$162+ Cheap flights from Eugene (EUG) 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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
EUG — CHI
Sep 25 — Oct 21
Round-trip
1 adult, Economy
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Find cheap flights from Eugene to Chicago with Cheapflights
1. Tell us where you want to go
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Cheapest flights from Eugene to ChicagoExplore the most affordable flight options available from Eugene to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 26, 2026.
Explore the most affordable flight options available from Eugene to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 26, 2026.
This Expedia deal was found by Cheapflights users on 8/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:08 am -
1 stop10h 13m
Tue 9/292:18 pm -
1 stop8h 06m
Deal found 8/25![Alaska Airlines logo]()
$323
This United Airlines deal was found by Cheapflights users on 8/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:15 pm -
Nonstop4h 11m
Thu 10/19:05 am -
Nonstop4h 45m
Deal found 8/24![United Airlines logo]()
$339
This Alaska Airlines deal was found by Cheapflights users on 8/22. 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 9/252:29 pm -
1 stop20h 53m
Wed 9/302:18 pm -
1 stop8h 06m
Deal found 8/22![Alaska Airlines logo]()
$340
This Alaska Airlines deal was found by Cheapflights users on 8/25. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:08 am -
1 stop28h 14m
Fri 10/23:52 pm -
1 stop6h 58m
Deal found 8/25![Alaska Airlines logo]()
$341
This United Airlines deal was found by Cheapflights users on 8/22. 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 9/192:19 pm -
Nonstop4h 11m
Sat 9/268:40 am -
1 stop6h 32m
Deal found 8/22![United Airlines logo]()
$345
This Alaska Airlines deal was found by Cheapflights users on 8/22. 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.
Mon 9/147:08 am -
1 stop28h 14m
Mon 9/218:17 pm -
1 stop26h 07m
Deal found 8/22![Alaska Airlines logo]()
$353
This Alaska Airlines deal was found by Cheapflights users on 8/25. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:08 am -
1 stop28h 14m
Mon 9/286:00 am -
1 stop9h 44m
Deal found 8/25![Alaska Airlines logo]()
$358
This Delta deal was found by Cheapflights users on 8/25. 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.
Sun 9/2012:32 pm -
1 stop9h 25m
Thu 10/15:44 pm -
1 stop8h 15m
Deal found 8/25![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 8/24. 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.
Thu 10/81:10 pm -
1 stop9h 25m
Tue 10/136:05 am -
1 stop6h 35m
Deal found 8/24![Southwest logo]()
$359
This Delta deal was found by Cheapflights users on 8/24. 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 10/216:05 am -
2 stops10h 05m
Mon 10/265:30 pm -
1 stop8h 29m
Deal found 8/24![Delta logo]()
$364
This Southwest deal was found by Cheapflights users on 8/22. 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 9/197:00 am -
2 stops10h 15m
Sat 9/266:50 am -
1 stop6h 00m
Deal found 8/22![Southwest logo]()
$364
This Southwest deal was found by Cheapflights users on 8/21. 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 9/2411:20 am -
1 stop10h 30m
Mon 9/286:15 am -
2 stops8h 25m
Deal found 8/21![Southwest logo]()
$365
Best flights from Eugene to ChicagoDiscover carefully curated flight deals from Eugene to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 26, 2026.
Discover carefully curated flight deals from Eugene to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 26, 2026.
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Tue 9/152:19 pm -
Nonstop4h 11m
Wed 11/186:00 am -
1 stop9h 09m
Deal found 8/25![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 8/21. 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 9/2412:32 pm -
1 stop9h 25m
Mon 9/287:00 am -
1 stop7h 58m
Deal found 8/21![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 8/21. 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 10/141:35 pm -
1 stop7h 35m
Tue 10/206:05 am -
1 stop6h 35m
Deal found 8/21![Southwest logo]()
$359
This Alaska Airlines deal was found by Cheapflights users on 8/22. 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 9/92:29 pm -
1 stop20h 53m
Tue 9/156:00 am -
1 stop9h 44m
Deal found 8/22![Alaska Airlines logo]()
$394
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Tue 9/222:19 pm -
Nonstop4h 11m
Tue 9/294:20 pm -
1 stop6h 52m
Deal found 8/25![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 8/23. 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 9/2012:32 pm -
1 stop9h 25m
Thu 10/15:44 pm -
1 stop8h 15m
Deal found 8/23![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 8/24. 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.
