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20 Things to Do in Chicago in the Summer

Summertime in Chicago just cannot be beat. We wait all year for the sun to come out and temps to rise, and from May – September, we do it right.

Having lived in the city for nearly five years now, just like any Chicagoan, I’ve learned how to maximize the summer season with all that Chicago has to offer. From the beach to festivals, my favorite rooftops and walking paths, here are a few of my go-to summer activities + new Chicago to-do’s on this summer’s bucket list.

  1. Millennium Park Movie in the Park Series – I’m putting this as #1 because it’s my favorite-ever thing to do in the summer in Chicago. In fact, we try to go as much as we can! Perfect for a family night, date night, or wine picnic with friends, there are a ton of great movies to choose from. Movies are Tuesdays at 6:30, and lawn spots fill up fast. Get there an hour early if you can.
  2. Old Town Art Fair – One of the best Chicago summer festivals. Walk around, libation in-hand, peeking through tons of awesome local artwork, and then enjoy the Old Town bar and restaurant scene after. Perfect!
  3. Cindy’s – Located in the Chicago Athletic Association Hotel right on Michigan Ave, Cindy’s is a new but already-legendary rooftop spot. Be prepared to wait, but the views and cocktails are worth it. 
  4. Go See Anything at Ravinia – Yes, anything. If you haven’t been to Ravinia yet, it’s sooo fun. Pack a picnic (with lots of wine) and camp out on the lawn while listening to the artist of the day. If you’re not picky like me, any artist will do. But they do have an outstanding lineup of performers this year – including John Legend and One Republic! Plus, you can get there via Metra.
  5. Windy City Smokeout – Haven’t yet been to this one, but heard really good things. On my list for this summer! Bands, BBQ and beer – what could be bad?
  6. RM Champagne Salon – Nestled in the West Loop, their back patio bar is one of the best kept secrets. Adorable lights, paved brick stone and yummy wine selections, this is the ultimate gals happy hour or romantic date night.
  7. Walk the River Walk – I love me some River Walk. Hop on anywhere in the Loop and walk along the serene river in the midst of downtown Chi. Stopping for a bevy on the way is not optional. (Hello, City Winery!)
  8. Green City Market – The farmer’s market of all farmer’s markets. Get fresh produce + fresh-made eats, like breakfast sandwiches and more. The one I know best is in Lincoln Park, which is open Wednesday and Saturday mornings. However, they also have locations in West Loop and Wrigley.
  9. Walk, Bike or Run the Lakeshore Path – Us Chicagoans are mighty proud of our lake. When Dan and I lived in River North, we regularly devoted a weekend morning to doing something active along the lake. Even in the heat, you get a great breeze (and views!) 
  10. Do Division Street Fest – Yummy food, drinks and fun bands. Definitely more of a lively fest. (Also, Division St. in Wicker is the best.)
  11. The Dawson – One of my all-time favorite outdoor patios in the city. Plus, their food is outstanding! Arrive early and park yourself for the afternoon.  
  12. Monday Movies at ROOF on theWit – One of Chicago’s premier rooftop bars at theWit hotel does outdoor movie screenings on Monday nights. Get there early – because seats fill up. And fair warning – the movies don’t start until sundown, so it may be a bit of a late Monday (#YOLO).
  13. Cubs Game – Enough said. And if you haven’t yet experienced the bleachers, you totally should (sans kids, with a ride home). 
  14. Big Star – An iconic Wicker Park spot with the best tacos you’ll ever eat. Get a pitcher of margaritas and see ya later. Also underrated: their queso fundido. Ta die for! But get there early – they open at 11 am and usually already have a line at that time.
  15. Fireworks at Navy Pier – The pier offers fireworks after sunset every Wednesday and Saturday from Memorial Day to Labor Day. Whether watching from the pier itself or from a nearby downtown location, this is an iconic Chicago to-do.
  16. The Beach – I prefer Oak Street Beach to North Avenue Beach, which can get a little college-spring-break-y after 2 pm. But if you must hit up North Ave, I’d recommend going early or planning to booze up and join the fun. I also hear Montrose Beach is really nice and dog-friendly.
  17. Parson’s – OK, I’m a little biased on this one because it’s close to where I live. But seriously – their outdoor scene cannot be beat! Grab a friend (or your dog) and indulge in fried chicken and slushy cocktails. Nom.
  18. Double Decker Bus Tour – Yes, this is for you, Chicagoans! When’s the last time you acted like a tourist in your own city? We did this last summer and had a ton of fun uncovering facts about our beloved Chicago that we never knew. The best-known hop-on/hop-off tours are Big Bus and Chicago Double Decker & Trolley.
  19. Park & Field – This one is on my to-do list, because I haven’t been yet — but I’ve heard good things! New to the Logan Square neighborhood, this hot spot is set in a vintage sports bar scene and boasts delish cocktails.
  20. Millennium Park Summer Music Series – Though I’ve been a summer movie goer for years, last summer was the first time I experienced the park’s summer music series. Same idea: pack a picnic (with lots of vino) and enjoy a night outdoors, with new (free!) shows every Monday and Thursday. And pssst…if you don’t have time to pack food or beverages in advance, pick up something delish at Pastoral on Lake St.

Chicagoans – what did I miss?

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