New York to Midway Chicago. It sounds simple enough on paper, right? You hop on a plane at LGA or EWR, cruise over Pennsylvania and Ohio, and land right in the middle of the South Side. But honestly, if you treat this like a standard Newark-to-O'Hare hop, you’re basically setting yourself up for a headache. New York and Chicago are two of the busiest airspace corridors in the entire world, and the Midway connection is the "in-the-know" choice that can either save your day or leave you stranded at a gate in Queens.
Most travelers just default to O’Hare because it’s the giant on the map. They don’t realize that O’Hare is a sprawling monster where you might taxi for forty minutes—literally long enough to watch an entire sitcom episode—before you even hit the gate. Midway is different. It’s compact. It’s scrappy. It’s also the primary fortress for Southwest Airlines, which fundamentally changes how you should book this route.
Why Everyone Messes Up the New York to Midway Chicago Choice
First off, let’s talk geography. If you are staying in the Loop or heading to Hyde Park, Midway is objectively better. You can take the Orange Line train and be downtown in about 25 minutes. Try doing that from O’Hare on the Blue Line during rush hour; you’ll be underground for an hour feeling every single bump in the track.
But here is the catch: your departure airport in New York dictates everything. If you are flying New York to Midway Chicago, you are almost certainly looking at LaGuardia (LGA) or Newark (EWR). JFK rarely touches Midway because it’s a heavy international and long-haul hub. Southwest dominates the Midway routes out of LGA.
Wait, why does that matter? Because Southwest doesn't show up on Google Flights or Expedia in the same way other airlines do. If you’re just searching on a third-party site, you’re seeing a distorted version of the market. You’re seeing the random Delta or United connection, but you’re missing the actual heartbeat of the route.
The Weather Factor (It’s Not Just the Wind)
People call Chicago the Windy City, but the wind isn't usually what ruins your trip. It’s the "Lake Effect." Because Midway is tucked further south and closer to the heart of the city than O'Hare, the visibility patterns can be totally different. I’ve seen days where O'Hare is clear and Midway is socked in with fog so thick you can't see the tail of the plane.
New York weather is its own beast. LaGuardia is notorious for delays the moment a single cloud looks at the runway funny. If you’re flying this route in February, you need a backup plan. You’re connecting two of the most delay-prone regions in the United States. According to Bureau of Transportation Statistics data, the LGA-MDW corridor often sees higher-than-average ground delay programs.
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Breaking Down the Airlines: Who Actually Wins?
You basically have two main contenders and a few outliers.
Southwest Airlines is the king here. They run a "bus-style" service. They have multiple flights a day from LaGuardia. The perks are obvious: two free checked bags. In a world where Delta and United are nickel-and-diming you for a carry-on in basic economy, Southwest feels like a fever dream from 1998. But you have to deal with the "boarding group" cattle call. If you don't check in exactly 24 hours before, you’re sitting in a middle seat between two guys who definitely didn't skip breakfast.
Delta operates out of LGA too. It’s a more "premium" feel, sure. You get the seatback screens. You get the reliable Wi-Fi. But you’re paying for it. If you’re a business traveler with status, the Delta Sky Club at LGA’s new Terminal C is a literal palace compared to the cramped waiting areas you’ll find elsewhere. It’s worth the extra $50 if you need to actually get work done.
United mostly handles the Newark (EWR) to Midway side of things. Newark is... well, it’s Newark. It has improved immensely with the new Terminal A, but getting there from Manhattan can be a soul-crushing experience if the Holland Tunnel is backed up.
The Logistics of the "Short" Flight
It’s about 700 miles. In the air? You’re looking at roughly two hours and fifteen minutes. But the "block time"—the time from gate to gate—is usually padded to about two hours and forty-five minutes.
Pro tip: Fly the early bird. The 6:00 AM or 7:00 AM flights are the only ones that actually run on time. By 3:00 PM, the delays from the rest of the country have cascaded. A thunderstorm in Atlanta can somehow delay a flight from New York to Midway Chicago because the incoming aircraft was stuck in Georgia. Aviation is a giant, fragile web.
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The Midway Experience: What to Expect When You Land
Midway is tiny. Well, tiny for a major city.
