$156+ Cheap flights from Medford (MFR) 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 8/9. Fares are subject to change and may not be available on all flights or dates of travel.
MFR — CHI
Jul 30 — Aug 61
Round-trip
1 adult, Economy
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Find cheap flights from Medford 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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Medford to Chicago
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Cheapest flights from Medford to ChicagoExplore the most affordable flight options available from Medford to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 30, 2026.
Explore the most affordable flight options available from Medford to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/79:17 pm
MFR
- ORD
1 stop30h 20m
Multiple Airlines
Wed 8/129:57 pm
ORD
- MFR
2 stops24h 51m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/259:22 am
MFR
- ORD
1 stop18h 20m
Multiple Airlines
Mon 9/286:50 am
ORD
- MFR
1 stop10h 00m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/39:11 pm
MFR
- ORD
1 stop30h 26m
Multiple Airlines
Fri 8/79:20 am
ORD
- MFR
2 stops13h 07m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$385
This Alaska Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 10/315:59 am
MFR
- ORD
1 stop6h 54m
Alaska Airlines
Wed 11/49:31 am
ORD
- MFR
1 stop7h 05m
Alaska Airlines
Deal found 6/28![Alaska Airlines logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/259:22 am
MFR
- ORD
1 stop18h 20m
Multiple Airlines
Sun 9/271:02 pm
ORD
- MFR
1 stop27h 48m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$415
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:15 am
MFR
- ORD
2 stops10h 04m
Delta
Tue 8/257:00 am
ORD
- MFR
1 stop7h 53m
Delta
Deal found 6/29![Delta logo]()
$418
This Delta deal was found by Cheapflights users on 6/25. 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 10/276:05 am
MFR
- MDW
2 stops8h 45m
Delta
Mon 11/21:00 pm
MDW
- MFR
2 stops12h 49m
Delta
Deal found 6/25![Delta logo]()
$423
This Alaska Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2610:33 am
MFR
- ORD
1 stop11h 26m
Alaska Airlines
Sat 11/77:00 am
ORD
- MFR
1 stop9h 36m
Alaska Airlines
Deal found 6/29![Alaska Airlines logo]()
$433
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:05 am
MFR
- ORD
1 stop8h 54m
Delta
Sat 11/711:19 am
ORD
- MFR
2 stops12h 40m
Delta
Deal found 6/29![Delta logo]()
$438
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:30 am
MFR
- ORD
2 stops8h 54m
Delta
Mon 11/211:19 am
ORD
- MFR
2 stops13h 49m
Delta
Deal found 6/29![Delta logo]()
$443
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 9/256:15 am
MFR
- MDW
2 stops10h 18m
Delta
Mon 9/282:00 pm
MDW
- MFR
2 stops11h 55m
Delta
Deal found 6/28![Delta logo]()
$464
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 8/186:15 am
MFR
- MDW
2 stops10h 18m
Delta
Tue 8/251:51 pm
MDW
- MFR
2 stops12h 04m
Delta
Deal found 6/28![Delta logo]()
$474
Best flights from Medford to ChicagoDiscover carefully curated flight deals from Medford to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 30, 2026.
Discover carefully curated flight deals from Medford to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 30, 2026.
