$113+ Cheap flights from Chicago (CHI) to Salem, OR
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Mar 3 — Mar 101
1 adult, Economy
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Find cheap flights from Chicago to Salem with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to Salem are usually found in September or May, booked 60 days in advance, depart on a Wednesday or Tuesday and return on a Friday
Cheap flight deals from Chicago to Salem
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Cheapest flights from Chicago to SalemExplore the most affordable flight options available from Chicago to Salem. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 1, 2026.
Explore the most affordable flight options available from Chicago to Salem. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 1, 2026.
This CheapOair deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/229:18 pm
ORD
- PDX
1 stop13h 41m
Frontier
Mon 4/2712:52 pm
PDX
- ORD
1 stop15h 55m
Frontier
Deal found 1/31![Frontier logo]()
$201
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/306:05 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Sat 6/611:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 1/31![Southwest logo]()
$202
This United Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:15 pm
ORD
- PDX
Nonstop4h 41m
United Airlines
Sat 3/71:00 pm
PDX
- ORD
1 stop6h 29m
United Airlines
Deal found 1/31![United Airlines logo]()
$203
This American Airlines deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:20 am
ORD
- PDX
Nonstop4h 25m
American Airlines
Wed 6/311:30 pm
PDX
- ORD
Nonstop4h 01m
American Airlines
Deal found 1/30![American Airlines logo]()
$204
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/105:45 am
MDW
- PDX
2 stops10h 45m
Southwest
Sat 3/146:20 pm
PDX
- MDW
1 stop9h 35m
Southwest
Deal found 1/31![Southwest logo]()
$206
This Southwest deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2012:05 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Tue 2/246:30 am
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 1/29![Southwest logo]()
$207
This Alaska Airlines deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/42:07 pm
ORD
- PDX
Nonstop4h 43m
Alaska Airlines
Sun 3/87:00 am
PDX
- ORD
Nonstop4h 11m
Alaska Airlines
Deal found 1/30![Alaska Airlines logo]()
$207
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:30 pm
MDW
- PDX
Nonstop4h 30m
Southwest
Sun 3/89:25 pm
PDX
- MDW
1 stop6h 30m
Southwest
Deal found 1/31![Southwest logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/68:42 pm
ORD
- PDX
2 stops39h 27m
Multiple Airlines
Mon 3/912:04 pm
PDX
- ORD
1 stop10h 53m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$208
This Orbitz deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:21 pm
ORD
- PDX
1 stop18h 36m
Multiple Airlines
Sun 4/267:55 am
PDX
- ORD
Nonstop4h 13m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:30 am
MDW
- PDX
1 stop8h 05m
Southwest
Sat 3/146:20 pm
PDX
- MDW
1 stop9h 35m
Southwest
Deal found 1/31![Southwest logo]()
$210
This Alaska Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/113:54 pm
ORD
- PDX
1 stop8h 47m
Alaska Airlines
Sat 3/143:52 pm
PDX
- ORD
1 stop6h 04m
Alaska Airlines
Deal found 2/1![Alaska Airlines logo]()
$210
Best flights from Chicago to SalemDiscover carefully curated flight deals from Chicago to Salem that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 1, 2026.
Discover carefully curated flight deals from Chicago to Salem that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 1, 2026.
