Chicago street festivals are hands-down one of the best things to do during the summer months.
From free music festivals in downtown Chicago to neighborhood food festivals, these are exactly why locals brave the winter months.
But navigating them can be overwhelming if you’re not prepared. After years of festival hopping across the city, I’ve learned the key to a stress-free and fun festival experience is all about planning and packing light.
Whether you’re a first-timer or a pro-festival hopper like me, here are 9 expert tips for experiencing and enjoying Chicago festivals.
Planning Your Chicago Festival Adventure: A Step-by-Step Guide
1. Research the Festivals
Before attending any Chicago festival, be sure to do your research.
Whether it’s one of the bigger Chicago music festivals like Lollapalooza or a smaller neighborhood festival, research is key.
Check resources like Choose Chicago, Block Club Chicago, and (of course) The Haute Seeker to find out what’s happening. Then visit the official festival websites for details on admission fees, schedules, maps, and prohibited items. Knowing the performances, vendors, and activities ahead of time will help you prioritize and avoid missing anything you’re excited about.
Haute Tip: Some festivals require advance ticket purchases, so lock those in early when needed.
2. Take Public Transit
When thinking about how to get to a Chicago festival, CTA is almost always the right move. Many festivals are located right off of major train routes like the Red or Blue Line, making public transit your most reliable option.
Download the Ventra app to plan your route and pay your fare easily. Trust me, you don’t want to spend half your day looking for parking or sitting in festival traffic.
3. Bring Cash
While credit cards are widely accepted these days, many Chicago neighborhood festivals still ask for a small cash “donation” at the entrance instead of charging an official fee.
Having cash on hand makes getting into festivals smoother, and it helps if you come across a vendor that’s cash-only.
4. Dress Comfortably
Dressing comfortably for street festivals in Chicago, especially during the summer, is essential.
Opt for breathable fabrics like cotton or linen. Comfortable walking shoes are a must, as you’ll be on your feet for hours. A light jacket or sweater is also a good idea for cooler evenings.
If, like me, you get hot or cold easily, I highly recommend dressing in layers. The temperatures can fluctuate throughout the day, and layering will help you stay comfortable while enjoying the festivities.
5. Travel Light
One of the biggest tips for Chicago festivals? Travel light.
You’ll likely have your bag searched, and you’ll want your hands free to dance, eat, and shop without being weighed down. Pack just the essentials: phone, sunglasses, sunscreen, portable charger, and a refillable water bottle.
A small backpack or crossbody bag is ideal. Leave anything you can’t afford to lose at home.
6. Coordinate a Meetup Spot
If you plan to attend a festival with a group of friends, determine a designated meetup spot before the festival.
Make sure that you set a time when you’ll meet at this spot after the festival. This spot should be something obvious, like in front of a restaurant stand or pop-up booth. This is important to set up, should someone lose their phone or get caught up in the festival spirit.
It’s a simple planning step that can save you from a lot of stress.
8. Remain Vigilant
Chicago street festivals are generally safe, but it’s always good to stay aware.
- Keep your bags zipped and close to your body.
- Store your phone in a front pocket or secure bag compartment.
- Stick with your group, and if you’re going solo, share your location with someone you trust ahead of time.
- Know where the exits are. And, if you ever feel uncomfortable, trust your gut and leave.
Festival safety is just as important as having a good time.
7. Stay Hydrated
Between the sun, walking, and excitement, it’s easy to get dehydrated at a Chicago festival. Bring a refillable water bottle and fill up at hydration stations or water fountains whenever you can.
Skip overly sugary or alcoholic drinks until you’ve had enough water, you’ll thank yourself later.
9. Have Fun, Be Open to New Experiences
Above all, the best tip for Chicago festivals? Have fun!
Festivals are a chance to discover new foods, artists, neighborhoods, and communities. Say yes to that dish you’ve never tried, check out an artist you’ve never heard of, and discover a brand you would’ve never known otherwise.
Some of my best festival memories came from moments I didn’t plan. And I am confident yours will too.
Making the Most of Chicago’s Street Festivals
The first Chicago street festival I ever attended was Taste of Chicago. The legendary food and music festival in Chicago was busy, exciting, and fun. But, also very overwhelming.
Over the years, I’ve put these festival tips into practice to make every experience better. And now, with this Chicago festival guide, you can too!
Whether it’s your first time or your fiftieth, these 9 festival tips will help you make the most out of your experience.
One response to “9 Expert Tips For Chicago Street And Neighborhood Festivals”
Great tips. This festival looks like a lot of fun. Will have to put it on my to do list. Thank you.
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