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!
Los Angeles (LAX), CA to Chicago (Midway), IL
departing on 11/04
one-way starting at*$57
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 16 travel days available.
Middle seats open through November 30
Full exchange of fresh, outdoor air every 2-3 minutes while inflight
Face coverings required
Average flight time: 3 hours 55 minutes
Departing from: Los Angeles International Airport (LAX)
Arriving at: Chicago Midway International Airport (MDW)
Nonstop flightsper day
Other popular flights from Los AngelesView our interactive map
†Based on DOT published scheduled average flights Monday-Friday between 8/20/2020 and 4/11/2021, as of 8/20/2020.
While 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.
A memorable trip from Los Angeles (LAX) to Chicago (Midway) (and back again, or maybe to parts beyond) is made up of more than cheap flights from Los Angeles International Airport to Chicago Midway International Airport. Find out more about the Southwest Travel Experience while you book your Los Angeles (LAX) to Chicago (Midway) flight.
Whether you're flying from Los Angeles (LAX) to Chicago (Midway) or anywhere else we go, traveling with Southwest Airlines is simple and fun—and straightforward. When you search for your next flight, you'll find low fares and no hidden fees—that's our Transfarency® promise. Stay up to date with our latest flight deals: Enroll in our Click 'N Save® emails. Looking for tours, activities, and more hidden gems? Check out Southwest Airlines® Experiences and earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.