Use the Orange Line train for a quick, cost-effective trip to MDW, taking less than 30 minutes from downtown Chicago.

Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $177 (Southwest) |
One-way from | $95 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $564 |
Good round-trip deal | $157 or less |
Good one-way deal | $153 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSeattle
MDW - SEA
MDWSEA
Chicago Midway
Wed 2/4
10:35 am-1:15 pm
Nonstop4h 40m
Seattle/Tacoma Intl
Sat 2/7
10:45 am-4:45 pm
Nonstop4h 00m
ChicagoSeattle
MDW - SEA
MDWSEA
Chicago Midway
Tue 3/3
10:35 am-1:15 pm
Nonstop4h 40m
Seattle/Tacoma Intl
Fri 3/6
11:55 pm-5:50 am
Nonstop3h 55m
ChicagoSeattle
MDW - SEA
MDWSEA
Chicago Midway
Wed 1/21
10:35 am-1:15 pm
Nonstop4h 40m
Seattle/Tacoma Intl
Sun 1/25
6:35 am-12:35 pm
Nonstop4h 00m
ChicagoSeattle
MDW - SEA
MDWSEA
Chicago Midway
Thu 1/22
10:35 am-1:15 pm
Nonstop4h 40m
Seattle/Tacoma Intl
Tue 1/27
6:45 am-12:40 pm
Nonstop3h 55m
ChicagoSeattle
MDW - SEA
MDWSEA
Chicago Midway
Sat 1/24
8:15 am-11:00 am
Nonstop4h 45m
Seattle/Tacoma Intl
Wed 1/28
6:45 am-12:40 pm
Nonstop3h 55m
ChicagoSeattle
MDW - SEA
MDWSEA
Chicago Midway
Thu 2/26
11:00 am-1:35 pm
Nonstop4h 35m
Seattle/Tacoma Intl
Sun 3/1
7:25 am-1:30 pm
Nonstop4h 05m
ChicagoSeattle
MDW - SEA
MDWSEA
Chicago Midway
Thu 3/5
9:55 pm-12:30 am
Nonstop4h 35m
Seattle/Tacoma Intl
Sun 3/8
11:55 pm-5:50 am
Nonstop3h 55m
ChicagoSeattle
MDW - SEA
MDWSEA
Chicago Midway
Sun 1/25
8:10 am-2:05 pm
1 stop7h 55m
Seattle/Tacoma Intl
Sun 2/1
6:35 am-12:35 pm
Nonstop4h 00m
ChicagoSeattle
MDW - SEA
MDWSEA
Chicago Midway
Thu 2/26
7:55 am-2:25 pm
1 stop8h 30m
Seattle/Tacoma Intl
Mon 3/2
6:35 am-12:35 pm
Nonstop4h 00m
ChicagoSeattle
MDW - SEA
MDWSEA
Chicago Midway
Tue 1/27
10:05 am-5:50 pm
1 stop9h 45m
Seattle/Tacoma Intl
Tue 2/3
6:45 am-12:40 pm
Nonstop3h 55m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars |
Booking 58 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago Midway Airport to Seattle. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Seattle (average of $121). Flying from Chicago Midway Airport to Seattle in December is currently the most expensive (average of $464). 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.
It’s typically best to fly out from Chicago Midway Airport to Seattle in the evening. Doing so could potentially save you 48% on the flight price compared to flying in the afternoon, which is usually more expensive.
Entertainment
Overall
Comfort
Food
Crew
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Overall
Comfort
Food
Crew
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Overall
Comfort
Food
Crew
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$142 | Average$270 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$194 | Average$413 | FlexibilityNo cancel fee | On-time63% |