$151+ 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 6/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Jun 8 — Jun 151
Round-trip
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 January or February, booked 42 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday
Cheap flight deals from Chicago to Salem
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Best
Last-minute
One-way
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 May 9, 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 May 9, 2026.
This Expedia deal was found by Cheapflights users on 5/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/107:15 am
ORD
- PDX
1 stop12h 49m
Multiple Airlines
Fri 8/1410:59 pm
PDX
- ORD
Nonstop4h 01m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$294
This SmartFares deal was found by Cheapflights users on 5/5. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:18 pm
ORD
- PDX
Nonstop4h 32m
Alaska Airlines
Sat 5/307:00 am
PDX
- ORD
Nonstop4h 22m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$304
This Southwest deal was found by Cheapflights users on 5/4. 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 7/118:25 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Wed 7/1511:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 5/4![Southwest logo]()
$305
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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 6/177:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Wed 7/110:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$305
This American Airlines deal was found by Cheapflights users on 5/5. 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.
Thu 5/2812:09 pm
ORD
- PDX
Nonstop4h 26m
American Airlines
Sat 6/611:30 am
PDX
- ORD
Nonstop4h 17m
American Airlines
Deal found 5/5![American Airlines logo]()
$306
This American Airlines deal was found by Cheapflights users on 5/6. 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.
Thu 5/289:25 pm
ORD
- PDX
Nonstop4h 27m
American Airlines
Sat 5/3010:59 pm
PDX
- ORD
Nonstop4h 03m
American Airlines
Deal found 5/6![American Airlines logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 5/7. 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.
Thu 6/48:03 pm
MDW
- PDX
1 stop20h 16m
Multiple Airlines
Sun 6/74:06 pm
PDX
- MDW
2 stops27h 56m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$309
This Expedia deal was found by Cheapflights users on 5/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/237:20 am
ORD
- PDX
Nonstop4h 25m
Multiple Airlines
Sun 7/265:42 pm
PDX
- ORD
1 stop10h 35m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 5/9. 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 6/239:10 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Tue 6/3011:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 5/9![Southwest logo]()
$310
This American Airlines deal was found by Cheapflights users on 5/9. 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 7/39:30 pm
ORD
- PDX
Nonstop4h 35m
American Airlines
Tue 7/710:57 pm
PDX
- ORD
Nonstop3h 59m
American Airlines
Deal found 5/9![American Airlines logo]()
$310
This Southwest deal was found by Cheapflights users on 5/7. 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 7/35:00 am
MDW
- PDX
1 stop6h 55m
Southwest
Tue 7/711:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 5/7![Southwest logo]()
$311
This Expedia deal was found by Cheapflights users on 5/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/129:48 pm
ORD
- PDX
1 stop21h 09m
Multiple Airlines
Tue 6/1610:59 pm
PDX
- ORD
Nonstop4h 01m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$313
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 May 9, 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 May 9, 2026.
This United Airlines deal was found by Cheapflights users on 5/6. 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.
Sun 5/247:05 am
ORD
- PDX
Nonstop4h 34m
United Airlines
Fri 5/2911:53 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Deal found 5/6![United Airlines logo]()
$305
This Southwest deal was found by Cheapflights users on 5/4. 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 7/118:25 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Tue 7/147:50 pm
PDX
- MDW
1 stop7h 55m
Southwest
Deal found 5/4![Southwest logo]()
$315
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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.
Sun 6/217:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Tue 6/2310:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$316
This Delta deal was found by Cheapflights users on 5/8. 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 6/265:57 pm
ORD
- PDX
1 stop7h 21m
Delta
Tue 6/309:45 am
PDX
- ORD
1 stop7h 13m
Delta
Deal found 5/8![Delta logo]()
$341
This United Airlines deal was found by Cheapflights users on 5/7. 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 5/295:00 am
ORD
- PDX
1 stop6h 47m
United Airlines
Wed 7/111:40 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Deal found 5/7![United Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 5/4. 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 7/115:10 pm
MDW
- PDX
2 stops7h 10m
Southwest
Wed 7/1511:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 5/4![Southwest logo]()
$320
This Alaska Airlines deal was found by Cheapflights users on 5/7. 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.
Thu 5/282:18 pm
ORD
- PDX
Nonstop4h 32m
Alaska Airlines
Sat 6/65:46 pm
PDX
- ORD
1 stop10h 34m
Alaska Airlines
Deal found 5/7![Alaska Airlines logo]()
$320
This Delta deal was found by Cheapflights users on 5/6. 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.
