If the Second City calls you away from the Big Apple, Southwest Airlines® has you covered with low fares on nonstop flights. Southwest® is proud to offer flights from New York (LaGuardia) to Chicago (Midway) at prices that'll melt a hardened New Yorker heart with their Midwestern nice. Booking is straightforward, no matter if you're traveling for fun, family, business, or something else. Have flexible dates? Search for your New York (LaGuardia) to Chicago (Midway) flight on our Low Fare Calendar and find our lowest fares within your timetable. Check out Southwest Vacations® and build yourself a package deal with flights, hotels, rental cars, and more to make the most of our low prices.
Explore New York (LaGuardia) to Chicago (Midway) flights and book your next trip to Chi-Town now!
New York (LaGuardia), NY to Chicago (Midway), IL
departing on 4/9
one-way starting at*$88
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 16 travel days available.
|LaGuardia Airport (LGA)
|Chicago Midway International Airport (MDW)
|Average flight time
|2 hours 32 minutes
|Nonstop flights per day Monday through Friday
|Nonstop flights on Saturday
|Nonstop flights on Sunday
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 3/1/2024 and 3/31/2024. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 3/1/2024 and 3/31/2024.
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.
One child over 14 days and under two (2) years of age, not occupying a seat, may be carried free of charge when traveling with an adult (12 years of age or older). Learn more.
Customers flying with a pet are subject to a pet fare. To learn more about traveling with your furry friend, explore the Southwest® pet policy.
Minors under the age of 18 are not permitted to fly unaccompanied on international flights or any itinerary that includes an international flight. Learn more.
Chicago Midway International Airport is a quick 30-minute 'L' ride from downtown Chicago. Get going—adventure awaits.
At Southwest, we know it takes more than great deals on Chicago (Midway) airfares and convenient scheduling options to make your trip memorable. So from booking to boarding, we offer services and features designed to make your travel from New York (LaGuardia) to Chicago (Midway) the best it can be. Learn more about the Southwest® travel experience before you book your flight from LaGuardia Airport to Chicago Midway International Airport.
Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. When you search for your next flight to Chicago (Midway), know that you won’t be surprised at checkout. Low fares and no hidden fees. That's Transfarency®. And as always, two bags fly free®1. Want the latest news, information, and promotional offers from Southwest? Sign up to receive email from us. Book your flight today and know that you'll earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
3Failure to cancel a reservation at least 10 minutes prior to departure may result in forfeited Travel Funds.
4Flight credits unexpired on or created on or after July 28, 2022, do not expire and will show an expiration date until our systems are updated. See full details here.
5Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
6Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
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.