One of my favorite Chicago flea markets is Wolff's Flea Market. This market happens every Sunday from April through October. Of course, the 3rd Sunday I'm busy with the Vintage Garage, but the rest of the month, early Sunday mornings at Wolff's are the best.
Vintage and antiques are plentiful. More so in the west lot of Allstate Arena where Wolff's is held. I like to arrive as early as possible. For me that means 5:30 am. I always begin in the west lot since vintage and antiques is what I'm looking for. I make sure my phone is fully charged so I can also use it as a flashlight. Each week there can easily over 1000 vendors present. I always take a run through the other section and usually pick up flowers and fruit. Farmer's come each week and flowers are fresh and priced right. The best thing about Wolff's is being back home by 10:00am (even after you stop for breakfast) because you can take care of business so early. Being an aviation geek, the show happens directly under one of O'Hare's runways so the plane spotting is excellent. If it's not a Garage weekend (always 3rd Sunday) in the city, head out to Wolff's. It's worth your time.