The 5 Most Underrated Cities in the US

New York and Los Angeles are so old fashioned. This Australian expat fills us in on the cities you should include on your bucket list.

Because there’s one thing you can always count on America to deliver: excess. The highest roller coaster, the largest music festival, the most caloric burger, the largest in the Great Lakes. The entire continent is a gluttonous clam for the senses. And that, frankly, is why we like it.

I have lived and traveled in the United States for over half a decade and it continues to be a fascinating continent. But with so many options, there are still places that rise above the grits, cementing themselves as the best cities to make money. Because these places will give you more for your money without skimping on that sugar-coated sensory overload America is known for.

Cloud Gate (also known as The Bean) in Millennium Park in Chicago, Illinois. Image: Alamy


Because: Oprah, Playboy and No 23: all synonymous with the Windy City. Chicago looks a lot like your cool uncle, and while the Bulls and Cubs may be world famous, Chicago is much more than just a great sports bar. From oceanic Lake Michigan to the world-leading Art Institute of Chicago, it’s as if someone has taken everything we travel through and dropped it in the middle of America. The food reigns supreme, from the deep-dish pizza to the high-end Alinea, one of the most famous restaurants in the world. Just be sure to pair it with Malört, a Chicago-only herbal liqueur, or risk missing out on a true taste of America’s most American city.

When to visit: Summer (or patio season as the locals call it) is without a doubt the busiest time to be in Chicago. Catch events from Lollapalooza to Ravinia, the oldest music festival in North America.

The Chicago Athletic Association hotel.

Where to stay: The Chicago Athletic Association, with its Venetian Gothic shell and almost Masonic lodge-like renovation, is ideally located in The Loop (downtown Chicago) for your Al Capone-laden adventures.

Do not miss: Home to the world’s first skyscrapers, Chicago has plenty of river tours to get a better look at the city’s architecture, but the First Lady cruise is considered by many to be the best boat tour in the entire US of A.

Local advice: Shermann Dilla Thomas, or simply Dilla to his Instagram and TikTok fans, is known as Chicago’s urban historian and runs Chicago Mahogany Tours on the city’s South Side. He says that the best way to see Chicago is simply by taking a bus. “Take the Halsted Street Bus from 63rd Street to Lawrence – the variety of people, sights, and parts of Chicago you see will be truly astounding. And it’s only about $2.”

Sixth Street music and entertainment district in downtown Austin, Texas.


Because: If America were steak, Texas would be fat. Austin takes that fat and turns it into the best confection you’ve ever tasted. You only need to head to Lala’s Little Nugget to experience Christmas all year long, or The Little Longhorn Saloon for Chicken Sh#t Bingo, to see what I mean. It’s also the Live Music Capital of the World, a trademark but not one that’s not guaranteed; there are more than 250 places. Austinites like it weird, too. Honky Tonks and hybrid cars, cowboy boots and lunchtime lectures. Somehow, the hippie haven combines all the dichotomous things America is known for into one bombastic ball.

When to visit: The best time is mid-March when South By Southwest is on. The city is teeming with film, music and media nerds. You can’t go a quarter turn without some culture smacking you in the face.

The historic Driskill Hotel in Austin, Texas. Image: Mark Knight

Where to stay: With a prime location, The Driskill was built in 1886 for a cattle magnate and is Austin’s most opulent hotel in the capital city. Think cowhide stools and breakfast waffles in the shape of Texas.

Do not miss: Customs officers won’t let you go until you try a barbecue. Food trucks abound, but if you can, take the hour drive to Snow’s BBQ, considered the best in Texas, only open on Saturdays, and the head waiter, Ms. Tootsie, 87, is a living legend.

Local advice: Michael Fojtasek, founder and executive chef of Olamaie restaurant (which has been named Austin’s best many times), says Austin’s outdoor spaces are where they’re at. “See an outdoor show, play golf at Butler Pitch and Putt, or run around Lady Bird Lake in the heart of the city.”

Amazon Spheres at Amazon headquarters in Seattle.


