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Cheap flights from Seattle to Chicago Midway Airport from C$ 226

SEA — MDW
25 Nov — 2 Dec1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Seattle to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Seattle to Midway

Sat 5/126:45 a.m. -
2 stops8h 20m
Thu 10/128:45 p.m. -
Nonstop4h 50m
Deal found 25/10C$ 398
Wed 2/126:30 a.m. -
Nonstop3h 55m
Mon 7/128:45 p.m. -
1 stop13h 45m
Deal found 26/10C$ 399
Mon 7/126:30 a.m. -
Nonstop3h 55m
Fri 11/129:45 p.m. -
Nonstop4h 50m
Deal found 23/10C$ 402
Mon 30/1112:15 a.m. -
Nonstop3h 50m
Fri 4/1210:10 a.m. -
Nonstop4h 40m
Deal found 26/10C$ 405
Tue 17/116:30 a.m. -
Nonstop3h 55m
Mon 23/119:45 p.m. -
Nonstop4h 50m
Deal found 23/10C$ 408
Wed 2/126:30 a.m. -
Nonstop3h 55m
Wed 2/128:45 p.m. -
Nonstop4h 50m
Deal found 22/10C$ 410
Mon 16/118:15 p.m. -
1 stop7h 40m
Mon 23/113:35 p.m. -
1 stop11h 45m
Deal found 26/10C$ 412
Thu 12/1112:15 a.m. -
Nonstop3h 50m
Wed 18/118:45 p.m. -
Nonstop4h 50m
Deal found 24/10C$ 413
Mon 9/115:30 a.m. -
Nonstop3h 50m
Tue 17/1110:15 a.m. -
2 stops9h 35m
Deal found 23/10C$ 415
Sat 5/126:45 a.m. -
2 stops8h 20m
Mon 7/128:45 p.m. -
1 stop13h 45m
Deal found 26/10C$ 420

Find flight deals from Seattle to Midway

Round-trip from

C$ 398

One-way from

C$ 226

Popular in

March

Cheapest in

January

Average price

C$ 676
Southwest
  • Southwest
  • 5/12-10/12
  • 2 total stops
  • 13h 10m total
  • Seattle to Chicago
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Southwest
  • Southwest
  • 15/12-31/12
  • 2 total stops
  • 11h 05m total
  • Seattle to Chicago
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 53 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease (C$ 22 potential savings vs. average RT price).
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Average for round-trip flights in October 2026
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Seattle to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

SeattleChicago

SEA Seattle/Tacoma Intl - MDW Chicago Midway

SEAMDW

Seattle/Tacoma Intl

Thu 3/12

6:10 a.m.-5:05 p.m.

2 stops8h 55m

Chicago Midway

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 227

SeattleChicago

SEA Seattle/Tacoma Intl - MDW Chicago Midway

SEAMDW

Seattle/Tacoma Intl

Mon 21/12

8:40 p.m.-8:20 a.m.

1 stop9h 40m

Chicago Midway

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 227

SeattleChicago

SEA Seattle/Tacoma Intl - MDW Chicago Midway

SEAMDW

Seattle/Tacoma Intl

Sat 14/11

5:30 a.m.-5:25 p.m.

2 stops9h 55m

Chicago Midway

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 231

SeattleChicago

SEA Seattle/Tacoma Intl - MDW Chicago Midway

SEAMDW

Seattle/Tacoma Intl

Tue 8/12

6:30 a.m.-12:25 p.m.

Nonstop3h 55m

Chicago Midway

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 231

SeattleChicago

SEA Seattle/Tacoma Intl - MDW Chicago Midway

SEAMDW

Seattle/Tacoma Intl

Mon 7/12

8:05 a.m.-5:15 p.m.

1 stop7h 10m

Chicago Midway

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 245

SeattleChicago

SEA Seattle/Tacoma Intl - MDW Chicago Midway

SEAMDW

Seattle/Tacoma Intl

Sat 9/1

7:05 a.m.-1:10 p.m.

Nonstop4h 05m

Chicago Midway

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 265
Quickest round-trip

SeattleChicago

SEA Seattle/Tacoma Intl - MDW Chicago Midway

SEAMDW

Seattle/Tacoma Intl

Fri 20/11

12:15 a.m.-6:05 a.m.

Nonstop3h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 265

SeattleChicago

SEA Seattle/Tacoma Intl - MDW Chicago Midway

SEAMDW

Seattle/Tacoma Intl

Sat 19/12

7:50 p.m.-5:45 a.m.

1 stop7h 55m

Chicago Midway

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 279

SeattleChicago

SEA Seattle/Tacoma Intl - MDW Chicago Midway

SEAMDW

Seattle/Tacoma Intl

Thu 24/12

11:59 p.m.-11:01 a.m.

1 stop9h 02m

Chicago Midway

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 304

SeattleChicago

SEA Seattle/Tacoma Intl - MDW Chicago Midway

SEAMDW

Seattle/Tacoma Intl

Wed 25/11

11:47 p.m.-10:25 a.m.

1 stop8h 38m

Chicago Midway

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 307

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/10

Showing 1-10 of 21 resultsSorted by cheapest first
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Best time to book a flight from Seattle to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Seattle with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Seattle to Chicago Midway Airport

What is the cheapest month to book a flight from Seattle to Chicago Midway Airport?

Currently, January is the cheapest month in which you can book a flight from Seattle to Chicago Midway Airport (average of C$ 444). Flying from Seattle to Chicago Midway Airport in March is currently the most expensive (average of C$ 794). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from SEA to MDW?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Seattle to Chicago Midway Airport as you normally would.

How much does it cost to fly round-trip from Seattle to Chicago Midway Airport?

Airfare is below average for this route at the moment.

Seattle to Chicago Midway Airport flights typically cost between C$ 485 and C$ 932 in December.
The cheapest round-trip price found within the last 5 days was C$ 398 on Southwest (5 Dec-10 Dec).

Related info for your journey

  • What airport do you fly from for flights from Seattle to Chicago Midway?

    If you book a flight to Chicago Midway from Seattle, you will be flying from Seattle/Tacoma Intl, which is the city’s only airport. Seattle/Tacoma Intl (SEA) is located 18.4 km from the centre of Seattle. There is 1 flight from Seattle/Tacoma Intl to Chicago Midway per day from 0 different airlines.

  • How long is the flight from Seattle to Chicago Midway Airport?

    Southwest can get you from Seattle to Chicago Midway Airport in just under 3h 55m. Your travel time will be generally consistent. The distance between Seattle and Chicago Midway Airport is about 2781 km. Generally, flights for this route are direct.

  • Can I find deals for flights from Seattle to Midway that include hotel bookings?

    Yes. In addition to deals on Seattle to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Seattle to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Seattle to Midway.

  • Can I find deals for business class flights from Seattle to Midway?

    Yes. Cheapflights offers flight deals from Seattle to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Seattle to Chicago Midway Airport?

    Currently, January is the cheapest month in which you can book a flight from Seattle to Chicago Midway Airport (average of C$ 444). Flying from Seattle to Chicago Midway Airport in March is currently the most expensive (average of C$ 794). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Seattle to Midway

Seattle to O'Hare Intl flights

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Why should you use Cheapflights to find cheap flight tickets from Seattle to Midway?

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Can Cheapflights find flights from Seattle to Midway with no change fees?

Certainly. Search results for flights to Midway from Seattle shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Midway from Seattle today and book when prices fit your budget.

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