If you read my post from last month on how to travel 120 days each year with a full time job, you know that the best way to travel more with a full time job is to take advantage of your weekends. With that said, there are certain cities that are more ideal for weekend trips than others. Having traveled to most of the U.S. states and most major cities in the U.S., I took a minute to think about what is most important to me in a weekend destination and compiled the list below of the 10 best weekend trips to take in the U.S. Some factors I take into consideration when determining whether a destination is a good destination for a weekend trip are walkability, activities, food, and cost. Typically, the more walkable a city is, the more activities there are to do, the better the food, and the lower cost a place is, the more likely I am to recommend it as a top weekend destination.
1. Chicago, Illinois
I may be a bit biased since I live in Chicago, but I would highly recommend it as a destination for a weekend trip. Flying into O’Hare Airport, you can take the train from the airport to downtown, nonstop. There is only one train that goes to O’Hare (the blue line), and it ends at the airport, so it will be impossible for you to get on the wrong train. Once you get into the city, you can go pretty much anywhere via train or bus, so there is no need to spend more money on a car rental.
In terms of activities, you will have plenty to do and see in one weekend, so there is no chance you’ll be bored. If you’re a big foodie, there are a number of foods native to Chicago you may have heard of and want to try, such as deep dish pizza and Chicago style hot dogs, as well as a quickly growing number of Michelin rated restaurants and craft beer offerings. It has really become somewhat of a foodie’s paradise.
Although Chicago, like many big cities, tends to be more expensive than other parts of the country, you have the option of making your trip as expensive or as cheap as you’d like it to be. For fancy, high-end restaurants, you’ll want to spend more time in the River North neighborhood for popular clubs and fine dining. For more budget friendly, casual restaurants and bars, head to the Lakeview or Logan Square neighborhoods. You can even go a whole weekend without spending a penny – just check out this list of 35 free things to do in Chicago.
2. New York City, New York
I have taken at least 10 weekend trips to New York City in my adult life, and it has always been one of my favorite cities in the country. The diversity, culture, and availability of good food here is really unrivaled by any other city. I’m always amazed by the quantity of good ethnic food available from every corner of the world, and of course you can find good bars and cafes all over the city (make sure you check out this list of the 15 coffee shops with the best New York City coffee).
Once you visit New York, you will understand why this is the city that never sleeps. Regardless of the hour, you will feel an immediate energy and aliveness walking through Times Square, which is always lit (literally – by lights – and figuratively – lit af – as the kids are saying) and bustling with people. Whether 4 AM or 4 PM, you will feel an energy in this city that simply does not exist elsewhere.
New York City is also very walkable, although my biggest gripe with the city is how confusing its public transportation is. Some trains are labeled by number, some are labeled by letter, some are referred to by color – I have an easier time navigating train systems abroad in foreign languages than I do in NYC. However, it is very easy to understand the set up of the streets, as it’s mainly set up in a grid system with a numeric naming system.
There is no doubt that you’ll have more than enough to do to keep you occupied for a weekend. And while New York is one of the most expensive cities in the country, there are also plenty of budget options. Hope traveled to NYC quite a bit as a full time student living in Boston last year, and she was able to spend only $20 USD total for the entire weekend, including transportation, by eating street food and taking advantage of the many free activities there. One of my personal favorites for a cheap meal is a lamb gyro for $6.99 USD from the gyro trucks, which you’ll find on the streets all throughout Manhattan.
3. Austin, Texas
Austin is a beer and coffee lover’s paradise, and I can’t even begin to talk about their tacos. I ate tacos for breakfast, lunch, and dinner during my weekend there and could not get sick of it. Most of the bars and restaurants here offer outdoor seating, and many bars have free live music at night as well. Having grown up in primarily cold weather cities, I felt like I was in paradise sitting outside in 80 degree Fahrenheit weather with my beer and tacos in February, when I was just sitting in 10 degree Fahrenheit weather in Chicago hours earlier.
In terms of walkability, I did not find the city to be as walkable as some of the larger cities like Chicago or New York City. However, it is a smaller city, and if you stay in a central location, you’ll be able to walk most places. I would also recommend renting a bike and exploring the city by bike. There is a large park in the middle of the city called Zilker Park, where you can go for a bike ride or a run/walk, and there are also activities there like kayaking, stand up paddleboarding, and swimming.