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/105:45 am
MDW
- PDX
2 stops10h 45m
Southwest
Sat 3/146:20 pm
PDX
- MDW
1 stop9h 35m
Southwest
Deal found 1/31![Southwest logo]()
$206
This United Airlines deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/249:10 am
ORD
- PDX
Nonstop4h 45m
United Airlines
Thu 2/2611:59 pm
PDX
- ORD
Nonstop3h 54m
United Airlines
Deal found 1/29![United Airlines logo]()
$207
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/112:05 pm
MDW
- PDX
1 stop8h 20m
Delta
Fri 3/1312:30 am
PDX
- MDW
1 stop6h 20m
Delta
Deal found 2/1![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2012:05 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Wed 2/256:30 am
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 1/29![Southwest logo]()
$207
This United Airlines deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/149:10 am
ORD
- PDX
Nonstop4h 45m
United Airlines
Sat 2/2111:59 pm
PDX
- ORD
Nonstop3h 54m
United Airlines
Deal found 1/30![United Airlines logo]()
$214
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/241:49 pm
MDW
- PDX
1 stop8h 41m
Delta
Tue 3/312:09 pm
PDX
- MDW
1 stop8h 24m
Delta
Deal found 1/31![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/288:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Mon 5/411:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 1/30![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/241:49 pm
MDW
- PDX
1 stop8h 41m
Delta
Sat 2/289:45 pm
PDX
- MDW
1 stop10h 09m
Delta
Deal found 1/29![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/109:06 am
ORD
- PDX
Nonstop4h 45m
United Airlines
Sat 3/144:07 pm
PDX
- ORD
1 stop5h 45m
United Airlines
Deal found 1/31![United Airlines logo]()
$217
This Southwest deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/298:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Mon 5/411:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 1/30![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/32:20 pm
ORD
- PDX
1 stop8h 35m
Delta
Wed 3/111:45 pm
PDX
- ORD
1 stop5h 49m
Delta
Deal found 1/30![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/126:17 am
ORD
- PDX
1 stop8h 16m
United Airlines
Sun 3/1511:59 pm
PDX
- ORD
Nonstop3h 54m
United Airlines
Deal found 1/31![United Airlines logo]()
$227
This Southwest deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2012:05 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Tue 2/246:30 am
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 1/29![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:40 am
ORD
- PDX
1 stop9h 31m
Delta
Wed 3/412:09 pm
PDX
- ORD
1 stop9h 47m
Delta
Deal found 1/30![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/109:25 pm
ORD
- PDX
Nonstop4h 33m
United Airlines
Sat 4/188:40 am
PDX
- ORD
1 stop8h 14m
United Airlines
Deal found 1/31![United Airlines logo]()
$227
This Southwest deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/510:20 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Wed 3/1111:55 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 1/30![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1812:14 pm
ORD
- PDX
1 stop7h 18m
Delta
Mon 4/2012:30 am
PDX
- ORD
1 stop6h 08m
Delta
Deal found 2/1![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/295:30 pm
MDW
- PDX
1 stop6h 30m
Southwest
Tue 5/511:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 1/30![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/42:20 pm
ORD
- PDX
1 stop6h 28m
Delta
Sat 3/712:05 am
PDX
- ORD
1 stop5h 35m
Delta
Deal found 2/1![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/258:25 am
MDW
- PDX
1 stop7h 10m
Southwest
Sat 2/2810:00 am
PDX
- MDW
1 stop8h 00m
Southwest
Deal found 1/29![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/137:10 pm
ORD
- PDX
1 stop6h 44m
Delta
Mon 3/1612:30 am
PDX
- ORD
1 stop6h 10m
Delta
Deal found 1/30![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/510:20 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Sun 3/86:15 am
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 1/29![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/137:10 pm
ORD
- PDX
1 stop6h 44m
Delta
Sat 3/141:49 pm
PDX
- ORD
1 stop8h 02m
Delta
Deal found 1/31![Delta logo]()
$227
This Delta deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/22:20 pm
ORD
- PDX
1 stop8h 35m
Delta
Tue 3/106:30 am
PDX
- ORD
1 stop8h 19m
Delta
Deal found 1/30![Delta logo]()
$227
Last-minute flights from Chicago to SalemDiscover last-minute flight deals from Chicago to Salem. Data last updated February 1, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Salem. Data last updated February 1, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/149:46 pm
ORD
- PDX
Nonstop4h 31m
American Airlines
Wed 2/1811:35 pm
PDX
- ORD
Nonstop3h 57m
American Airlines
Deal found 1/31![American Airlines logo]()
$211
This Southwest deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/148:30 pm
