Whether you're traveling for business or pleasure, solo, or with the whole family, you'll enjoy the flexibility of flying Southwest®.
Find your next flight from New York (LaGuardia) to Chicago (Midway) now!
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Whether you're traveling for business or pleasure, solo, or with the whole family, you'll enjoy the flexibility of flying Southwest®.
Find your next flight from New York (LaGuardia) to Chicago (Midway) now!
New York (LaGuardia), NY to Chicago (Midway), IL
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 23 travel days available. Fares are updated hourly. Fares displayed on external channels may no longer be available at time of booking. To find the most updated fare, please visit Southwest.com.
Southwest seats are first come, first served based on check-in order. But there are ways to board the plane earlier!
Take advantage of inflight entertainment with free movies4, free live TV5, free texting6, and $8 inflight Internet7.
We also offer free sodas, coffee, and snacks8—learn more about the inflight food and beverage experience.
Have a change of travel plans? We offer free same-day standby for all fare types. This means that you can retain your current flight while listing for standby on an earlier flight. If a seat becomes available, it’s yours at no charge!
Rapid Rewards Members can redeem their points for flights, hotel stays, rental cars, gift cards, and more. And your points never expire!
| Fare | Fly one-way from $89 (departing on 5/27)* |
|---|---|
| Departing from | LaGuardia Airport (LGA) |
| Arriving at | Chicago Midway International Airport (MDW) |
| Average flight time | 2 hours 25 minutes |
| Distance | 725 miles |
| 148† | Weekly flights |
|---|---|
| 7‡ | Nonstop flights per day Monday through Friday |
| 3 ‡ | Nonstop flights on Saturday |
| 5 ‡ | Nonstop flights on Sunday |
Other popular flights from New York (LaGuardia):
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 4/1/2025 and 4/30/2025. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 4/1/2025 and 4/30/2025.
There's no chip on the City of the Big Shoulders about folks thinking they're lesser than New York City. That's like comparing the Big Apple to oranges, frankly. The Second City is second to none when it comes to pizza, improv, cursed baseball teams, fires started by cows, and so much more. The ...skyline boasts the tallest building in the Western hemisphere—NYC doesn't have that. New York City has Broadway; Chicago has Broadway in Chicago, where Broadway comes to visit. Chicago also happens to be the market where stage shows test before heading to the East Coast. One might say, if you can make it in Chicago, you can really make it anywhere.
Faux competition aside, New Yorkers can find a lot to love in Chicago. Freshwater abounds thanks to the shores of Lake Michigan; take a dip if your visit is during the summer, or consider joining a Polar Plunge if you're around during the arctic depths of a Midwestern winter. New Yorkers are no strangers to public transit, and so will likely take to the CTA like ducks to water. When deplaning at Midway, it's just a half hour Orange Line elevated train ride to the Loop—Chicago's downtown. From there, the city is at your feet thanks to the train and bus system. And like NYC, Chicago is on a grid system—getting lost? Fuggetaboutit.
When you fly from New York (LaGuardia) to Chicago (Midway), you can put the money you save on your nonstop flight toward enjoying the Windy City. Take a Chicago River boat ride, an architectural walking tour, or sit down for a Michelin-starred meal. Maximize your savings by exploring our deals on rental cars, hotels, and more. We even have whole vacation packages if you'd like to round out your trip while protecting your wallet. Whether you're in Chicago just briefly or for an extended period of time, your trip will go smoothly with Southwest.
1EarlyBird Check-In® pricing starts at $15 one-way, and is subject to availability. Pricing may vary based on the popularity and length of each (one-way) flight. Please see optional travel charges for more details.
2Upgraded boarding prices and benefits are per eligible segment. Flights must be within 24 hours of departure to be eligible for upgraded boarding.
4Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
5Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
6Texting only allows access to iMessage and WhatsApp (which must be downloaded and activated before connecting to SouthwestWiFi).
7Internet access for $8 per device from takeoff to landing. Price is subject to change. May not be available for the full duration of flight. In order to provide a top-notch Internet experience, we prohibit access to certain high-bandwidth applications and websites. We also prohibit access to certain obscene or offensive content.
8Flights traveling 175 miles or less will have only water available. Complimentary snacks are served on flights over 175 miles. If you’re flying between Hawaii and the continental U.S., you’ll have even more snacks to choose from.
9Free same-day standby: You can list for same-day standby for an earlier flight via a Southwest Customer Service Agent at the airport or the Southwest app or mobile web. You must request to be added to the same-day standby list at least 10 minutes prior to the scheduled departure of your original flight or the no-show policy will apply. If using the app or mobile web, you must list your name 30 minutes ahead of scheduled departure. You will receive a message based on the contact preference selected during booking if you are cleared on the flight. Group bookings and Unaccompanied Minors are not eligible for same-day standby. You will be required to pay any government taxes and fees associated with these itinerary changes but refunds will be provided. Your original boarding position is not guaranteed on your standby flight. Southwest Business Customers booked through travel agencies may need to see a Southwest agent at the airport for a standby listing. See Southwest.com/standby for more details.