Best of all, the prices here are one of the lowest on this list. We were pleasantly surprised by the number of bars offering live music without charging a cover, and we were also delighted to find that our beers only cost a few dollars, so $20 took us pretty far for a night out. I would recommend Austin for a more relaxed weekend trip in the winter months consisting of a lot of relaxing outside with a beer and walks in the park.
4. San Francisco, California
San Francisco is a hodgepodge of the laid-back California vibe, forward thinking tech innovations, and an open-minded attitude. Everyone fits in here, and with mild temperatures year round, there’s never a bad time to visit. I visited just a couple of weeks ago in February, and it was 60 and sunny the entire weekend we were there.
The city is mostly walkable, but I noticed that it is a lot more common for young people living in the city to have cars and to use their cars to get around the city. This is in significant contrast to Chicago, where the only “young” people with cars in the city are those with jobs outside the city. But what San Francisco (and the west side of the U.S.) lacks in the form of good public transportation, it makes up for with its perfect weather, relaxed vibes, and abundance of nature and outdoor activities. You can easily spend a weekend in San Francisco without a car, but if you’re interested in doing any hikes or checking out the redwoods, you will need a car to get to those places.
While San Francisco is undeniably the most expensive city in the U.S., its costs come mainly the form of living expenses and not food, activities, etc., so you likely will not notice significantly higher costs here than in any other major city. I stayed in a hotel in the financial district that was very reasonably priced and in close proximity to many sights. Restaurants and bars there are also on par with other major cities like New York City, and rivals New York City equally in its abundance of delicious foods of all types.
5. Washington, D.C.
Our nation’s capital is one of my favorite places for a weekend trip. There is just enough to do and see in a weekend, and going for a walk around the monuments is not only a meaningful experience, but there is no place in the country that will make you feel more patriotic than Washington, D.C. It is also entirely possible to keep your weekend under budget, as all the monuments and the majority of the Smithsonian museums are free.
Washington, D.C. is extremely walkable, and there’s no reason for you to rent a car for a weekend there. Public transportation is available from several nearby airports, and none takes longer than one hour to get downtown. Once downtown, the subway system will get you just about anywhere you want to go.
As is true with any major city, you will find a diverse range of food options here. From vegetarian options to Chinese food to rooftop beer gardens, D.C. has it all.
6. Seattle, Washington
Seattle offers the best of city life and nature, with several parks within city limits and a number of more challenging hikes a short drive outside the city. You’ll feel a more alternative, artsy culture here, which is reflected in the prevalence of independent coffee shops and organic, vegan food options. On a nice day, take the ferry out to Alki Beach or another nearby island.
In terms of food options, Seattle also has a great selection of Asian food, including the largest bowl of pho in the world, and fresh seafood. Similar to San Francisco, I noticed a much stronger culture of driving than taking public transportation, but you can certainly get around for a weekend without renting a car. However, there are quite a few hikes outside of the city that are worth doing, and you would need a car to access those mountains.
I have visited Seattle a few times, and it is a city that has grown on me. As a visitor, it’s sometimes hard to know which areas to spend time in and what sights to see. After going back and visiting friends who live in the city, I gained a much better perspective of Seattle and felt like I had a better understanding of the culture there. If you do not have privilege of visiting friends in Seattle, I would recommend booking your accommodations through Airbnb or Couchsurfing, which will allow you to connect with a local and see Seattle from a local’s perspective.
7. Portland, Oregon
If you’ve watched the TV show Portlandia or heard any stereotypes of Portland, you probably have a pretty accurate image of Portland in your head. You will see the alternative culture of this city seep through in its art, music, and food. In terms of food, the first place you want to check out is the food truck park, an entire street block of food trucks with food options ranging from Mexican to Greek to Asian. There are also a number of outdoor markets in the summer months, where you will get a sense of the local focus on organic, whole foods and drinks.
One thing you may not have known about Portland is how poor its economy is. As such, there is a large number of independent artists and entrepreneurs in Portland. Since it’s hard to find a job, locals create their own jobs. One such local is a guy who started a free walking tour company in Portland. After living in Spain and working as a tour guide for several years, he was surprised to see that, unlike in Europe, free walking tours aren’t prevalent at all in the U.S., so he decided to create his own job working as a tour guide in Portland. To this day, the only free walking tour I’ve been on in the U.S. was in Portland. I would highly recommend starting your weekend off with a free walking tour, which will provide you with an overview of the city and its history.
