Best of Chicago (Chicago Reader): How Voting Works & How to Win

The one thing most entrants get wrong about Best of Chicago

People assume Best of Chicago is a syndicated franchise, one entry in a chain of "Best of [City]" polls stamped out across the country by a shared corporate parent. It isn't. The Chicago Reader runs it in-house, the same independent alt-weekly newsroom that has covered the city since 1971, not a licensing arrangement bolted onto a media conglomerate's local paper.

Why that matters for anyone entering: the rules, the category list, and the close date can move year to year at the Reader's own discretion, with no shared playbook from a sister publication in another city to fall back on. The 2025 cycle is active now, voting through December 31, across every category citywide. No opening date for the next cycle has surfaced yet.

That last row is the gap worth flagging. Most best-of pages in this state either publish a cap or stay silent on it; the Reader hasn't said either way in public materials, so treat the live ballot page, not this table, as the final word if that detail changes mid-cycle. For state-level comparisons, the Illinois contest hub lists what else is running.

Picking the right category before the ballot fills up

Guessing a category name from last year's memory is the single most avoidable mistake here. Best of Chicago spans every category citywide (food and drink, retail, services, arts, nightlife, professionals), and the exact label a business needs can shift slightly between cycles. A bakery entered under "Best Bakery" one year might find that label folded into a broader "Best Sweets" category the next.

So check the live ballot first. Not a bookmark from last spring, not a screenshot a competitor posted. The current page is the only place the real category structure lives right now.

Matching the category to who already knows you

A neighborhood coffee shop in Pilsen and a downtown steakhouse are not competing for the same reader attention, even inside a single citywide ballot. Pick the category your existing customers would recognize instantly, the one that matches the sign above your door, not an aspirational label a marketing team might prefer. Confusion here costs votes; a customer who can't find the right listing usually just closes the tab.

For a broader campaign framework beyond category selection, best business award voting covers general planning. Return to the live Best of Chicago ballot for the exact, current-year labels.

Planning around a hard close date with no fixed open date

December 31 is confirmed. That's the one date on this page a business can build a calendar around. What isn't confirmed: when the next cycle opens, or whether it'll follow the same New Year's Eve close going forward. That asymmetry, one locked deadline, one open question, is the actual planning problem here, more than any generic "vote early and often" advice would suggest.

Practically, that means printing QR cards or buying ad space too far in advance risks targeting a ballot that hasn't opened yet. Reminders staged in the final week of December, timed against a confirmed close rather than a guessed open, tend to waste less effort.

Restaurants and bars weighing a citywide push may also find restaurant award voting useful for timing reminders around a similarly hard close date.

What a reminder actually needs to say

Four things, in order: award name, category, business name, direct link. Nothing else. A customer who has to search the Reader's homepage to find the right ballot page is a customer who probably won't finish voting.

Because the ballot is 100% reader-driven, with no editorial panel deciding outcomes, the only lever a business actually controls is how many real supporters see that four-part message and act on it. So the shape of the campaign matters more than its size. One splashy launch post rarely beats several smaller touches spaced across the window: a receipt insert in December, a staff mention at checkout, a QR code by the register, timed to land before the confirmed close rather than crammed into it.

Multi-location businesses should split by neighborhood but keep the ballot instruction word-for-word identical across locations. Inconsistent category names across a chain's own social accounts is a small, avoidable way to lose votes to confusion rather than to a competitor.

Where does 'citywide' actually stop?

Chicago is not one audience. A River North boutique and a Pilsen taqueria are both eligible on the same ballot, but they don't share customers, and treating the city as a single homogenous readership is how campaigns waste reach. The program's scope is citywide across all categories; nothing published narrows it to downtown or the North Side.

Suburbs are trickier. Evanston, Oak Park, Cicero, Naperville, Aurora: these are real Chicago-area communities with their own readership overlap, but whether a suburban business actually qualifies under a given year's category list is a live-ballot question, not something this page can promise. Rockford, Joliet, Peoria, and Springfield sit further out; a downstate business assuming Chicago Reader reach extends that far should verify eligibility before spending a dime on the campaign.

A comparably structured readers-choice program runs in New Jersey; see Best of New Jersey for how a different alt-weekly market handles the same reader-vote format.

The email list beats the social post here

Not always true for every contest, but true for this one. A citywide readers-choice ballot with no editorial filter rewards volume of genuine supporters over volume of impressions. An email to 2,000 past customers who already like the business tends to convert better than a public Instagram post seen by 20,000 strangers who have never walked through the door.

That doesn't mean skip social. It means sequence it: email first (people who already trust the brand), staff mentions second (people already in the building), QR codes third (people about to leave), public social posts last (the widest, least-warm audience). Keep the ballot instruction (category, business name, link) identical across every channel, because a Reader-run ballot with no shared franchise rulebook means there's no fallback "standard" phrasing to lean on if a post gets the category label wrong.

Businesses also running a trophy or plaque campaign alongside the vote can check award voting basics for general framing on separating the vote push from award-usage claims.

No winners list exists yet. Here's what to do about that.

This page won't invent one. That's deliberate. Best-of results tend to circulate as old PDFs and reseller screenshots long after they've gone stale, and a business copying last cycle's "winner" tag onto this year's window is a fast way to look careless in front of the exact readership the award is supposed to impress.

Checking a competitor's claim? Get the exact award year and category name before believing it. Promoting your own entry? "Best of Chicago 2025 nominee, [category]" survives scrutiny. A bare "Chicago's best" with no year attached does not.

Paid promotion fits into this the same way online vote campaigns work anywhere: reminders, landing pages, and real voter outreach can extend reach among people who'd support the business anyway, but no honest provider promises a reader-driven citywide outcome. Businesses leaning on a recognizable local personality to drive attention can adapt the framing in influencer vote campaigns to this format, but the ballot itself stays reader-decided either way.