When is it cheapest to stay in Chicago (IL)?

The 10 cheapest nights

The 10 cheapest of the next 71 measured nights in Chicago (IL) ask a median of $144 to $149, against $160 across all 71 nights.

Each figure is the median asking price for one night; a date opens that night's places on the town page.

The cheapest 7 nights in a row

The cheapest 7 nights in a row in Chicago (IL) run from 2 January 2027 to 8 January 2027: their nightly medians add up to $1 062, with a middle night of $149.

• Runs of 7 consecutive measured nights compared: 65; a night that was not measured breaks a run.
• The dearest 7 nights in a row run from 13 November 2026 to 19 November 2026, adding up to $1 701.

The sum of nightly medians is the 7 nights' median asking prices added together; it is not a price offered for the week.

The cheapest weekend

The cheapest Friday and Saturday nights in Chicago (IL) are 8 January 2027 and 9 January 2027: medians of $159 and $163, $322 for the two nights (sum of nightly medians).

• Weekends compared: 10, each a measured Friday night followed by a measured Saturday night.

Each row is a Friday night and the Saturday night after it; places are counted Friday / Saturday.

Month by month

The cheapest month of the next 71 measured nights in Chicago (IL): January 2027, a median of $152 over 22 nights; the dearest: November 2026, $217 over 18 nights.

A month counts only its nights in this window, and only with at least 15 of them; its month page also counts nights already past.

Places at $150 or less on the cheapest night

On the cheapest night, 20 December 2026, 57% of the places with a price in Chicago (IL) (113 of 197) asked $150 or less.

$150 is the median of all 71 nights ($160) rounded to a round price, the same ceiling the town page uses; the date opens the list of places by name.

Night-by-night price calendar

Nightly medians in Chicago (IL) over the next 71 measured nights, 13 November 2026 to 22 January 2027, run from $144 to $273; the median of all of them is $160.

A place with no price that night (sold out or closed) is counted but carries no price; a date missing from the table was not measured.

What was measured

Nights measured in Chicago (IL): 71, from 13 November 2026 to 22 January 2027; each with at least 30 places showing a price.

• Up to 208 places checked per night; a place with no price that night (sold out or closed) is counted but carries no price.
• Prices in USD, as shown on the day each night was read, on 25 October 2026.
• Asking prices seen while searching for one night: not prices paid, and not a forecast; prices move after the scan.