In case no one has told you lately, you don’t need to go far in order for it to be considered “traveling” – there are so many places worth exploring just around the corner. Each city has their own unique way of celebrating the season and with affordable flights*, winter is the time to experience somewhere new. So bundle up and get ready to fall in love with a new city.
Affordable destinations for winter
01
Most affordable winter destination
New York
New York
Hacker tip
Admit it, you’ve fantasized seeing New York City covered in snow. Though we can’t control the weather, we can tell you where to go. Venture outside the usual tourist traps for bites and a skate at Winter Village at Westlight. Located on the roof of The William Vale hotel, skating at this skyline-facing rink will only set you back about $20. If you have more cash to spare, stay after your skate for drinks and alpine-style fondue at one of the cozy rink-side chalets.
01
Most affordable winter destination
New York
New York
Hacker tip
Admit it, you’ve fantasized seeing New York City covered in snow. Though we can’t control the weather, we can tell you where to go. Venture outside the usual tourist traps for bites and a skate at Winter Village at Westlight. Located on the roof of The William Vale hotel, skating at this skyline-facing rink will only set you back about $20. If you have more cash to spare, stay after your skate for drinks and alpine-style fondue at one of the cozy rink-side chalets.
Median flight price by month**
Median hotel price by month**
November
$338 / night
December
$402 / night
January
$196 / night
February
$192 / night
Median rental car price by month**
Median flight price by month**
November
$287
December
$297
January
$247
February
$257
Median hotel price by month**
November
$338 / night
December
$402 / night
January
$196 / night
February
$192 / night
Median rental car price by month**
November
$68 / day
December
$79 / day
January
$69 / day
February
$64 / day
02
Most affordable winter destination
Minneapolis
Minnesota
Hacker tip
Minneapolis is a whole other kind of cold during the winter – there’s no getting around it. Except, there actually is – Minneapolis has its own “Skyway System” that connects all of downtown through indoor sky bridges. In fact, it’s actually the largest contiguous system in the world, so you can explore 9.5 miles of the city without spending a dime or having to be out in the cold.
02
Most affordable winter destination
Minneapolis
Minnesota
Hacker tip
Minneapolis is a whole other kind of cold during the winter – there’s no getting around it. Except, there actually is – Minneapolis has its own “Skyway System” that connects all of downtown through indoor sky bridges. In fact, it’s actually the largest contiguous system in the world, so you can explore 9.5 miles of the city without spending a dime or having to be out in the cold.
Median flight price by month**
Median hotel price by month**
November
$165 / night
December
$161 / night
January
$160 / night
February
$121 / night
Median rental car price by month**
Median flight price by month**
November
$322
December
$377
January
$294
February
$297
Median hotel price by month**
November
$165 / night
December
$161 / night
January
$160 / night
February
$121 / night
Median rental car price by month**
November
$68 / day
December
$72 / day
January
$61 / day
February
$73 / day
03
Most affordable winter destination
Seattle
Washington
Hacker tip
Seattle isn’t your typical winter island destination, but does have a few surrounding archipelagos in the San Juan Islands that you can visit for less than $16 round trip. Take the ferry to Orcas Island and get yourself a cozy beverage to warm you up during the ride. Then, take a hike through Moran State Park or meander around the shops at Eastsound Village to discover local galleries and boutiques.
03
Most affordable winter destination
Seattle
Washington
Hacker tip
Seattle isn’t your typical winter island destination, but does have a few surrounding archipelagos in the San Juan Islands that you can visit for less than $16 round trip. Take the ferry to Orcas Island and get yourself a cozy beverage to warm you up during the ride. Then, take a hike through Moran State Park or meander around the shops at Eastsound Village to discover local galleries and boutiques.
Median flight price by month**
Median hotel price by month**
November
$190 / night
December
$188 / night
January
$166 / night
February
$176 / night
Median rental car price by month**
Median flight price by month**
November
$312
December
$354
January
$259
February
$317
Median hotel price by month**
November
$190 / night
December
$188 / night
January
$166 / night
February
$176 / night
Median rental car price by month**
November
$63 / day
December
$72 / day
January
$47 / day
February
$62 / day
04
Most affordable winter destination
Chicago
Illinois
Hacker tip
Fun games and cozy vibes – that’s exactly what you want from a night out in Chicago. Luckily, we know just the spot – Gwen & Rooftop Terrace is a great spot for food and drinks that offers a glimpse of Chicago higher up. Be sure to check out their “curling and cocktails” on the roof – for $40, you can try your hand at a new winter sport (and the first cocktail is included).
