This American city is one of the most popular destinations in the world, according to experts

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TripAdvisor just dropped its “Travelers’ Choice Awards Best of the Best” for 2026, and while the usual suspects like Bali and London top the overall lists, the “Trending Destinations” category has created a huge curve.

Sit comfortably number three worldwide– beating exotic heavyweights like Quy Nhon, Vietnam and Puerto Escondido, Mexico – is Chicago.

Yes, you read that correctly. The Windy City isn’t just an American favorite anymore; it is currently one of the most popular tickets in the world.

Look, I know what you’re thinking. “Chicago? The place where the wind chill hurts your face?” I get it.

I’ve been there when the wind from the lake cut right through your coat. But here’s the thing: Chicago in 2026 is growing into an absolute beast of a destination, and the experts finally understand what the locals have known for years.

It’s world-class, it’s rugged, and honestly, it’s way more interesting than another week of all-inclusive if that’s been your annual trip (no judgement!).

Here’s why Chicago is booming right now and how you can do it without going crazy in traffic.

Why 2026 is pushing Chicago to new heights

If you think Chicago is all The Bean and deep dish, you’re wrong. We’ll dive into that in more detail below, but here are two things that are actually driving the hype this year.

The ‘Sports Illustrated’ resort

In a move that feels very 2026, the Virgin Hotel near Michigan Avenue is turning into the first urban Sports illustrated resort. It is expected to be fully online by the end of 2026. It’s a huge shift from the ‘rock and roll’ atmosphere to an energetic sports center. If you come to town for a Bears or Cubs game, try this to be your new headquarters.

The “Bear” effect is permanent

We can’t ignore it: the TV show The Bear changed the city’s culinary reputation overnight. It was no longer about heavy pizzas, but about precision and pizzazz.

• The reality: Yes, there are still people queuing Mr. Beef at Orleans. It’s timeless, it’s delicious, and you have to go.
• The upgrade: The real movement is on the high side. Places like Kasama (the world’s first Filipino restaurant with a Michelin star) and Ever are now some of the hardest tables to book in the country. Chicago doesn’t just feed you anymore; it challenges you.

Add it to another trip: my favorite stop

Let’s talk logistics. Chicago traffic is legendary, and not in a good way. Getting from O’Hare to the Loop during rush hour can take forever.

But I’ve done Chicago a few times and I’ve found a game-changing loophole, especially if you’re only there for a short trip or long layover.

Forget booking a hotel in the city and fighting for an Uber. Stay with the Hilton Chicago O’Hare Airport.

This is not an airport-adjacent hotel where you have to stand in the freezing cold waiting for a shuttle bus that smells of diesel. This hotel is literal inside the airport. You get off your plane, grab your bag and walk underground straight to the lobby.

Here’s the best part: The hotel has direct indoor access to the CTA Blue Line train.

You can wake up at the airport, hop on a train in the basement and be in the heart of downtown Chicago in about 40-45 minutes for about five dollars.

You party in town, eat the food, see the Boon and then ride the train back to your bed. No traffic, no stress and you literally can’t miss your flight the next morning.

It’s the most solid travel hack I’ve found for this city, and I’ve done it a few times now on my way to other destinations connecting through Chicago.

The only “tourist trap” you have to do

I usually tell people to avoid the obvious touristy things, but the River cruise through the Chicago Architecture Foundation Center is the exception to the rule.

On paper it sounds incredibly boring – ‘looking at buildings from a boat’ – but it’s without a doubt the best 90 minutes you’ll spend in the city. You grab a drink, sit on the top deck and float through the canyons of steel and glass as a docent (who really knows their stuff) explains how this city was built from the ashes of the Great Fire. It gives you a perspective of the skyline that you literally can’t get from the street. Just book it.

My advice? Do it early in your trip so that you can revisit all the places that catch your interest during the tour, as there will be plenty.

Winter is hell, summer is heaven

We need to validate the pain: Chicago is a frozen test of human endurance from January to March. The wind from the lake will hurt your face.

But that’s exactly why Chicago is one of the best cities in the world in the summer. Because the locals have earned it, the energy from June to September is manic and infectious.

The city has 42 kilometers of public beaches, right on the edge of the skyscrapers. You can have a Michelin-star meal in the Loop and dig your toes in the sand at North Avenue Beach twenty minutes later.

Get out of the loop (go west)

Most tourists get stuck in the ‘Mag Mile’ trap: shopping at home stores and eating at chains. Don’t do that.

Go to the West Loop (Fulton Market). This used to be the meatpacking district (gritty, industrial) and now it’s the culinary capital of the Midwest.

The concentration of incredible restaurants here is absurd. You don’t go here to see the sights; You’re going to eat here until you can’t walk anymore. If you want the ‘cool’ factor without the downtown prices, head north Logan Square or Thatched park for the dive bars, vintage shops and real local culture.

The bottom line

Chicago deserves the hype. It’s one of the few American cities that feels like a truly global metropolis without the pretension of New York or the sprawl of LA. I’ve enjoyed it every time and always leave wanting more.

Sure, winters are brutal. If you go in January, bring a jacket that resembles a sleeping bag. But with the 2026 line-up and the sheer energy of the city right now, it’s easily one of the best trips you can take this year.

Don’t bet the house on the weather cooperating, but you can certainly count on having a great time.

Tyler Fox

Tyler is our editor-in-chief and writer. After years of reading, writing, and obsessing about travel (while traveling as often as possible, of course!), he wants to give readers the best and most balanced experience possible when exploring the site.