Hotels in Chicago measured, not claimed
We record what hotels in Chicago actually cost, day after day. A price appears below only when it is genuinely under its own usual level, or under the median of comparable hotels here on the same dates — never under a crossed-out number. See the exact thresholds.
- 3hotels below their usual level
- 1,320hotels we can search here
- €188.24lowest measured, per night
- −59%median gap of the offers below
Dates measured right now: 31 Oct 26 to 14 Aug 27. Average guest rating of these hotels: 9.2/10. Last re-measured 3 hours ago.
What a night costs in Chicago
Measured median across all hotels of each class in Chicago, on the dates we track. Not an average of the deals below — the level they are measured against.
- €6595-star · median per night6 date windows measured
What a week costs in Chicago, by arrival date
Median price of a night for a seven-night stay, measured across at least 80 hotels on each of these 37 arrival dates. Same city, same length of stay — only the date changes, so what you see is the season and nothing else.
- €511 a nightarriving 17 Oct 26
- €325 a nightarriving 24 Oct 26
- €257 a nightarriving 31 Oct 26
- €254 a nightarriving 7 Nov 26
- €269 a nightarriving 14 Nov 26
- €183 a nightarriving 21 Nov 26
- €247 a nightarriving 28 Nov 26
- €187 a nightarriving 5 Dec 26
- €175 a nightarriving 12 Dec 26
- €160 a nightarriving 19 Dec 26
- €192 a nightarriving 26 Dec 26
- €157 a nightarriving 2 Jan 27
- €162 a nightarriving 9 Jan 27
- €196 a nightarriving 27 Feb 27
- €228 a nightarriving 6 Mar 27
- €238 a nightarriving 13 Mar 27
- €229 a nightarriving 20 Mar 27
- €238 a nightarriving 27 Mar 27
- €323 a nightarriving 3 Apr 27
- €278 a nightarriving 10 Apr 27
- €352 a nightarriving 17 Apr 27
- €293 a nightarriving 24 Apr 27
- €330 a nightarriving 1 May 27
- €330 a nightarriving 8 May 27
- €383 a nightarriving 15 May 27
- €442 a nightarriving 22 May 27
- €490 a nightarriving 29 May 27
- €556 a nightarriving 5 Jun 27
- €483 a nightarriving 12 Jun 27
- €422 a nightarriving 19 Jun 27
- €437 a nightarriving 26 Jun 27
- €389 a nightarriving 3 Jul 27
- €463 a nightarriving 10 Jul 27
- €421 a nightarriving 17 Jul 27
- €482 a nightarriving 24 Jul 27
- €477 a nightarriving 31 Jul 27
- €416 a nightarriving 7 Aug 27
Cheapest arrival we measure: 2 Jan 27 at €157 a night. Dearest: 5 Jun 27 at €556 — 72% more for the same week in the same city. We measure Saturday arrivals, and we do not measure January or most of February, so this is a season, not a full year. See how that compares with every city we measure.
What is underpriced in Chicago right now
Hilton Vacation Club Hotel Blake Chicago5★ · 9/10 · 24 Apr 27 → 1 May 27 · 7 nightsUnder the median for 5-star hotels in Chicago€470.09€188.24−60% · per night- Hilton Vacation Club Hotel Blake Chicago5★ · 9/10 · 19 Jun 27 → 26 Jun 27 · 7 nightsSaves 392 EUR a nightUnder the median for 5-star hotels in Chicago
€657.77€265.82−60% · per night - Hilton Vacation Club Hotel Blake Chicago5★ · 9/10 · 7 Aug 27 → 14 Aug 27 · 7 nightsSaves 391 EUR a nightUnder the median for 5-star hotels in Chicago
€660.20€268.85−59% · per night 
Hampton Inn Chicago-Midway Airport3★ · 9/10 · 29 May 27 → 5 Jun 27 · 7 nightsUnder the median for 3-star hotels in Chicago€467.44€193.34−59% · per night
Trump International Hotel & Tower Chicago5★ · 9.4/10 · 7 Nov 26 → 14 Nov 26 · 7 nightsRefurbished in 2024, still priced below its class€871.78€447.01−49% · per night- Trump International Hotel & Tower Chicago5★ · 9.4/10 · 31 Oct 26 → 14 Nov 26 · 14 nightsRefurbished in 2024, still priced below its class
€735.04€464.26−37% · per night - Trump International Hotel & Tower Chicago5★ · 9.4/10 · 14 Nov 26 → 21 Nov 26 · 7 nightsRefurbished in 2024, still priced below its class
€555.03€403.67−27% · per night
The crossed-out figure is the measured median for hotels of the same class in Chicago on the same dates — not a number anyone invented. Prices are re-checked live when you search. The deepest gap on this page is −60%; we discard anything beyond −60%, because past that point the hotel’s own star rating is more likely wrong than its price low.
Search Chicago for your dates
The offers above are the terms we happen to be measuring. For your own dates we ask the supplier live and compare every hotel there.
Search hotels in ChicagoOther destinations we measure
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These are the places where enough hotels are currently priced below their usual level to fill a page. See every hotel we measure — every country, plain links, no dates required.