
My 2019 Chicago Summer Bucket List
Happy June! After the longest winter ever, I could not be any more excited that summer is (unofficially) here! I’ve been cooped up in my apartment for the last six months, so I can’t wait to get outside and do all these items on my Chicago Summer Bucket List. Chicago comes alive in the summer and there’s truly no better place to be!
- Go to a few Cubs games. I didn’t go to any last year and need to make up for it this summer! There’s nothing better than Wrigley Field, a cold beer, and a Chicago hot dog.
- Go to all the street festivals. Some of my favorites are Belmont-Sheffield Music Festival, Do Division Street Fest, Chicago Blues Festival, Wells Street Art Fair, Ribfest, Southport Art Festival, and last but certainly not least, Chicago Hot Dog Fest.
- Walk down the Chicago Riverwalk. Even though it opened in 2016, I’ve only been once and would like to go back. I’m especially looking forward to visiting City Winery.
- Go on a boat. This is on my list every year and it never happens…fail. If you own a boat, hit me up!
- Go to the beach. It’s the quintessential summer activity, after all. North Ave. is one of Chicago’s best beaches, and I like hanging out at Castaways while I’m there.
- Ride a Divvy down the Lakefront Trail. I’ve lived in Chicago for four years now and am still yet to rent a Divvy. This is the year!
- Have a drink on a rooftop. Cindy’s is a popular spot with its amazing view of Millennium Park. I’d like to check out some new places as well, including the Parker, LondonHouse Chicago, and Z Bar.
- Wander around the farmer’s market. I went to the Green City Market in Lincoln Park last year and thoroughly enjoyed myself. I sampled the doughnuts (highly recommend!), ate all the free samples, and bought a fresh loaf of bread and cheese to take home.
- Eat ice cream at Jeni’s. As the temperature rises, so do my cravings for ice cream 😊
- Go to Jazzin’ at the Shedd. There’s live jazz at the Shedd every Wednesday night, which you can enjoy with a drink on the terrace. I’ve never been to the Shedd Aquarium, and this would be a unique way to experience it for the first time.
- Play shuffleboard at Royal Palms. This place looks like so much fun! I haven’t played shuffleboard since I was a kid. Also, there are different food trucks on site every night to try out.
- Dine at some new-to-me restaurants. One of my favorite things to do in every city is to try the local cuisine, and even though I live here, Chicago should be no different! Parson’s Chicken & Fish, Le Colonial, Smoque BBQ, and Piccolo Sogno are on my list.
What’s on your Chicago Summer Bucket List? Leave a comment and let me know!
P.S. Follow me on Instagram to see all of my summer adventures in real-time!

