$115+ 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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
EUG — CHI
Aug 11 — Aug 181
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
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
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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 July 12, 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 July 12, 2026.
This American Airlines deal was found by Cheapflights users on 7/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/91:41 pm
EUG
- ORD
1 stop8h 49m
American Airlines
Tue 9/156:59 am
ORD
- EUG
1 stop8h 08m
American Airlines
Deal found 7/7![American Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 7/8. 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.
Thu 8/271:15 pm
EUG
- MDW
1 stop9h 10m
Southwest
Mon 8/316:40 am
MDW
- EUG
1 stop7h 00m
Southwest
Deal found 7/8![Southwest logo]()
$230
This Southwest deal was found by Cheapflights users on 7/7. 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.
Wed 8/1211:15 am
EUG
- MDW
2 stops9h 35m
Southwest
Tue 8/183:50 pm
MDW
- EUG
1 stop8h 40m
Southwest
Deal found 7/7![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 7/8. 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.
Wed 8/512:25 pm
EUG
- MDW
2 stops15h 15m
Southwest
Wed 8/126:50 am
MDW
- EUG
1 stop8h 05m
Southwest
Deal found 7/8![Southwest logo]()
$241
This American Airlines deal was found by Cheapflights users on 7/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/291:41 pm
EUG
- ORD
1 stop8h 49m
American Airlines
Fri 10/25:00 am
ORD
- EUG
1 stop10h 07m
American Airlines
Deal found 7/7![American Airlines logo]()
$259
This Southwest deal was found by Cheapflights users on 7/10. 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 9/181:15 pm
EUG
- MDW
1 stop9h 10m
Southwest
Mon 9/216:15 am
MDW
- EUG
2 stops8h 25m
Southwest
Deal found 7/10![Southwest logo]()
$260
This Southwest deal was found by Cheapflights users on 7/7. 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.
Mon 8/103:55 pm
EUG
- MDW
1 stop11h 05m
Southwest
Fri 8/146:40 am
MDW
- EUG
1 stop7h 00m
Southwest
Deal found 7/7![Southwest logo]()
$265
This Southwest deal was found by Cheapflights users on 7/8. 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 10/234:05 pm
EUG
- MDW
1 stop6h 50m
Southwest
Tue 10/275:45 pm
MDW
- EUG
1 stop6h 30m
Southwest
Deal found 7/8![Southwest logo]()
$287
This Alaska Airlines deal was found by Cheapflights users on 7/8. 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.
Thu 8/612:34 pm
EUG
- ORD
1 stop14h 26m
Alaska Airlines
Thu 8/136:00 am
ORD
- EUG
1 stop9h 01m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$289
This Southwest deal was found by Cheapflights users on 7/7. 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.
Thu 9/31:15 pm
EUG
- MDW
1 stop9h 10m
Southwest
Tue 9/83:50 pm
MDW
- EUG
1 stop8h 40m
Southwest
Deal found 7/7![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 7/10. 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 8/235:50 pm
EUG
- MDW
1 stop9h 10m
Southwest
Thu 8/276:15 am
MDW
- EUG
2 stops8h 25m
Southwest
Deal found 7/10![Southwest logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:55 pm
EUG
- ORD
1 stop9h 42m
Multiple Airlines
Sat 8/87:29 am
ORD
- EUG
1 stop29h 47m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$302
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 July 12, 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 July 12, 2026.
This Southwest deal was found by Cheapflights users on 7/10. 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 8/271:15 pm
EUG
- MDW
1 stop9h 10m
Southwest
Mon 8/314:25 pm
MDW
- EUG
1 stop8h 15m
Southwest
Deal found 7/10![Southwest logo]()
$230
This United Airlines deal was found by Cheapflights users on 7/10. 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 8/132:19 pm
EUG
- ORD
Nonstop4h 11m
United Airlines
Sat 8/296:00 am
ORD
- EUG
1 stop7h 43m
United Airlines
Deal found 7/10![United Airlines logo]()
$335
This Alaska Airlines deal was found by Cheapflights users on 7/7. 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.
Tue 9/17:10 am
EUG
- ORD
1 stop28h 12m
Alaska Airlines
Wed 9/26:54 pm
ORD
- EUG
1 stop6h 59m
Alaska Airlines
Deal found 7/7![Alaska Airlines logo]()
$348
This Delta deal was found by Cheapflights users on 7/8. 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.
Mon 8/3112:29 pm
EUG
- ORD
1 stop9h 00m
Delta
Wed 9/91:50 pm
ORD
- EUG
2 stops11h 57m
Delta
Deal found 7/8![Delta logo]()
$354
This Southwest deal was found by Cheapflights users on 7/9. 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 8/251:40 pm
EUG
- MDW
1 stop7h 10m
Southwest
Sat 8/295:05 pm
MDW
- EUG
1 stop6h 10m
Southwest
Deal found 7/9![Southwest logo]()
$230
This Southwest deal was found by Cheapflights users on 7/7. 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.
Wed 8/1211:15 am
EUG
- MDW
2 stops9h 35m
Southwest
Tue 8/186:40 am
MDW
- EUG
2 stops8h 15m
Southwest
Deal found 7/7![Southwest logo]()
$240
This Southwest deal was found by Cheapflights users on 7/8. 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 12/45:50 am
EUG
- MDW
2 stops9h 55m
Southwest
Mon 12/76:05 am
MDW
- EUG
1 stop6h 35m
Southwest
Deal found 7/8![Southwest logo]()
$292
This Delta deal was found by Cheapflights users on 7/8. 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 12/46:15 am
EUG
- MDW
2 stops8h 35m
Delta
Mon 12/712:30 pm
MDW
- EUG
2 stops13h 23m
Delta
Deal found 7/8![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 7/7. 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.
Thu 9/32:19 pm
EUG
- ORD
Nonstop4h 11m
United Airlines
Tue 9/84:20 pm
ORD
- EUG
1 stop6h 57m
United Airlines
Deal found 7/7![United Airlines logo]()
$370
This Southwest deal was found by Cheapflights users on 7/11. 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
EUG
- MDW
1 stop7h 30m
Southwest
Sun 11/1510:10 am
MDW
- EUG
1 stop8h 50m
Southwest
Deal found 7/11![Southwest logo]()
$319
This United Airlines deal was found by Cheapflights users on 7/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/152:19 pm
EUG
- ORD
Nonstop4h 11m
United Airlines
Tue 8/188:40 am
ORD
- EUG
1 stop8h 56m
United Airlines
Deal found 7/9![United Airlines logo]()
$387
This Southwest deal was found by Cheapflights users on 7/7. 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.
Thu 8/611:20 am
EUG
- MDW
1 stop10h 25m
Southwest
Thu 8/136:15 am
MDW
- EUG
2 stops8h 25m
Southwest
Deal found 7/7![Southwest logo]()
$330
This United Airlines deal was found by Cheapflights users on 7/11. 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 8/132:19 pm
EUG
- ORD
Nonstop4h 11m
United Airlines
Mon 8/1710:25 am
ORD
- EUG
Nonstop4h 45m
United Airlines
Deal found 7/11![United Airlines logo]()
$429
This Southwest deal was found by Cheapflights users on 7/6. 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.
Tue 8/42:50 pm
EUG
- MDW
1 stop12h 10m
Southwest
Tue 8/116:40 am
MDW
- EUG
1 stop5h 55m
Southwest
Deal found 7/6![Southwest logo]()
$354
This United Airlines deal was found by Cheapflights users on 7/8. 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.
Mon 8/312:19 pm
EUG
- ORD
Nonstop4h 11m
United Airlines
Wed 9/99:05 am
ORD
- EUG
Nonstop4h 45m
United Airlines
Deal found 7/8![United Airlines logo]()
$429
This Southwest deal was found by Cheapflights users on 7/9. 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.
Thu 8/611:20 am
EUG
- MDW
1 stop10h 25m
Southwest
Sun 8/96:30 am
MDW
- EUG
1 stop5h 55m
Southwest
Deal found 7/9![Southwest logo]()
$354
This United Airlines deal was found by Cheapflights users on 7/11. 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 8/132:19 pm
EUG
- ORD
Nonstop4h 11m
United Airlines
Tue 8/1810:25 am
ORD
- EUG
Nonstop4h 45m
United Airlines
Deal found 7/11![United Airlines logo]()
$429
This United Airlines deal was found by Cheapflights users on 7/11. 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 9/171:19 pm
EUG
- ORD
Nonstop4h 11m
United Airlines
Mon 9/215:55 am
ORD
- EUG
1 stop9h 00m
United Airlines
Deal found 7/11![United Airlines logo]()
$439
This Southwest deal was found by Cheapflights users on 7/9. 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.
Thu 8/611:20 am
EUG
- MDW
2 stops11h 05m
Southwest
Mon 8/106:40 am
MDW
- EUG
1 stop7h 00m
Southwest
Deal found 7/9![Southwest logo]()
$388
This Southwest deal was found by Cheapflights users on 7/10. 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 8/12:45 pm
EUG
- MDW
2 stops11h 55m
Southwest
Thu 8/66:15 am
MDW
- EUG
1 stop10h 55m
Southwest
Deal found 7/10![Southwest logo]()
$394
This Southwest deal was found by Cheapflights users on 7/8. 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.
Sun 8/24:50 pm
EUG
- MDW
1 stop10h 10m
Southwest
Wed 8/54:40 pm
MDW
- EUG
2 stops7h 50m
Southwest
Deal found 7/8![Southwest logo]()
$439
Last-minute flights from Eugene to ChicagoDiscover last-minute flight deals from Eugene to Chicago. Data last updated July 12, 2026 and is based on user searches.
