Southwest® flights to Chicago (Midway) starting at $49

Flights to Chicago – Midway International Airport (MDW)

Book your flight to Chicago, IL and land right in the action at Midway International Airport (MDW). Whether you're here for business or you've just always wanted to hang out at a huge metal bean, your Chicago adventure starts right here.

Chicago Midway International Airport (MDW) vs. O’Hare International Airport (ORD)

Choosing between Chicago's airports? While O'Hare International Airport (ORD) is a major global hub, many travelers prefer Midway because it's smaller, easier to navigate, and closer to the downtown Loop area.

If an easy travel day is your top priority, Midway is a great choice for your flight to Chicago. Its compact layout means you'll spend less time walking to your gate or baggage claim. Just like O'Hare, it also has a train line that provides direct service—but unlike the relatively long ride from ORD, Midway's Orange Line can get you downtown in just 20 to 25 minutes.

Getting From MDW to Downtown Chicago

Take note of your best options for getting into the city once your flight to Midway has arrived:

• CTA Orange Line: This train provides a reliable and affordable ride downtown in under 30 minutes, and it leaves directly from the airport.
• Rideshares & taxis: Find these waiting right outside baggage claim. Depending on traffic, you can get to neighborhoods like River North or the West Loop in about 30 to 45 minutes.
• Rental cars: If you plan on exploring more of the Chicagoland area, rental cars are a quick shuttle ride away.

How to Find Cheap Flights to Chicago Midway

Planning and flexibility are the keys for finding cheap flights to Chicago Midway. Here's a few tips for the fare-hunters out there:

• Check flexible dates: Use the Southwest Low Fare Calendar to spot great deals if you have some wiggle room on your travel dates.
• Travel midweek: Flying on Tuesdays or Wednesdays usually means lower fares and less crowded airports.
• Book in advance: Secure your seat early to lock in the best prices. The sooner you book, the more you’re likely to save, and you’ll have more flight options than if you wait until the last minute.
• Set up alerts: Sign up for Southwest email alerts so you can be the first to know about fare sales and special offers.