This Alaska Airlines deal was found by Cheapflights users on 6/25. 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 10/2710:33 am
MFR
- ORD
1 stop11h 26m
Alaska Airlines
Mon 11/26:33 pm
ORD
- MFR
1 stop7h 26m
Alaska Airlines
Deal found 6/25![Alaska Airlines logo]()
$413
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:15 am
MFR
- ORD
2 stops10h 04m
Delta
Tue 8/257:00 am
ORD
- MFR
1 stop7h 53m
Delta
Deal found 6/29![Delta logo]()
$418
This Delta deal was found by Cheapflights users on 6/25. 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 10/275:55 am
MFR
- ORD
2 stops8h 38m
Delta
Mon 11/21:35 pm
ORD
- MFR
2 stops11h 37m
Delta
Deal found 6/25![Delta logo]()
$423
This Alaska Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 10/2610:33 am
MFR
- ORD
1 stop11h 26m
Alaska Airlines
Sat 11/77:00 am
ORD
- MFR
1 stop9h 36m
Alaska Airlines
Deal found 6/28![Alaska Airlines logo]()
$433
This Delta deal was found by Cheapflights users on 6/25. 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 9/246:15 am
MFR
- ORD
2 stops13h 37m
Delta
Mon 9/281:55 pm
ORD
- MFR
2 stops12h 00m
Delta
Deal found 6/25![Delta logo]()
$423
This Delta deal was found by Cheapflights users on 6/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:05 am
MFR
- ORD
1 stop8h 54m
Delta
Sat 11/711:19 am
ORD
- MFR
2 stops12h 40m
Delta
Deal found 6/27![Delta logo]()
$438
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 9/2612:22 pm
MFR
- ORD
1 stop9h 35m
Delta
Mon 9/285:10 pm
ORD
- MFR
2 stops8h 45m
Delta
Deal found 6/28![Delta logo]()
$438
This Delta deal was found by Cheapflights users on 6/26. 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 9/111:31 pm
MFR
- ORD
1 stop6h 21m
Delta
Sun 9/137:00 am
ORD
- MFR
1 stop7h 46m
Delta
Deal found 6/26![Delta logo]()
$453
This Delta deal was found by Cheapflights users on 6/26. 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 9/116:15 am
MFR
- ORD
1 stop9h 46m
Delta
Mon 9/147:00 am
ORD
- MFR
1 stop7h 46m
Delta
Deal found 6/26![Delta logo]()
$453
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:15 am
MFR
- ORD
2 stops13h 05m
Delta
Wed 8/55:56 pm
ORD
- MFR
1 stop7h 27m
Delta
Deal found 6/29![Delta logo]()
$469
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 8/186:15 am
MFR
- MDW
2 stops10h 18m
Delta
Tue 8/251:51 pm
MDW
- MFR
2 stops12h 04m
Delta
Deal found 6/28![Delta logo]()
$474
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 9/246:15 am
MFR
- MDW
2 stops10h 18m
Delta
Mon 9/282:00 pm
MDW
- MFR
2 stops11h 55m
Delta
Deal found 6/28![Delta logo]()
$496
This Delta deal was found by Cheapflights users on 6/25. 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.
Mon 10/266:05 am
MFR
- MDW
2 stops8h 45m
Delta
Sat 11/79:30 am
MDW
- MFR
2 stops9h 13m
Delta
Deal found 6/25![Delta logo]()
$614
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 8/176:15 am
MFR
- MDW
2 stops9h 46m
Delta
Wed 8/191:25 pm
MDW
- MFR
2 stops12h 30m
Delta
Deal found 6/28![Delta logo]()
$716
This Delta deal was found by Cheapflights users on 6/25. 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.
Fri 7/106:15 am
MFR
- MDW
2 stops10h 10m
Delta
Tue 7/141:18 pm
MDW
- MFR
2 stops11h 53m
Delta
Deal found 6/25![Delta logo]()
$758
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 9/267:00 am
MFR
- MDW
2 stops9h 19m
Delta
Mon 9/282:00 pm
MDW
- MFR
2 stops11h 55m
Delta
Deal found 6/28![Delta logo]()
$786
This Delta deal was found by Cheapflights users on 6/24. 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 8/16:15 am
MFR
- MDW
2 stops9h 52m
Delta
Sat 8/81:51 pm
MDW
- MFR
2 stops10h 42m
Delta
Deal found 6/24![Delta logo]()
$878
Last-minute flights from Medford to ChicagoDiscover last-minute flight deals from Medford to Chicago. Data last updated June 30, 2026 and is based on user searches.
Discover last-minute flight deals from Medford to Chicago. Data last updated June 30, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/25. 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.
Fri 7/106:15 am
MFR
- MDW
2 stops10h 10m
Delta
Tue 7/141:18 pm
MDW
- MFR
2 stops11h 53m
Delta
Deal found 6/25![Delta logo]()
$758
This Kiwi.com deal was found by Cheapflights users on 6/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/139:11 pm
MFR
- ORD
1 stop30h 26m
Multiple Airlines
Sat 7/185:13 pm
ORD
- MFR
2 stops29h 30m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$483
This Alaska Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/147:50 pm
MFR
- ORD
1 stop8h 30m
Alaska Airlines
Sat 7/187:17 pm
ORD
- MFR
1 stop6h 47m
Alaska Airlines
Deal found 6/29![Alaska Airlines logo]()
$515
This United Airlines deal was found by Cheapflights users on 6/26. 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.
