Cheap Flights from Seattle to Chicago Midway

Compare Seattle to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from Seattle to Chicago Midway Airport

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 $444. Find the lowest prices on one-way and return tickets right here.

Chicago.$444 per passenger.Departing Sat, 9 May, returning Tue, 12 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Seattle / Tacoma International on Sat, 9 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 12 May, arriving in Seattle / Tacoma International.Price includes taxes and charges.From $444, select.

Chicago.$448 per passenger.Departing Wed, 29 Apr, returning Sat, 2 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Seattle / Tacoma International on Wed, 29 Apr, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 2 May, arriving in Seattle / Tacoma International.Price includes taxes and charges.From $448, select.

Chicago.$532 per passenger.Departing Tue, 21 Apr, returning Wed, 29 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Seattle / Tacoma International on Tue, 21 Apr, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 29 Apr, arriving in Seattle / Tacoma International.Price includes taxes and charges.From $532, select.

Chicago.$536 per passenger.Departing Wed, 13 May, returning Thu, 11 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Seattle / Tacoma International on Wed, 13 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 11 Jun, arriving in Seattle / Tacoma International.Price includes taxes and charges.From $536, select.

Chicago.$619 per passenger.Departing Wed, 15 Jul, returning Mon, 20 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Seattle / Tacoma International on Wed, 15 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 20 Jul, arriving in Seattle / Tacoma International.Price includes taxes and charges.From $619, select.

Chicago.$619 per passenger.Departing Wed, 1 Jul, returning Sat, 1 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Seattle / Tacoma International on Wed, 1 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 1 Aug, arriving in Seattle / Tacoma International.Price includes taxes and charges.From $619, select.

Chicago.$619 per passenger.Departing Wed, 10 Jun, returning Tue, 16 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Seattle / Tacoma International on Wed, 10 Jun, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 16 Jun, arriving in Seattle / Tacoma International.Price includes taxes and charges.From $619, select.

Chicago.$619 per passenger.Departing Fri, 14 Aug, returning Sun, 16 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Seattle / Tacoma International on Fri, 14 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 16 Aug, arriving in Seattle / Tacoma International.Price includes taxes and charges.From $619, select.

Chicago.$619 per passenger.Departing Tue, 15 Sep, returning Sun, 20 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Seattle / Tacoma International on Tue, 15 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 20 Sep, arriving in Seattle / Tacoma International.Price includes taxes and charges.From $619, select.

Chicago.$623 per passenger.Departing Fri, 25 Sep, returning Fri, 2 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Seattle / Tacoma International on Fri, 25 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 2 Oct, arriving in Seattle / Tacoma International.Price includes taxes and charges.From $623, select.

Chicago.$623 per passenger.Departing Thu, 25 Jun, returning Mon, 6 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Seattle / Tacoma International on Thu, 25 Jun, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 6 Jul, arriving in Seattle / Tacoma International.Price includes taxes and charges.From $623, select.

Chicago.$624 per passenger.Departing Sat, 24 Oct, returning Sat, 31 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Seattle / Tacoma International on Sat, 24 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 31 Oct, arriving in Seattle / Tacoma International.Price includes taxes and charges.From $624, select.

Chicago.$655 per passenger.Departing Sat, 29 Aug, returning Mon, 7 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Seattle / Tacoma International on Sat, 29 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 7 Sep, arriving in Seattle / Tacoma International.Price includes taxes and charges.From $655, select.

Chicago.$944 per passenger.Departing Thu, 31 Dec, returning Sun, 3 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Seattle / Tacoma International on Thu, 31 Dec, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sun, 3 Jan, arriving in Seattle / Tacoma International.Price includes taxes and charges.From $944, select.

Chicago.$1,380 per passenger.Departing Thu, 20 Aug, returning Sun, 20 Dec.Return flight with Delta.Outbound indirect flight with Delta, departs from Seattle / Tacoma International on Thu, 20 Aug, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sun, 20 Dec, arriving in Seattle / Tacoma International.Price includes taxes and charges.From $1,380, select.

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 May.

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Direct flights from Seattle to Chicago Midway

Seattle to Chicago Midway: Alternative routes

Compare routes from Seattle to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Seattle to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$224
Cheapest month to fly	May
Average flight time	3 hrs, 59 mins
Most popular airline	Southwest Airlines
Average flights per week	13

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

How much are return flights from Seattle to Chicago Midway?

The best price we found for a return flight from Seattle to Chicago Midway is $444. 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.

How long does it take to fly from Seattle to Chicago Midway?

3 hours and 59 minutes is the average flight time from Seattle to Chicago Midway.

Which airlines fly direct from Seattle to Chicago Midway?

Southwest Airlines flies direct from Seattle to Chicago Midway.

How many flights are there a week from Seattle to Chicago Midway?

As of April 2026, there are 13 flights per week flying from Seattle to Chicago Midway.

When is the cheapest time to fly from Seattle to Chicago Midway?

The cheapest month to fly from Seattle to Chicago Midway is usually May.

Which upcoming date is cheapest to fly from Seattle to Chicago Midway Airport on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Seattle to Chicago Midway Airport on Saturday, 9 May 2026.

Can I get a direct flight from Seattle to Chicago Midway Airport?

Yes – the average flight time is 3 hours and 59 minutes.

How can I find the best flight deal to Chicago Midway?

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.