04
Most affordable winter destination
Chicago
Illinois
Hacker tip
Fun games and cozy vibes – that’s exactly what you want from a night out in Chicago. Luckily, we know just the spot – Gwen & Rooftop Terrace is a great spot for food and drinks that offers a glimpse of Chicago higher up. Be sure to check out their “curling and cocktails” on the roof – for $40, you can try your hand at a new winter sport (and the first cocktail is included).
Median flight price by month**
Median hotel price by month**
November
$208 / night
December
$175 / night
January
$158 / night
February
$147 / night
Median rental car price by month**
Median flight price by month**
November
$297
December
$313
January
$272
February
$277
Median hotel price by month**
November
$208 / night
December
$175 / night
January
$158 / night
February
$147 / night
Median rental car price by month**
November
$74 / day
December
$81 / day
January
$74 / day
February
$65 / day
05
Most affordable winter destination
Montreal
Québec, Canada
Hacker tip
It can be tempting to spend all of your time exploring Montreal – but, if you’re in need of some chill time and have a little room in the budget to splurge, go have yourself a day at Bota Bota. Not your typical spa, Bota Bota is an old ferry-turned-spa and restaurant moored on the Saint Lawrence River. Treat yourself to pampering and once you’re feeling zen, walk over to Old Montreal for relaxing drinks with dinner.
05
Most affordable winter destination
Montreal
Québec, Canada
Hacker tip
It can be tempting to spend all of your time exploring Montreal – but, if you’re in need of some chill time and have a little room in the budget to splurge, go have yourself a day at Bota Bota. Not your typical spa, Bota Bota is an old ferry-turned-spa and restaurant moored on the Saint Lawrence River. Treat yourself to pampering and once you’re feeling zen, walk over to Old Montreal for relaxing drinks with dinner.
Median flight price by month**
Median hotel price by month**
November
$184 / night
December
$199 / night
January
$186 / night
February
$153 / night
Median rental car price by month**
Median flight price by month**
November
$330
December
$383
January
$330
February
$388
Median hotel price by month**
November
$184 / night
December
$199 / night
January
$186 / night
February
$153 / night
Median rental car price by month**
November
$48 / day
December
$64 / day
January
$82 / day
February
$72 / day
06
Most affordable winter destination
Denver
Colorado
Hacker tip
Believe it or not, there’s plenty to do in Denver during the cooler months besides skiing. If you’re seeking a magical night out, visit Denver Botanic Gardens to walk through their expansive holiday light show for $24 a person (from 11/18 – 1/7). Afterwards, head to one of the city’s many dinner spots that offer heated outdoor seating for a cozy meal in an igloo or chalet to round out the night.
06
Most affordable winter destination
Denver
Colorado
Hacker tip
Believe it or not, there’s plenty to do in Denver during the cooler months besides skiing. If you’re seeking a magical night out, visit Denver Botanic Gardens to walk through their expansive holiday light show for $24 a person (from 11/18 – 1/7). Afterwards, head to one of the city’s many dinner spots that offer heated outdoor seating for a cozy meal in an igloo or chalet to round out the night.
Median flight price by month**
Median hotel price by month**
November
$156 / night
December
$162 / night
January
$159 / night
February
$164 / night
Median rental car price by month**
Median flight price by month**
November
$286
December
$361
January
$306
February
$367
Median hotel price by month**
November
$156 / night
December
$162 / night
January
$159 / night
February
$164 / night
Median rental car price by month**
November
$65 / day
December
$74 / day
January
$80 / day
February
$79 / day
07
Most affordable winter destination
Vancouver
British Columbia, Canada
Hacker tip
Regardless of when you’re traveling to Vancouver, Capilano Suspension Bridge Park is always a hot spot for visitors. The holidays are a good time to brave this popular attraction – not only will you be able to appreciate the park during the Canyon Lights Winter Festival (from 11/18 – 1/22), but you can see the suspension bridge lit up for the season. Just FYI, entry tickets to the park are the pricier side (think $63 for adults) so this is definitely an activity where you’ll want to save up ahead of time.
07
Most affordable winter destination
Vancouver
British Columbia, Canada
Hacker tip
Regardless of when you’re traveling to Vancouver, Capilano Suspension Bridge Park is always a hot spot for visitors. The holidays are a good time to brave this popular attraction – not only will you be able to appreciate the park during the Canyon Lights Winter Festival (from 11/18 – 1/22), but you can see the suspension bridge lit up for the season. Just FYI, entry tickets to the park are the pricier side (think $63 for adults) so this is definitely an activity where you’ll want to save up ahead of time.
