Flying from Chicago Midway to New York's LaGuardia is a rite of passage for many Midwest travelers. It’s a route defined by convenience, specifically the kind of convenience that lets you skip the massive footprint of O'Hare and the long haul from JFK or Newark. Southwest Airlines has basically staked its reputation on this specific corridor. If you've ever stood in that long security line at MDW at 5:00 AM, you know exactly what I’m talking about.
People choose Southwest MDW to LGA for a few very specific reasons. First, Midway is a hub. It’s Southwest’s territory. Second, LaGuardia isn't the "Third World country" airport it used to be. The multi-billion dollar renovation actually turned it into something quite nice. But flying this route isn't always as simple as picking the cheapest fare and showing up. There are nuances to the boarding process, the baggage situation, and the weird weather patterns of the Great Lakes and the Atlantic Coast that can mess up your day in a heartbeat.
The Reality of the Midway Experience
Midway is small. That’s the draw. You can get from the orange line train to your gate in twenty minutes if the TSA gods are smiling on you. Southwest owns this place. Unlike O'Hare, where you might walk a mile to reach a regional jet, Midway is compact. However, that compactness means that when things go wrong—like a winter storm rolling off Lake Michigan—the whole operation feels the squeeze.
Southwest operates dozens of daily flights on the Southwest MDW to LGA route. It’s a high-frequency shuttle for business travelers and weekenders alike. One thing you've gotta realize is that because Midway is a secondary airport, it handles delays differently than larger hubs. If Southwest has a ground stop at MDW, you aren't just delayed; you're sitting in a very crowded terminal with limited seating.
Honestly, the "Midway Shuffle" is real. You’ll see people racing from the food court to the A or B gates the second a boarding group is called. Since Southwest doesn't do assigned seating, your "position" in line is everything. If you're flying to New York for a quick meeting, paying for that EarlyBird Check-In is basically a tax you have to pay to ensure you aren't stuck in a middle seat between two linebackers.
Why LaGuardia is Actually Good Now
For years, saying you were flying into LGA was an apology. Not anymore. The new Terminal B, which Southwest shares with several other carriers, is a legitimate marvel. It’s got high ceilings, actual sunlight, and food that doesn't just come from a heat lamp. When you land on a Southwest MDW to LGA flight today, you aren't walking into a basement; you're walking into a modern transportation hub.
The big win for LGA is its proximity to Manhattan. If you land at JFK, you’re looking at an hour-plus trek. From LGA, you can be in Midtown in thirty minutes if traffic behaves.
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But here is the catch. LGA is notorious for "congested airspace." You can be ten minutes away from landing and find yourself circling over Long Island for twenty minutes because the runways are backed up. It's a dance. The pilots are used to it, but your schedule might not be. Always build in a thirty-minute buffer for your arrival time in New York. Seriously. Don't book a Broadway show for 7:00 PM if your flight lands at 5:30 PM. You won't make it.
The Southwest Boarding Game on the LGA Route
We have to talk about the boarding process because it defines the Southwest MDW to LGA experience. A, B, and C groups. No assigned seats. Two free checked bags.
This last point is huge for New York trips. If you're heading to NYC for a wedding or a long winter weekend, those heavy coats and extra shoes add up. On United or American out of ORD, you’re paying $35 or more for that bag. On Southwest, it’s included. That’s often the "hidden" savings that makes the MDW to LGA route more economical, even if the base fare looks similar to competitors.
Timing Your Booking
When should you buy? Usually, the "sweet spot" for Chicago to New York is about three to five weeks out. Southwest doesn't appear on Google Flights in the same way other airlines do, though that’s started to change recently with their new data-sharing agreements. You still get the best experience searching directly on their site.
Keep an eye on the "Wanna Get Away" fares. They are non-refundable but reusable as flight credits. If you see a flight for under $150 round trip, grab it. That's a steal for this corridor. Anything over $300 is pushing it unless it’s a holiday weekend or Lollapalooza is happening in Chicago.
Weather and Technical Delays
Let's get technical for a second. The Southwest MDW to LGA route crosses several air traffic control sectors that are among the busiest in the world. When a thunderstorm hits Pennsylvania or Ohio, it creates a "gate" issue. Planes can't fly through the storm, so they have to be spaced out.
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Chicago winters are another beast. De-icing at Midway is an efficient process, but it adds time. If you see "De-icing" on your flight status, add 45 minutes to your mental timeline. Southwest is great at quick turns—getting a plane in and out in 30-40 minutes—but ice and snow break that efficiency.
