The Street Fair Strategy You’ll Use All Summer

Confession: There's nothing I look forward to more than street fair season. Literally. My birthday, Hanukkah, and Halloween have nothing on this baby. Every Chicagoan knows the where and when of their favorite street fair, and your calendars are probably already marked. But rather than push my favorite fest on you (c'mon, how great is Do Division?!), I'm going to share my strategy for making the most out of Chicago street fairs. Our sunny, warm days are a precious few, so read on and max-out your fun. Have a few stellar tips of your own? Please share...helpful comments make us happy!
While I'm a huge fan of stumbling upon a new street fair by accident, it's all about strategy. Before you take to the streets, a few quick prep-steps are key.
1. Cash No one likes getting hosed by street fair ATM fees. Visit your bank prior, and make sure you've got enough green to cover your booze, munchies, incidental craft purchases, and donation at the door. (These donations are optional, but they matter! It's what keeps street fairs happening year after year).
2. Music We're not sure why the entire world hasn't discovered that you can see tons of great bands, like, for free at Chicago street fairs. These "festivals" can span many, many blocks, so make sure you take a peek at the music lineup at your fest ahead of time, and type your faves into your BlackBerry or iPhone so you don't miss a beat. And don't forget to jot down which stage you're headed to, as street fairs often have several. Bonus: If you forget to do this, most fairs hand out a schedule as you walk in the gate.
3. SPF The Midwestern sunshine can creep up on ya. If you want to avoid showing up to work on Monday looking like a summertime rookie, spray on a good waterproof sunblock before you leave home. And take along a travel-size sunblock, too. You'll be able to give yourself a touch-up, and forgetful (crispy) friends will be very grateful.

Hawaiian Tropic Sheer Touch SPF 30 Travel Size, $2.99, available at

1. Tote
A good canvas tote can easily take the place of a traditional bag during street fair season. Comfy canvas feels much better than leather in sticky summer conditions. Plus, there's plenty of room to stash fab handmade finds you spot at the fest. Eco-Friendly Canvas Tote Bag, $8, available at Etsy.
2. Sandals

Be sweet to your feet this summer, you're going to need them! Investing in a great pair of comfy, stylish sandals is money well spent—you'll feel the difference after hours on your feet trolling up and down Lincoln Avenue. Arden Ankle Cuff Sandals by ROSEGOLD, $168, available at Shopbop.

3. Digital Camera

We are all well aware that summer fun can't last forever, but the photos can. There is no greater mid-January pick-me-up then reminiscing over summertime photos. Okay, maybe a vacay to the Caribbean works too, but this is the low-budget version of therapy, k? If your go-to digicam has been dropped on the concrete one too many times, upgrade.
Canon PowerShot S95, $399.99, available at BestBuy.

Enjoy! Bask in the summer sun and soak up every bit of Chicago's best season. Take advantage of the fact that you're not wearing three layers plus a winter coat and relax together with the rest of the city. Head outside of your comfort zone and try a street fair in a neighborhood that's not your own. Any time you feel a little too toasty, remember the Blizzaster of 2011. Exactly. See you outside!
Street fair image via West Fest Chicago.

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