Ohhh Chicago in summertime 😍there’s nothing like it! Whether you already live here or if you’re planning a trip this summer (which you should be!), here’s my most updated bucket list of things to do in the city for summer 2018. I have lot of the typical tourist-y things you should do when visiting Chicago [in this older post here] if it’s your first time, but the list below is more of a local’s guide for things to do specifically over the next few months of summer here. ENJOY MY CITY! Tag your travel buddy in the comments of this Instagram post to start planning 🙂

Chicago Bucket List:

Summer Edition

1. Boating day on Lake Michigan in the ‘Play Pen’

Rent a boat with friends and head out to the “Playpen” – the no-wake area just south of Oak Street Beach in Lake Michigan (one of the most fun things I’ve done here since moving to Chicago).

2. Millenium Park Summer Film Series

Plan a movie night at Millennium Park to sit, picnic and watch movies on a 40-foot LED screen (June 5 – August 21) see the full movie schedule here.

3. Divvy Bike Day 

Rent Divvy bikes for a day to explore the city.

4. Lollapalooza 

August 2-5

5. Windy City Smokeout

July 13-15

6. Sheffield Music Fest & Garden Walk

July 21 + 22, so excited about this! Lincoln Park residents open up their homes to showcase their home gardens.

7. Cubs Game at Wrigley 

Watch the Cubs play then go to the new Big Star across the street after for tacos and margaritas.

8. Castaways at the Beach

9. Rooftop pool at the Viceroy Hotel – Devereaux

10. Rooftop Sushi at Noyane (rooftop of the Conrad)

11. Watch the Air & Water Show

Aug. 18 +19 —> Best view: rooftop of Eugenie Terrace

12. Lincoln Park Farmers Market

13. Free Concerts at Millenium Park

Get the concert schedule here.

14. Navy Pier Fireworks

15. Wicker Park Fest


16. Parson’s Patio

A great summer patio spot with table table tennis & negroni slushies!

17. Rent a Cabana at the beach at Shore Club

18. Punch Bowl Social Game Night

A fun place for music, food, games, and drinks. Where brunch turns into a bowling party and a bowling parties turning into all-you-can-sing karaoke.

19. Drinks at Violet Hour

My favorite spot in my neighborhood for drinks!

20. Night out at The Disco

For a marathon dancing night – check it out here.



Recent Posts
Showing 2 comments

Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.