Thu 5/2812:47 pm
ORD
- PDX
1 stop8h 39m
Delta
Sun 6/710:53 am
PDX
- ORD
1 stop10h 25m
Delta
Deal found 5/6![Delta logo]()
$341
This United Airlines deal was found by Cheapflights users on 5/4. 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 6/161:30 pm
ORD
- PDX
Nonstop4h 27m
United Airlines
Sun 6/2111:40 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Deal found 5/4![United Airlines logo]()
$316
This Southwest deal was found by Cheapflights users on 5/6. 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 6/68:25 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Sat 6/138:20 pm
PDX
- MDW
1 stop6h 50m
Southwest
Deal found 5/6![Southwest logo]()
$325
This Alaska Airlines deal was found by Cheapflights users on 5/4. 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 6/29:00 am
ORD
- PDX
1 stop9h 58m
Alaska Airlines
Sat 6/67:15 am
PDX
- ORD
1 stop9h 35m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 5/8. 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 6/206:55 am
ORD
- PDX
1 stop6h 47m
Delta
Thu 6/2511:15 pm
PDX
- ORD
1 stop6h 50m
Delta
Deal found 5/8![Delta logo]()
$346
This United Airlines deal was found by Cheapflights users on 5/5. 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 7/149:00 am
ORD
- PDX
Nonstop4h 38m
United Airlines
Fri 7/1710:40 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Deal found 5/5![United Airlines logo]()
$316
This Southwest deal was found by Cheapflights users on 5/8. 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 5/297:40 pm
MDW
- PDX
1 stop7h 15m
Southwest
Tue 6/26:40 am
PDX
- MDW
2 stops7h 55m
Southwest
Deal found 5/8![Southwest logo]()
$346
This Alaska Airlines deal was found by Cheapflights users on 5/6. 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 5/307:49 pm
ORD
- PDX
1 stop14h 13m
Alaska Airlines
Fri 6/55:46 pm
PDX
- ORD
1 stop10h 34m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 5/8. 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 7/247:06 pm
MDW
- PDX
1 stop6h 12m
Delta
Tue 7/2812:33 am
PDX
- MDW
1 stop6h 04m
Delta
Deal found 5/8![Delta logo]()
$366
This United Airlines deal was found by Cheapflights users on 5/8. 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 5/284:15 pm
ORD
- PDX
Nonstop4h 32m
United Airlines
Sun 5/317:00 am
PDX
- ORD
Nonstop4h 13m
United Airlines
Deal found 5/8![United Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 5/5. 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 5/2610:10 am
MDW
- PDX
Nonstop4h 20m
Southwest
Sun 5/3111:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 5/5![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 5/7. 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 5/294:35 pm
MDW
- PDX
2 stops10h 20m
Southwest
Wed 7/13:20 pm
PDX
- MDW
1 stop6h 45m
Southwest
Deal found 5/7![Southwest logo]()
$350
This Southwest deal was found by Cheapflights users on 5/8. 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 6/138:25 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Mon 6/158:15 pm
PDX
- MDW
1 stop7h 30m
Southwest
Deal found 5/8![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 5/5. 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 7/229:10 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Wed 7/2911:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 5/5![Southwest logo]()
$375
Last-minute flights from Chicago to SalemDiscover last-minute flight deals from Chicago to Salem. Data last updated May 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Salem. Data last updated May 9, 2026 and is based on user searches.
This SmartFares deal was found by Cheapflights users on 5/5. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:18 pm
ORD
- PDX
Nonstop4h 32m
Alaska Airlines
Sat 5/307:00 am
PDX
- ORD
Nonstop4h 22m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$304
This American Airlines deal was found by Cheapflights users on 5/5. 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.
Thu 5/2812:09 pm
ORD
- PDX
Nonstop4h 26m
American Airlines
Sat 6/611:30 am
PDX
- ORD
Nonstop4h 17m
American Airlines
Deal found 5/5![American Airlines logo]()
$306
This American Airlines deal was found by Cheapflights users on 5/6. 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.
Thu 5/289:25 pm
ORD
- PDX
Nonstop4h 27m
American Airlines
Sat 5/3010:59 pm
PDX
- ORD
Nonstop4h 03m
American Airlines
Deal found 5/6![American Airlines logo]()
$308
This Southwest deal was found by Cheapflights users on 5/6. 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 5/287:40 pm
MDW
- PDX
1 stop7h 15m
Southwest
Sat 6/611:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 5/6![Southwest logo]()
$315
This Southwest deal was found by Cheapflights users on 5/7. 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 5/299:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Wed 7/111:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 5/7![Southwest logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 5/7. 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.
Thu 6/48:03 pm
MDW
- PDX
1 stop20h 16m
Multiple Airlines
Sun 6/74:06 pm
PDX
- MDW
2 stops27h 56m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$309
This Expedia deal was found by Cheapflights users on 5/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/129:48 pm
ORD
- PDX
1 stop21h 09m
Multiple Airlines
Tue 6/1610:59 pm
PDX
- ORD
Nonstop4h 01m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/129:48 pm
ORD
- PDX
1 stop21h 09m
Frontier
Mon 6/155:42 pm
PDX
- ORD
2 stops25h 01m
Frontier
Deal found 5/5![Frontier logo]()
$314
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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 6/177:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Wed 7/110:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$305
This American Airlines deal was found by Cheapflights users on 5/8. 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.