Wed 11/112:35 pm -
1 stop7h 35m
Fri 11/132:30 pm -
2 stops10h 10m
Deal found 8/24![Southwest logo]()
$364
This United Airlines deal was found by Cheapflights users on 8/21. 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 10/2112:52 pm -
1 stop7h 00m
Mon 10/262:30 pm -
1 stop8h 59m
Deal found 8/21![United Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 8/22. 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 9/1712:32 pm -
1 stop9h 25m
Mon 9/215:10 pm -
2 stops8h 37m
Deal found 8/22![Delta logo]()
$364
This Southwest deal was found by Cheapflights users on 8/23. 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.
Fri 11/132:25 pm -
1 stop5h 35m
Mon 11/161:20 pm -
2 stops11h 00m
Deal found 8/23![Southwest logo]()
$364
This Delta deal was found by Cheapflights users on 8/23. 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.
Thu 11/191:40 pm -
1 stop6h 07m
Sun 11/227:35 am -
2 stops11h 26m
Deal found 8/23![Delta logo]()
$364
This Southwest deal was found by Cheapflights users on 8/21. 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 9/2411:20 am -
1 stop10h 30m
Mon 9/286:15 am -
1 stop10h 55m
Deal found 8/21![Southwest logo]()
$370
This Delta deal was found by Cheapflights users on 8/24. 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 9/156:04 am -
2 stops13h 51m
Wed 9/231:55 pm -
2 stops12h 04m
Deal found 8/24![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 8/21. 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 9/2312:25 pm -
2 stops15h 15m
Mon 9/286:15 am -
2 stops8h 25m
Deal found 8/21![Southwest logo]()
$371
This Delta deal was found by Cheapflights users on 8/22. 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 9/256:04 am -
2 stops10h 29m
Wed 9/302:00 pm -
2 stops11h 47m
Deal found 8/22![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 8/22. 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 11/612:35 pm -
2 stops9h 30m
Mon 11/95:20 pm -
2 stops7h 20m
Deal found 8/22![Southwest logo]()
$403
This Delta deal was found by Cheapflights users on 8/24. 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 9/265:20 am -
2 stops11h 02m
Tue 9/291:19 pm -
2 stops12h 40m
Deal found 8/24![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 8/21. 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 12/66:15 am -
2 stops9h 30m
Thu 12/101:20 pm -
2 stops11h 00m
Deal found 8/21![Southwest logo]()
$403
This Delta deal was found by Cheapflights users on 8/25. 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 1/66:15 am -
2 stops13h 38m
Tue 1/127:00 am -
1 stop6h 54m
Deal found 8/25![Delta logo]()
$384
This Southwest deal was found by Cheapflights users on 8/25. 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.
Thu 9/101:15 pm -
1 stop9h 15m
Mon 9/144:25 pm -
1 stop8h 20m
Deal found 8/25![Southwest logo]()
$429
This Delta deal was found by Cheapflights users on 8/23. 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 9/95:51 pm -
2 stops13h 16m
Tue 9/159:29 am -
2 stops9h 42m
Deal found 8/23![Delta logo]()
$404
This Southwest deal was found by Cheapflights users on 8/22. 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 9/69:00 am -
1 stop8h 55m
Thu 9/106:15 am -
2 stops8h 25m
Deal found 8/22![Southwest logo]()
$430
Last-minute flights from Eugene to ChicagoDiscover last-minute flight deals from Eugene to Chicago. Data last updated August 26, 2026 and is based on user searches.
Discover last-minute flight deals from Eugene to Chicago. Data last updated August 26, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:00 pm -
1 stop23h 02m
Wed 9/91:21 pm -
1 stop24h 10m
Deal found 8/25![Multiple Airlines logo]()
$465
This United Airlines deal was found by Cheapflights users on 8/22. 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 8/305:45 am -
1 stop7h 05m
Sun 9/610:25 am -
Nonstop4h 45m
Deal found 8/22![United Airlines logo]()
$479
This Alaska Airlines deal was found by Cheapflights users on 8/21. 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.
Mon 8/319:56 am -
2 stops8h 14m
Tue 9/16:05 am -
1 stop8h 36m
Deal found 8/21![Alaska Airlines logo]()
$440
This United Airlines deal was found by Cheapflights users on 8/23. 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.
