img#mv-trellis-img-1::before{padding-top:66.666666666667%; }img#mv-trellis-img-1{display:block;}img#mv-trellis-img-2::before{padding-top:100%; }img#mv-trellis-img-2{display:block;}img#mv-trellis-img-3::before{padding-top:100%; }img#mv-trellis-img-3{display:block;}img#mv-trellis-img-4::before{padding-top:100%; }img#mv-trellis-img-4{display:block;}img#mv-trellis-img-5::before{padding-top:100%; }img#mv-trellis-img-5{display:block;}img#mv-trellis-img-6::before{padding-top:100%; }img#mv-trellis-img-6{display:block;}img#mv-trellis-img-7::before{padding-top:74.418604651163%; }img#mv-trellis-img-7{display:block;}Have fall plans yet?
Most avid travelers have already scoped out their favorite mountain towns, sunny beaches, and basically anywhere with an excuse to cozy up by the fireplace with a hot cocoa.
But one iconic U.S. city is calling practically the whole world to visit before frigid winters give credence to the “Windy City” moniker.
That’s right — one of our favorite urban escapes here at Travel Off Path was just crowned America’s most connected destination, meaning just about anyone from anywhere can get here faster than I can scoff down a famous Portillo’s hot dog (don’t try it at home, kids).
Home to astounding architecture, classy hotels, seemingly endless vibrant neighborhoods, world-class eats, and so much more, now is the perfect time to plan a trip to Chicago, no matter how long you plan to stay.
Did You Know Chicago Has 3 Airports?
Let’s just let the cat out of the bag — but be careful! Mr. Whiskers is feisty!
As you’ve probably guessed, Chicago’s sprawling O’Hare International Airport is currently the most connected U.S. airport.
But before we dive into that, there’s one thing all travelers have in common — we love to avoid crowds.
No matter if you’re a seasoned vet like me or just beginning to branch out beyond the confines of your hometown, the potential of long lines, grumpy TSA agents, being herded like cattle, and then packed in like sardines can scare off any of us.
There’s no doubt O’Hare is the easiest to reach with so many flights, both domestic and abroad, and the ease of access into the city by public transit is unmatched.
However, Chicago is home to much smaller (yet still very popular) Midway International Airport, anchored by Southwest and a select few others.
Midway is no secret, but nearby Chicago Rockford International Airport (RFD) certainly is if you’re not a “sunseeker” loyalist to one of America’s trendiest budget airlines as of late.
Set an hour or so outside the city limits, RFD makes for a much calmer entry point to one of America’s few true metropolises, even offering an American Airlines-backed bus to transfer between airports beginning October 20, 2025.
Serving only Allegiant Air, this increasingly popular low-cost carrier offers direct flights to Rockford from 7 cities.
The World Is Your Oyster At O’Hare
While I’ve personally never understood why anyone would want their world to be a slimy sea booger, we’ll go with the old adage here for argument’s sake.
Not only is O’Hare the most reachable American airport, sitting ahead of Atlanta (ATL) and Dallas (DFW), it’s now the 7th most connected in the world, sitting right behind Seoul (ICN).
Speaking of bucket-list destinations, whether you’re going to or from, O’Hare has no shortage of stunners to make use of your passport.
As of September 1, 2025, O’Hare declared there are an estimated 126 daily direct flights to 67 international destinations — yeah, you read that right…
If you own a scratch map like me, it seems like the best strategy to turn your map into Swiss cheese is to fly out of O’Hare.
Though there’s obviously even more domestic flights — an estimated 1020 daily direct flights to 181 U.S. cities.
While everyone has their own travel wishlists, if I lived in the region, the following routes out of O’Hare would certainly top mine as they’re less common compared to other major airports:
- Belgrade, Serbia (BEG) — Air Serbia
- Krakow, Poland (KRK) — LOT Polish Airlines
- Amman, Jordan (AMM) — Royal Jordanian
New International Flights Coming To O’Hare
Perhaps the most exciting addition to O’Hare in recent months is American’s new route to Naples, Italy, which launched in May 2025.
There’s a lot more to look forward to, though.
These 6 international routes are coming soon to O’Hare:
- Tel Aviv, Israel (TLV) — United, 4x weekly, beginning November 1, 2025
- San José, Costa Rica (SJO) — American, daily, beginning November 2, 2025
- Guatemala City, Guatemala (GUA) — American, up to 3x weekly, beginning November 6, 2025
- St. Maarten (SXM) — American, Saturday-only, beginning November 8, 2025
- St. Croix (STX) — American Airlines, Saturday-only, beginning December 6, 2025
- Curaçao (CUR) — American, Saturday-only, beginning December 6, 2025
- Bucharest, Romania (OTP) — HiSky, 2x weekly, beginning June 4, 2026.
Sam SearsSam, our Lead Writer & Journalist based in San Diego has visited 36 countries and written over 1000 articles with a focus on sharing his own travel experiences and shining a light on lesser-known gems.
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