When is the best time to book flights to Chicago?

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.

Which is the cheapest airline to fly from Seattle to Chicago Midway with?

The cheapest airline that flies to Chicago Midway is Southwest Airlines .

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

Your journey comes together at Seattle's main airport, Seattle-Tacoma International Airport (SEA). Check out your options for booking a flight from Seattle to Chicago Midway International Airport (MDW) leaving from this base.
Around 4 hours is how long you'll be travelling on a direct Seattle to Chicago Midway International Airport flight.
Chicago is two hours ahead of Seattle. Chicago Midway International Airport is located in Chicago, which runs on the UTC-5 timezone.
The busiest route is from Seattle-Tacoma International Airport (SEA) to Chicago Midway International Airport (MDW). Choose from 8 direct services each week. Southwest Airlines operates a 5:15am departure between SEA and MDW.
Arrive at the airport on time so you don't miss your flight from Seattle to MDW. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid any last-minute rush.
Travelling during a peak time like a bank holiday? Expect longer queues at check-in and security. For peace of mind, arrive up to four hours before international flights and two hours before domestic departures.

Airports in Seattle

Seattle-Tacoma International Airport (SEA)

You can hop on a direct flight from Seattle to Chicago Midway International Airport (MDW) leaving from Seattle-Tacoma International Airport (SEA).
Southwest Airlines is a popular airline that offers direct flights from Seattle to Chicago Midway International Airport jetting out of SEA.
Southwest Airlines is the most frequently chosen airline for flights from SEA to MDW.
Southwest Airlines leads the way as the most punctual carrier on this route, with 100.0% of services arriving as scheduled.
Located around 23 kilometres from the centre of Seattle, SEA can be reached in about 20 minutes by car (depending on traffic). The journey by public transport takes roughly 55 minutes.
Want a hassle-free start to your travels? Stay near Seattle-Tacoma International Airport. Whether you're catching an early flight from Seattle to Chicago Midway International Airport or aren't a fan of being rushed, these hotels are just the thing:
Seattle-Tacoma International Airport gets high marks for on-time performance. 81.27% of flights that depart SEA arrive at their destination on time.

Lake Union Sea Plane Base Airport (LKE)

You can arrive at LKE from the centre of Seattle in about 10 minutes by car, depending on traffic. The ride by public transport takes roughly 25 minutes to cover the 3 kilometres or so.
Catching the earliest flight? You might like to check in to one of these accommodation options near Lake Union Sea Plane Base Airport the day before your Seattle to MDW flight:

About Chicago Midway International Airport (MDW)

Consider booking a hotel near MDW if you have a late flight from Seattle to Chicago Midway International Airport. Pick one of these options and be in bed sooner:
Explore without limits with a Chicago Midway International Airport rental car. Book your wheels from Dollar, Hertz or Budget and see more of Chicago and beyond.
Booking your ride around four weeks ahead of your Seattle to Chicago Midway International Airport flight can help you get the lowest rate.
You'll find MDW at 5700 South Cicero.

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

Chicago Midway International Airport is roughly 14 kilometres from central Chicago. How long it'll take to get there by cab or car hire depends on the time of day. Do a little research before your trip.
If you're using public transport, expect a journey of about 45 minutes.

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

Currently, $224 is the best price we've found for a one-way ticket from Seattle to Chicago Midway International Airport. The cheapest price for a return flight is $444. Remember fares can change due to availability at the time of booking.
Lock in cheap flights from Seattle to MDW by booking three months ahead. According to our research, that's the sweet spot for picking up a bargain.
August is when you're most likely to land a bargain on a Seattle to Chicago Midway International Airport ticket. If you want to travel at a different time of year, the 'Whole month' tool will show you the lowest prices for every month.
There's no need to check back in every day to find out if fares have dropped when you set up a Price Alert. We'll notify you as soon as a new deal shows up on flight tickets from Seattle to MDW.
Discover the best deal on a flight from Seattle to Chicago Midway International Airport with the help of the filters. Pick your ideal departure and arrival times, airlines and number of stops. You can also sort your results by 'Cheapest,' 'Best' or 'Fastest.'

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

It's time to work out your travel dates for your flight from Seattle to Chicago Midway International Airport (MDW). July is when most people travel to Chicago. If crowds aren't your thing, think about going in May.
Book a Seattle to MDW flight ticket departing in July if you want to experience the city during its warmest month. Expect temperatures in Chicago to range from 15ºC to 29ºC.
Look for cheap tickets from Seattle to Chicago Midway International Airport in January if you'd rather travel during cooler conditions. Temperatures are at their lowest then, ranging between -12ºC and 3ºC.

More about Chicago

After booking your flight from Seattle to Chicago Midway International Airport, find a hotel that's got location and comfort covered. Make one of these accommodation options your base for exploring Chicago:
You'll find loads of terrific things to do in Chicago when you're in the mood to sightsee. Head straight for Millennium Park followed by Lollapalooza and Art Institute of Chicago.

Explore more of the United States

You've seen Chicago, now it's time to explore other parts of the United States. Travel around 257 kilometres south-east to Indianapolis to check off its top sights. From 9-11 Memorial to Lucas Oil Stadium and Eiteljorg Museum, you'll have a packed itinerary ahead.
Around 137 kilometres north of Chicago, Milwaukee is another essential stop in the United States. Experience major highlights starting with Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo.