15 things to see in Chicago this summer

June 13, 2019

*updated March 2022*

Summer is just around the corner. I really can’t believe how fast it’s going, time needs to slow down! I truly believe Chicago is one of the best places in the summer, who else agrees with me?! Especially since we are not pretty much full open with limited COVID restrictions. All of Chicago has been literally waiting for summer all winter long.

If you are looking for a more detail itinerary for something like a bachelorette or birthday party in Chicago, specifically the West Loop, here is a full 3 day detailed guide with discounts up to $65 dollars for local places! Shop the West Loop itinerary here.

I wanted to round out a list of everything you should do this summer. Many of the things listed are family friendly and a few for the adults only. Summertime Chi is like no other, so enjoy every moment.

My List:

Explore Parks– Chicago has some of the best public parks like Palmisano Park in Bridgeport or the Osaka Gardens in Jackson Park

Osaka Gardens

Patio and rooftop hop– Chicago has some of the best views, so why not check out some of the rooftops and patios around town? I wrote a post all about my favorites here.

rooftop in west town chicago at the six06 bar
Rooftop at the Six06

Gallagher Park -So many activities for the family like green city market, yoga, kids sing alongside, etc. They are also starting to have concerts, which would be great for a night out.

Gallagher Way in the summer

Montrose Beach/Bird Conservatory– I like this beach because it’s less crowded and parking is so much easier. Did you know that there’s a bird conservatory, Montrose Point as well. I just found out and we took Noah, he loved it.

Garfield Park Conservatory– Ideal for a rainy summer day! They don’t serve food, but pack a picnic and there’s a huge patio and lawn you can eat at. Perfect for families and lots of free activities for kids. Goat yoga is really popular over the summer too.

Chicago Water Taxi We just did this recently and took the taxi up and down the Chicago River. IT WAS SO SO SO MUCH FUN! Noah was free and adults are $6 each, just make sure to buy your tickets online. We then ended up in Chinatown and grabbed some dumplings at Qing Xiang Yuan Dumplings. It was one of the best days of the summer. All the photos above are from our adventure from that day.

Water Taxi on the Chicago River is perfect for families in the summer
Water Taxi on the Chicago River

Movies in the park- One of my favorite things to do in the summer. You can make it a date or bring the whole family.

Hang out along the Chicago river– We did this over Memorial Day weekend and had so much fun watching the boats and people watching. There are splash pads that are perfect for kids, and adults can get their wine at City Winery 🙂 There are also Kayaking on the Chicago River ,not kid friendly, but it would be a really fun day date! I’ve always wanted to try it, maybe for a day date…

Ravinia– Take the train up, pack and picnic, and enjoy a summer night.

Concerts in Millenium Park –Grab food and drinks at the Gage or Remingtons before the concert and make an whole evening out of it.  Manny and I did this for our anniversary last year and it was nice to do something different than dinner. Remington’s also has premade picnic baskets you can pick up before you head to the park. Wine, utensils, cups and chocolate for dessert!

Picnic basket from Remington's Chicago is perfect for concerts at Millenium Park
Picnic from Remingtons’s for concerts in Millenium Park

Chicago Fire Boat– Best way to see the city for even non tourists. It’s an old fireboat that a family has renovated and it’s a fun way to see the city. There is a full bar aboard too!

Rent Jet Ski’s- I know this might sound crazy, but a year ago, Manny and I ditched the worked day and rented jet skis at 31st Street Beach and it was SO FUN! I hadn’t done anything like it before. I do have to say, the water was freeeezing….but lots of fun!

Navy Pier- So i know this is a super tourist spot, but we all went last month to the Children’s Museum and walked around after. It has changed so much! First, there’s open container laws so you can grab a drink and walk around. The views at sunset are awesome and the food options have come a long way. There are some much better restaurants, anything from falafel to sushi. Lastly, now that the rooftop and country’s largest rooftop is open, Offshore, I think I want to go back and check it out!

Live Comedy Show- Makes for a great date night. We had a date at Zanie’s and it was our first time. The place is iconic, I could just spend an hour looking at the photos on the walls of every performer.

Zanie's Comedy show makes the perfect summer date night
Zanie’s Live Comedy Show

Festivals– This the most obvious I think, but festival season is here and I am loving it. Some of my favorites: Pilsen Food Truck Social, Greek Fest, Roscoe Burger Fest, the Pride Parade and more!

Hopefully, this list helps you enjoy your summer and everything Chicago has to offer! And as always, thanks for following me. You can sign up for weekly blog posts here and follow my adventures on Instagram.

Until next time,

Leave a Reply

Your email address will not be published. Required fields are marked *