Discover last-minute flight deals from Eugene to Chicago. Data last updated July 12, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 7/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/24:00 pm
EUG
- ORD
1 stop11h 00m
Alaska Airlines
Wed 8/58:20 pm
ORD
- EUG
1 stop14h 47m
Alaska Airlines
Deal found 7/7![Alaska Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 7/6. 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.
Tue 8/412:25 pm
EUG
- MDW
1 stop14h 05m
Southwest
Tue 8/114:40 pm
MDW
- EUG
2 stops7h 50m
Southwest
Deal found 7/6![Southwest logo]()
$300
This Southwest deal was found by Cheapflights users on 7/8. 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.
Wed 8/512:25 pm
EUG
- MDW
2 stops15h 15m
Southwest
Wed 8/126:50 am
MDW
- EUG
1 stop8h 05m
Southwest
Deal found 7/8![Southwest logo]()
$241
This Southwest deal was found by Cheapflights users on 7/8. 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.
Wed 8/512:25 pm
EUG
- MDW
2 stops15h 15m
Southwest
Sat 8/82:25 pm
MDW
- EUG
2 stops8h 50m
Southwest
Deal found 7/8![Southwest logo]()
$305
This Alaska Airlines deal was found by Cheapflights users on 7/8. 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.
Thu 8/612:34 pm
EUG
- ORD
1 stop14h 26m
Alaska Airlines
Thu 8/136:00 am
ORD
- EUG
1 stop9h 01m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:55 pm
EUG
- ORD
1 stop9h 42m
Multiple Airlines
Sat 8/87:29 am
ORD
- EUG
1 stop29h 47m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$302
This Southwest deal was found by Cheapflights users on 7/7. 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.
Mon 8/103:55 pm
EUG
- MDW
1 stop11h 05m
Southwest
Fri 8/146:40 am
MDW
- EUG
1 stop7h 00m
Southwest
Deal found 7/7![Southwest logo]()
$265
This Southwest deal was found by Cheapflights users on 7/7. 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.
Wed 8/1212:25 pm
EUG
- MDW
1 stop14h 05m
Southwest
Tue 8/186:50 am
MDW
- EUG
1 stop8h 05m
Southwest
Deal found 7/7![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 7/9. 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.
Wed 8/1212:25 pm
EUG
- MDW
1 stop14h 05m
Southwest
Sat 8/156:55 am
MDW
- EUG
1 stop8h 25m
Southwest
Deal found 7/9![Southwest logo]()
$295
This United Airlines deal was found by Cheapflights users on 7/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/122:19 pm
EUG
- ORD
Nonstop4h 11m
United Airlines
Sat 8/1510:25 am
ORD
- EUG
Nonstop4h 45m
United Airlines
Deal found 7/9![United Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 7/10. 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 8/235:50 pm
EUG
- MDW
1 stop9h 10m
Southwest
Thu 8/276:15 am
MDW
- EUG
2 stops8h 25m
Southwest
Deal found 7/10![Southwest logo]()
$290
This Southwest deal was found by Cheapflights users on 7/8. 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.
Thu 8/271:15 pm
EUG
- MDW
1 stop9h 10m
Southwest
Mon 8/316:40 am
MDW
- EUG
1 stop7h 00m
Southwest
Deal found 7/8![Southwest logo]()
$230
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 July 12, 2026.
Search for one-way flight options from Eugene to Chicago. Find affordable one-way fares based on user searches. Data last updated July 12, 2026.
This Southwest deal was found by Cheapflights users on 7/10. 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 8/2412:20 pm
EUG
- MDW
1 stop7h 40m
Southwest
Deal found 7/10![Southwest logo]()
$115
This Southwest deal was found by Cheapflights users on 7/8. 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.
Wed 8/1212:25 pm
EUG
- MDW
1 stop14h 05m
Southwest
Deal found 7/8![Southwest logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:09 pm
EUG
- ORD
1 stop15h 48m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$122
This Southwest deal was found by Cheapflights users on 7/8. 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.
Wed 8/512:25 pm
EUG
- MDW
2 stops15h 15m
Southwest
Deal found 7/8![Southwest logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 7/10. 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
EUG
- ORD
1 stop23h 02m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$132
This Southwest deal was found by Cheapflights users on 7/10. 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 8/71:15 pm
EUG
- MDW
1 stop9h 10m
Southwest
Deal found 7/10![Southwest logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 7/8. 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.
Thu 8/135:55 pm
EUG
- ORD
1 stop9h 42m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$151
This American Airlines deal was found by Cheapflights users on 7/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:07 pm
EUG
- ORD
1 stop8h 21m
American Airlines
Deal found 7/7![American Airlines logo]()
$165
This Alaska Airlines deal was found by Cheapflights users on 7/8. 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.