MDW
- PDX
Nonstop4h 30m
Southwest
Fri 2/206:45 am
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 1/30![Southwest logo]()
$224
This Alaska Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/182:07 pm
ORD
- PDX
Nonstop4h 43m
Alaska Airlines
Tue 2/247:00 am
PDX
- ORD
Nonstop4h 11m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$214
This Alaska Airlines deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/182:07 pm
ORD
- PDX
Nonstop4h 43m
Alaska Airlines
Thu 2/197:00 am
PDX
- ORD
Nonstop4h 11m
Alaska Airlines
Deal found 1/29![Alaska Airlines logo]()
$224
This Southwest deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2012:05 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Wed 2/256:30 am
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 1/29![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/251:49 pm
MDW
- PDX
1 stop8h 41m
Delta
Fri 2/2712:40 am
PDX
- MDW
1 stop8h 23m
Delta
Deal found 1/30![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:25 am
ORD
- PDX
1 stop8h 13m
United Airlines
Sat 2/287:00 am
PDX
- ORD
Nonstop4h 04m
United Airlines
Deal found 1/29![United Airlines logo]()
$217
This American Airlines deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/279:46 pm
ORD
- PDX
Nonstop4h 31m
American Airlines
Sun 3/111:35 pm
PDX
- ORD
Nonstop3h 57m
American Airlines
Deal found 1/30![American Airlines logo]()
$220
This United Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:15 pm
ORD
- PDX
Nonstop4h 41m
United Airlines
Sat 3/71:00 pm
PDX
- ORD
1 stop6h 29m
United Airlines
Deal found 1/31![United Airlines logo]()
$203
This Alaska Airlines deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/282:07 pm
ORD
- PDX
Nonstop4h 43m
Alaska Airlines
Fri 3/67:00 am
PDX
- ORD
Nonstop4h 11m
Alaska Airlines
Deal found 1/30![Alaska Airlines logo]()
$207
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:30 pm
MDW
- PDX
Nonstop4h 30m
Southwest
Sun 3/89:25 pm
PDX
- MDW
1 stop6h 30m
Southwest
Deal found 1/31![Southwest logo]()
$208
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/283:15 pm
MDW
- PDX
1 stop9h 15m
Southwest
Sat 3/76:20 pm
PDX
- MDW
1 stop9h 35m
Southwest
Deal found 1/31![Southwest logo]()
$220
One-way flights from Chicago to SalemSearch for one-way flight options from Chicago to Salem. Find affordable one-way fares based on user searches. Data last updated February 1, 2026.
Search for one-way flight options from Chicago to Salem. Find affordable one-way fares based on user searches. Data last updated February 1, 2026.
This Trip.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:00 am
ORD
- PDX
1 stop6h 33m
Hawaiian Airlines
Deal found 1/31![Hawaiian Airlines logo]()
$113
This Southwest deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/185:45 am
MDW
- PDX
2 stops10h 45m
Southwest
Deal found 2/1![Southwest logo]()
$114
This Southwest deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/178:10 am
MDW
- PDX
Nonstop4h 35m
Southwest
Deal found 1/30![Southwest logo]()
$116
This Alaska Airlines deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/172:07 pm
ORD
- PDX
Nonstop4h 43m
Alaska Airlines
Deal found 1/30![Alaska Airlines logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/158:25 am
ORD
- PDX
2 stops28h 38m
Frontier
Deal found 1/30![Frontier logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/279:18 pm
ORD
- PDX
2 stops17h 44m
Frontier
Deal found 1/31![Frontier logo]()
$118
This Delta deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/132:12 pm
MDW
- PDX
1 stop7h 53m
Delta
Deal found 1/30![Delta logo]()
$119
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:25 pm
ORD
- PDX
1 stop8h 20m
Southwest
Deal found 1/31![Southwest logo]()
$119
This Southwest deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/283:15 pm
MDW
- PDX
1 stop9h 15m
Southwest
Deal found 2/1![Southwest logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/24:55 pm
ORD
- PDX
2 stops20h 08m
Frontier
Deal found 1/31![Frontier logo]()
$121
This Frontier deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/239:18 pm
ORD
- PDX
1 stop13h 41m
Frontier
Deal found 2/1![Frontier logo]()
$122
This Southwest deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/178:45 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 2/1![Southwest logo]()
$123
Find flight deals from Chicago to Salem
Keep the following information in mind while searching for Chicago to Salem flight deals. Data was last updated February 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $201 (CheapOair) |
One-way from | $113 (Trip.com) |
Popular in | March |
Cheapest in | September |
Average price | $309 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Salem that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 1, 2026.
Use the filters below to find and compare flights from Chicago to Salem that are best for you.
