The Top 10 Most Fun Cities In America (And What To Do In Each)

Whether you’re trying to figure out where to go on vacation or simply planning what to do this weekend in the city nearest you, one thing is for sure: we all just want to have a little fun! 

So what makes a fun city? 

When it comes to the best cities in America to have fun, it’s all very subjective. While fun for me means lots of breweries within walking distance of each other, someone else’s idea of fun might be a city that hosts a different music festival every weekend.

But that doesn’t make it impossible to rank U.S. cities by funness, and Wallethub recently took on the task of doing just that. The site compared 182 American cities to find out where the most fun happens on the regular, ranking each based on entertainment and recreation, nightlife and parties, and perhaps most importantly, costs. 

What follows is a list of the top contenders, plus personal recommendations for where to stay and things to do in each place.

10. Los Angeles, California

Whether you’re a big Hollywood fan, prefer a beachy vibe, or want to go on a hike with vast city views, the “City of Angels” has a little bit of something for everyone. One of the most expensive U.S. cities to live in, Los Angeles is all that much more exotic to visit — no wonder 50 million people visited it just last year!

L.A. came in at number 8 of 182 in entertainment and recreation and is 12th in nightlife and parties. Unsurprisingly, though, it’s number 159 in costs, making it one of the most expensive cities on the list.

Where to stay: For a homey feel and gorgeous views, try one of Outsite’s four Venice-based locations (plus you’ll get $50 towards your stay with my referral code).

Best brewery in Los Angeles: Highland Park Brewery

Things to do in Los Angeles:

  1. Hike to the Hollywood sign

  2. Griffith Observatory

  3. Universal Studios Hollywood

9. San Diego, California

Not far from Los Angeles is the 9th most fun city in the U.S., coming in at number 3 in entertainment and recreation and 17th in nightlife and parties. Much like its other California counterpart, though, at 142 in costs, San Diego is on the more expensive side.

Where to stay: Outsite’s co-living and co-working spaces are based in some of the most beautiful places in the world, so it’s no surprise they have two San Diego locations. (And my referral code will get you $50 towards your stay here too!).

Best brewery in San Diego: Modern Times Brewery

Things to do in San Diego:

  1. USS Midway Museum

  2. San Diego Zoo

  3. La Jolla Cove

8. Portland, Oregon

Let’s put California cities behind us for a second and move on to Portland, Oregon. Known for being a bit quirky, it’s no wonder Portland made the top 10 most fun cities in the U.S.!

So what makes Portland so fun? It ranked number 13 in recreation and entertainment and 7 in nightlife and parties. As far as costs, Portland is number 117 on the list, at least making it more affordable than both Los Angeles and San Diego.

Where to stay: Immerse yourself in Portland’s weirdness by staying at a unique Airbnb. Use this code to get $40 toward your stay and $15 towards an experience worth $50 or more.

Best brewery in Portland: Ecliptic Brewing

Things to do in Portland:

  1. Portland Japanese Garden

  2. International Rose Test Garden

  3. Washington Park

7. San Francisco, California

Back in Cali but a little farther north, San Fran is the 7th most fun city in the U.S. At number 4 in entertainment and recreation and 8 in nightlife and parties, there’s surely a little something for everyone. 

Like its other California counterparts, however, San Francisco is on the expensive side, coming in at 177 of 182 in costs. It’s also one of the top five in beer prices, so that pint might cost you a little more than a pretty penny!

Where to stay: Stay right in the heart of one of two of San Francisco’s most popular neighborhoods with Outsite

Best brewery in San Francisco: ThirstyBear Brewing Co.

Things to do in San Francisco:

  1. Alcatraz Island

  2. Golden Gate Bridge

  3. Twin Peaks

6. Atlanta, Georgia

Finally, a city east of the Rockies! Atlanta is 14th in entertainment and recreation and 5th in nightlife and parties. If you like dancing, Atlanta is the place for you! According to Wallethub, it has the 4th most dance clubs per capita.