Because: Microsoft, Amazon and Starbucks anchor Seattle as three giant capitalist drags. Giants also make their presence known. The city’s latest attraction, colloquially known as Bezos’ Balls (also known as The Amazon Spheres), acts as a giant glass greenhouse for more than 40,000 plants. And while it has the classic seductions that every big city boasts (in Seattle’s case, Pike Place Market, the Space Needle, and Chihuly Garden and Glass), it’s the unexpected attractions that make it worthy. Like the hidden Walrus and the Carpenter restaurant, where you can slurp oysters straight out of Puget Sound, or the aptly named Hot Tub Boats. Add to that some spectacular natural environments – green mountains, lush forests – and you have an ideal launching pad for Alaska, Canada and the rest of North America.

When to visit: Early fall (or fall, if you want to be a Yank about it) is the sweet spot for Seattle: warm and hospitable, but with less chance of Frasier-esque downpours that the city is known for.

Seattle’s Inn at the Market is located in the famous Pike Place Market.

Where to stay: For a true Seattle experience, head straight to the Inn at the Market, the only lodging inside Pike Place Market.

Do not miss: When a fire in 1889 buried downtown Seattle, the powers that be simply built a new one on top of it. Since 1954, Bill Speidel’s Underground has been running tours of the underground city left behind, and it’s every bit as spooky as it gets.

Local advice: Bill Radke, host of NPR Network affiliate KUOW Seattle radio show and podcast Week in Review, says if you want to eat like a local, head to Chinatown. “My 13-year-old daughter and I love taking the bus to the Uwajimaya food hall for fish waffles and poke, and Beard Papa cream puffs.”

Bourbon Street, New Orleans, Louisiana. Image: US Tourism


Because: The crescent-shaped city is the birthplace of jazz, dental floss and, perhaps surprisingly, poker. It’s also home to The Causeway, a bridge that police have had to bail out drivers for so long that they couldn’t proceed when they lost sight of land. There’s a lot more to it than Mardi Gras and Voodoo, is what I’m saying. Although it would be difficult to visit without experiencing at least a little revelry, New Orleans’ open container laws make drinking in public completely legal and definitely consensual. But you can also go just for the food, it has a culinary wish list of its own.

When to visit: Spring is the season for Goldilocks to come to NOLA. That’s when the New Orleans Jazz & Heritage Festival takes place. It’s more eclectic than the name suggests (this year’s acts include Lizzo and Wu-Tang Clan).

The Hotel Monteleone’s Carousel Bar is a New Orleans institution. Image: Stephen Young

Where to stay: One of the iconic buildings in the French Quarter, the Hotel Monteleone has a revolving bar and suites named after past guests like Truman Capote and Ernest Hemingway.

Do not miss: New Orleans’ greatest invention: the cocktail. The Sazerac, considered the first to be invented, was invented in New Orleans and is best served at the Sazerac Bar at The Roosevelt Hotel.

Local advice: Singer-songwriter Judith Owen is exactly the type of performer NOLA is known for. And the hot tip of her? Forget Bourbon street. “Eat in Bayonne, then walk down Frenchman Street instead – you’ll see music spilling onto the sidewalk, amongst markets, food and swing dancers. And there’s nothing about it that doesn’t feel completely authentic.”

Waterfront homes in Old Charleston, South Carolina.


Because: I declare that Charleston has more history than Stephen King’s bookshelf. Not only is it the site of the beginning of the American Civil War, but the fact that it can boast the first public university, museum, theater and golf club in the United States is a testament. Everything moves a little slower to the south to the point where you’ll feel like human molasses. But you knew. What you didn’t know is that you can go horseback riding on the beach or paddle board at sunset with dolphins. After which you’ll want to kick back with shrimp and grits: invented in Charleston in 1950, it became so popular that in 1976 South Carolina declared it the official state food.

When to visit: Charleston has two peak seasons: spring and fall. That’s when the weather is mild and the lowland boil tastes its best.

View from Wentworth Mansion, Charleston. Image: Small luxury hotels of the world

Where to stay: For a true taste of southern hospitality, make a beeline for Wentworth Mansion. Crystal chandeliers, marble fireplaces – it’s everything you’d expect from the former Gilded Age home of a wealthy cotton merchant.

Do not miss: Pineapple stains, which is easy enough since they are absolutely everywhere. In fountains, lampposts and houses. The tradition goes back to when captains would place pineapples on their porches to symbolize their safe return from the sea.

Local advice: Jason Kempf, broadcaster for the Charleston RiverDogs minor league baseball team, says the Holy City is surprisingly competitive. “When there’s no baseball season, there’s college football and basketball, plus professional hockey, soccer and tennis. There is always a game worth watching.”