Chicago, IL

Chicago Ditch Day

Wed, Aug 19 Take the day off. We're playing hooky.

Only 20 spots available

Save my spot

Chicago Ditch Day Chicago Pizza Tours

You work alone.
You don't have to play alone.

Chicago Ditch Day is a single, glorious summer Wednesday for solopreneurs, freelancers, creatives, and small-shop founders to skip work and remember why we live in this city.

Close the laptop. Silence Slack. We'll handle the agenda.

Your Day

Three stops, a small group, and a roomful of other professionals from around Chicago worth knowing.

  1. 9:00 AM

    Coffee & Networking

    Cupitol Coffee & Eatery

    Show up. Drink and pastry of your choice are included. Meet a few people who also said "screw it" to their inbox today.

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    Cupitol is in Streeterville, right in central downtown, easy to reach from anywhere in the city.

    Plan to park here for the day. We'll wrap a short walk away at Ohio Street Beach, so your car will be waiting when we're done.

    Parking nearby:

    • River East Center Garage (closest covered option)
    • Streeter Place Garage (backup just up the block)
    • Or grab a deal on SpotHero

    Coming by transit? The Red Line at Grand & State is about a 10 minute walk.

  2. 10–2 PIZZA

    Pizza Sampling

    with Chicago Pizza Tours

    Guided transportation to three iconic Chicago pizzerias to sample everything from tavern style to deep dish. Alcohol available for purchase along the way.

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    The Chicago Pizza Tours bus picks us up at Cupitol right after coffee and rolls out around 10 AM.

    Four hours, three iconic Chicago pizzerias, everything from tavern style to deep dish. The Chicago Pizza Tours crew handles the route, the seats, and the storytelling. You handle the chewing.

    Bus drops us at Ohio Street Beach around 2 PM, a short walk from the morning pickup point at Cupitol.

  3. 2–5 BEACH

    Beach Hang

    Caffè Oliva at Ohio Street Beach

    Sun, sand, and Lake Michigan. Drinks at Caffè Oliva, toes in the sand, conversations that wander. Stay until you can't.

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    We close the day at Caffè Oliva, the open-air beach restaurant at Ohio Street Beach. Your first drink is on the ticket. Lake views, sand between your toes.

    Lake breeze on your face. Sun on your skin. A well-earned nap after all that pizza. Real life can wait a few more hours before you make your way back to it.

    Pack a small bag with beach clothes and sandals. Change before we get on the bus or carry it with you between stops. Close the day out in proper ditch day style.

    Stay till 5. Stay till sunset. Up to you. You'll be a short walk from Navy Pier if you're not ready to call it.

Get Your Ticket

Only 20 spots. First come, first slice.

One ticket gets you

  • Drink & pastry at Cupitol Coffee
  • Guided pizza sampling at three iconic Chicago pizzerias (lunch covered)
  • Beach hang at Caffè Oliva on Ohio Street Beach (first drink included)
  • A day with 19 other Chicago professionals worth knowing

$199/ person

Get on the early list

Tickets open soon. Early-list gets first crack before we open it up wider.

Questions

Real ones. Asked by real people who almost ditched but had a question first.

What's included with the ticket?

Your $199 covers a drink and pastry of your choice at Cupitol, four hours of guided transportation to three iconic Chicago pizzerias sampling tavern style to deep dish (enough pizza for lunch), private bus between stops, and your first drink at Caffè Oliva on the beach. Alcohol on the bus and additional drinks at the beach are on you.

Who is this actually for?

Solopreneurs, freelancers, consultants, agency-of-one operators, small-shop founders. People in Chicago who run their own thing and rarely get a real day off with people who get it. If that sounds like you, this is for you.

I have dietary restrictions. Am I going to starve?

You won't starve. Chicago Pizza Tours can usually accommodate gluten-free, vegetarian, and most allergies with advance notice. When you buy your ticket, you'll tell us what to plan around. Vegan is the trickiest at deep-dish stops, but we'll make it work.

Where do I park, and where do we start?

We start at Cupitol Coffee & Eatery in Streeterville at 9 AM. Park nearby (River East Center Garage or Streeter Place are closest, or comparison-shop on SpotHero). We end the day a short walk away at Ohio Street Beach, so leave your car where you parked it in the morning.

What if it rains?

Chicago in August is mostly sunshine, occasionally apocalyptic. Coffee and pizza sampling happen rain or shine (both are indoors anyway). For the beach portion, light rain we'll move under Caffè Oliva's covered area. Severe weather is the only scenario where we'd cut the beach short, and we'll communicate that day-of.

What's the refund policy?

Full refund if you cancel by August 5 (two weeks out). After that, refunds aren't possible because pizzeria and beach reservations are committed. You're welcome to transfer your ticket to someone else (email Joe to swap names).

Can I bring a friend?

Yes, as long as they fit the spirit of the day (Chicago, runs their own thing, wants a real day off). They buy their own ticket. With only 20 spots, every seat counts, so encourage your friend to book early if they're in.

Is this an annual thing?

2026 is the first official Chicago Ditch Day. If it goes the way we want, yes, it becomes a yearly tradition. Get on the list below to hear about future Ditch Days even if you can't make this one.

Why "Ditch Day"?

In high school, "ditch day" was when seniors skipped class to go do something better. As adults running our own businesses, we don't get caught playing hooky, because nobody's checking. So we should do it on purpose, once a year, together.

Get on the list

Tickets aren't live yet. Drop your email and you'll be first in line when they open, plus you'll hear about future Ditch Days.