TripAdvisor just dropped its “Travelers’ Choice Awards Best of the Best” for 2026, and while the usual suspects like Bali and London are hanging out at the top of the general lists, the “Trending Destinations” category has thrown a massive curveball.
Sitting comfortably at number three worldwide—beating out exotic heavyweights like Quy Nhon, Vietnam, and Puerto Escondido, Mexico—is Chicago.
Yeah, you read that right. The Windy City isn’t just a U.S. favorite anymore; it’s currently one of the hottest tickets on the planet.
Look, I know what you’re thinking. “Chicago? The place with the wind chill that hurts your face?” I get it.
I’ve been there when the lake wind cuts right through your jacket. But here is the thing: Chicago in 2026 is stacking up to be an absolute beast of a destination, and the experts are finally catching on to what locals have known for years.
It’s world-class, it’s gritty, and frankly, it’s a lot more interesting than another week at an all-inclusive if that’s been your yearly trip go-to (no judgement!).
Here is why Chicago is blowing up right now and how to do it without losing your mind in traffic.
Why 2026 Is Pushing Chicago To New Heights
If you think Chicago is just “The Bean” and deep dish, you’re wrong. We’ll get into that more below, but here are 2 things actually driving the hype this year.
The “Sports Illustrated” Resort
In a move that feels very 2026, the Virgin Hotel near Michigan Avenue is rebranding into the first urban Sports Illustrated Resort. It’s slated to be fully online by late 2026. It’s a massive pivot from the “rock and roll” vibe to a high-energy sports hub. If you are coming into town for a Bears or Cubs game, this is trying 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 stopped being about heavy pizza and started being about precision and grit.
- The Reality: Yes, people still line up at Mr. Beef on Orleans. It’s timeless, it’s delicious, and you need to go.
- The Upgrade: The real movement is at the high end. Places like Kasama (the world’s first Michelin-starred Filipino restaurant) and Ever are now some of the hardest tables to book in the country. Chicago isn’t just feeding you anymore; it’s challenging you.
Add It To Another Trip: My Favorite Layover Hack
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 an eternity.
But I’ve done Chicago a few times, and I found a loophole that changes the game, especially if you’re just there for a quick trip or a long stopover.
Forget booking a hotel downtown and fighting for an Uber. Stay at the Hilton Chicago O’Hare Airport.
This isn’t some “airport adjacent” hotel where you have to stand in the freezing cold waiting for a shuttle bus that smells like diesel. This hotel is literally inside the airport. You walk off your plane, grab your bag, and walk underground directly to the lobby.
Here is the best part: The hotel has direct indoor access to the CTA Blue Line train.
You can wake up at the airport, jump on the train in the basement, and be in the heart of downtown Chicago in about 40-45 minutes for like five bucks.
You party in the city, eat the food, see the Bean, and then ride the train back to your bed. No traffic, no stress, and you literally cannot 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 One “Tourist Trap” You Must Do
I usually tell people to avoid the obvious tourist stuff, but the Chicago Architecture Foundation Center River Cruise is the exception to the rule.
It sounds incredibly boring on paper—”looking at buildings from a boat”—but it is hands-down the best 90 minutes you will spend in the city. You grab a drink, sit on the top deck, and float through the canyons of steel and glass while a docent (who actually knows their stuff) explains how this city was built from the ashes of the Great Fire. It gives you a perspective on the skyline you literally cannot get from the street. Just book it.
My advice? Do it early in your trip so you can revisit any places that grab your interest during the tour, because there will be plenty.
Winter is Hell, Summer is Heaven
We have to validate the pain: Chicago from January to March is a frozen test of human endurance. The wind off the lake will hurt your face.
But that is exactly why Chicago in the summer is one of the best cities on earth. Because the locals earned it, the energy from June to September is manic and infectious.
The city has 26 miles of public beaches right on the edge of the skyscrapers. You can finish a Michelin-star meal in the Loop and be digging your toes into 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 stores you have back home and eating at chains. Don’t do that.
Head to the West Loop (Fulton Market). This used to be the meatpacking district (gritty, industrial), and now it is the culinary capital of the Midwest.
The concentration of incredible restaurants here is absurd. You don’t go here to sightsee; you go here to eat until you can’t walk. If you want the “cool” factor without the downtown prices, head north to Logan Square or Wicker Park for the dive bars, vintage shops, and actual local culture.
The Bottom Line
Chicago deserves the hype. It’s one of the few American cities that feels like a true global metropolis without the pretension of New York or the sprawl of LA. I’ve loved it every time I visit, and always leave wanting more.
Sure, the winters are brutal. If you go in January, bring a coat that looks like a sleeping bag. But with the 2026 lineup 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 definitely bet on having a good time.
Subscribe To Our Latest Posts
Enter your email address to subscribe to Travel Off Path’s latest breaking travel news, straight to your inbox.
