$144 Cheap Southwest Airlines flights Chicago (ORD) to Milwaukee (MKE)

Grab affordable round-trip Southwest Airlines flights from $290 from ORD to MKE by organizing your results from “Price (lowest to highest)” on Expedia. Or search for options from $144 for a one-way journey.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

January is one of the least expensive months to jet away to Milwaukee with Southwest Airlines. You could also find great prices on one-way and round-trip fares in February.

Start searching one to three months ahead of your travel date to get cheaper fares on Southwest Airlines flights from O’Hare Intl. Airport (ORD) to General Mitchell Intl. Airport (MKE). You can save 25% by booking your domestic flight 34 to 86 days in advance compared to last-minute reservations made 6 to 12 days out. You could also reduce costs by buying your fare on a Sunday, as it’s 6% cheaper on average than a Monday, the most expensive day to book.* Nail your timing, and you can enjoy significant savings on domestic flights.*Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC’s global airline sales database.

Click on the “Nonstop” filter when searching for direct Southwest Airlines flights from ORD to MKE. It’s also an easy way to compare other airlines servicing the same nonstop route.

Find Southwest Airlines’s earliest flights from ORD to MKE by checking our “Early Morning” and “Morning” filters. Not only will you get to where you’re going sooner, early departures are also 20% less likely to be canceled.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.

Take a Southwest Airlines flight from O’Hare Intl. Airport (ORD) to Milwaukee, and you’ll likely touch down at General Mitchell Intl. Airport (MKE). This is the airline’s primary hub in this city.

It’s usually possible to cancel or change your flight, although additional fees may apply if you booked over 24 hours ago. Prefer to keep your options open? Apply the “No cancel fee” and “Changes included” filters to find flights that won’t penalize you if you need to revise your plans. To make changes, visit “Trips,” select your flight and click on “Manage Booking” for more information.