Thu 9/32:19 pm -
Nonstop4h 11m
Thu 9/175:00 am -
1 stop8h 43m
Deal found 8/23![United Airlines logo]()
$444
This Booking.com deal was found by Cheapflights users on 8/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:35 pm -
1 stop8h 45m
Thu 9/177:20 am -
1 stop17h 01m
Deal found 8/23![Alaska Airlines logo]()
$478
This Delta deal was found by Cheapflights users on 8/21. 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 9/45:20 am -
2 stops9h 39m
Mon 9/76:00 am -
2 stops7h 49m
Deal found 8/21![Delta logo]()
$439
This United Airlines deal was found by Cheapflights users on 8/21. 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 9/412:47 pm -
1 stop7h 59m
Mon 9/710:25 am -
Nonstop4h 45m
Deal found 8/21![United Airlines logo]()
$473
This Southwest deal was found by Cheapflights users on 8/24. 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.
Wed 9/91:40 pm -
1 stop7h 15m
Wed 9/233:10 pm -
2 stops9h 25m
Deal found 8/24![Southwest logo]()
$399
This Southwest deal was found by Cheapflights users on 8/22. 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 9/197:00 am -
2 stops10h 15m
Sat 9/266:50 am -
1 stop6h 00m
Deal found 8/22![Southwest logo]()
$364
This Southwest deal was found by Cheapflights users on 8/21. 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 9/2312:25 pm -
2 stops15h 15m
Mon 9/286:15 am -
2 stops8h 25m
Deal found 8/21![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 8/21. 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 9/2411:20 am -
1 stop10h 30m
Mon 9/286:15 am -
2 stops8h 25m
Deal found 8/21![Southwest logo]()
$365
This Southwest deal was found by Cheapflights users on 8/24. 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.
Thu 9/2411:20 am -
2 stops11h 10m
Thu 10/15:25 am -
1 stop10h 30m
Deal found 8/24![Southwest logo]()
$388
One-way flights from Eugene to ChicagoSearch for one-way flight options from Eugene to Chicago. Find affordable one-way fares based on user searches. Data last updated August 26, 2026.
Search for one-way flight options from Eugene to Chicago. Find affordable one-way fares based on user searches. Data last updated August 26, 2026.
This Alaska Airlines deal was found by Cheapflights users on 8/24. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:08 am -
1 stop10h 13m
Deal found 8/24![Alaska Airlines logo]()
$162
This Southwest deal was found by Cheapflights users on 8/23. 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.
Tue 9/1511:15 am -
1 stop7h 35m
Deal found 8/23![Southwest logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/47:48 pm -
3 stops50h 35m
Deal found 8/23![Multiple Airlines logo]()
$189
This Southwest deal was found by Cheapflights users on 8/23. 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.
Tue 9/2212:25 pm -
2 stops15h 15m
Deal found 8/23![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 8/25. 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.
Tue 10/201:35 pm -
1 stop7h 35m
Deal found 8/25![Southwest logo]()
$204
This Gotogate deal was found by Cheapflights users on 8/25. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/203:16 pm -
2 stops12h 24m
Deal found 8/25![Alaska Airlines logo]()
$207
This American Airlines deal was found by Cheapflights users on 8/23. 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.
Sun 10/41:41 pm -
1 stop8h 49m
Deal found 8/23![American Airlines logo]()
$214
This Southwest deal was found by Cheapflights users on 8/23. 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 10/45:10 pm -
2 stops10h 35m
Deal found 8/23![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 8/25. 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.
Tue 9/812:25 pm -
1 stop14h 05m
Deal found 8/25![Southwest logo]()
$220
This Southwest deal was found by Cheapflights users on 8/25. 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.
Fri 9/2512:20 pm -
2 stops8h 05m
Deal found 8/25![Southwest logo]()
$232
This Booking.com deal was found by Cheapflights users on 8/21. 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 12/168:00 am -
2 stops13h 59m
Deal found 8/21![Alaska Airlines logo]()
$256
This Booking.com deal was found by Cheapflights users on 8/21. 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.
Mon 8/312:29 pm -
1 stop7h 30m
Deal found 8/21![Alaska Airlines logo]()
$275
Find flight deals from Eugene to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Eugene (EUG) 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 August 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $323 (Expedia) |
One-way from | $162 (Alaska Airlines) |
Popular in | March |
Cheapest in | May |
Average price | $383 |
Good round-trip deal | $359 or less |
Good one-way deal | $280 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Eugene 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 7,457,451 searches. Data last updated August 26, 2026.
