When the City of the Big Shoulders calls you away from the City of Angels, Southwest Airlines® has you covered. Southwest® is proud to offer flights from Los Angeles International Airport to Chicago Midway International Airport at Midwest-nice prices. Book with confidence—flying with Southwest is smooth, whether you're traveling for fun, family, or business. Have flexible travel dates? Search for your Los Angeles (LAX) flight with our Low Fare Calendar, and find extra savings for yourself. Check out Southwest Vacations® and build yourself a package deal with flights, hotels, rental cars, and more to make the most of our prices.
Check out Los Angeles (LAX) to Chicago (Midway) flights and book yours now!
Best Airline in the U.S. and North America & Best Economy Class and Low Cost Airline in North America.
Los Angeles (LAX), CA to Chicago (Midway), IL
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 20 travel days available.
During the ongoing COVID-19 pandemic, the availability, health and safety procedures, operations, and schedules for local attractions are changing constantly. Please contact attractions directly for hours of operation, potential temperature screenings, and other possible health and safety procedures and restrictions. Visit our COVID-19 Travel Information page for information about potential restrictions on air travel.
Departing from: Los Angeles International Airport (LAX)
Arriving at: Chicago Midway International Airport (MDW)
Other popular flights from Los Angeles (LAX)
View our interactive mapWhile Los Angeles may have unseated Chicago as the Second City by population size, there's still plenty that keeps the City of the Big Shoulders standing tall. Take the skyline, for example: This iconic collection of skyscrapers and high rises is famous for a reason. Visit the Willis Tower (or the Sears Tower, as many locals still call it)—the tallest building in the Western hemisphere—and step out onto the famous, four-foot-long Chicago Skydeck Ledge that lets you gaze straight down onto the city streets from 1,353 feet up in the air. Prefer to stay planted on terra firma? There are walking tours in nearly every corner of the City of Neighborhoods, from gangster-era crime tours about Al Capone to architectural tours for lovers of Frank Lloyd Wright. If you'd dig a river-roaming adventure rather than air or land, check out the boat tours on the Chicago River.
Hungry for more of Chicago? When you disembark from Midway, a quick ride on the Orange Line of the CTA will bring you right into the Loop—Chicago's downtown. From there, you can make it to nearly every portion of the city by hopping on the train line of your choosing (or transferring to the vast network of buses). Cabs, rideshares, and rental cars are options too, of course, but the public transit of the Windy City can be an adventure all its own. Connect to sleepy neighborhoods with hidden gems, venture to the Magnificent Mile for world-class shopping, or explore Restaurant Row for Michelin-starred cuisine. Neighborhood bars and hole-in-the-wall hotdog joints, though, are worth the trek into the Bungalow belts (either north or south, your pick) to explore.
Flying from Los Angeles (LAX) to Chicago (Midway) with Southwest lets you spend less on the trip and more on taking in your destination. 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.
Start packing! Every ticketed Customer’s first two checked bags are free. 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 Los Angeles (LAX) to Chicago (Midway) the best it can be. Learn more about the Southwest® travel experience before you book your flight from Los Angeles International 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. Looking for tours, activities, and more hidden gems to add to your Chicago (Midway) adventure? Explore getaways with Southwest®. 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.
To find the cheapest day and time to fly Los Angeles (LAX) to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
You can rent a car at Chicago Midway International Airport—book yours with your flight.
Yes! Flights from Los Angeles (LAX) to Chicago (Midway)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Check the status of your upcoming Southwest flight here.
Check out the Southwest Airlines® FAQs for answers about everything Southwest.
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