21 Things to Add to Your Chicago Summer Bucket List

21 Things to Add to Your Chicago Summer Bucket List

Update 2019

We wait – through the cold and wind and as we thaw out, our ray of light is summertime Chi. I always question why people love this time of year. People are quick to talk about the festivals or movies in the park or Lollapollza and I’m here to tell you while those all sound great, and I have some tips about them, there’s more to living in Chicago than that. I’m here to show you the magical aspects of summertime in Chicago.

This is a list of everything -okay well some things to do in Chicago this summer. There is so much more to do, but it’s a good taste of Chicago’s summer from outdoor sports to beach days, to patios and Chicago’s rooftops.

1. Yoga (or any sport) in the park

Every summer in Chicago there are endless Meetup groups and also free Pilates and boot camps in parks throughout Chicago. The last series in Millennium Park is Labor Day Weekend!

May 25 – August 31

  • Tai Chi at 7am
  • Yoga at 8am
  • Pilates at 9am
  • Zumbaยฎ at 10am

There is also free neighborhood yoga. In Wicker Park, Lululemon hosts free yoga from 6:30 -7:30 pm at the Wicker Park Softball Field. Bring a mat and friends. I’ve already done this and it was amazing to go outside and do yoga, but I still love my Bottom Line Yoga membership in the loop (at the Board of Trade and Civic Opera House locations) because rain and humidity are also part of summer (have you seen these isolated thunderstorms!).

2. Go to a wedding.

If you don’t have an invite, you’re sure to see beautiful brides taking pictures on street corners or near Navy Pier. I went to one of the most beautiful weddings at the Ivy Room in State and Ohio St. There were flowers hanging from the ceiling with tea lights and a live band. Going to a Chicago wedding is an honor.

3. Have a girl’s night in the city at museums with al fresco martinis.

While summer is a great time to be outside, you might want to mix it up. One of the most amazing nights was having a girls night at the Chicago History Museum where we learned about fashion and then went a mile south to the Waldorf Astoria for cocktails al fresco and makeovers from Dior. Chicago has so many fun mixers like this and pulling off a multi-destination event could only be done when it’s still warm outside.

Girl’s Night Out Idea: The Chicago Museum of Contemporary Art has free admission on Tuesdays and a program called Tuesday’s on the Park. From June to September 5:30-8 pm, they have drinks and food and a picnic area with live music. It really is a low cost way for a fun night. And if you’re girls don’t want to go, it’s also a really cute date idea for your Bumble Boo.ย 

4. Go to a Chicago rooftop and experience a Silent DJ.

When I heard Silent DJ, I was confused, but it’s becoming very popular. You get a headset and it has three different stations played by live DJ’s. The headset lights up a different color to match each DJ. So, if you’re not feeling the red station and you seem someone partying on the blue, you can join them. Throughout the night, it’s fun to watch people dance. Check out an AIRE Rooftop Silent Party here.ย 


5. Enjoy shopping on State Street or Michigan Ave.

Summertime is amazing because you can actually start your shopping spree on State Street, then walk along the Chicago River walk and all along the Magnificent Mile. Stores are always hosting events and having blowout sales.

For instance The NikeLab Chicago Re-Creation Center c/o Virgil Abloh opens from May 31 to July 28 at 673 N. Michigan Avenue. It serves a creative hub where cool and creative projects are taking place like the Reuse-a-Show Program that reuses worn-out athletic shoes by turning them into Nike Grind. Nike Grind will then be used to build a basketball court for the community, designed by Abloh, for the Chicago community in advance of NBA All-Star 2020.

For my shopping adventures, I like Nordstrom Rack, Express and for the crazy summer look, Akira.

6. Get that mani and pedi.

During the winter, your feet always are covered up with socks on them and your hands always have gloves. Summertime is that one opportunity to enjoy a fresh manicure. You don’t have to go with the nude polish if you don’t want to!ย  I tried Groupon’s beauty booking app, Beauty Now. In less than 5 minutes, I could book an appointment for the same afternoon without waiting. And that, my love, is nice.

