$77+ Cheap flights from Portland, ME (PWM) to Chicago (CHI)
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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Mar 29 — Apr 51
1 adult, Economy
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Find cheap flights from Portland to Chicago 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 Portland to Chicago are usually found in April or September, booked 70 days in advance, depart on a Thursday or Friday and return on a Tuesday
Cheap flight deals from Portland to Chicago
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Cheapest flights from Portland to ChicagoExplore the most affordable flight options available from Portland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 27, 2026.
Explore the most affordable flight options available from Portland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 27, 2026.
This Delta deal was found by Cheapflights users on 2/24. 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 4/86:03 am
PWM
- ORD
2 stops8h 14m
Delta
Fri 4/102:32 pm
ORD
- PWM
1 stop7h 50m
Delta
Deal found 2/24![Delta logo]()
$209
This Delta deal was found by Cheapflights users on 2/25. 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 5/712:55 pm
PWM
- MDW
1 stop6h 38m
Delta
Sun 5/106:23 am
MDW
- PWM
1 stop5h 47m
Delta
Deal found 2/25![Delta logo]()
$213
This Delta deal was found by Cheapflights users on 2/26. 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 4/86:03 am
PWM
- MDW
2 stops7h 26m
Delta
Fri 4/101:10 pm
MDW
- PWM
2 stops9h 12m
Delta
Deal found 2/26![Delta logo]()
$214
This United Airlines deal was found by Cheapflights users on 2/23. 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 4/147:33 pm
PWM
- ORD
1 stop5h 10m
United Airlines
Sat 4/186:10 pm
ORD
- PWM
Nonstop2h 30m
United Airlines
Deal found 2/23![United Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 2/23. 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 5/84:48 pm
PWM
- ORD
1 stop4h 26m
Delta
Sun 5/106:00 am
ORD
- PWM
1 stop6h 10m
Delta
Deal found 2/23![Delta logo]()
$220
This Delta deal was found by Cheapflights users on 2/23. 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 4/145:26 pm
PWM
- ORD
1 stop5h 49m
Delta
Sat 4/186:04 am
ORD
- PWM
1 stop7h 07m
Delta
Deal found 2/23![Delta logo]()
$224
This Delta deal was found by Cheapflights users on 2/24. 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 5/2212:55 pm
PWM
- ORD
1 stop6h 10m
Delta
Sun 5/247:00 am
ORD
- PWM
1 stop4h 00m
Delta
Deal found 2/24![Delta logo]()
$229
This American Airlines deal was found by Cheapflights users on 2/25. 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.
Tue 4/77:23 pm
PWM
- ORD
1 stop5h 11m
American Airlines
Sun 4/127:49 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 2/25![American Airlines logo]()
$230
This Delta deal was found by Cheapflights users on 2/25. 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 4/75:48 pm
PWM
- ORD
1 stop5h 24m
Delta
Sun 4/127:10 am
ORD
- PWM
1 stop3h 59m
Delta
Deal found 2/25![Delta logo]()
$233
This Delta deal was found by Cheapflights users on 2/26. 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 4/112:51 pm
PWM
- MDW
1 stop6h 03m
Delta
Mon 4/61:10 pm
MDW
- PWM
2 stops9h 02m
Delta
Deal found 2/26![Delta logo]()
$234
This United Airlines deal was found by Cheapflights users on 2/26. 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 7/84:51 pm
PWM
- ORD
Nonstop3h 00m
United Airlines
Sat 7/116:18 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 2/26![United Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 2/25. 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 4/86:03 am
PWM
- ORD
2 stops8h 14m
Delta
Sun 4/127:10 am
ORD
- PWM
1 stop3h 59m
Delta
Deal found 2/25![Delta logo]()
$238
Best flights from Portland to ChicagoDiscover carefully curated flight deals from Portland to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 27, 2026.
Discover carefully curated flight deals from Portland to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 27, 2026.
