Ah, the nostalgia of vintage clothing. The thrill of finding that perfect pair of shorts from a bygone era can be a daunting task. With so many stores and options to choose from, where do you even start? Fear not, for we have done the leg work for you (pun intended). Here are 10 vintage stores in Chicago where you can find that perfect pair of shorts.

1. Kokorokoko - This Wicker Park store is a staple in the vintage clothing world. Their collection of shorts range from floral prints to denim cutoffs. Prices range from $20-$60.
2. The Silver Umbrella - This vintage shop in Pilsen carries more unique items like high waisted shorts and retro sports shorts. Prices range from $25-$60.
3. Shangri-La Vintage - In Ukrainian Village, this store has an extensive collection of vintage shorts in a variety of styles and sizes. Prices range from $20-$60.
4. Dovetail - A Wicker Park boutique that specializes in vintage designer clothing. They have a small collection of high-end vintage shorts with prices ranging from $100-$200.
5. Lost Girls Vintage - This vintage store in Logan Square has a great selection of vintage shorts, including high waisted and patterned styles. Prices range from $25-$60.
6. Kairos Vintage - Located in Humboldt Park, this store has a fun selection of shorts in various prints and colors. Prices range from $20-$60.
7. The Brown Elephant - With locations in Andersonville and Lakeview, this thrift store carries a mix of vintage and modern clothing. Their selection of shorts varies, with prices ranging from $5-$25.
8. Tusk - This Bucktown store specializes in vintage western wear, but also has a great selection of denim cutoff shorts. Prices range from $30-$60.
9. State Street Thrift - Located in the heart of downtown Chicago, this thrift store is a great spot for affordable vintage shorts. Prices range from $5-$20.
10. Ragstock - With multiple locations throughout the city, this store is known for their fun and affordable vintage clothing. They have a great selection of shorts, with prices ranging from $10-$30.

In conclusion, shopping for vintage shorts in Chicago may seem like a tall order, but rest assured, there are plenty of stores with a plethora of options to choose from. Whether you’re looking for floral prints, high waisted styles, or retro sports shorts, there’s a store for you. So, ditch the mall and take a stroll through these ten vintage shops in search of the perfect pair of shorts.