Southwest Airlines flights to Chicago
The best Southwest Airlines flight deals to Chicago
Looking for a last minute deal or the best direct flight? Find the biggest savings on one-way and return trips to Chicago with Southwest Airlines.Find which Chicago airports Southwest Airlines flies to
Compare routes to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier.Flying to Chicago with Southwest Airlines
The things to know before you go.| Cheapest month to fly | November |
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How to find cheap flights to Chicago with Southwest Airlines
Looking for cheap flight tickets to Chicago? Here are a few tips on how to find the best price.Simply hit 'search'
We've compared every online travel agent and flight provider out there to find the cheapest Southwest Airlines flight tickets to Chicago. And with us, there are no added fees – what you see is what you pay.
Flex your dates for the best rates
If you're flexible on your departure dates, use Skyscanner's whole month tool to find the cheapest month, and even day to get flights to Chicago with Southwest Airlines.
Set up a Price Alert
We'll let you know when the price of your flight to Chicago goes up or down so you can book when the time is just right. You're even able to watch specific Southwest Airlines flights.
Book your Southwest Airlines flight to Chicago with extra peace of mind
Find flexible Southwest Airlines flights to Chicago
Southwest Airlines might offer amendable tickets to Chicago, which means you won't lose out if your booking has to be changed or cancelled.
Add travel cost protection
Make sure you have the right travel insurance before flying to Chicago. That way you can cover the costs of any unexpected events, such as delays or lost luggage.
Reduce your carbon footprint
To check whether there are any lower emissions flights available on your route, simply check the “only show flights with lower CO₂ emissions” box when you search for a flight with us.