This Delta deal was found by Cheapflights users on 2/25. 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 5/712:55 pm
PWM
- MDW
1 stop6h 38m
Delta
Sun 5/106:23 am
MDW
- PWM
1 stop5h 47m
Delta
Deal found 2/25![Delta logo]()
$213
This United Airlines deal was found by Cheapflights users on 2/25. 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 5/77:10 pm
PWM
- ORD
1 stop5h 34m
United Airlines
Sun 5/107:15 am
ORD
- PWM
Nonstop2h 38m
United Airlines
Deal found 2/25![United Airlines logo]()
$219
This Southwest deal was found by Cheapflights users on 2/26. 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 4/104:50 pm
PWM
- MDW
1 stop6h 30m
Southwest
Mon 4/132:10 pm
MDW
- PWM
2 stops8h 15m
Southwest
Deal found 2/26![Southwest logo]()
$311
This Delta deal was found by Cheapflights users on 2/24. 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 7/226:50 pm
PWM
- ORD
1 stop6h 05m
Delta
Tue 7/289:30 am
ORD
- PWM
1 stop7h 31m
Delta
Deal found 2/24![Delta logo]()
$229
This Delta deal was found by Cheapflights users on 2/26. 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 4/1112:51 pm
PWM
- ORD
1 stop4h 27m
Delta
Sun 4/127:10 am
ORD
- PWM
1 stop3h 59m
Delta
Deal found 2/26![Delta logo]()
$233
This Southwest deal was found by Cheapflights users on 2/26. 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 6/185:20 pm
PWM
- MDW
2 stops8h 20m
Southwest
Sun 6/217:55 pm
MDW
- PWM
Nonstop2h 15m
Southwest
Deal found 2/26![Southwest logo]()
$347
This Delta deal was found by Cheapflights users on 2/24. 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 3/284:48 pm
PWM
- ORD
1 stop4h 29m
Delta
Tue 3/311:57 pm
ORD
- PWM
2 stops8h 15m
Delta
Deal found 2/24![Delta logo]()
$300
This Southwest deal was found by Cheapflights users on 2/26. 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 5/14:50 pm
PWM
- MDW
1 stop6h 30m
Southwest
Fri 5/82:10 pm
MDW
- PWM
2 stops8h 15m
Southwest
Deal found 2/26![Southwest logo]()
$351
This Delta deal was found by Cheapflights users on 2/26. 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 8/2011:38 am
PWM
- MDW
1 stop7h 27m
Delta
Sun 8/236:00 am
MDW
- PWM
1 stop5h 22m
Delta
Deal found 2/26![Delta logo]()
$304
This Southwest deal was found by Cheapflights users on 2/23. 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.
Sun 8/26:45 am
PWM
- MDW
Nonstop2h 35m
Southwest
Tue 8/47:40 am
MDW
- PWM
1 stop5h 35m
Southwest
Deal found 2/23![Southwest logo]()
$359
This Delta deal was found by Cheapflights users on 2/23. 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 4/1411:42 am
PWM
- ORD
2 stops9h 58m
Delta
Sun 4/191:36 pm
ORD
- PWM
2 stops10h 10m
Delta
Deal found 2/23![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 2/26. 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 4/15:30 am
PWM
- MDW
1 stop5h 20m
Southwest
Mon 4/610:35 am
MDW
- PWM
1 stop5h 10m
Southwest
Deal found 2/26![Southwest logo]()
$380
This Delta deal was found by Cheapflights users on 2/26. 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 4/1012:51 pm
PWM
- ORD
1 stop6h 43m
Delta
Wed 4/155:04 pm
ORD
- PWM
2 stops6h 42m
Delta
Deal found 2/26![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 2/26. 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 7/2212:50 pm
PWM
- MDW
1 stop6h 41m
Delta
Tue 7/289:30 am
MDW
- PWM
1 stop5h 45m
Delta
Deal found 2/26![Delta logo]()
$374
This Southwest deal was found by Cheapflights users on 2/23. 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 3/215:30 am
PWM
- MDW
2 stops7h 30m
Southwest
Sun 3/292:10 pm
MDW
- PWM
2 stops8h 55m
Southwest
Deal found 2/23![Southwest logo]()
$468
This Delta deal was found by Cheapflights users on 2/23. 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.
Sun 8/26:50 pm
PWM
- ORD
1 stop6h 05m
Delta
Tue 8/46:00 am
ORD
- PWM
1 stop6h 21m
Delta
Deal found 2/23![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 2/24. 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 4/2112:46 pm
PWM
- MDW
1 stop6h 12m
Delta
Mon 4/279:27 am
MDW
- PWM
2 stops6h 18m
Delta
Deal found 2/24![Delta logo]()
$434
Last-minute flights from Portland to ChicagoDiscover last-minute flight deals from Portland to Chicago. Data last updated February 27, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Chicago. Data last updated February 27, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 2/25. 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 3/115:45 am
PWM
- ORD
Nonstop3h 12m
United Airlines
Mon 3/165:47 pm
ORD
- PWM
Nonstop2h 24m
United Airlines
Deal found 2/25![United Airlines logo]()
$272
This American Airlines deal was found by Cheapflights users on 2/25. 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 3/115:40 pm
PWM
- ORD
Nonstop3h 10m
American Airlines
Mon 3/168:02 pm
ORD
- PWM
Nonstop2h 32m
American Airlines
Deal found 2/25![American Airlines logo]()
$274
This American Airlines deal was found by Cheapflights users on 2/26. 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 3/135:40 pm
PWM
- ORD
Nonstop3h 10m
American Airlines
Tue 3/178:05 pm
ORD
- PWM
Nonstop2h 32m
American Airlines
Deal found 2/26![American Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 2/26. 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 3/134:48 pm
PWM
- ORD
1 stop4h 29m
Delta
Tue 3/172:38 pm
ORD
- PWM
1 stop7h 44m
Delta
Deal found 2/26![Delta logo]()
$269
This American Airlines deal was found by Cheapflights users on 2/25. 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 3/185:58 pm
PWM
- ORD
Nonstop3h 10m
American Airlines
Sat 3/218:02 pm
ORD
- PWM
Nonstop2h 32m
American Airlines
Deal found 2/25![American Airlines logo]()
$229
This American Airlines deal was found by Cheapflights users on 2/23. 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 3/216:49 pm
PWM
- ORD
1 stop4h 57m
American Airlines
Sat 3/288:02 pm
ORD
- PWM
Nonstop2h 32m
American Airlines
Deal found 2/23![American Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 2/24. 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 3/234:48 pm
PWM
- ORD
2 stops8h 06m
Delta
Wed 3/257:00 am
ORD
- PWM
1 stop5h 50m
Delta
Deal found 2/24![Delta logo]()
$234
This American Airlines deal was found by Cheapflights users on 2/23. 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.
