There’s a certain sadness that comes with a summer’s end. The sun lingers a little longer, the air gets colder a bit quicker, and there’s the feeling of needing to savor every second of it until it ends. But later season excursions don’t need a fixed price menu or require a hefty bill. The best dates are often the least expensive ones that don’t leave your wallet empty. Especially in a city like Chicago, where culture, history, and community exist on every street, no restrictions or reservations required.
In a generation thriving on fancy cocktails and overpriced appetizers, free museums are an underrated kind of romance. It’s a quiet space, you only get smarter, and there’s something curiously intimate about the excursion. Museums in many cities are affordable and even free. In Chicago, the National Museum of Mexican Art in Pilsen is one of the city’s most underappreciated gems. It’s completely free, deeply rich in history, and has artwork bound to start conversation, perhaps even flirtation.
If the weather is nice, a well-packed picnic is a score in any playbook. Fun, satiating, and a guaranteed photo op. Throwing together a charcuterie board doesn’t have to break your bank account when assembled strategically. Picnics are never short of romance, and parks reside in any city. Humboldt Park is a beautiful gem; you’re more likely to stumble upon live music, and it’s a great place for bird watching (another no-cost activity!). Promontory Point, located in Hyde Park on the south side of Chicago, cosplays as a beach with grass. It’s perfect for hanging a hammock and lounging by the lake.
For a more adventurous (or rather quirky) group, there’s always an IKEA date. It’s not just a furniture store, it’s a relationship simulator. You hold at your fingertips a fake domestic future by picking out your dream home. Remake 500 Days of Summer, eat the meatballs, lie on every bed, and judge the people judging you. It’s an absurd thought, but skipping through staged bedrooms is a surprisingly effective form of modern courtship.
And if you like a (perhaps questionable) adventure, test drive a car. You can go to a dealership and pick out something you could never afford. Honoring your inner child is what summer is really all about. Pretend like you’re planning a road trip, argue about the colors, and press play on the list that feels like a rom-com. It’s a low-stakes outing that feels like a vision and nostalgia. (So long as you don’t let them run your credit.)
Exclusive to Chicago, the streets are exceptionally alive. Fiesta del Sol, one of the largest Latino festivals in the Midwest, transforms Pilsen into a four-day celebration of culture, food, and music, completely free to attend. Glenwood Avenue Arts Fest takes place in the tight-knit neighborhood of Rogers Park and lasts a whole weekend. The festival features art, music, dance, and more, all for the price of showing up. Wandering around tasting local eateries, dancing to a local band you’ve never heard of, and people-watching the crowds makes for a load of effortless memories. Chicago summer lives for its street festivals, and late August is peak season. Other bigger ones are Edge Fest and Wicker Park Fest. Pick any neighborhood, though, and they’re probably throwing a street party for something. It’s the simplest recipe in the book, shared bites, laughing, music in the air, and none of it even dents your wallet.
The end of summer celebrations don’t have to require a spending cap. All you need is a little intention, imagination, and spontaneity to make memories. And in a city like Chicago, where beauty hides in back alleys and street corners, memories aren’t hard to make, they’re just a CTA ride away. The end of summer is a time to appreciate whether you’re back-to-school shopping or just putting away your summer stock. It’s time to be present, and even if it’s cheap, you won’t miss an overpriced cocktail. You’ll be too busy falling in love with the moment.
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