With daily nonstop service and our legendary discount fares, Southwest makes it convenient – and cheap – to enjoy the Navy Pier, shop along Michigan Avenue, or just see the sights in the Windy City.
Flying for business? Taking a last-minute weekend getaway? No matter why you’re traveling, you can land great deals on direct flights to Chicago on southwest.com. Book your direct flight online to get our lowest discount fares, or check out our vacation packages for some of our best deals on nonstop travel to Chicago and other favorite destinations. Then relax and enjoy your trip on Southwest Airlines!
Are your travel dates flexible? Search for our lowest fares by date.
At Southwest, we know it takes more than great deals on discount air fares and convenient daily nonstop flights to make your trip memorable. So from booking to boarding, we offer services and features designed to help ensure your travel is hassle free.
Find out more about the Southwest Experience.