Boston is heading into its most expensive month. October hotel rates there hit $458 a night, up from $166 in January, the widest swing of any major U.S. market. New York is doing the same thing, $458 in September and $541 by December.
In cities like these, the month on the calendar changes the hotel bill more than the choice of hotel does. In other cities, it barely matters. The first thing to figure out is which kind of city you are booking.
Engine, a platform companies use to book work travel, analyzed 128.5 million hotel searches across 50 U.S. markets over two years, from May 2024 to April 2026, to find where timing matters most, and where it does not matter at all.
The 10 biggest swings
Boston and New York: the two widest swings
Both cities spread 64% between their cheapest and most expensive months. Boston has two peaks. May hits $390 when commencement weekends stack up across dozens of colleges, and October reaches $458 when leaf season and conference season overlap. January is $166.
New York never gets cheap. Its cheapest month, January at $196, is higher than the most expensive month in 30 of the other 49 markets. December is $541, nearly double November's $352 and the single priciest city-month in the data. The peaks track the corporate and holiday calendars more than the weather.
"In Boston and New York the event calendar stacks on top of the weather," said Jack Swiatoschik, a data analyst at Engine. "Boston peaks in October when the Head of the Charles falls in the same weeks as conference season, and New York's December is holiday tourism, with September already crowded by UN General Assembly week and Fashion Week."
Phoenix and Chicago swing the same amount in opposite directions
Phoenix peaks at $246 in February and March, when Cactus League spring training fills ten area ballparks, and the weather is at its best. By August, it is 110 degrees, and the rate is $96, a 61% drop: the cheapest big-market month in the data.
Chicago runs the other way. January is $127. June is $319, when good weather and convention season at McCormick Place, the largest convention center in North America, overlap. Anyone booking a trip that has to happen in one of these two cities should first check which half of the year it is in.
Weather cities and event cities
Most of the rest of the top 10 track the weather. Palm Springs spreads 57%, from $369 in March to $158 in August, and prices follow the weather almost exactly, since there is little year-round business demand to flatten it out. Seattle spreads 53%, from $139 in January to $297 in July, with no specific event behind any of it. Norfolk, Virginia's summer doubles its winter, $96 to $216. Miami runs the opposite way, peaking with the snowbirds in February at $267 and bottoming out in September at $128.
Omaha, Nebraska, and Milwaukee are the event cities. Omaha sits between $95 and $126 for eleven months, then June jumps to $182 for the College World Series, which has been played there every June since 1950. Milwaukee's June and July, $163 and $194, line up with Summerfest. Both are flat and affordable the rest of the year, so a trip that can move two weeks clears the spike.
Where the month does not matter
El Paso moves 10% across the whole year. Los Angeles moves 13%, Dallas 19%. Steady business demand keeps those markets level, so book them whenever the calendar says and spend the effort somewhere else.
"Boston and New York get big weather swings like a lot of cities, but they also concentrate demand into a small core in a way most don't," Swiatoschik said. "Everything competes for the same hotels, so the swings are bigger. Los Angeles is the opposite on both counts. Steady weather and demand spread across the whole county, so the curve stays flat."
Honolulu swings only 23%, but its cheapest month is $169, the third-highest low in the data. With no drive-in market and no fast way to add rooms, rates hold a narrow, high band, and timing buys less there than anywhere else.
How to use timing to your advantage
Forty of the 50 markets are cheapest between November and February. The other ten, almost all in the Sun Belt, are cheapest in summer. If the city is on the top-10 list, the month is worth negotiating over. If it is one of the flat ones, it is not.
In the seasonal cities, choosing the right month can save 40% to 64% compared to the wrong one, with no promo code or negotiation involved. Each city in the table has its own page in Engine's hotel price data, with all twelve months and the markets nearest it in price.
Methodology: Figures are the median nightly rate for searches made 10 to 180 days before check-in, on business accounts, from May 2024 through April 2026. Rates are public shelf prices shown in a live search, not negotiated company rates, which typically run lower. Event explanations describe what is on the calendar in a given month and are Engine's reading of why a rate moves, not a separate measurement.
