When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 59 days in advance, which can save you up to 23% on flights from Oregon to Chicago Midway Airport compared to booking the week you need them. Waiting 59 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $331. For sooner than that we have options available in the next 3 days from $615.
Our data shows that November tends to be the cheapest month to fly to Chicago Midway Airport from Oregon. Users have commonly found prices around $365 for the month, but tickets can be as low as $127. Due to multiple factors, prepare for potentially higher prices in June.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oregon to Chicago Midway Airport as you normally would.
Fly from
Fly to
Budget
$169 - $278
Route
Depart
Return
Price
PortlandChicago Midway
PDX - MDW
PDXMDW
Portland
Tue 6/4
1 stop7h 05m
Chicago Midway
Tue 6/11
1 stop11h 50m
PortlandChicago Midway
PDX - MDW
PDXMDW
Portland
Mon 6/3
1 stop11h 14m
Chicago Midway
Thu 6/13
1 stop10h 04m
PortlandChicago Midway
PDX - MDW
PDXMDW
Portland
Mon 9/9
1 stop12h 03m
Chicago Midway
Thu 9/12
1 stop19h 54m
PortlandChicago Midway
PDX - MDW
PDXMDW
Portland
Wed 5/29
1 stop18h 54m
Chicago Midway
Mon 6/3
1 stop17h 15m
PortlandChicago Midway
PDX - MDW
PDXMDW
Portland
Fri 6/7
1 stop18h 41m
Chicago Midway
Sun 6/16
1 stop20h 51m
PortlandChicago Midway
PDX - MDW
PDXMDW
Portland
Sat 6/1
1 stop8h 36m
Chicago Midway
Sat 6/15
1 stop12h 11m
PortlandChicago Midway
PDX - MDW
PDXMDW
Portland
Wed 6/5
2 stops11h 29m
Chicago Midway
Thu 6/13
1 stop10h 04m
Boise Air Term. Gowen FldChicago Midway
BOI - MDW
BOIMDW
Boise Air Term. Gowen Fld
Fri 8/30
1 stop6h 26m
Chicago Midway
Sat 9/7
2 stops11h 38m
Boise Air Term. Gowen FldChicago Midway
BOI - MDW
BOIMDW
Boise Air Term. Gowen Fld
Fri 6/14
2 stops11h 49m
Chicago Midway
Mon 6/17
2 stops8h 12m
No data available for this route at this time. Please check back soon.
Boarding
Crew
Food
Overall
Comfort
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Boarding
Crew
Food
Overall
Comfort
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Boarding
Crew
Food
Overall
Comfort
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Boarding
Crew
Food
Overall
Comfort
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Boarding
Crew
Food
Overall
Comfort
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Boarding
Crew
Food
Overall
Comfort
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
76%of flight departures | Early morningMidnight to 6 am |
---|---|
12%of flight departures | Morning6 am to noon |
12%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Oregon to Midway. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.
It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Oregon to Midway.
Yes, we can. To see specific flights from Oregon to Midway with no change fees, users can toggle flexible booking options after using the search form above to find flights.
Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Midway from Oregon today and book when prices fit your budget.