preload

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

New York, NY

Minneapolis, MN

Seattle, WA

Chicago, IL

Montreal, QC, CA

Denver, CO

Vancouver, BC, CA

Cincinnati, OH

Hartford, CT

Portland, OR

New York, NY

Minneapolis, MN

Seattle, WA

Chicago, IL

Montreal, QC, CA

Denver, CO

Vancouver, BC, CA

Cincinnati, OH

Hartford, CT

Portland, OR

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**

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


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**

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


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**

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


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**

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


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**

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


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


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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**

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


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**

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


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**

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


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**

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


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**

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


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.

See the spots

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.

Show me more

     Methodology

Methodology

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*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.