Wed 6/178:00 am
ORD
- PDX
Nonstop4h 25m
American Airlines
Wed 7/110:59 pm
PDX
- ORD
Nonstop4h 01m
American Airlines
Deal found 5/8![American Airlines logo]()
$310
This Southwest deal was found by Cheapflights users on 5/9. 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 6/239:10 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Tue 6/3011:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 5/9![Southwest logo]()
$310
This Alaska Airlines deal was found by Cheapflights users on 5/4. 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 6/277:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Wed 7/110:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$315
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 May 9, 2026.
Search for one-way flight options from Chicago to Salem. Find affordable one-way fares based on user searches. Data last updated May 9, 2026.
This Frontier deal was found by Cheapflights users on 5/4. 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 6/117:20 am
ORD
- PDX
1 stop14h 27m
Frontier
Deal found 5/4![Frontier logo]()
$151
This Southwest deal was found by Cheapflights users on 5/4. 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 5/299:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 5/4![Southwest logo]()
$153
This Alaska Airlines deal was found by Cheapflights users on 5/8. 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.
Fri 7/37:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Deal found 5/8![Alaska Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 5/276:00 am
MDW
- PDX
2 stops36h 46m
Frontier
Deal found 5/6![Frontier logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 5/271:50 pm
ORD
- PDX
2 stops28h 56m
Frontier
Deal found 5/6![Frontier logo]()
$155
This CheapOair deal was found by Cheapflights users on 5/5. 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.
Sat 7/119:13 pm
ORD
- PDX
1 stop16h 25m
Frontier
Deal found 5/5![Frontier logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 6/312:04 pm
MDW
- PDX
2 stops27h 44m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$157
This Booking.com deal was found by Cheapflights users on 5/8. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/159:13 pm
ORD
- PDX
1 stop16h 25m
Frontier
Deal found 5/8![Frontier logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 8/16:00 am
MDW
- PDX
2 stops33h 58m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$158
This Alaska Airlines deal was found by Cheapflights users on 5/7. 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 8/57:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Deal found 5/7![Alaska Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 5/8. 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.
Tue 6/26:00 am
MDW
- PDX
2 stops57h 48m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$159
This Super.com deal was found by Cheapflights users on 5/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/219:37 pm
ORD
- PDX
1 stop21h 09m
Frontier
Deal found 5/5![Frontier logo]()
$159
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 May 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $304 (SmartFares) |
One-way from | $151 (Frontier) |
Popular in | March |
Cheapest in | January |
Average price | $305 |
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 May 9, 2026.
Use the filters below to find and compare flights from Chicago to Salem that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Sun 5/24
7:05 am-9:39 am
Nonstop4h 34m
Portland
Fri 5/29
11:53 pm-5:58 am
Nonstop4h 05m
$305
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Sat 7/11
8:25 pm-10:45 pm
Nonstop4h 20m
Portland
Tue 7/14
7:50 pm-5:45 am
1 stop7h 55m
$315
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Fri 5/29
5:00 am-9:47 am
1 stop6h 47m
Portland
Wed 7/1
11:40 pm-5:45 am
Nonstop4h 05m
$315
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Sun 6/21
7:20 am-9:45 am
Nonstop4h 25m
Portland
Tue 6/23
10:59 pm-5:00 am
Nonstop4h 01m
$316
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Tue 6/16
1:30 pm-3:57 pm
Nonstop4h 27m
Portland
Sun 6/21
11:40 pm-5:45 am
Nonstop4h 05m
$316
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Tue 7/14
9:00 am-11:38 am
Nonstop4h 38m
Portland
Fri 7/17
10:40 pm-4:45 am
Nonstop4h 05m
$316
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Sat 7/11
5:10 pm-10:20 pm
2 stops7h 10m
Portland
Wed 7/15
11:30 pm-5:20 am
Nonstop3h 50m
$320
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Thu 5/28
2:18 pm-4:50 pm
Nonstop4h 32m
Portland
Sat 6/6
5:46 pm-6:20 am
1 stop10h 34m
$320
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Sat 6/6
8:25 pm-10:45 pm
Nonstop4h 20m
Portland
Sat 6/13
8:20 pm-5:10 am
1 stop6h 50m
$325
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Fri 6/26
5:57 pm-11:18 pm
1 stop7h 21m
Portland
Tue 6/30
9:45 am-6:58 pm
1 stop7h 13m
$341
Showing 1-10 of 40 resultsSorted by cheapest first
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
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 May 9, 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 20% 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 May 9, 2026.
Travelers seeking maximum savings on their Chicago to Salem flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday 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 May 9, 2026.
The most flights from CHI to SA8 are scheduled on a Wednesday (27 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 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 May 9, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, andHawaiian 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
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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.
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Alternative routes for Chicago to Salem
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Complete your trip
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Search flights from Chicago to Salem by cabin class
Find flights from Chicago to Salem, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Salem flights
Browse other Chicago and Salem flight options. Last updated on May 9, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on May 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 May 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$178 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$124 | Average$346 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$150 | Average$248 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$189 | Average$350 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$192 | Average$468 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$198 | Average$319 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$199 | Average$389 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$227 | Average$358 | FlexibilityNo cancel fee | On-time63% |