Things to do in Chicago in the Summer

Summer in Chicago.

Three of my favorite words. If you haven’t had the opportunity to visit Chicago during the summer, you are missing out!

Chicago is my favorite city and I will argue until I’m blue in the face that it’s one of the best cities in the world, especially during the summer months.

There are so many things to do in Chicago during the summer and there’s such a vibrant energy all around. I love being a part of it.

So what are some of those things that you can do when visiting? Here is a list so you can start planning a trip:

Pin it!

Summertime in Chicago

  • Book an architectural boat tour with the Chicago Architecture Foundation (or Wendella or Shoreline. They’re all good). Rumor has it the architectural boat tours in Chicago are the second most popular tour in the world (after the Vatican).
  • Visit the Bean (formally named Cloudgate) in Millennium Park. It is nicknamed “the Bean” due to its shape. Go early in morning to avoid the big crowds. If you have kids, I also encourage you to check out Maggie Daly Park and its playground nearby.
Cloudgate, aka “the Bean”
  • Go to a concert, movie or show at Millennium Park. Pack a picnic and grab a blanket and hang out in the pavilion area for some free entertainment. The NPR podcast “Wait, Wait Don’t Tell Me” is one of my favorite shows to catch there during the summer along with concerts showcasing the Broadway shows currently showing or coming soon.
Jay Pritzker Pavilion during a taping of the NPR podcast “Wait, Wait Don’t Tell Me.”
  • Head to Cindy’s Rooftop for great views of Millennium Park and Lake Michigan. You can enjoy the views while having some apps and cocktails.
The view of Millennium Park from the terrace at Cindy’s Rooftop
  • Explore the Lincoln Park Zoo. This is the free zoo on the north side of the city. It’s not as big as the zoo out in Brookfield but for the price, you can’t beat it. Check out my favorites, the zebras and polar bears while you’re there!
  • Catch the fireworks at Navy Pier. They have fireworks shows on Wednesday and Saturday nights. It’s definitely worth checking out if you’re downtown around 9:30 on those evenings.
  • Go to a baseball game at Wrigley Field. Ignore what you’re told. Skip the bleachers and sit in the stands where it’s shaded (important for a fair gal like me) and cooler when the lake breeze is blowing. Don’t forget to have a beer and hot dog.
Beautiful Wrigley Field. Go Cubs Go!
  • Hang out along Lake Michigan. One of the most popular destinations for locals and tourists alike during the summer months is the lakefront. There are beaches. There are beach bars scattered about where you can enjoy some drinks while enjoying the views. There’s also a lot of grassy park space for picnics or relaxing on a blanket while reading a good book (pup pictured below not included).
The view of Lake Michigan Stella and I often enjoy
  • Go for a walk or bike ride along the 606. The 606 goes through neighborhoods west of the city, such as Wicker Park. It’s a great walking and bike path that allows you to explore different areas of the city. There are also lots of great restaurants and bars in Wicker Park and Bucktown if you decide to stop along the way. Tip: Don’t have a bike? Look for the blue Divvy bike stations located all over the city where you can easily rent a bike.
  • Have a meal on the patio at the many places available around the city. El fresco dining is definitely one of my favorite summer activities in Chicago and there are hundreds of restaurants that have great patios. If you want a list to choose from, check out Shelley from @chicagoismyboyfriend’s story highlights on Instagram. She lists lots of amazing Chicago patio and rooftop options in that reel.
  • Walk around the city and enjoy all the art and murals along with the beautiful flowers the city plants and maintains. These are the things that I think make Chicago so unique. There is so much care put into the plantings and the art. I try to remember to stop and appreciate it often and encourage you to do the same.
Possibly my favorite mural in the city. It’s 4,000-square-feet and located at the intersection of Lincoln, Ashland and Belmont in the Lakeview neighborhood.
The bright red 53-foot-tall steel stabile “Flamingo” in Federal Plaza in downtown Chicago

So there is my list. If you have visited during the summer and think I missed something, let me know in the comments below.

Looking for more ideas for things to do in Chicago? Check out some of my other Chicago posts here and here.

The Best Broadway Shows

Several years ago, I was out with some friends and their friends. We were at a bar, talking and having a good time. The discussion turned to whatever the popular TV shows or movies were at the time and I zoned out, not interested in the conversation. I don’t watch much TV and usually fall asleep during movies. If you like to recite movie or TV quotes, unless it’s from “Friends,” “Big Bang Theory” or the prior day’s Cubs’ game, I’m going to look at you like you’re crazy.

One of the friends of friends started asking me about what shows I watch and when I told her I don’t really watch TV, she told me “you have no culture.”

I remember being taken aback when she said that. What? What does that even mean? Because I don’t watch TV, I lack “culture?” Again, what? I’m pretty sure I rolled my eyes at her and said “Whatever, you don’t know me.”

Her comment crosses my mind from time to time because I look at my life and know that I am pretty well cultured. I have traveled all around the USA and to many different countries throughout the world. I have friends from all over the world as well. Visiting museums and going to concerts and sporting events are things I do often. I also love to go to live theater and I have had the opportunity to see several shows on Broadway in New York. However, most of the time, I see shows here in Chicago through Broadway in Chicago.