Fly from
Chicago
Fly to
Salem
Route
Depart
Return
Price
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Tue 3/10
5:45 am-2:30 pm
2 stops10h 45m
Portland
Sat 3/14
6:20 pm-5:55 am
1 stop9h 35m
$206
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Tue 2/24
9:10 am-11:55 am
Nonstop4h 45m
Portland
Thu 2/26
11:59 pm-5:53 am
Nonstop3h 54m
$207
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Fri 2/20
12:05 pm-2:30 pm
Nonstop4h 25m
Portland
Wed 2/25
6:30 am-12:25 pm
Nonstop3h 55m
$207
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Tue 4/28
8:50 pm-11:10 pm
Nonstop4h 20m
Portland
Mon 5/4
11:55 pm-5:50 am
Nonstop3h 55m
$207
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Wed 4/29
8:50 pm-11:10 pm
Nonstop4h 20m
Portland
Mon 5/4
11:55 pm-5:50 am
Nonstop3h 55m
$207
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Fri 2/20
12:05 pm-2:30 pm
Nonstop4h 25m
Portland
Tue 2/24
6:30 am-12:25 pm
Nonstop3h 55m
$207
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Thu 3/5
10:20 pm-12:45 am
Nonstop4h 25m
Portland
Wed 3/11
11:55 pm-5:45 am
Nonstop3h 50m
$207
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Wed 4/29
5:30 pm-10:00 pm
1 stop6h 30m
Portland
Tue 5/5
11:55 pm-5:50 am
Nonstop3h 55m
$207
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Sat 2/14
9:10 am-11:55 am
Nonstop4h 45m
Portland
Sat 2/21
11:59 pm-5:53 am
Nonstop3h 54m
$214
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Wed 3/11
2:05 pm-8:25 pm
1 stop8h 20m
Portland
Fri 3/13
12:30 am-8:50 am
1 stop6h 20m
$217
Showing 1-10 of 41 results
Best time to book a flight from Chicago to Salem
Have a flexible travel schedule? Discover the best time to fly to Salem from Chicago with our price prediction graph.
ORD-PDX
MDW-PDX
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Salem
CHI-SA8
ORD-PDX
MDW-PDX
How far ahead should I book a flight from Chicago to Salem?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Salem. Price data was last updated on January 30, 2026.
Booking 60 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Salem. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Chicago to Salem?
Currently, March is the cheapest month in which you can book a flight from Chicago to Salem (average of $122). Flying from Chicago to Salem in December is currently the most expensive (average of $207). 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 CHI to SA8?
Find hourly flight availability from Chicago to Salem. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 1, 2026.
One of the essential ways to save on airfare from Chicago to Salem is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 25% on airfare.
What is the cheapest day to fly from Chicago to Salem?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Salem. Price data was last updated on January 31, 2026.
Travelers seeking maximum savings on their Chicago to Salem flight should consider departing on Saturday mornings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Salem
Explore weekly flight availability from Chicago to Salem. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 1, 2026.
The most flights from CHI to SA8 are scheduled on a Friday (19 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 on average).
How much does it cost to fly round-trip from Chicago to Salem?
Reviews of airlines servicing Salem
Get insights into the airlines that provide service to Salem. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Salem. Reviews last updated February 1, 2026.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Hawaiian Airlines from Chicago to Salem by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Comfort
7.8
Entertainment
7.0
Boarding
8.1
Crew
8.5
Food
7.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Overall
8.0
Comfort
7.8
Entertainment
7.0
Boarding
8.1
Crew
8.5
Food
7.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Overall
8.0
Comfort
7.8
Entertainment
7.0
Boarding
8.1
Crew
8.5
Food
7.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Overall
8.0
Comfort
7.8
Entertainment
7.0
Boarding
8.1
Crew
8.5
Food
7.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Overall
8.0
Comfort
7.8
Entertainment
7.0
Boarding
8.1
Crew
8.5
Food
7.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Overall
8.0
Comfort
7.8
Entertainment
7.0
Boarding
8.1
Crew
8.5
Food
7.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Related info for your journey
Find useful and relevant information for your journey from Chicago to Salem. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes for Chicago to Salem
See prices for flight routes from nearby airports that may be better suited for you.
Top 8 airlines flying from Chicago to Salem
Discover the top 8 airlines that operate flights from Chicago to Salem. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$178 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$88 | Average$430 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$128 | Average$358 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$150 | Average$227 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$194 | Average$379 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$202 | Average$404 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$204 | Average$312 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$234 | Average$413 | FlexibilityNo cancel fee | On-time63% |