Mon 3/236:00 pm
PWM
- ORD
Nonstop3h 10m
American Airlines
Mon 3/303:16 pm
ORD
- PWM
1 stop6h 34m
American Airlines
Deal found 2/23![American Airlines logo]()
$264
This Southwest deal was found by Cheapflights users on 2/24. 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.
Mon 3/235:30 pm
PWM
- MDW
1 stop7h 05m
Southwest
Wed 3/253:35 pm
MDW
- PWM
1 stop6h 30m
Southwest
Deal found 2/24![Southwest logo]()
$294
This United Airlines deal was found by Cheapflights users on 2/26. 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 3/266:00 am
PWM
- ORD
1 stop5h 51m
United Airlines
Thu 4/21:55 pm
ORD
- PWM
Nonstop2h 37m
United Airlines
Deal found 2/26![United Airlines logo]()
$245
This American Airlines deal was found by Cheapflights users on 2/27. 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 3/286:17 am
PWM
- ORD
Nonstop3h 17m
American Airlines
Tue 3/318:05 pm
ORD
- PWM
Nonstop2h 32m
American Airlines
Deal found 2/27![American Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 2/25. 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.
Mon 3/305:30 pm
PWM
- MDW
1 stop7h 05m
Southwest
Tue 3/315:40 pm
MDW
- PWM
1 stop4h 25m
Southwest
Deal found 2/25![Southwest logo]()
$316
One-way flights from Portland to ChicagoSearch for one-way flight options from Portland to Chicago. Find affordable one-way fares based on user searches. Data last updated February 27, 2026.
Search for one-way flight options from Portland to Chicago. Find affordable one-way fares based on user searches. Data last updated February 27, 2026.
This JetBlue deal was found by Cheapflights users on 2/26. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
PWM
- ORD
1 stop5h 17m
JetBlue
Deal found 2/26![JetBlue logo]()
$77
This Expedia deal was found by Cheapflights users on 2/23. 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.
Wed 6/106:00 am
PWM
- ORD
1 stop5h 17m
JetBlue
Deal found 2/23![JetBlue logo]()
$89
This Delta deal was found by Cheapflights users on 2/23. 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 4/225:26 pm
PWM
- ORD
1 stop5h 49m
Delta
Deal found 2/23![Delta logo]()
$99
This Delta deal was found by Cheapflights users on 2/24. 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 4/2312:46 pm
PWM
- MDW
1 stop6h 12m
Delta
Deal found 2/24![Delta logo]()
$99
This Southwest deal was found by Cheapflights users on 2/24. 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 7/37:40 am
PWM
- MDW
Nonstop2h 35m
Southwest
Deal found 2/24![Southwest logo]()
$105
This Delta deal was found by Cheapflights users on 2/23. 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 4/244:43 pm
PWM
- ORD
1 stop4h 57m
Delta
Deal found 2/23![Delta logo]()
$106
This Delta deal was found by Cheapflights users on 2/24. 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 4/2412:46 pm
PWM
- MDW
1 stop6h 12m
Delta
Deal found 2/24![Delta logo]()
$106
This Delta deal was found by Cheapflights users on 2/24. 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 3/235:23 am
PWM
- ORD
1 stop9h 15m
Delta
Deal found 2/24![Delta logo]()
$115
This Delta deal was found by Cheapflights users on 2/24. 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 3/245:23 am
PWM
- MDW
1 stop7h 39m
Delta
Deal found 2/24![Delta logo]()
$115
This American Airlines deal was found by Cheapflights users on 2/23. 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 3/255:58 pm
PWM
- ORD
Nonstop3h 10m
American Airlines
Deal found 2/23![American Airlines logo]()
$116
This Delta deal was found by Cheapflights users on 2/23. 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 8/253:00 pm
PWM
- ORD
2 stops9h 57m
Delta
Deal found 2/23![Delta logo]()
$120
This Delta deal was found by Cheapflights users on 2/25. 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 4/251:23 pm
PWM
- MDW
2 stops10h 05m
Delta
Deal found 2/25![Delta logo]()
$120
Find flight deals from Portland to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $209 (Delta) |
One-way from | $77 (JetBlue) |
Popular in | December |
Cheapest in | April |
Average price | $389 |
Good round-trip deal | $348 or less |
Good one-way deal | $178 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Chicago 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 27, 2026.