I would say that by now, I have seen 50 or so Broadway shows. Reading reviews before going to a show is something I try to avoid because I love to go in without preconceived notions so I can make my own opinions. Since I have been to so many shows, I thought you might be interested in knowing which are my favorites and which I thought were underwhelming. So here is my list of the best Broadway shows

Disclaimer: This list turned out to be longer than I planned but I love theater so I guess it shouldn’t surprise me.

The Best Broadway Shows


  1. Wicked – This is the story of the witches from the Wizard of Oz. I saw it at least three times when it was here in its first run in Chicago and saw it again last year when it came back. I gasped the first time I saw the surprise at the end and officially decided I loved it then. It’s my favorite of all the shows I’ve seen. I HIGHLY recommend Wicked if you have the opportunity to go see it.
  2. Hamilton – I cannot do a list of the best Broadway shows and not mention Hamilton, right? Hamilton ranks second on my favorites list. It won 11 Tony Awards. I have also seen this show multiple time. A friend and I got to see Wayne Brady playing Aaron Burr the first time I was in the room where it happened. I thought the actress who played Alexander Hamilton’s wife, Aliza, stole the show. She has an amazing voice! Fun fact: JPMorgan Chase Bank owns the pistols used in the dual fight that killed Alexander Hamilton. They are housed in one of its NY offices.

    The Best Broadway Shows
    Kelley and me before seeing Hamilton for the first time.
  3. Mama Mia – I’ve seen this one in Chicago and also on Broadway in New York. I love the music – it’s all music from the band Abba if you don’t know. The play is better than the movie, although I love the movie too.
  4. Mary Poppins –The classic movie done live. This was a show I decided to go to on a whim by myself one night and I am so glad I did. Supercalifragilisticexpialidocious is the best musical number I’ve seen. I loved loved loved it!  I wanted to get up and sing along.
  5. Jersey Boys – This play is the story of Frankie Valli and the Four Seasons. I also loved the music in this one and wanted to sing along because it included so much of the music I grew up listening to with my parents.
  6. Beauty and the Beast – This was the first show I say on Broadway in New York. It was so good – it felt like I was watching the Disney animated version.
  7. Aladdin – I saw this one in Chicago with my friend Kelley. The set and costumes were amazing! And the music was good too. The magic carpet flies – and I still wonder how they did it! I didn’t see any wires.
  8. Newsies – This is a musical based on the 1992 musical film Newsies, which in turn was inspired by the real-life Newsboys Strike of 1899 in New York City.
  9. Escape to Margaritaville – Okay, this one is definitely not for everyone. It is very cheesy. BUT, as a self declared Parrothead who has been to 15ish Jimmy Buffett concerts, I loved this one. I knew most of the music and loved singing along.
  10. Something Rotten – I also went into this one not knowing what to expect. While it wasn’t quite “The Play that Goes Wrong” funny, it was pretty close. I would recommend it. What I remember most about this show was going with a friend who was struggling through a break up. Hearing her laugh during this show was the best music to my ears.
  11. Once on this Island – A couple of friends and I decided to go to this show at the last minute and I am glad we did. The cast was entirely Black, which I loved. The costumes were great and the story was okay too.


  1. The Play that Goes Wrong – I had no idea what to expect when I went to this show and it ended up being the funniest show Broadway show I have seen. EVERYTHING goes wrong, according to plan. It was incredible! I laughed and gasped a lot in this one. I loved the lightness of this one for a change of pace.
  2. What the Constitution Means to Me – This one isn’t going to be everyone’s cup of tea but as a political junkie and strong advocate for women’s rights, I really enjoyed it. This was part of a season ticket package and is one of the reasons why I like the packages. I probably wouldn’t have gone to see this one on its own. I really recommend it if political history and women’s rights are your thing.
  3. Oslo – This is the Tony award-winning play by J. T. Rogers, recounting the true-life, previously secret, back-channel negotiations in the development of the pivotal 1990s Oslo Peace Accords between Israel and the Palestinian Liberation Organization. I remember the photos from when this happened but never knew the significance or the story behind it. This is a long play and is not a musical. But it is a good history lesson.

There are two shows that I hope to see sometime in 2021 or 2022, “Six” and “Come From Away.” My friends saw Six when it was at Navy Pier last summer and still rave about it. In “Six,” the “six wives of Henry VIII take the mic to remix five hundred years of historical heartbreak into an exuberant celebration of 21st century girl power!”

“Come Away From” was also in Chicago last year. I missed it because my schedule wasn’t cooperative. Hopefully, it comes back in 2021 or 2022. If not, I may have to go to New York to check it out.

Now it’s your turn. What are the best Broadway shows in your opinion? Did I miss any? Tell me in the comments below.

To check out more from this blog, see my favorite memories from Jimmy Buffett concerts here and a Letter to My Younger Self here.

Save this post to Pinterest!

The Best Broadway Shows