of my favorites!

When You Don't Want to Spend Any Money...
(Some of the items in the Tourism category work here, too!)

  • Walk around and explore the Lincoln Park Zoo
  • Relax on the Beach & Try Out Beach Volleyball
  • Explore one of the many Street Festivals All Summer Long (see the full calendar here!)
  • Bring a Picnic + Wine/Beer and Enjoy one of the weekly free concerts at Millenium Park
  • Find a good spot along the Lakeshore to watch the Wednesday Night Navy Pier firework show
  • Rent Divvy Bikes for a Day and Ride around the Parks or along the Lakeshore
  • Find a comfortable spot by the Lakeshore to relax and picnic (my favorite is the grassy area at Fullerton & North Ave)
  • Get Lou Malnati's Deep Dish Pizza as Carry-Out and bring some wine/beer to a free movie in the park (schedule) under the stars

Everything Else...

  • Get Cubs Rooftop Tickets for a day of all you can eat/drink and an amazing view of the game (OR grab bleacher tickets the day of for cheap and find an empty seat!)
  • Get tickets to one of your favorite concerts at Wrigley Field (I've got my eye on Lady Gaga or Zac Brown Band this year - here's the full list of upcoming concerts!)
  • Rent a Trolley & do a Bar Crawl with friends (and get some amazing views of the city)
  • If you're lucky, you might have a friend with a boat willing to take you out on the lake. If you don't, renting one is really easy and affordable when split with a group! I always check Groupon to find a good deal! 
I think the biggest detail this list is missing is an in-depth guide to my favorite rooftops, patios and happy hour specials around the city. I'm planning on doing a much more in-depth guide of all of those really soon, so stay tuned! 

What are your favorite Chicago activities, or activities in your city during the warmer seasons? I love to travel - so please comment below with some of your top choices and maybe it will inspire me to make a weekend trip out of it!

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