Chicago Finds, Food & Recipes

The Thriftista guide to Chicago street fests

chicago street festival

We love Chicago street fests — all the food, live music, fun vendors, and the whole city coming out to enjoy the amazing weather.

You’ll find a comprehensive listing of fests on our calendar, but we’d never leave you high and dry! Check out our tips below for thriftier, safer, and healthier festing. Drop your favorite tips in the comments!

Street fest survival tips

Bring a fest-friendly bag:
Go for a cross-body or a backpack you won’t mind getting dusty.

Comfy shoes only:
We know those cute new shoes are tempting, but several hours on pavement (and possibly gravel or grass) may have you hobbling. Opt for sneakers or cushioned sandals — your future self will thank you.

Stock your bag with these essentials:

  • Water or a sports drink — Why pay $5 for a bottle? Even 7-Eleven is cheaper.
  • Antibacterial hand gel or wipes — Crucial for portapotties and food trucks.
  • Blotting wipes or a small face mist — A face mist is essential when it’s over 90.
  • Sunscreen — Even if it’s cloudy. Mini travel sticks or roll-ons are a great, no-mess option.
  • Cash — Avoid outrageous ATM fees or long lines. Many fests accept cards or mobile payments now, but vendors may still prefer cash.
  • Napkins or mini toilet paper rolls — Not all porta-potties are stocked.
  • Granola bar or protein snack — In case the food lines are long or options are limited.
  • Portable phone charger — You’ll burn through battery taking pics or pulling up maps. A mini power bank is worth it.

About those “entry fees:”

If a fest is on a public street, it’s technically a suggested donation — your tax dollars already cover the permits, security, and cleanup. Don’t feel guilty about paying less or nothing; support vendors or artists instead — or treat yourself to another cocktail.

Bonus tip:

Check fest websites or social accounts ahead of time for info on stage lineups, vendor lists, and any bag policy or restricted items.