Use the filters below to find and compare flights from Portland to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
PortlandChicago
PWM - MDW
PWMMDW
Portland
Thu 5/7
12:55 pm-6:33 pm
1 stop6h 38m
Chicago Midway
Sun 5/10
6:23 am-1:10 pm
1 stop5h 47m
$213
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 5/7
7:10 pm-11:44 pm
1 stop5h 34m
Chicago O'Hare Intl
Sun 5/10
7:15 am-10:53 am
Nonstop2h 38m
$219
PortlandChicago
PWM - ORD
PWMORD
Portland
Wed 7/22
6:50 pm-11:55 pm
1 stop6h 05m
Chicago O'Hare Intl
Tue 7/28
9:30 am-6:01 pm
1 stop7h 31m
$229
PortlandChicago
PWM - ORD
PWMORD
Portland
Sat 4/11
12:51 pm-4:18 pm
1 stop4h 27m
Chicago O'Hare Intl
Sun 4/12
7:10 am-12:09 pm
1 stop3h 59m
$233
PortlandChicago
PWM - ORD
PWMORD
Portland
Sat 3/28
4:48 pm-8:17 pm
1 stop4h 29m
Chicago O'Hare Intl
Tue 3/31
1:57 pm-11:12 pm
2 stops8h 15m
$300
PortlandChicago
PWM - MDW
PWMMDW
Portland
Thu 8/20
11:38 am-6:05 pm
1 stop7h 27m
Chicago Midway
Sun 8/23
6:00 am-12:22 pm
1 stop5h 22m
$304
PortlandChicago
PWM - MDW
PWMMDW
Portland
Fri 4/10
4:50 pm-10:20 pm
1 stop6h 30m
Chicago Midway
Mon 4/13
2:10 pm-11:25 pm
2 stops8h 15m
$311
PortlandChicago
PWM - ORD
PWMORD
Portland
Tue 4/14
11:42 am-8:40 pm
2 stops9h 58m
Chicago O'Hare Intl
Sun 4/19
1:36 pm-12:46 am
2 stops10h 10m
$339
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 4/10
12:51 pm-6:34 pm
1 stop6h 43m
Chicago O'Hare Intl
Wed 4/15
5:04 pm-12:46 am
2 stops6h 42m
$339
PortlandChicago
PWM - MDW
PWMMDW
Portland
Thu 6/18
5:20 pm-12:40 am
2 stops8h 20m
Chicago Midway
Sun 6/21
7:55 pm-11:10 pm
Nonstop2h 15m
$347
Showing 1-10 of 39 resultsSorted by cheapest first
Compare providers for flights from Portland to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to Chicago in February.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Portland, Maine-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland, Maine-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland, Maine-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Portland, Maine-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Portland, Maine-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Portland to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Portland with our price prediction graph.
PWM-CHI
PWM-ORD
PWM-MDW
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 Portland to Chicago
PWM-CHI
PWM-ORD
PWM-MDW
How far ahead should I book a flight from Portland, Maine to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Portland to Chicago. Price data was last updated on February 20, 2026.
Booking 70 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland, Maine to Chicago. 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 Portland, Maine to Chicago?
Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Chicago (average of $91). Flying from Portland, Maine to Chicago in January is currently the most expensive (average of $123). 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 PWM to CHI?
Find hourly flight availability from Portland to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 27, 2026.
One of the essential ways to save on airfare from Portland, Maine to Chicago is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 41% on airfare.
Weekly flight availability from Portland, Maine to Chicago
Explore weekly flight availability from Portland to Chicago. 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 27, 2026.
The most flights from PWM to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated February 27, 2026.
See what other customers who have flown with Southwest, United Airlines, and American Airlines from Portland to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from Portland to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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Other flights to Chicago
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Complete your trip
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Portland and Chicago flights
Browse other Portland and Chicago flight options. Last updated on February 27, 2026.
Other flights from Portland
Browse through other flights departing from Portland. Flights are based on user searches made on Cheapflights and were last updated on February 27, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Portland to Chicago
Discover the top 4 airlines that operate flights from Portland to Chicago. 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 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$114 | Average$351 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$209 | Average$305 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$223 | Average$370 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$246 | Average$397 | FlexibilityNo cancel fee | On-time63% |