Aug 21, 2025 - Things to Do
Your guide to Chicago's end of summer fun
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Navy Pier Fireworks. Photo: Moyo Adeolu/Axios
Summer in Chicago is unmatched, but the days are limited.
The big picture: Summer officially ends Monday, Sept. 22, so if you're trying to squeeze in a few more perfect days, here's my go-to guide.
- My first stop was this popular Black-owned restaurant in Hyde Park. I ordered my go-to meal — the Brioche French toast ($16) with a side of turkey bacon ($6).
- 1642 E. 56th St.
- Then I went for a peaceful stroll just east of Hyde Park. People were swimming, having picnics and just enjoying the outdoors.
- My next stop was the Field Museum. I strategically visited on a Wednesday to take advantage of the Free Illinois Resident discount day, available with a valid ID.
- Open 9am-5pm. Last entry is 4pm. Every Wednesday.
- Another free experience for Illinois residents. To my surprise, the line was long and seemed like we all had the same plan! This is a great place to take the kids.
- 4-10pm every Wednesday.
- By this point in the day, I was feeling fatigued and rented a Divvy bike from the Museum Campus to head toward the Loop. It was my first time on an e-bike, which I found heavier and harder to handle. ($11.40)
- If you're looking for other forms of transportation and want to stay active, e-scooters are also an option.
- My dream day was supposed to include kayaking on the Chicago River for the first time, but with heavy traffic and nerves setting in, I decided to pass. Instead, I grabbed a ($16) frozen cocktail at City Winery and enjoyed some people-watching.
- On my walk toward Navy Pier, I picked up some street tacos from a local food truck. I ordered two birria tacos, which were extremely flavorful and gave me the authentic Mexican vibe I was hoping for. ($9)
If you go: If you can't catch their food truck, stop by their local walk-in spot located at 2247 E. 71st St. in the South Shore neighborhood.
- Before the night ended, I headed down to Navy Pier and boarded the Shoreline Sightseeing boat to catch their summer fireworks show as I sailed along Lake Michigan. It was a historic, yet romantic evening. A possibly perfect date night. ( $50)
- You can also watch the show for free on the pier.
- 10-10:10pm Saturday, Aug. 23 and 30.
- 9-9:10pm Wednesday, Aug. 27.
- My final stop of the night was on Taylor Street in Little Italy. With just 30 minutes until closing, there were still many people outside. ($6)
💭 Moyo's thought bubble: If you're looking to make the most of these warmer days, start early. If you're driving, find free parking in a residential area and opt for walking or public transportation.
- A good pair of walking shoes is helpful.
- Have alternative ideas? Share your perfect summer day with us!