Tue 7/142:11 pm
MFR
- ORD
2 stops9h 04m
United Airlines
Sat 7/184:12 pm
ORD
- MFR
1 stop6h 57m
United Airlines
Deal found 6/26![United Airlines logo]()
$552
This Alaska Airlines deal was found by Cheapflights users on 6/26. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1712:30 pm
MFR
- ORD
1 stop14h 30m
Alaska Airlines
Sun 7/196:20 am
ORD
- MFR
1 stop18h 00m
Alaska Airlines
Deal found 6/26![Alaska Airlines logo]()
$539
This Delta deal was found by Cheapflights users on 6/26. 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 7/176:15 am
MFR
- MDW
2 stops10h 03m
Delta
Sun 7/191:18 pm
MDW
- MFR
2 stops11h 53m
Delta
Deal found 6/26![Delta logo]()
$2,178
This Delta deal was found by Cheapflights users on 6/25. 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 7/216:15 am
MFR
- ORD
2 stops13h 14m
Delta
Tue 7/282:02 pm
ORD
- MFR
2 stops11h 09m
Delta
Deal found 6/25![Delta logo]()
$474
This American Airlines deal was found by Cheapflights users on 6/25. 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.
Sat 7/251:23 pm
MFR
- ORD
1 stop9h 28m
American Airlines
Wed 8/51:59 pm
ORD
- MFR
1 stop7h 21m
American Airlines
Deal found 6/25![American Airlines logo]()
$413
This Alaska Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:11 am
MFR
- ORD
1 stop11h 26m
Alaska Airlines
Wed 8/58:20 pm
ORD
- MFR
1 stop15h 31m
Alaska Airlines
Deal found 6/29![Alaska Airlines logo]()
$464
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:15 am
MFR
- ORD
2 stops13h 05m
Delta
Wed 8/55:56 pm
ORD
- MFR
1 stop7h 27m
Delta
Deal found 6/29![Delta logo]()
$469
This American Airlines deal was found by Cheapflights users on 6/27. 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.
Wed 7/291:23 pm
MFR
- ORD
1 stop9h 28m
American Airlines
Thu 8/131:59 pm
ORD
- MFR
1 stop7h 21m
American Airlines
Deal found 6/27![American Airlines logo]()
$522
This Delta deal was found by Cheapflights users on 6/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:15 am
MFR
- ORD
1 stop8h 28m
Delta
Thu 8/132:00 pm
ORD
- MFR
2 stops11h 23m
Delta
Deal found 6/27![Delta logo]()
$527
One-way flights from Medford to ChicagoSearch for one-way flight options from Medford to Chicago. Find affordable one-way fares based on user searches. Data last updated June 30, 2026.
Search for one-way flight options from Medford to Chicago. Find affordable one-way fares based on user searches. Data last updated June 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/79:17 pm
MFR
- ORD
1 stop30h 20m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/39:11 pm
MFR
- ORD
1 stop30h 26m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 6/25. 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 8/99:38 pm
MFR
- ORD
1 stop29h 59m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/209:11 pm
MFR
- ORD
2 stops25h 38m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/283:40 pm
MFR
- ORD
2 stops27h 55m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$190
This United Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/52:11 pm
MFR
- ORD
2 stops9h 04m
United Airlines
Deal found 6/29![United Airlines logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/209:11 pm
MFR
- MDW
3 stops35h 56m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$231
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:15 am
MFR
- MDW
2 stops11h 18m
Delta
Deal found 6/29![Delta logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/57:50 pm
MFR
- MDW
3 stops36h 01m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$647
Find flight deals from Medford to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Medford (MFR) 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 June 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $331 (Kiwi.com) |
One-way from | $156 (Kiwi.com) |
Popular in | January |
Cheapest in | December |
Average price | $554 |
Cheapflights Fare Finder
Customize your flight search to find flights from Medford 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 June 30, 2026.
