Chicago · Halloween 2026
Chicago Halloween Bar Crawls 2026, Compared
Ten companies sell a Halloween bar crawl in Chicago this year. Most of them do not show a price on their own website. Here is what each one costs and what each one says you get, so you can decide without opening six checkout pages.
The short version
Chicago Halloween bar crawl tickets in 2026 run from about $9 to about $62, depending on the operator and how early you buy. Most operators price between $15 and $25 early and $30 to $45 in the final week.
Cheapest is not the useful question. The three things worth checking before you buy any of them: whether the venue list is published before you pay, whether "drinks included" means an actual credit or the bar's public specials, and whether the ticket can be transferred if your plans change.
Prices
Chicago Halloween crawls, 2026
| Operator | Price | Price shown on their own site |
|---|---|---|
| Crawlloween | Publishes with the ladder | Yes, full ladder with step-up dates |
| Bar Crawl LIVE | $20 flat, all 3 dates | No, Eventbrite only |
| Trick or Drink | $15 day one, $21.22+ multi-day | No, Eventbrite only |
| Boos Fest | $19.99 GA to $39.99 VIP | No, Eventbrite only |
| Wrigleyville Crawl | $15.97 in May, escalating | No, Eventbrite only |
| Boos & Booze | from $9.40, badged up to 50% off | No, Bucketlisters only |
| PubCrawls.com | "from $15" | Partial |
Prices verified 2026-08-03. Every operator on this list raises prices as the date approaches, several of them more than once, so check the current tier before you buy. If you find one of these out of date, tell us and we will fix it.
Inclusions
What "included" means, operator by operator
This is where the category gets slippery, so read the wording rather than the headline.
Crawlloween
A free welcome shot at check-in, plus one drink token for every stop on your route, plus entry without a cover during each venue's published window. Drink specials exist at most venues and we publish them, and we do not count them as part of your ticket because the bar offers them to everyone.
Every other operator on this list
Each operator's own published wording goes here, quoted and dated, so you can read what they actually promise rather than our summary of it.
Before you buy
Three questions to ask any of them, including us
Is the venue list published before I pay?
Ask for the list and the door windows, not a neighborhood name. If a list only appears after purchase, or arrives the week of the event, you are buying a promise.
Crawlloween publishes every venue and every door window on a date we name in advance, and the 2025 routes for River North and West Loop are already on this site so you can see what a locked list looks like.
What does "drinks included" actually mean?
Ask whether it is a credit you redeem or a discount the bar was already running. The single most common complaint across this category is buyers finding out at the bar that "included drinks" meant a special the public already had.
Crawlloween gives you a free welcome shot and one drink token per stop, torn off a card printed with each venue's name. The bar's own specials are published separately, labelled as the bar's, and each one carries its own window.
What happens if the plan changes?
Ask what happens if a venue drops out, and whether the ticket can be transferred. "All sales final, venues subject to change" hands you all of the risk and none of the flexibility.
Crawlloween tells every holder within 24 hours if a venue changes after the lock date, names the replacement, and lets you transfer to another night or another person at no cost.
Collecting a wristband is part of the answer to all three. Wristband pickup times, window caps and backup locations are published on their own page.
Reviews
Nobody in this category publishes any. We checked every operator selling a Chicago Halloween crawl this year and found no reviews, ratings or testimonials on any of their sites, including ours.
So look outside the site. Search the operator's name plus "review," check the BBB, and read the TripAdvisor pages for whoever is selling you a wristband. That is advice we are giving you about us as much as about anyone.
Commitments
What we do not do
All four are checkable on this site in about ten seconds, which is the only reason they are worth writing down.
No countdown timer on this site.
No "only 3 left" when there are not.
No venue list that appears after you have paid.
No drink special sold to you as an included drink.
If Crawlloween is not the right one, buy the right one
Neighborhood crawls across three nights, prices and step-up dates on the page, venue list locked on a date we publish in advance.
21+ with valid government-issued photo ID. Rain or shine.