Chicago's Best Summer Flea Markets

The thrill of the hunt is not lost on us. That's why we've honed our skills and sharpened our senses so we can sniff out the coolest, rarest, most make-your-friends-jealous finds ever. We know you've got some stellar skills of your own, too, but all of our talents are for naught if we're not shopping at the city's top flea markets. There's a ton of summer left (OMG, heat wave!), and while it's still here, make the most of it by attacking Chicago's best markets and pop-ups with all the fashion-warrior vigor we know you've got. If you think you've scored the best deal ever, let us know! We'll be so proud.

AdvertisementADVERTISEMENT

Ashland Swap-O-Rama
Something about calling it a swap meet lights a fire under our collective shopping ass. We're ready to make deals and break hearts with our stellar flea finds. This is a year-round market, but we love going in summertime to do our dirty work in the open air. Bonus: Admission is only a dollar.
Ashland Swap-O-Rama, 4200 S. Ashland Avenue (at 42nd Street); 708-344-7300.

Eskell & Dovetail's Backyard Flea Market
This first-time market has a focus we can totally get behind—vintage. Two local heroes, Dovetail and Eskell, are teaming up on July 30 and 31 for a vintage sale of gorgeous proportions. Dig for gold of yesteryear, but you'll have to beat us to it.
Eskell & Dovetail's Vintage Flea Market, 1509 North Milwaukee (at Honore Street); 773-486-0830.

The Vintage Bazaar
Some markets overwhelm even the most seasoned flea-veterans (?), and the Vintage Bazaar has the potential to make the mind reel. Our advice? Baby steps. Don't stare directly at the market. Look at each booth, take your time, and breathe. There's so much good stuff here that there will be plenty to go around. Trust us.
The Vintage Bazaar, 2135 North Milwaukee Avenue (at North Rockwell Street); 773-276-1235.

Dose Market
Have a little patience, please. This market won't be back in our lives again until August 14, but as we've learned, the wait is worth it. Look for a new crop of delectable clothing and food vendors that are sure to become household names around your pad. Bring your appetite, a reusable shopping bag, and some cold hard cash.
Dose Market at The River East Art Center, 435 East Illinois Street (East of McClurg Court); 312-321-1001.

Sandwich Antiques Market
Come on, would you miss a market with this name? For those on the hunt for true antiques, this is a winner. Whether you're looking for fixer-upper furniture or just good old-fashioned inspiration, your mind will reel after a trip to Sandwich. Who's hungry?
Sandwich Fairgrounds, 1401 Suydam Road (North of Route 34); 847-227-4464.

Chicago Antique Market
Welcome to the big leagues. If you make it through this market without crying over a piece of furniture that already has a "sold" tag on it, we'll be shocked. There's an incredible selection of all the vintage furniture you're on the hunt for (including every single midcentury piece you want from Grandma's house). Show up ready to rock and buy big, this market will help you arrange for home delivery.
Chicago Antique Market, 1300 West Randolph Street (at North Elizabeth Street); 312-666-1200.