Discover the Magic of Chicago’s Summertime: A 2023 Bucket List

Discover the Magic of Chicago’s Summertime: A 2023 Bucket List

This post was updated for Chicago Summer 2023.

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. I’m here to show you the magical aspects of summertime in Chicago.

This Chicago summer bucket list 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!

Saturdays, May 27–September 2, 2023 • 8-11:45am
Millennium Park Great Lawn • Free Admission

  • Tai Chi 8:30-9:15am
  • Yoga 9:30-10:15am
  • Pilates 10:30-11:15am
  • Zumba 11:30-12:15pm

There is also free neighborhood yoga. I haven’t seen any yoga at Wicker Park, but typically during the summer, there are some free sessions.

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 girl’s 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. 


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. AIRE Rooftop hasn’t announced any for 2023. The Gwen also hosts silent DJ parties. Here’s a list of silent DJ events and you can check by city.

And also, rooftops are the best places to be in Chicago in general. This is a solid Chicago rooftop list. I usually start the night at one of these for happy hour.

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 Riverwalk. If you’re at the Riverwalk, I would suggest renting out kayaks – I loved that experience. Kayak rentals are usually $30 per hour for a single and $40 per hour for a double.  Stores are always hosting events and having blowout sales.

For my shopping adventures, I like Nordstrom Rack and Anthropologie.

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!

I recently stopped getting gel nail polish because it’s harsh on my nails. As an alternative, I’ve tried dazzle manicures, which don’t use any UV lights and can be removed with regular nail polish remover. As a bonus it’s vegan, and my nails lasted for 3 weeks. I loved my experience at Mitazi Salon in Lincoln Park.

7. Go to the movies.

I think movie theatres are happening this summer. It wouldn’t be summertime without a summer movie. I had so many amazing movie experiences. If you haven’t been going 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.

The other spot to check out is The Music Box Theater. It’s actually celebrated its 90th Anniversary two years ago. The Music Box Theatre opened on August 22, 1929. 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. Pro tip: Millennium Park Music series is back this year, June 22 – Aug. 21, 2023.

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.

Another favorite is the Millennium Park Summer Film Series (Jay Pritzker Pavilion): Tuesdays, July 11 – Aug. 29, 2023. Enter the Park at Michigan Ave. and Washington St. or Michigan Ave. and Madison St.
Tuesdays at 6:30pm (Gates open at 5pm) • Free Admission.

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. 

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 a 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. Note: Due to COVID-19, as of May 2021, Razzmatazz is still closed.

10. Go to a conference or a talk.

Chicago has so many amazing opportunities to learn from professionals in your field – the good, the bad, and the ugly. One place that has fascinating events is 1871. They even label their events so you know if it’s a good fit for you from an early stage, to a growth stage to corporate. 1871 is geared towards entrepreneurs. They most recently developed an accelerator for Black founders to help diversify Chicago’s startup scene.

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.  

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.

Also, I pulled together some spots to go for a weekend away road trip with your boyfriend – from cabins in the woods, to state parks, and cute towns.

13. Ride Divvy bikes

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. You can also easily see if a bike is available through Lyft and reserve it there. I love this feature. I still think you should experience seeing Chicago by bike. We’re still waiting to hear whether scooters are making a comeback in Chicago. 

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. Here’s a bigger list of ice cream spots to try in Chicago. I’ve been to over half of them, and they are worth it 🙂

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. Honestly, if you have a big enough group, renting a boat for half a day is less than $150/person.

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 for 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.

Pro Tip: There’s a beautiful new bar on Navy Pier, Offshore Chicago. It’s absolutely gorgeous (during the day). Make sure to get reservations ahead of time because it does fill up quickly, and Navy Pier isn’t close to anything.

19. Try something new with your hair.

I don’t know about you, but while summertime in Chicago is nice, my hair is not. And also during quarantine, I feel like a lot of us put our hair on the back burner in the name of safety so we’re overdue for a chop and color. 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 a 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 the list. The best festivals of summer are honestly Taste of Chicago 2023.  This year it will not take place in July, the Taste of Chicago will be at Grant Park from September 8-10, 2023. Greek Fest is usually lit (you can ride a camel downtown).

21. Date or not.

Chicago, oh Chicago is known for its dating scene.

Dating should definitely be added to your Chicago Summer Bucket List. It is so much better than any other season because you actually get to do things and explore the city together. Also,a few years ago I did a segment on WGN radio – with a glimpse into my dating stories.

Amanda Whitfield
Amanda Whitfield

Amanda Whitfield 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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