Use the filters below to find and compare flights from Medford to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MedfordChicago
MFR - ORD
MFRORD
Medford
Tue 10/27
10:33 am-11:59 pm
1 stop11h 26m
Chicago O'Hare Intl
Mon 11/2
6:33 pm-11:59 pm
1 stop7h 26m
$413
MedfordChicago
MFR - ORD
MFRORD
Medford
Tue 8/18
6:15 am-6:19 pm
2 stops10h 04m
Chicago O'Hare Intl
Tue 8/25
7:00 am-12:53 pm
1 stop7h 53m
$418
MedfordChicago
MFR - ORD
MFRORD
Medford
Tue 10/27
5:55 am-4:33 pm
2 stops8h 38m
Chicago O'Hare Intl
Mon 11/2
1:35 pm-11:12 pm
2 stops11h 37m
$423
MedfordChicago
MFR - ORD
MFRORD
Medford
Thu 9/24
6:15 am-9:52 pm
2 stops13h 37m
Chicago O'Hare Intl
Mon 9/28
1:55 pm-11:55 pm
2 stops12h 00m
$423
MedfordChicago
MFR - ORD
MFRORD
Medford
Mon 10/26
10:33 am-11:59 pm
1 stop11h 26m
Chicago O'Hare Intl
Sat 11/7
7:00 am-2:36 pm
1 stop9h 36m
$433
MedfordChicago
MFR - ORD
MFRORD
Medford
Mon 10/26
6:05 am-4:59 pm
1 stop8h 54m
Chicago O'Hare Intl
Sat 11/7
11:19 am-9:59 pm
2 stops12h 40m
$438
MedfordChicago
MFR - ORD
MFRORD
Medford
Sat 9/26
12:22 pm-11:57 pm
1 stop9h 35m
Chicago O'Hare Intl
Mon 9/28
5:10 pm-11:55 pm
2 stops8h 45m
$438
Quickest round-trip
MedfordChicago
MFR - ORD
MFRORD
Medford
Fri 9/11
1:31 pm-9:52 pm
1 stop6h 21m
Chicago O'Hare Intl
Sun 9/13
7:00 am-12:46 pm
1 stop7h 46m
$453
MedfordChicago
MFR - ORD
MFRORD
Medford
Fri 9/11
6:15 am-6:01 pm
1 stop9h 46m
Chicago O'Hare Intl
Mon 9/14
7:00 am-12:46 pm
1 stop7h 46m
$453
MedfordChicago
MFR - ORD
MFRORD
Medford
Sat 7/25
6:15 am-9:20 pm
2 stops13h 05m
Chicago O'Hare Intl
Wed 8/5
5:56 pm-11:23 pm
1 stop7h 27m
$469
Showing 1-10 of 28 resultsSorted by cheapest first
Compare providers for flights from Medford 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 Medford to Chicago in June.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Medford-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Medford-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Medford-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Medford-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 Medford-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 Medford to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Medford with our price prediction graph.
MFR-CHI
MFR-ORD
MFR-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 Medford to Chicago
MFR-CHI
MFR-ORD
MFR-MDW
What is the cheapest month to book a flight from Medford to Chicago?
Currently, September is the cheapest month in which you can book a flight from Medford to Chicago (average of $96). Flying from Medford to Chicago in July is currently the most expensive (average of $412). 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.
How much does it cost to fly round-trip from Medford to Chicago?
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 June 30, 2026.
Get a feel of what it's like to fly with Alaska Airlines,Delta, andUnited Airlines from Medford to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.5
Overall
7.9
Boarding
8.1
Comfort
7.8
Entertainment
7.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Crew
8.5
Overall
7.9
Boarding
8.1
Comfort
7.8
Entertainment
7.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Crew
8.5
Overall
7.9
Boarding
8.1
Comfort
7.8
Entertainment
7.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Crew
8.5
Overall
7.9
Boarding
8.1
Comfort
7.8
Entertainment
7.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Related info for your journey
Find useful and relevant information for your journey from Medford 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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Medford and Chicago flights
Browse other Medford and Chicago flight options. Last updated on June 30, 2026.
Other flights from Medford
Browse through other flights departing from Medford. Flights are based on user searches made on Cheapflights and were last updated on June 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Medford to Chicago
Discover the top 3 airlines that operate flights from Medford 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 June 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$273 | Average$477 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$302 | Average$421 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$306 | Average$419 | FlexibilityNo cancel fee | On-time75% |