Since Portland is a smaller city, if you are able to rent a car for a day, I would recommend driving out to Mt. Hood and hiking or skiing there. Mt. Hood is one of the few mountains in the U.S. that offers year round skiing/snowboarding, so if you really wanted a range of activities, you could spend a day exploring the city in shorts and a tank top and spend the next day skiing down a mountain just a short drive away.
8. Denver, Colorado
If I had to guess, I would say that at least 75% of the time, when I hear about someone moving out of Chicago, they are moving to Denver. It has become such a hot commodity for young people that housing prices have sky rocketed over the last few years. This comes at no surprise, as Denver has plenty to offer locals and travelers alike.
The two main things that come to mind when I think of Denver are beer and nature. Denver (and the surrounding area) is home to nearly 100 breweries, according to this list published by the Denver Brewery Guide. The last time I was there in April 2016, I randomly walked into a few breweries, and even the small ones that most people haven’t heard about were wonderful. I love the rustic, farmhouse style that characterizes many of the breweries in Denver.
Denver is also a nature lover’s paradise. It is hard to believe that the Rocky Mountain Arsenal National Wildlife Refuge, home to numerous species of animals, including bisons, is located a stone’s throw away from downtown Denver. Or that a two hour drive from Denver will land you in some of the nation’s most prominent ski resorts. Needless to say, there are numerous hikes in and around Denver for you hikers and non-city dwellers.
In terms of cost, Denver is very reasonable, although prices are rising due to the city’s growing popularity and growing population. However, it is still much more affordable than cities like New York and San Francisco.
9. Boston, Massachusetts
If I had to pick one city in the United States that most closely resembles Europe, I would pick Boston. Boston’s North End consists of narrow, cobble stone streets lined with small, independently owned restaurants and shops in old buildings. It is a smaller city but exudes a strong air of class and sophistication. Don’t miss Mike’s Pastry for the best cannolis in town and James Hook for the most delicious seafood in a small shack on the river.
The city is entirely walkable, as is true with most east coast cities, but if you happen to have a car, I would recommend visiting some of the neighboring cities. As Hope spent a year living in Wenham, on the north shore of Boston, we have taken a number of roadtrips around the north shore. Salem is known for its famous witch trials, and Manchester-by-the-sea and Gloucester are beautiful fishing towns where you can find delicious seafood. Whether you choose to stay in the city or explore neighboring towns, Boston is the perfect “European” weekend trip without actually traveling to Europe.
10. Toronto, Ontario (Canada)
If you have a passport and live in the Midwest or East Coast, Toronto is one of the best cities for a weekend trip. Our parents have lived in Toronto for the last eight years, and Hope spent her formative middle school and high school years in Toronto, so it is a city near and dear to our hearts. I’ve taken at least 30 weekend trips there over the last eight years and could not recommend it more highly.
Interestingly enough, my second home of Toronto reminds me a lot of my first home: Chicago. Toronto is a bit smaller than Chicago and much more laid back. Many people think Canada and the United States are one in the same, but in many ways, the culture and mindset in Canada much more closely resembles that of Europe than of the United States. For example, Canada leans much more toward a socialist society than does the United States, and people are a lot more content with the life they live, whether they are a doctor or garbage collector, and are not constantly hustling for that promotion or higher paying job. Toronto is also one of the most diverse cities in the world, with less than half of its residents carrying a Canadian birth certificate. People of all colors, ages, and backgrounds are welcome here.
Toronto is often referred to as a City Within a Park, and it will be obvious to you where this label comes from once you visit the city. There are large parks scattered throughout this city, and in the summer months, you can take the ferry downtown to one of the Toronto islands. There are endless activities to do here, from walks in the park to world class museums to Michelin rated restaurants that you will surely not find yourself bored by the end of your weekend here. In terms of cost, Toronto is a great place for Americans to travel to right now because of the favorable exchange rate for Americans.
Disclaimer: This post may contain affiliate links. That means we receive a commission when you click and buy through our links. You don't have to use our links, but we're very grateful when you do.
Hi, I’m Diana, the big sister in the sister duo. I left my job as an attorney in March 2017 to pursue the work-from-anywhere/travel-everywhere life aka The Dream. I blog about off the beaten trail travel destinations, adventure travel, immersing in local cultures, and publish plenty of travel guides for all you who are too lazy to plan your own trips. I’ve traveled to 53 countries to date, and some of my recent adventures include hiking Mt. Kilimanjaro, visiting a child I’ve sponsored for over 10 years in Rwanda, and exploring the Middle East.