When you land, you’re not walking two miles to baggage claim. It’s all right there. The food scene has actually gotten better lately. You can get a real Chicago hot dog (no ketchup, don't even ask) at Gold Coast Dogs or a slice of Home Run Inn pizza. It beats the soggy sandwiches at LGA any day.
Transportation from Midway:
- The "L" (Orange Line): $2.50. Fastest way to the Loop. Cheap. Real.
- Rideshare (Uber/Lyft): There is a specific pickup garage. Follow the signs. It’s a bit of a hike from the gate, but manageable. Expect to pay $40-$70 depending on the surge.
- Go Airport Express: A shuttle service. Good if you have massive suitcases, but honestly, just take a cab.
Hidden Costs and Travel Hacks
Don't book "Basic Economy" on this route unless you are traveling with nothing but a backpack. Both United and JetBlue (who occasionally runs seasonal or codeshare routes nearby) are ruthless about bag sizes.
If you’re flying out of LGA, try to use the new Terminal B or C. They are world-class. If your flight is out of the old Marine Air Terminal, you’re in for a nostalgic but very "retro" (read: zero food options) experience.
Another weird quirk? The "Ground Stop." If there is heavy rain in Northern New Jersey, the FAA will often halt all flights heading into the New York area. This means you might be sitting on the tarmac at Midway, ready to go, but the pilot comes on and says, "Sorry folks, New York won't let us into their air." This happens more often on the Midway route than the O'Hare route because Midway flights are often handled by smaller regional jets or shorter-range 737s that don't have the fuel capacity to circle for three hours.
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Is Midway Actually Better Than O'Hare?
Honestly, it depends on your final destination.
- Go to Midway if: You are staying in the Loop, South Side, or West Loop. You are flying Southwest. You want a shorter walk from the gate to the exit.
- Go to O'Hare if: You are staying in the North Side, Evanston, or the Northwest suburbs. You want more options for "re-booking" if a flight gets cancelled (O'Hare has 10x the flight volume).
Navigating the Return: Midway back to New York
The security lines at Midway can be deceptive. Because the terminal is small, the line for TSA can look like a nightmare, stretching back toward the parking garage. However, it usually moves fast. If you have TSA PreCheck, you can usually clear it in under seven minutes.
One thing most people miss: Midway has a yoga room. If your flight back to New York is delayed—and let’s be real, it might be—go find the yoga room in Concourse C. It’s quiet, it’s clean, and it’s a great place to hide from the screaming toddlers at the gate.
Actionable Insights for Your Trip
To make the most of your New York to Midway Chicago journey, follow these specific steps:
- Book directly on Southwest.com: If you want the Midway advantage, you have to go to the source. Don't rely on aggregators.
- Check the "LGA Terminal C" status: If you’re flying Delta, verify which terminal you’re in. The walk between terminals at LGA is not something you want to do with a rolling suitcase.
- Download the Ventra App: Before you land in Chicago, get the Ventra app on your phone. You can load a "CTA" pass instantly. When you get off the plane, you just tap your phone at the turnstile for the Orange Line. No fumbling with vending machines while people behind you sigh loudly.
- Watch the "Flow Control": Use an app like FlightAware to see where your plane is coming from. If your flight to Midway is supposed to leave at 2 PM, but the plane is currently stuck in a snowstorm in Buffalo, you know you have time for a long lunch.
- The "South Side" Food Rule: If you have a long layover at Midway or your flight is delayed, don't just eat at the terminal. If you have two hours, take a quick 5-minute Uber to Vito & Nick’s Pizzeria. It’s legendary thin-crust Chicago pizza (tavern style) and it’s way better than anything in the airport.
Flying between these two cities is a rite of passage for any East Coast or Midwest traveler. It’s a route defined by efficiency and the occasional weather-induced chaos. If you plan for the gate distances at LGA and the train connections at MDW, you’ll be blocks ahead of the tourists who are still wandering around O’Hare Terminal 3 trying to find the exit.
Next Steps for Your Trip:
Check your departure terminal at LaGuardia at least 24 hours in advance, as construction still occasionally shifts gate assignments. If you are flying Southwest, set an alarm for exactly 24 hours before departure to snag an "A" boarding group. Finally, verify your ground transport; if you're arriving at Midway after 11 PM, the Orange Line runs less frequently, and a pre-booked car might save you a long wait in the taxi line.