7. Go to the movies.

It wouldn’t be summertime without a summer movie. I had so many amazing movie experiences. If you haven’t been go to the VIP room at the movie theatre, the Showplace Icon Theatre in The Roosevelt Collection. They had red recliners and you can get dinner and cocktails there. It’s truly one of the best date nights I have had. Very comfy. Shout out to Aladdin for also bringing me back to childhood.

The other spot to check out is The Music Box Theater. A little secret is that they have a bar and a game room and a gorgeous patio with twinkle lights.

8. Enjoy the parks.

Whether it’s Lincoln Park or Millennium Park or Museum Campus. Don’t miss the opportunity to sit and read in the park and soak up the sun.ย  Another favorite activity is seeing people tightrope in Oz Park – if you’re lucky, they’ll let you try it but you might need someone to hold on to as you walk across from tree to tree.

9. Try a new work out.

When you get out of your house and into a new neighborhood, it’s amazing what you can discover. One of my favorite ways to do is try a workout class in a different neighborhood. In the winter, I don’t like to travel far, but in the summer – exploring is the best part.

One of the coolest workout experiences I had was at a new virtual cycling experience, Cycmode in the South Loop. The bikes literally swerved left to right with you and as you stare at the big screen it takes you on a journey going uphill and downhill. You no longer have to visualize hills.

I also recently tried my first aerial yoga class at AIR Chicago in River North. They started the class by having us hang upside down – something I didn’t think was possible. I highly recommend doing this with a friend because from the moment we got into the fabric, we couldn’t stop laughing. Plus, there are a few partner moves that are fun to try. I did this class with Allie from Allie’s Fashion Alley.ย 

I also tried a rowing class in Old Town at the Row House. The energy and enthusiasm the instructor has literally made my Saturday morning and I also did the class for National Best Friends Day with Once Upon a Dollhouse – so workouts with friends are just better. It was perfect because after class was the Old Town Art Fest. Getting your sweat on and then walking around looking at beautiful art is half the fun. We also grabbed a table at Topo Gigio – which has the cutest patio and really good pasta at pretty amazing price. When the bill is under $15, it’s something to write home about…

If you really want to go for an adventure, there’s a place on the south side called Razzmatazz which has indoor bubble soccer and an adult obstacle course. You get to be a kid again but it’s also difficult to keep a bubble around you while playing soccer. Seriously, though, it was a fun way to workout.

10. Go to a conference or a talk.

Chicago has so many amazing opportunities to learn from professionals inย  your field – the good, the bad, and the ugly. July 17th, you can grab $10 tickets to hear from what was named Best Literary Event in the 2017 Chicago Reader’s Reader poll, The First Time. The night of unique live storytelling and music experience includes stories from one of the greatest Chicago female entrepreneur, Nicole Vasquez, Deskpass Co-Founder.

11. Volunteer.

I joined the Chicago Cares group for their volunteer day, where 5k people came together to connect and build relationships for a stronger, more unified city. I painted murals and classrooms with positive messages at Burnside Scholastic Academy one summer. Our collective work will save CPS $3 million in facility impacts!

Love making a difference?

If you have vacations planned and want to still volunteer when you’re free, sign up for Chicago Cares 200 monthly volunteer projects.ย ย 

12. Take a weekend trip to another Midwest city (no car necessary).

While it’s hard to leave Chicago, it’s also nice to explore other cities. I’ve taken weekend trips to St. Louis. If you go, experience their famous BBQ and art scene and find the Ferris Wheel on the roof – it’s pretty epic. I also have taken a trip to Detroit, MI using the Amtrak and Cincinnati, OH using the Greyhound Bus. Another fun trip is to Valparaiso, IN for the popcorn festival. You can take the train down and enjoy a popcorn parade and beer and popcorn for the day. It’s quite the experience. There’s so much to explore in the Midwest and if you time it right, you can get a round trip for as low as $18 to some of these cities, just saying.

