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 (Delta) |
One-way from | $91 (Southwest) |
Popular in | December |
Cheapest in | January |
Average price | $564 |
Good one-way deal | $138 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSeattle
MDW - SEA
MDWSEA
Chicago Midway
Mon 3/2
8:05 am-10:50 am
Nonstop4h 45m
Seattle/Tacoma Intl
Sat 3/7
11:55 pm-5:50 am
Nonstop3h 55m
ChicagoSeattle
MDW - SEA
MDWSEA
Chicago Midway
Thu 1/8
2:10 pm-11:05 pm
2 stops10h 55m
Seattle/Tacoma Intl
Tue 1/13
11:20 am-9:50 pm
2 stops8h 30m
ChicagoSeattle
MDW - SEA
MDWSEA
Chicago Midway
Mon 1/12
9:55 am-5:50 pm
2 stops9h 55m
Seattle/Tacoma Intl
Wed 1/21
8:45 am-7:55 pm
2 stops9h 10m
ChicagoSeattle
MDW - SEA
MDWSEA
Chicago Midway
Sat 1/17
8:20 am-8:10 pm
1 stop13h 50m
Seattle/Tacoma Intl
Mon 1/19
6:15 pm-5:15 am
2 stops9h 00m
ChicagoSeattle
MDW - SEA
MDWSEA
Chicago Midway
Mon 3/2
8:10 am-2:05 pm
1 stop7h 55m
Seattle/Tacoma Intl
Sun 3/8
7:55 pm-10:20 am
1 stop12h 25m
ChicagoSeattle
MDW - SEA
MDWSEA
Chicago Midway
Thu 2/12
11:00 am-1:35 pm
Nonstop4h 35m
Seattle/Tacoma Intl
Sun 2/15
6:35 am-12:35 pm
Nonstop4h 00m
ChicagoSeattle
MDW - SEA
MDWSEA
Chicago Midway
Fri 1/16
8:05 am-5:40 pm
1 stop11h 35m
Seattle/Tacoma Intl
Mon 1/19
6:15 pm-5:15 am
2 stops9h 00m
ChicagoSeattle
MDW - SEA
MDWSEA
Chicago Midway
Fri 1/16
6:45 am-2:18 pm
1 stop9h 33m
Seattle/Tacoma Intl
Fri 1/23
11:10 pm-8:52 am
1 stop7h 42m
ChicagoSeattle
MDW - SEA
MDWSEA
Chicago Midway
Fri 1/16
1:49 pm-8:46 pm
1 stop8h 57m
Seattle/Tacoma Intl
Mon 1/19
11:10 pm-8:52 am
1 stop7h 42m
ChicagoSeattle
MDW - SEA
MDWSEA
Chicago Midway
Fri 2/6
4:15 pm-10:50 pm
1 stop8h 35m
| 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 $112). Flying from Chicago Midway Airport to Seattle in October is currently the most expensive (average of $304). 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 43% on the flight price compared to flying in the afternoon, which is usually more expensive.
Travelers seeking maximum savings on their Chicago Midway Airport to Seattle flight should consider departing on Tuesday mornings when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Comfort
Overall
Food
Crew
Entertainment
Boarding
Reviews
William Drew,Nov 2025
SJC - HNL
Comfort
Overall
Food
Crew
Entertainment
Boarding
Reviews
William Drew,Nov 2025
SJC - HNL
Comfort
Overall
Food
Crew
Entertainment
Boarding
Reviews
William Drew,Nov 2025
SJC - HNL
Comfort
Overall
Food
Crew
Entertainment
Boarding
Reviews
William Drew,Nov 2025
SJC - HNL
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$142 | Average$270 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$169 | Average$353 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$189 | Average$422 | FlexibilityNo cancel fee | On-time63% |