Have fall plans but?
Most avid vacationers have already scoped out their favourite mountain cities, sunny seashores, and mainly anyplace with an excuse to cozy up by the fireside with a sizzling cocoa.
However one iconic U.S. metropolis is looking virtually the entire world to go to earlier than frigid winters give credence to the “Windy Metropolis” moniker.
That is proper — considered one of our favourite city escapes right here at Journey Off Path was simply topped America’s most connected vacation spot, which means nearly anybody from anyplace can get right here quicker than I can scoff down a well-known Portillo’s sizzling canine (do not attempt it at residence, youngsters).
House to astounding structure, stylish resorts, seemingly countless vibrant neighborhoods, world-class eats, and a lot extra, now’s the right time to plan a visit to Chicago, regardless of how lengthy you propose to remain.
Did You Know Chicago Has 3 Airports?
Let’s simply let the cat out of the bag — however watch out! Mr. Whiskers is feisty!
As you have most likely guessed, Chicago’s sprawling O’Hare Worldwide Airport is presently probably the most linked U.S. airport.
However earlier than we dive into that, there’s one factor all vacationers have in widespread — we like to keep away from crowds.
Regardless of in case you’re a seasoned vet like me or simply starting to department out past the confines of your hometown, the potential of lengthy traces, grumpy TSA brokers, being herded like cattle, after which packed in like sardines can scare off any of us.
There isn’t any doubt O’Hare is the simplest to succeed in with so many flights, each home and overseas, and the benefit of entry into town by public transit is unmatched.
Nevertheless, Chicago is residence to a lot smaller (but nonetheless very fashionable) Halfway Worldwide Airport, anchored by Southwest and a choose few others.
Halfway is not any secret, however close by Chicago Rockford Worldwide Airport (RFD) actually is in case you’re not a “sunseeker” loyalist to considered one of America’s trendiest finances airways as of late.
Set an hour or so exterior town limits, RFD makes for a a lot calmer entry level to considered one of America’s few true metropolises, even providing an American Airways-backed bus to switch between airports starting October 20, 2025.
Serving solely Allegiant Air, this more and more fashionable low-cost provider provides direct flights to Rockford from 7 cities.
The World Is Your Oyster At O’Hare
Whereas I’ve personally by no means understood why anybody would need their world to be a slimy sea booger, we’ll go along with the previous adage right here for argument’s sake.
Not solely is O’Hare probably the most reachable American airport, sitting forward of Atlanta (ATL) and Dallas (DFW), it is now the seventh most linked on the planet, sitting proper behind Seoul (ICN).
Talking of bucket-list locations, whether or not you are going to or from, O’Hare has no scarcity of stunners to utilize your passport.
As of September 1, 2025, O’Hare declared there are an estimated 126 each day direct flights to 67 worldwide locations — yeah, you learn that proper…
In the event you personal a scratch map like me, it looks as if one of the best technique to show your map into Swiss cheese is to fly out of O’Hare.
Although there’s clearly much more home flights — an estimated 1020 each day direct flights to 181 U.S. cities.
Whereas everybody has their very own journey wishlists, if I lived within the area, the next routes out of O’Hare would definitely prime mine as they’re much less widespread in comparison with different main airports:
- Belgrade, Serbia (BEG) — Air Serbia
- Krakow, Poland (KRK) — LOT Polish Airways
- Amman, Jordan (AMM) — Royal Jordanian
New Worldwide Flights Coming To O’Hare
Maybe probably the most thrilling addition to O’Hare in current months is American’s new path to Naples, Italy, which launched in Could 2025.
There’s much more to stay up for, although.
These 6 worldwide routes are coming quickly to O’Hare:
- Tel Aviv, Israel (TLV) — United, 4x weekly, starting November 1, 2025
- San José, Costa Rica (SJO) — American, each day, starting November 2, 2025
- Guatemala Metropolis, Guatemala (GUA) — American, as much as 3x weekly, starting November 6, 2025
- St. Maarten (SXM) — American, Saturday-only, starting November 8, 2025
- St. Croix (STX) — American Airways, Saturday-only, starting December 6, 2025
- Curaçao (CUR) — American, Saturday-only, starting December 6, 2025
- Bucharest, Romania (OTP) — HiSky, 2x weekly, starting June 4, 2026.
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