$130+ 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 7/13. Fares are subject to change and may not be available on all flights or dates of travel.
MFR — CHI
Jun 6 — Jun 131
Round-trip
1 adult, Economy
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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 May 7, 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 May 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 6/89:13 pm
MFR
- ORD
2 stops21h 30m
Multiple Airlines
Mon 9/146:50 am
ORD
- MFR
1 stop10h 00m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$372
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/269:13 pm
MFR
- ORD
1 stop29h 54m
Multiple Airlines
Fri 7/37:20 am
ORD
- MFR
1 stop9h 26m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$383
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:01 am
MFR
- ORD
1 stop8h 44m
Delta
Sat 6/205:55 pm
ORD
- MFR
1 stop7h 37m
Delta
Deal found 5/5![Delta logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/269:13 pm
MFR
- ORD
1 stop29h 54m
Multiple Airlines
Wed 7/89:57 pm
ORD
- MFR
2 stops24h 46m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$387
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:15 am
MFR
- ORD
2 stops13h 35m
Delta
Sat 5/307:12 am
ORD
- MFR
1 stop7h 48m
Delta
Deal found 5/6![Delta logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/229:13 pm
MFR
- ORD
1 stop29h 54m
Multiple Airlines
Mon 7/137:15 am
ORD
- MFR
1 stop9h 31m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$391
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:15 am
MFR
- ORD
2 stops13h 35m
Delta
Sat 5/307:12 am
ORD
- MFR
1 stop7h 48m
Delta
Deal found 5/7![Delta logo]()
$395
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:15 am
MFR
- MDW
2 stops10h 18m
Delta
Fri 5/291:59 pm
MDW
- MFR
2 stops11h 56m
Delta
Deal found 5/6![Delta logo]()
$395
This Alaska Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:08 am
MFR
- ORD
1 stop9h 42m
Alaska Airlines
Tue 6/92:10 pm
ORD
- MFR
1 stop10h 11m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$397
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/89:13 pm
MFR
- ORD
2 stops25h 35m
Multiple Airlines
Mon 6/157:20 am
ORD
- MFR
1 stop9h 29m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$401
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/109:11 pm
MFR
- ORD
2 stops16h 57m
Multiple Airlines
Mon 7/137:15 am
ORD
- MFR
1 stop9h 31m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$404
This United Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/62:11 pm
MFR
- ORD
1 stop6h 48m
United Airlines
Mon 6/156:00 am
ORD
- MFR
1 stop9h 00m
United Airlines
Deal found 5/6![United Airlines logo]()
$412
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 May 7, 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 May 7, 2026.
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:21 pm
MFR
- ORD
1 stop9h 34m
Delta
Wed 6/107:45 am
ORD
- MFR
2 stops10h 59m
Delta
Deal found 5/4![Delta logo]()
$390
This United Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/152:11 pm
MFR
- ORD
1 stop6h 48m
United Airlines
Wed 7/226:10 am
ORD
- MFR
1 stop7h 54m
United Airlines
Deal found 5/6![United Airlines logo]()
$413
This Alaska Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/257:35 pm
MFR
- ORD
1 stop7h 25m
Alaska Airlines
Fri 7/35:42 pm
ORD
- MFR
1 stop8h 22m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$445
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 7/256:01 am
MFR
- ORD
1 stop8h 42m
Delta
Wed 8/57:00 am
ORD
- MFR
1 stop7h 58m
Delta
Deal found 5/2![Delta logo]()
$413
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:15 am
MFR
- ORD
1 stop8h 34m
Delta
Fri 6/53:47 pm
ORD
- MFR
2 stops9h 55m
Delta
Deal found 5/5![Delta logo]()
$420
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:01 am
MFR
- ORD
2 stops13h 47m
Delta
Wed 7/227:45 am
ORD
- MFR
2 stops11h 02m
Delta
Deal found 5/4![Delta logo]()
$423
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/412:21 pm
MFR
- ORD
1 stop9h 34m
Delta
Thu 6/115:55 pm
ORD
- MFR
1 stop7h 17m
Delta
Deal found 5/4![Delta logo]()
$442
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 7/96:01 am
MFR
- ORD
2 stops10h 56m
Delta
Sat 7/185:55 pm
ORD
- MFR
1 stop7h 16m
Delta
Deal found 5/2![Delta logo]()
$445
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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
- ORD
2 stops9h 52m
Delta
Mon 11/27:30 am
ORD
- MFR
1 stop7h 06m
Delta
Deal found 5/3![Delta logo]()
$445
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:15 am
MFR
- MDW
2 stops10h 41m
Delta
Fri 5/291:59 pm
MDW
- MFR
2 stops11h 56m
Delta
Deal found 5/6![Delta logo]()
$455
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:15 am
MFR
- MDW
2 stops10h 18m
Delta
Fri 6/51:22 pm
MDW
- MFR
2 stops12h 20m
Delta
Deal found 5/5![Delta logo]()
$495
