This page answers one question with numbers: in which month does a night out in Chicago cost least? Every morning we take the cheapest resale listing for each dated event in the city and group them by month. The table below is today's result.
On today's numbers, September 2026 has the lowest typical cheapest seat ($57) among months with a full calendar, and July 2027 the highest ($142). October 2026 has the most dates on sale (851).
Month by month
| Month | Dates | Typical cheapest seat | Concerts | Theater & shows |
|---|---|---|---|---|
| September 2026 | 137 | $57 | $54 | $58 |
| October 2026 | 851 | $62 | $57 | $77 |
| November 2026 | 669 | $68 | $59 | $84 |
| December 2026 | 456 | $73 | $61 | $83 |
| January 2027 | 153 | $84 | $75 | $89 |
| February 2027 | 160 | $74 | $62 | $89 |
| March 2027 | 108 | $61 | $66 | $89 |
| April 2027 | 109 | $75 | $60 | $99 |
| May 2027 | 95 | $80 | $66 | $82 |
| June 2027 | 88 | $86 | $67 | $137 |
| July 2027 | 49 | $142 | $130 | $144 |
| August 2027 | 31 | $98 | — | $168 |
| September 2027 | 24 | $95 | $419 | — |
| October 2027 | 2 | $528 | $970 | $87 |
“Typical” is the median of each event's lowest listing. Months far ahead have few dates on sale and swing more.
How to read it
These are asking prices on a resale marketplace, not what seats sold for, and they move. The mix of events drives each month's number: a month full of nightly shows has many modest listings, while one big arena tour can pull a month up on its own. Check the month's calendar to see which is which. For any single show, compare its dates on its own page.
Cheapest dates on sale right now
The lowest listings in the whole feed at the last refresh, across every category: