SEARCH ONE AND DONE. - Compare hundreds of travel sites at once.
Choose where to book.
Find deals from over 400 airlines worldwide.

Cheap Flights from Chicago to Portland (MDW - PDX)

DepartReturn
1 adult
Note: some airlines charge for infants in laps.
The price shown for each flight will be the average for all passengers including any infants.
Choose Sites to Compare vs. KAYAK all | none

Best fares from MDW to PDX (Found by others)

Sun Mon Tue Wed Thu Fri Sat
        1 $326 2 $326 3 $302
4 $369 5 $326 6 $326 7 $326 8 $350 9 $320 10 $330
11 $413 12 $350 13 $350 14 $320 15 $380 16 $388 17 $354
18 $470 19 $482 20 $409 21 $388 22 $492 23 $433 24 $349
25 $366 26 $461 27 $394 28 $373 29 $359 30 $342 31 $352
KAYAK searches hundreds of sites to find the best rate for your next flight from Chicago to Portland. Get the best flight deal for your Portland trip!
Here's how it works. Search KAYAK for a flight ticket from Chicago to Portland. Sort, filter and compare results on one web page. Then book your plane ticket direct on the airline or travel agent site of your choice!
Select an airline:  AirTran
Direct flights MDW to PDX on AirTran
Flight # Depart MDW Arrive PDX Sun Mon Tue Wed Thu Fri Sat Valid Between
5232 8:30 am 10:50 am May 25 - May 25
5383 8:30 am 10:50 am Apr 27 - May 23
5383 8:30 am 10:50 am May 27 - Jun 6
3296 9:10 am 11:30 am Apr 19 - Apr 26
3296 9:10 am 11:30 am May 3 - May 17
4446 9:10 am 11:30 am May 24 - May 24
2493 7:15 pm 9:40 pm May 27 - Jun 6
2493 7:15 pm 9:40 pm Apr 27 - May 23
2948 7:15 pm 9:35 pm May 25 - May 25
2948 7:15 pm 9:35 pm May 26 - May 26