It’s roughly middle-of-the-line in costs at 100 on the list.

Where to stay: Stay in the heart of downtown at the iconic Hyatt Regency hotel.

Best brewery in Atlanta: Terrapin Brew Co.

Things to do in Atlanta: 

  1. Atlanta Botanical Garden

  2. Georgia Aquarium

  3. Martin Luther King Jr. National Historic Site

5. Chicago, Illinois

The Windy City is 5th on the list of the most fun cities in America and ranks in the top 10 for both entertainment and recreation as well as nightlife and parties. 

Where to stay: Chicago has a ton of different neighborhoods to choose from, all with their own pros and cons. But since you’re looking for fun, the River North area is for you — book a room at the FOUND hotel.

Best brewery in Chicago: Lagunitas Brewing Company

Things to do in Chicago:

  1. Millennium Park

  2. 360 Chicago Observation Deck

  3. Catch a game at Wrigley Field

4. Miami, Florida

Its tropical climate makes Miami a hotspot (literally) all year round, so it’s no wonder it’s considered one of the most fun cities in America. Miami lands at number 9 in entertainment and recreation and 4 in nightlife and parties. 

Miami has a few other bragging rights. It has the 3rd most restaurants per capita of all the cities included in the study as well as the most fitness centers per capita — you know, if getting a workout in is your idea of fun.

Where to stay: South Beach is the place to be if you’re staying in Miami. Get the full experience by staying in a boutique hotel just seconds from the beach. Don’t forget you can use this code for $40 toward your stay and $15 towards an experience worth $50 or more!

Best brewery in Miami: J Wakefield Brewing

Things to do in Miami:

  1. Wynwood Walls

  2. South Beach

  3. Bayside Marketplace

3. New York, New York

Is it any surprise that the City That Never Sleeps is in the top three most fun cities in the U.S.? Known for its incredible culinary scene, nightlife, and an abundance of shopping, there is truly something for everyone here. 

In fact, NYC ranks at number 1 in entertainment and recreation. However, it’s also the most costly city of all 182 cities on the list. The price might be worth it, though, as NYC ranks in the top 5 for categories like most restaurants per capita, most park playgrounds per capita, most fitness centers per capita, and most importantly, most accessible bars. 

Where to stay: New York City is the least affordable city to live in in the whole United States, but you can get a taste of the life when you stay in Outsite’s Brooklyn location. Don’t forget you’ll get $50 towards your stay with my referral code!

Best brewery in New York City: Brooklyn Brewery

Things to do in NYC:

  1. Central Park

  2. Times Square

  3. Brooklyn Bridge

2. Orlando, Florida

Home to Disney World, the most magical place on Earth, how could Orlando not make the list? 

Aside from Disney, Orlando also ranks in the top 5 for most restaurants and dance clubs per capita. The best part? It’s ranked 17th in costs, meaning it’s the most affordable city on this list.

Where to stay: Stay in the midst of all the action in this bright and airy condo located close to Orlando’s theme parks and International Drive. Don’t forget you can use my code for $40 toward your stay and $15 towards an experience worth $50 or more.

Best brewery in Orlando: Orlando Brewing

Things to do in Orlando:

  1. Check out the theme parks

  2. Visit I-Drive

  3. Walk around Lake Eola Park

And the most fun city in the U.S. is…

1. Las Vegas, Nevada

They don’t call it Sin City for nothing! Whether you’re an early bird or a night owl, Vegas has something going on at all hours of the night and day. As far as rankings go, Vegas is 5th in entertainment and recreation, and unsurprisingly ranks as number 1 in nightlife and parties. 

What’s more, Vegas ranks in the top 5 for most festivals per capita, most restaurants per capita, most accessible bars, and most dance clubs per capita.

Where to stay: One of the casino hotels on The Strip, of course!

Best brewery in Las Vegas: Ellis Island Casino & Brewery

Things to do in Las Vegas:

  1. Explore The Strip

  2. Downtown Container Park

  3. Hike in Red Rock Canyon National Park

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