Tue 8/117:50 am
EUG
- ORD
1 stop9h 07m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$173
This Alaska Airlines deal was found by Cheapflights users on 7/8. 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.
Thu 8/272:29 pm
EUG
- ORD
1 stop7h 30m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$175
This Southwest deal was found by Cheapflights users on 7/9. 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.
Mon 8/36:40 pm
EUG
- MDW
1 stop8h 20m
Southwest
Deal found 7/9![Southwest logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 7/8. 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.
Thu 8/65:55 pm
EUG
- ORD
1 stop9h 42m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$178
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 July 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $229 (American Airlines) |
One-way from | $115 (Southwest) |
Popular in | March |
Cheapest in | May |
Average price | $409 |
Good round-trip deal | $402 or less |
Good one-way deal | $209 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 2,558,603 searches. Data last updated July 12, 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 - MDW
EUGMDW
Eugene
Thu 8/27
1:15 pm-12:25 am
1 stop9h 10m
Chicago Midway
Mon 8/31
4:25 pm-10:40 pm
1 stop8h 15m
$230
EugeneChicago
EUG - MDW
EUGMDW
Eugene
Tue 8/25
1:40 pm-10:50 pm
1 stop7h 10m
Chicago Midway
Sat 8/29
5:05 pm-9:15 pm
1 stop6h 10m
$230
EugeneChicago
EUG - MDW
EUGMDW
Eugene
Wed 8/12
11:15 am-10:50 pm
2 stops9h 35m
Chicago Midway
Tue 8/18
6:40 am-12:55 pm
2 stops8h 15m
$240
EugeneChicago
EUG - MDW
EUGMDW
Eugene
Fri 12/4
5:50 am-5:45 pm
2 stops9h 55m
Chicago Midway
Mon 12/7
6:05 am-10:40 am
1 stop6h 35m
$292
EugeneChicago
EUG - MDW
EUGMDW
Eugene
Fri 11/13
2:25 pm-11:55 pm
1 stop7h 30m
Chicago Midway
Sun 11/15
10:10 am-5:00 pm
1 stop8h 50m
$319
EugeneChicago
EUG - MDW
EUGMDW
Eugene
Thu 8/6
11:20 am-11:45 pm
1 stop10h 25m
Chicago Midway
Thu 8/13
6:15 am-12:40 pm
2 stops8h 25m
$330
EugeneChicago
EUG - ORD
EUGORD
Eugene
Thu 8/13
2:19 pm-8:30 pm
Nonstop4h 11m
Chicago O'Hare Intl
Sat 8/29
6:00 am-11:43 am
1 stop7h 43m
$335
EugeneChicago
EUG - ORD
EUGORD
Eugene
Tue 9/1
7:10 am-1:22 pm
1 stop28h 12m
Chicago O'Hare Intl
Wed 9/2
6:54 pm-11:53 pm
1 stop6h 59m
$348
EugeneChicago
EUG - ORD
EUGORD
Eugene
Mon 8/31
12:29 pm-11:29 pm
1 stop9h 00m
Chicago O'Hare Intl
Wed 9/9
1:50 pm-11:47 pm
2 stops11h 57m
$354
EugeneChicago
EUG - MDW
EUGMDW
Eugene
Tue 8/4
2:50 pm-5:00 am
1 stop12h 10m
Chicago Midway
Tue 8/11
6:40 am-10:35 am
1 stop5h 55m
$354
Showing 1-10 of 35 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 July.
| 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-MDW
EUG-ORD
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-MDW
EUG-ORD
What is the cheapest month to book a flight from Eugene to Chicago?
Currently, November is the cheapest month in which you can book a flight from Eugene to Chicago (average of $104). Flying from Eugene to Chicago in July is currently the most expensive (average of $277). 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 July 12, 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 July 12, 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?
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 59 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 July 12, 2026.
Peruse reviews from past customers who have flown with Alaska Airlines,Southwest, 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.
Overall
7.9
Crew
8.5
Entertainment
7.0
Food
7.0
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Overall
7.9
Crew
8.5
Entertainment
7.0
Food
7.0
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Overall
7.9
Crew
8.5
Entertainment
7.0
Food
7.0
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Overall
7.9
Crew
8.5
Entertainment
7.0
Food
7.0
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Overall
7.9
Crew
8.5
Entertainment
7.0
Food
7.0
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
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
Hammond
Lansing
Merrillville
Valparaiso
Porter
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Other flights to Chicago
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Complete your trip
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Eugene and Chicago flights
Browse other Eugene and Chicago flight options. Last updated on July 12, 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 July 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 2,558,603 searches. Data last updated July 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$335 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$198 | Average$396 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$279 | Average$415 | FlexibilityNo cancel fee | On-time69% |