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.

Girls’ Weekend in Chicago featuring Jimmy Buffett

Fun. So much laughter. Lots of good food and drinks. Girl talk….

All of these can be used to describe the weekend I had with my sister and our friend Meagan over the past couple of days. I was so excited for them to come visit!

They got in on Friday afternoon and we headed out for dinner that night at Cafe BaBa Reeba. If you’ve followed my blog, you know this is one of my favorite restaurants and my go-to when friends visit. It’s a tapas (small plates) restaurant near Halsted and Armitage in Lincoln Park. It never disappoints and didn’t this time either.

We followed Cafe BaBa Reeba with some drinks at Merkles. Merkles is a Hawkeye bar on N Clark St in Wrigleyville. The sign behind us in the photo below says “This is Hawkeye country.” I agree but Meagan may not since she is a Cyclone.

Brunch at Tuco and Blondie (on the corner of Southport and Roscoe in Lakeview) is quickly becoming one of my favorite weekend activities. I had been to Tuco and Blondie once before and really enjoyed it so I decided to take Meagan and Amber there on Saturday morning. I’m glad I did because was a hit! I had to laugh when we first got there at 10am because I opened the drink menu and Amber commented “You’re going to have a margarita at 10am with breakfast?” Yes, I was, and I did. And they did too. Apparenty, I previously failed to convey proper brunch etiquette to Amber. ????

I had the passion fruit margarita, Amber had strawberry and Meagan had the regular margarita. All were great and not too sweet (which can sometimes happen with flavored margaritas).


I had the gringo omelette and their famous potatoes. Their potatoes are more like a crispy on the outside but creamy on the inside potato casserole. Delicious!


Amber had the breakfast burrito

We finished brunch with the obligatory photo in front of the mural on the outside of the restaurant. Amber and Meagan coordinated their colors to the mural very well!

Next up, the Jimmy Buffet concert! This is one day I look forward to each summer. I have been to a Jimmy Buffett concert almost every year with my friend Joe since I first moved to Chicago in 2002. I would say that this was probably my 15th concert of his then. Does that make me an official parrothead? ???? It was Amber’s second Buffett concert and Meagan’s first. I was so excited to go with them!

We started the evening with a Buffett preparty drink at Sports Corner. (Nice photobomb by the gentleman behind us. He was very proud of himself for it).




Fins Up!

After a quick stop at the Sports Corner, we headed over to Brickhouse to meet my friends Joe and Chris. Brickhouse is a new bar that opened as part of the Park at Wrigley just west of the stadium (Clark and Waveland for street reference). I was skeptical as we were walking over but I ended up really enjoying the bar and our time there. The music was great! The wait staff was friendly and attentive. The food was good. The drinks were tasty. And it was steps to the entrance of the stadium. Wins all around!

Quick selfie in front of the marquee on our way to Brickhouse

Brickhouse is two stories. We were on the second floor patio pictured here. I highly recommend it if you’re heading to a game or concert or even just in the neighborhood not going to Wrigley.


I love this hula girls headband. (I should have left my sunglasses on for this photo).


Chris and me


My favorite Parrotheads, Joe and Chris

Quick photo with Ronny Woo Woo and my friend, Laura, at Brickhouse.

Time for the concert!


Tuco and Blondie gave away beach balls to its brunch patrons heading to the concert. Pretty neat marketing idea!

Joe and Chris opted for rooftop tickets to listen to the concert rather than be inside the stadium. As luck would have it, they are in the rooftop directly behind us. How funny!


Pretty sunset behind Wrigley


Cool coloring of the crowd during the show


It was such a great weekend. I miss Amber and Meagan already. I’m so glad we had the opportunity to spend the weekend together and have a ton of fun! I hope they come back soon!