C$177 Cheap Flights from Seattle (SEAA) to Chicago Midway (MDW)

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Flight deals from Seattle to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Seattle to Chicago Midway Airport? If you want to travel next month, return fares start from C$349. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Seattle to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Seattle to Chicago Midway flights are currently cheapest in April.

Which airlines fly from Seattle to Chicago Midway?

Seattle to Chicago: Flight information

The things to know before you go.
Cheapest flight foundC$177
Cheapest month to flyApril
Average flight time3 hrs, 59 mins
Most popular airlineSouthwest Airlines
Average flights per week15

Finding cheap flights from Seattle to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Seattle to Chicago Midway is C$349. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
3 hours and 59 minutes is the average flight time from Seattle to Chicago Midway.
Southwest Airlines flies direct from Seattle to Chicago Midway.
As of April 2026, there are 15 flights per week flying from Seattle to Chicago Midway.
The cheapest month to fly from Seattle to Chicago Midway is usually May.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Seattle to Chicago Midway Airport on Monday, May 4, 2026.
Yes – the average flight time is 3 hours and 59 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

Travelling from Seattle to Chicago Midway International Airport (MDW): what you need to know

  • Seattle's main airport is Seattle-Tacoma International Airport (SEA). Explore your options for departing from this terminal when searching for flights from Seattle to Chicago Midway International Airport (MDW).

  • Take a direct flight from Seattle to Chicago Midway International Airport and you'll be travelling for around 4 hours 1 minute.

  • Chicago is 2 hours ahead of Seattle. Chicago Midway International Airport is located in Chicago, which operates on the UTC-5 timezone.

  • With 9 direct weekly flights between the two airports, Seattle-Tacoma International Airport (SEA) to Chicago Midway International Airport (MDW) is the busiest route. Southwest Airlines operates the earliest flight at 05:10. If you prefer to get more out of your day before you fly, the last flight from SEA to MDW is with Southwest Airlines at 18:45.

  • Your flight from Seattle to MDW won't wait if you're late, so be at the airport on time. Arrive up to one hour in advance for domestic flights and two hours ahead when you're flying internationally.

  • If you're getting away during a peak month like July, get to the airport even earlier. It's wise to arrive up to four hours before an international flight and two hours ahead of domestic departures. Expect lines to be longer during peak periods like summer and spring break.

Airports in Seattle

Seattle-Tacoma International Airport (SEA)

  • Get there in one go from Seattle-Tacoma International Airport (SEA). Nonstop flights from Seattle to Chicago Midway International Airport (MDW) can be booked from here.

  • Southwest Airlines is a well-known airline that operates direct flights from Seattle to Chicago Midway International Airport jetting out of SEA.

  • The distance from central Seattle to SEA is around 23 kilometres. Use travel apps like Google Maps for the quickest way to get there, whether you want to drive or use public transport.

  • Catching an early flight from Seattle to Chicago Midway International Airport? Avoid the stress of rushing to the terminal (and get some extra shut-eye) by picking one of these stays close to Seattle-Tacoma International Airport:

Lake Union Sea Plane Base (LKE)

About Chicago Midway International Airport (MDW)

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • Chicago Midway International Airport to the centre of Chicago is around 21 minutes in a car. It's approximately 19 kilometres away. See what options are available, such as cabs, car rentals or ride-sharing.

  • If you're travelling by public transport, expect a journey of about 46 minutes.

How to find the cheapest flights from Seattle to Chicago Midway International Airport (MDW)

  • For a one-way ticket from Seattle to Chicago Midway International Airport, C$177 is the best price we've seen. You can also book a return flight starting from C$349. These are currently the lowest fares and may differ based on availability.

  • 11 months before your departure is the best time to score flight tickets from Seattle to MDW.

  • Organize your trip for August. That's the cheapest month for tickets from Seattle to Chicago Midway International Airport. If you're flexible with your dates, use the 'Whole month' tool to find the best price across each month.

  • Create a Price Alert for flight tickets from Seattle to MDW. There's no need to check back in every day to find out if fares have dropped. We'll update you the moment there's a change in price.

  • Use the filters to tailor your flights from Seattle to Chicago Midway International Airport. Simply select your ideal departure and arrival times, number of stops and airlines. You can also sort your results by 'Cheapest' to find the best deals.

The best time to fly from Seattle to Chicago Midway International Airport (MDW)

  • July is the most popular month to catch a flight from Seattle to Chicago Midway International Airport while May is the quietest. To work out the ideal time to go to Chicago, consider the pace you prefer to travel at.

  • Think about the kind of weather that'll suit your plans for Chicago. July is known as the warmest month. Book your flights from Seattle to MDW during then and you can expect temperatures of between 15ºC and 29ºC.

  • January sees average temperatures of between -12ºC and 3ºC. Look for cheap flights from Seattle to Chicago Midway International Airport sometime around then if you like cooler conditions.

More about Chicago

Complete your Chicago trip with a car rental

  • We use the same magic that helped you find your cheap flight from Seattle to Chicago Midway International Airport to track down your perfect ride. Browse our car rentals in Chicago and compare offers in one place. Plus we give you all the info you need to know, from the most popular rental company to the average daily price.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.