I’ve only found one trick to save money on hotel rooms in expensive cities, and that’s strategically choosing when to travel.
Head to New York City in mid-December, for example, and the Hampton Inn in Brooklyn can set you back $400 a night. The hotel isn’t particularly special, but between the holidays and SantaCon, a citywide pub crawl of people dressed in varying degrees of Santa, this particularly weekend sees high demand for hotel rooms. Wait until January, and you can pay half that in Brooklyn or Manhattan.
If you travel for food and theater and don’t mind the cold, January and February are excellent months to visit New York and Chicago, two notoriously expensive U.S. destinations. Schedule a winter trip to find deep discounts on luxury hotel rooms, restaurant promotions worth traveling for and deals on theater and attraction tickets.
In Chicago, restaurant week is a 17-day celebration that runs from mid-January through early February. These deals offer a great way to have mini-tasting menu experiences at some of the city’s top restaurants at bargain prices.
This year, Chicago Restaurant Week runs from January 19 through Feb 4, 2024. Several of my favorite Chicago restaurants— including The Press Room, Vermilion, Gilt Bar and Esme— are on the list. Expect to pay $25 for price fixe brunches and lunches and between $42 and $59 for dinner.
In New York, which has a better known and well-earned reputation as a food mecca, restaurant week runs from early January through mid-February. New York also runs a hotel week promotion that cuts 23% from room rates around the same time.
If you’re looking to splurge, check out the William Vale or the Hoxton in Williamsburg, the Pierre near Central Park or Arlo Nomad near the Flatiron Building. If you’re looking to save and don’t mind a small room, you’ll find a variety of Marriott and Hyatt brands in Midtown.
2024 NYC Hotel Week Picks
- Thompson Central Park
- Conrad Midtown
- Arlo Nomad
- Hampton Inn New York Times Square
- Ace Hotel Brooklyn
- The Hoxton Williamsburg
If you need any more incentive to book a winter New York getaway, Broadway Week also happens from late January through mid-February. That means two-for-one tickets to shows including Harry Potter and the Cursed Child, The Lion King and Aladdin. Tickets to dozens of popular attractions—including the Empire State Building, Top of the Rock, One World Trade observatory and Yankee Stadium tours—are also buy one get one free.
I’ve seen a lot of live theater in a lot of cities, but I haven’t found any other place that makes it so easy to see your on-screen favorites on stage. Over the years, I’ve seen Neal Patrick Harris, Al Pacino, Mary Elizabeth Parker, John Slattery, Nathan Lane, John Goodman and Uma Thurman perform on Broadway.
Chicago doesn’t line up its discount weeks as well as New York, but you can still expect to find some very nice hotel rooms for under $150 a night in January and February. Plan your Chicago trip for mid-February, and you can score deals on theater tickets, too.
My Favorite Chicago Hotels
- Park Hyatt
- Waldorf Astoria
- Hyatt Place Wicker Park
- 21c Museum Hotel
- The Palmer House Hilton
- Virgin Hotels Chicago
Chicago theater week runs cuts prices on tickets to more than 100 different performances across the city from mid-February through the end of February. And just like Chicago’s restaurant scene, Chicago’s theater scene is underrated.
Whichever bargain winter break you choose, just don’t forget your coat.