- Check the inbound flight. Use a tool like FlightAware to see where your plane is coming from. If your MDW to LGA plane is coming from Denver and Denver is under a blizzard, your flight is late. It doesn't matter if Chicago is sunny.
- The "Bridge" effect. Sometimes flights are diverted to Philadelphia or Newark if LGA gets too crowded or the wind shifts. It’s rare, but it happens.
- Connection risks. Most MDW to LGA flights are non-stop. If you are offered a "1-stop" through Baltimore (BWI) or Nashville (BNA), think twice. Why add a failure point? Stick to the non-stops.
The Comfort Factor
Southwest flies Boeing 737s. Usually the 700 series or the newer, quieter MAX 8. The MAX 8 is a much better ride for the two-hour hop to New York. It’s quieter, the air feels less dry, and the overhead bins are massive.
There is no "First Class" on Southwest. Everyone gets the same pretzels and the same legroom. This is the great equalizer. Whether you’re a CEO or a college student, you’re all fighting for the same exit row. If you want extra legroom, you’ve got to be in that A-group. That means checking in exactly 24 hours before departure. Not 24 hours and one minute. Exactly 24 hours.
Navigating the Terminals
At Midway, Southwest is the king. You’ll find most of their gates in Concourses A and B. The food options have improved lately; there’s a Billy Goat Tavern if you want that classic "Cheezborger" experience before you leave the 312.
At LaGuardia, Southwest operates out of Terminal B. This is important because Terminal B is a separate building from Delta’s Terminal C. If you’re meeting someone at the airport, make sure they know which one you’re in. The walk between terminals isn't really a thing there; you have to take a shuttle bus.
Once you land at LGA, follow the signs for "Ground Transportation." If you're taking an Uber or Lyft, you have to go to a specific parking garage. It’s a bit of a hike from the gate, involving a series of escalators and a pedestrian bridge. It’s well-signed, but it takes about 10 minutes.
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The Commuter Vibe
The Tuesday morning Southwest MDW to LGA flight is a different beast than the Friday afternoon flight. Tuesday morning is full of consultants in Patagonia vests. It’s quiet. Everyone is working on laptops. Friday afternoon is a party. It’s people heading to Broadway, couples on dates, and Chicagoans looking for a change of scenery.
Knowing the vibe helps you prepare. If you want a quiet flight, the early morning departures are your best bet. If you want to land in New York and go straight to dinner, take the 2:00 PM out of Midway. You’ll land around 5:15 PM, giving you just enough time to drop your bags at a hotel in Chelsea or Queens and hit a 7:30 PM reservation.
What People Get Wrong About This Route
A common mistake is assuming O'Hare (ORD) is always better because it's "bigger." For New York, that’s rarely true. O'Hare is further from the city center, the security lines are often longer, and the taxi times on the runway can be thirty minutes alone. Midway is a "fast" airport.
Another misconception is that LGA is still "bad." Seriously, if you haven't been there since 2019, you won't recognize it. It’s arguably the best airport in the New York system now. Don't let old Yelp reviews scare you away from booking Southwest MDW to LGA.
Lastly, people forget about the time zone change. It sounds silly, but Chicago is Central Time and New York is Eastern. You lose an hour going there. You gain an hour coming back. That 6:00 PM flight from Midway doesn't land until 9:00 PM in New York. By the time you get to your hotel, it’s 10:30 PM. Plan your meals accordingly.
Actionable Steps for Your Trip
To make the most of your Southwest flight from Chicago to New York, follow these specific steps:
- Download the Southwest App: This is non-negotiable. You need it for the 24-hour check-in and to track your bags.
- Check-in exactly 24 hours out: Set an alarm for 24 hours and 2 minutes before your flight. Be ready to hit the button.
- Verify your terminal at LGA: If you are booking a car service, make sure they know you are at Terminal B.
- Pack for the "Micro-Climates": It can be 20 degrees in Chicago and 45 in New York. Layers are your friend.
- Use the L-Train or Bus: If you’re on a budget, the M60-SBS bus from LGA connects you to the subway for a few bucks. It’s much cheaper than a $70 Uber.
- Watch the "Wanna Get Away Plus" fares: For a few extra dollars, these fares allow for same-day confirmed changes. If you finish your meeting early in New York, you can jump on an earlier flight home to Chicago without paying a huge fare difference.
The Southwest MDW to LGA route remains one of the most efficient ways to travel between the two greatest cities in the United States. It’s built on the backs of commuters and savvy travelers who know that Midway’s speed and LaGuardia’s new facilities are a winning combination. As long as you manage your boarding position and keep an eye on the weather, it’s a seamless hop.