Summer Chicago Bucket List: What to do in DA BEST city!


You know you live in Chicago because we put a DA in front of everything! DA Bears, DA Bulls, DA BEST… this city is seriously so much fun…. and summer is here! There’s no better time to get out and explore than summer time in the Chi. SOOO many things to do that I have not done yet in the five years I’ve lived downtown! Time to be a tourist in my own city and make the most out of the warmer days! Here is a list of 15 things I want to do this summer to have DA BEST year yet!


  1. Take my God daughter to Maggie Daly Park! I so hope this happens sooner than later, cuz you all have to meet my lil girl! She’s full of sass (just like me) and the cutest little chuck of a mini human you will ever see. Her name is Maggie – so obviously we have to go to the coolest park in Chicago together with the same name… Maggie Daly Park! It’s so family friendly and she loves her days with “Auntie Kelly”. Mostly cuz I just give her ALL the snacks and hugs and kisses she wants!
  2. Do the paddle boat river tour with friends! This is new to Chicago as of this year. You basically get a bunch of friends together and pedal like you’re on a bike, and you’re powering the paddles to move you up and down the river…. while drinking! there’s a guide and you BYOB! How fun! I’ve done this in Nashville before, but not on the actual water. So pumped!
  3. Eat brunch at Cindy’s! Hands down the best view of Millennium park and the city! They have a really long waiting list and can be hard to make a reservation to actually sit down and eat. I’ve only ever had lunch there and drinks… I’m determined for brunch this summer because I hear it’s amazing!
  4. Shop the entire mag mile! Haven’t done this in a long time since I’m more an online shopper – however it’s such a fun way to spend a day in the city. Plus this blog gives me an excuse to do that for an entire day, right?!?
  5. Go to a Cubs game! This is a must every summer, especially in the bleachers. Cubs fans are so die hard and just the best. Just being in the park makes you feel so alive with Cubs spirit. My friends typically go to one game a year in the bleachers… so much fun, but somehow we missed last two years! Back on the to-do for this summer!
  6. Visit as many street festivals as possible! There are so many! Art festivals, music, jazz, film, wine, tacos, burgers, beer… music! Each neighborhood has their own festival with different music and bands, and you just wander the streets and have some drinks and eat lots of good food! Definitely going to try and make the Windy City Smokeout and the Lakeview Sam Adams Taco Fest this summer!
  7. Eat at every pizza place I haven’t been to! OK so maybe not EVERY place… but my love for pizza runs deep so I will never say no to any kind! There are a few places I have yet to hit up… Pequods being one of them. WHAT? I know I feel like I can’t even say that out loud in fear of my pizza crown being taken away!
  8. Rosé all day for Sunday Funday! Need I say more…rosé is the drink of the summer. If you can find some Frosé you’re just winning at life! Sunday’s, outdoor patios… gimme all the rosé please!
  9. Rooftop dance parties! Grew up dancing my whole life… and still love a night on the dance floor with some great music and friends. Just. Add. Rooftop! Maybe some twinkle lights too!
  10. Air and Water show from the lake! I am fortunate to have a very good friend who keeps a boat on the water in Chicago. Air and water show is one of my favorite weekends, mostly because it falls on my birthday each year…but viewing the air and water show from the boat is just an experience you need to have! The planes fly right over you, the sound of the military planes is just incredible, the tricks are happening right in front of you… it’s all just so much more amplified from the water. Find anyone with a boat this summer and get out there!
  11.  Drinking wine on the river walk! City winery is so fun to hang out at on the Chicago Riverwalk! If you have a boat, you can dock there and get lunch and some wine! Or you can just grab a glass and walk around! There are tons of food trucks docked in that area, you can watch the boats, take a walk, relax on the stone steps… such a great way to soak in the views!
  12. Paddle board in the lake! YES! This is also new at North Avenue beach! Sometimes the lake is super choppy, but other days its so calm and looks like glass! These are the days to get out on a paddle board. Such a good exercise too!
  13. Go to a concert at Northerly Island! I think this is the only place I haven’t been to a concert at. Such a fun smaller venue right on the water. You can hear the music from the boat, but it’s more fun to be there in person! There are some great artists coming this summer – so I need to choose fast!
  14. Ride the ferris wheel! They just rebuilt a new one last year – and it’s bigger and better than ever. Go Wednesday and Saturday nights and you can view the fireworks from capsule!
  15. Watch a free movie in Millenium Park! So many great free concerts and movies in the park all summer long! Tuesday night is movie night. Gather your friends, your babe, grab a blanket… and bring some wine and snacks for the perfect outdoor venue experience

What are you favorite things to do and explore in your city? Where should I visit next? Comment below- I need a vacation!

Shop my look below!…. use code SUNNY to get 25% off your purchase from Aerie! My top is on sale and I’m wearing a small…. the only size left! HURRY. Otherwise I posted a couple others that I also love. There are tons more too. My shorts are Levi’s… the same cut as my favorite distressed jeans I own from them… so you can’t go wrong!

And can we talk about how cute this bag is? TARGET for the win! Comes with a cute little stripe scarf and a detachable shoulder strap. You can wear it as a cross body or as a mini satchel!

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2 thoughts on “Summer Chicago Bucket List: What to do in DA BEST city!

  1. I just love this top!
    And don’t miss the amazing Architectural Tour on the Chicago River. Also Steves Lakefront Segway Tour!

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