Use the filters below to find and compare flights from Eugene to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
EugeneChicago
EUG Eugene - ORD Chicago O'Hare Intl
EUGORD
Eugene
Tue 9/15
2:19 pm-8:30 pm
Nonstop4h 11m
Chicago O'Hare Intl
Wed 11/18
6:00 am-1:09 pm
1 stop9h 09m
$349
Quickest round-trip
EugeneChicago
EUG Eugene - ORD Chicago O'Hare Intl
EUGORD
Eugene
Tue 9/22
2:19 pm-8:30 pm
Nonstop4h 11m
Chicago O'Hare Intl
Tue 9/29
4:20 pm-9:12 pm
1 stop6h 52m
$349
EugeneChicago
EUG Eugene - ORD Chicago O'Hare Intl
EUGORD
Eugene
Thu 9/24
12:32 pm-11:57 pm
1 stop9h 25m
Chicago O'Hare Intl
Mon 9/28
7:00 am-12:58 pm
1 stop7h 58m
$359
EugeneChicago
EUG Eugene - MDW Chicago Midway
EUGMDW
Eugene
Wed 10/14
1:35 pm-11:10 pm
1 stop7h 35m
Chicago Midway
Tue 10/20
6:05 am-10:40 am
1 stop6h 35m
$359
EugeneChicago
EUG Eugene - ORD Chicago O'Hare Intl
EUGORD
Eugene
Sun 9/20
12:32 pm-11:57 pm
1 stop9h 25m
Chicago O'Hare Intl
Thu 10/1
5:44 pm-11:59 pm
1 stop8h 15m
$359
EugeneChicago
EUG Eugene - ORD Chicago O'Hare Intl
EUGORD
Eugene
Wed 10/21
12:52 pm-9:52 pm
1 stop7h 00m
Chicago O'Hare Intl
Mon 10/26
2:30 pm-9:29 pm
1 stop8h 59m
$359
EugeneChicago
EUG Eugene - MDW Chicago Midway
EUGMDW
Eugene
Wed 11/11
2:35 pm-12:10 am
1 stop7h 35m
Chicago Midway
Fri 11/13
2:30 pm-10:40 pm
2 stops10h 10m
$364
EugeneChicago
EUG Eugene - ORD Chicago O'Hare Intl
EUGORD
Eugene
Thu 9/17
12:32 pm-11:57 pm
1 stop9h 25m
Chicago O'Hare Intl
Mon 9/21
5:10 pm-11:47 pm
2 stops8h 37m
$364
EugeneChicago
EUG Eugene - MDW Chicago Midway
EUGMDW
Eugene
Fri 11/13
2:25 pm-10:00 pm
1 stop5h 35m
Chicago Midway
Mon 11/16
1:20 pm-10:20 pm
2 stops11h 00m
$364
EugeneChicago
EUG Eugene - ORD Chicago O'Hare Intl
EUGORD
Eugene
Thu 11/19
1:40 pm-9:47 pm
1 stop6h 07m
Chicago O'Hare Intl
Sun 11/22
7:35 am-5:01 pm
2 stops11h 26m
$364
Showing 1-10 of 38 resultsSorted by cheapest first
Compare providers for flights from Eugene 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 Eugene to Chicago in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Eugene-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Eugene-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Eugene-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Eugene-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 Eugene-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 Eugene to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Eugene with our price prediction graph.
EUG-CHI
EUG-ORD
EUG-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 Eugene to Chicago
EUG-CHI
EUG-ORD
EUG-MDW
What is the cheapest month to book a flight from Eugene to Chicago?
Currently, May is the cheapest month in which you can book a flight from Eugene to Chicago (average of $319). Flying from Eugene to Chicago in December is currently the most expensive (average of $500). 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 EUG to CHI?
Find hourly flight availability from Eugene 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 August 26, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Eugene to Chicago as you normally would.
Weekly flight availability from Eugene to Chicago
Explore weekly flight availability from Eugene 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 August 26, 2026.
The most flights from EUG to CHI are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Eugene to Chicago?
Airfare is below average for this route at the moment.
Eugene to Chicago flights typically cost between $324 and $498 in September.The cheapest round-trip price found within the last 5 days was $323 on Alaska Airlines (Sep 22-Sep 29).
How far ahead should I book a flight from Eugene to Chicago?
The price you pay for your flight from Eugene to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 56 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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 August 26, 2026.
Peruse reviews from past customers who have flown with Southwest,Alaska Airlines, andDelta from Eugene to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Eugene 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 locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
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Eugene and Chicago flights
Browse other Eugene and Chicago flight options. Last updated on August 26, 2026.
Other flights from Eugene
Browse through other flights departing from Eugene. Flights are based on user searches made on Cheapflights and were last updated on August 26, 2026.
Popular flight searches
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Top 3 airlines flying from Eugene to Chicago
Discover the top 3 airlines that operate flights from Eugene 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 7,457,451 searches. Data last updated August 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$306 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$198 | Average$411 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$282 | Average$429 | FlexibilityNo cancel fee | On-time69% |