Median flight price by month**
Median hotel price by month**
November
$186 / night
December
$187 / night
January
$151 / night
February
$243 / night
Median rental car price by month**
Median flight price by month**
November
$322
December
$432
January
$388
February
$419
Median hotel price by month**
November
$186 / night
December
$187 / night
January
$151 / night
February
$243 / night
Median rental car price by month**
November
$51 / day
December
$69 / day
January
$79 / day
February
$73 / day
08
Most affordable winter destination
Cincinnati
Ohio
Hacker tip
There’s more to Cincinnati than their famous chili – and what could be better than experiencing the city through a spirited bar crawl? Explore the historic Over-the-Rhine neighborhood during the annual Ugly Sweater Bar Crawl (on 12/3) for $15 – $21 a ticket (not including drinks, though tickets do include discounts at certain bars). Of course, you can always do your own pub crawl sans sweaters with this guide to some of the city’s local breweries.
08
Most affordable winter destination
Cincinnati
Ohio
Hacker tip
There’s more to Cincinnati than their famous chili – and what could be better than experiencing the city through a spirited bar crawl? Explore the historic Over-the-Rhine neighborhood during the annual Ugly Sweater Bar Crawl (on 12/3) for $15 – $21 a ticket (not including drinks, though tickets do include discounts at certain bars). Of course, you can always do your own pub crawl sans sweaters with this guide to some of the city’s local breweries.
Median flight price by month**
Median hotel price by month**
November
$188 / night
December
$207 / night
January
$152 / night
February
$175 / night
Median rental car price by month**
Median flight price by month**
November
$325
December
$380
January
$262
February
$278
Median hotel price by month**
November
$188 / night
December
$207 / night
January
$152 / night
February
$175 / night
Median rental car price by month**
November
$69 / day
December
$74 / day
January
$71 / day
February
$119 / day
09
Most affordable winter destination
Hartford
Connecticut
Hacker tip
Hartford may not be known as a “foodie haven” but trust us, they have an incredible dining scene due to the city’s close proximity to many local farms. If you’re in the mood for barbecue, Bear’s Smokehouse is a favorite spot for smoked meats and zesty sauces at reasonable prices. Prefer a few brews over brisket? Find your way over to City Steam Brewery to see what kind of craft beers are on tap.
09
Most affordable winter destination
Hartford
Connecticut
Hacker tip
Hartford may not be known as a “foodie haven” but trust us, they have an incredible dining scene due to the city’s close proximity to many local farms. If you’re in the mood for barbecue, Bear’s Smokehouse is a favorite spot for smoked meats and zesty sauces at reasonable prices. Prefer a few brews over brisket? Find your way over to City Steam Brewery to see what kind of craft beers are on tap.
Median flight price by month**
Median hotel price by month**
November
$180 / night
December
$216 / night
January
$198 / night
February
$194 / night
Median rental car price by month**
Median flight price by month**
November
$355
December
$397
January
$287
February
$366
Median hotel price by month**
November
$180 / night
December
$216 / night
January
$198 / night
February
$194 / night
Median rental car price by month**
November
$75 / day
December
$90 / day
January
$79 / day
February
$61 / day
10
Most affordable winter destination
Portland
Oregon
Hacker tip
Having the “where do you want to go for dinner” debate? In Portland, the solution is simple: head on over to Division Street. This neighborhood has something for everyone and every price range – food carts, restaurants, desserts, beer gardens, wine bars – the list goes on. Plus, there are a handful of small boutiques and shops that are bound to have something for everyone on your list.
10
Most affordable winter destination
Portland
Oregon
Hacker tip
Having the “where do you want to go for dinner” debate? In Portland, the solution is simple: head on over to Division Street. This neighborhood has something for everyone and every price range – food carts, restaurants, desserts, beer gardens, wine bars – the list goes on. Plus, there are a handful of small boutiques and shops that are bound to have something for everyone on your list.
Median flight price by month**
Median hotel price by month**
November
$161 / night
December
$163 / night
January
$154 / night
February
$177 / night
Median rental car price by month**
Median flight price by month**
November
$376
December
$415
January
$334
February
$317
Median hotel price by month**
November
$161 / night
December
$163 / night
January
$154 / night
February
$177 / night
Median rental car price by month**
November
$72 / day
December
$73 / day
January
$77 / day
February
$80 / day
Roam through more of the guide
‘Tis the ski-son
Find out more about this season’s trendiest ski destinations and the must-have items to bring on your next winter adventure.
Swap a summer Euro trip for the winter
Rethink your summer vacation for a more affordable winter trip with less crowds – see where you can explore for less this season.
Methodology*KAYAK US considered round trip, economy flight destinations with the lowest median airfare that experience winter weather during travel dates 11/18/22 – 1/2/23 for search dates 6/1/22 – 9/15/22.
**Median airfare, median nightly hotel/vacation rental rates and median daily rental car rates by month for each destination are based on the above indicated search and travel dates. Airfare is round trip pricing with a US origin. Hotel and car rates are daily median rates excluding taxes and fees.