13. Ride Divvy bikes or this year, scooters.

There’s nothing more exciting than riding a bike. I would suggest riding a bike on the Lakefront path but you can also ride down Michigan Ave. They did raise the price a bit (it’s about $10 to rent a bike for the day). I still think you should experience seeing Chicago by bike.

14. Go to a baseball game.

I’ve gone to a White Sox game and then I went to a Cubs game. Baseball games are exciting to go to – the city comes alive and I must say there is nothing quite like singing baseball games with excited fans in Wrigley. P.S. if you go to a Sox game, go for the food. If you go to a Cubs game, go for the experience and go to the bars after. Win or lose you’ll have a good time.

15. Eat ice cream.

My favorite summertime treat is ice cream! I tried Bombobar and found out their shakes are actually frozen hot chocolate, which I tried and honestly they taste terrible. It’s very rich. Their gelato however is amazing and even better than Eataly’s gelato.

16. Go on a boat.

This is always the mission. Chicago has a beautiful river and lake and it’s really nice to experience them while on a boat. I did the Architecture Tour and it was a great experience to not only look at Chicago’s architecture, but also learn the stories behind the skyline and how Chicago’s skyline will continue to change.

17. Go to the beach.

Okay well the beach was actually amazing because I found a Pier at 31st beach where it was safe to jump off. Turns out you don’t have to go to Europe to jump off a pier. It was a pretty steep jump, but it was also one of my favorite moments of this summer. All of the beaches have a bit of charm to them. North Ave. Beach tends to be the most active with volleyball nets and the infamous, Castaways.

18. Ride the Ferris Wheel at Navy Pier.

I have to say that one of the scariest moments of summer was prepping myself to the Ferris Wheel at Navy Pier. I hate heights, so I almost didn’t do it. But the staff showed me the panic button in the Ferris Wheel. One thing you have to note is that this is an enclosed Ferris Wheel. So it doesn’t feel like you are as high up as you are. With your purchase, you get to see Chicago’s skyline three times before getting off.

19. Try something new with your hair.

I don’t know about you, but while summertime in Chicago is nice, my hair is not. So rather than putting it on my bucket list for another summer, I decided to do something about my hair and try Keratin treatment. I was sad to hear that you can’t go into a pool or the ocean with Keratin treated hair. Luckily, you can still go to the lake. I’m glad I did the treatment because now I just have to straighten my hair and I don’t need product. If I lived near the ocean, though, I wouldn’t have had the treatment done. I’m still debating whether to do Keratin treatment or a Brazilian blowout this summer.

20. Go to a foodie event or festival.

I would be remiss if I didn’t add this to list. The best festivals of summer are honestly Taste of Chicago (July 10-14)ย  or Greek Fest (you can ride a camel downtown).

21. Date or not.

Chicago, oh Chicago is known for its dating scene. Cuffing season happens right about the time when football comes back and Labor Day ends because everyone needs a cuddle buddy for the cold Chicago months ahead. But rather than dating and swiping – only dating one guy is nice. I think everyone should experience a summer with a guy they like. It is pretty magical going on date nights to steakhouses and The Grand Lux Cafe and having beach days and taking them to launch parties.

Dating in the summer is so much better than any other season because you actually get to do things and explore the city together. Also, if you missed my segment on WGN radio – you can listen to my dating stories here.

Amanda Elliott
Amanda Elliott

Amanda Elliott is a writer and speaker and a relationship builder. She believes that meeting people in person is important. After attending numerous fashion, startup, and creative events, she founded Windy City Cosmo is 2015 to help people make connections in the city as they build their businesses, start and end relationships and see and be seen. Over the past three years, the entrepreneurs she’s interviewed have become the most successful in Chicago and Windy City Cosmo won an award in 2017 for her work for female entrepreneurs.

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