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:15 am
MFR
- MDW
2 stops10h 18m
Delta
Sat 5/231:22 pm
MDW
- MFR
2 stops11h 13m
Delta
Deal found 5/4![Delta logo]()
$506
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:15 am
MFR
- MDW
2 stops24h 27m
Delta
Fri 5/291:59 pm
MDW
- MFR
2 stops11h 56m
Delta
Deal found 5/6![Delta logo]()
$518
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:15 am
MFR
- MDW
2 stops11h 18m
Delta
Sat 5/301:22 pm
MDW
- MFR
2 stops11h 13m
Delta
Deal found 5/6![Delta logo]()
$541
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:05 am
MFR
- MDW
2 stops10h 26m
Delta
Mon 9/281:00 pm
MDW
- MFR
2 stops12h 13m
Delta
Deal found 5/4![Delta logo]()
$603
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/126:01 am
MFR
- MDW
2 stops10h 30m
Delta
Fri 6/191:49 pm
MDW
- MFR
2 stops11h 23m
Delta
Deal found 5/3![Delta logo]()
$603
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 6/85:20 am
MFR
- MDW
2 stops10h 58m
Delta
Mon 9/141:00 pm
MDW
- MFR
2 stops12h 13m
Delta
Deal found 5/2![Delta logo]()
$722
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:00 am
MFR
- MDW
2 stops10h 18m
Delta
Mon 7/131:49 pm
MDW
- MFR
2 stops11h 22m
Delta
Deal found 5/6![Delta logo]()
$727
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:15 am
MFR
- MDW
2 stops10h 41m
Delta
Sun 5/241:59 pm
MDW
- MFR
2 stops10h 36m
Delta
Deal found 5/6![Delta logo]()
$727
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:01 am
MFR
- MDW
2 stops10h 24m
Delta
Sat 7/251:18 pm
MDW
- MFR
2 stops11h 14m
Delta
Deal found 5/5![Delta logo]()
$730
Last-minute flights from Medford to ChicagoDiscover last-minute flight deals from Medford to Chicago. Data last updated May 7, 2026 and is based on user searches.
Discover last-minute flight deals from Medford to Chicago. Data last updated May 7, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:15 am
MFR
- MDW
2 stops10h 18m
Delta
Fri 5/291:59 pm
MDW
- MFR
2 stops11h 56m
Delta
Deal found 5/6![Delta logo]()
$395
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:15 am
MFR
- ORD
2 stops13h 35m
Delta
Sat 5/307:12 am
ORD
- MFR
1 stop7h 48m
Delta
Deal found 5/6![Delta logo]()
$390
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:15 am
MFR
- ORD
2 stops13h 35m
Delta
Sat 5/307:12 am
ORD
- MFR
1 stop7h 48m
Delta
Deal found 5/7![Delta logo]()
$395
This Alaska Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:08 am
MFR
- ORD
1 stop9h 42m
Alaska Airlines
Tue 6/92:10 pm
ORD
- MFR
1 stop10h 11m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$397
This United Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/62:11 pm
MFR
- ORD
1 stop6h 48m
United Airlines
Mon 6/156:00 am
ORD
- MFR
1 stop9h 00m
United Airlines
Deal found 5/6![United Airlines logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 6/89:13 pm
MFR
- ORD
2 stops21h 30m
Multiple Airlines
Mon 9/146:50 am
ORD
- MFR
1 stop10h 00m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$372
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/89:13 pm
MFR
- ORD
2 stops25h 35m
Multiple Airlines
Mon 6/157:20 am
ORD
- MFR
1 stop9h 29m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$401
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:01 am
MFR
- ORD
1 stop8h 44m
Delta
Sat 6/205:55 pm
ORD
- MFR
1 stop7h 37m
Delta
Deal found 5/5![Delta logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/229:13 pm
MFR
- ORD
1 stop29h 54m
Multiple Airlines
Mon 7/137:15 am
ORD
- MFR
1 stop9h 31m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$391
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/269:13 pm
MFR
- ORD
1 stop29h 54m
Multiple Airlines
Fri 7/37:20 am
ORD
- MFR
1 stop9h 26m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/269:13 pm
MFR
- ORD
1 stop29h 54m
Multiple Airlines
Wed 7/89:57 pm
ORD
- MFR
2 stops24h 46m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$387
This Expedia deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/273:52 pm
MFR
- ORD
1 stop11h 08m
Alaska Airlines
Sat 7/48:02 am
ORD
- MFR
1 stop6h 48m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$413
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 May 7, 2026.
Search for one-way flight options from Medford to Chicago. Find affordable one-way fares based on user searches. Data last updated May 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/139:11 pm
MFR
- ORD
1 stop30h 17m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/109:17 pm
MFR
- ORD
2 stops25h 32m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/129:33 pm
MFR
- ORD
1 stop29h 55m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/109:11 pm
MFR
- ORD
1 stop30h 17m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/79:17 pm
MFR
- ORD
1 stop30h 11m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/139:11 pm
MFR
- MDW
3 stops35h 56m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/219:31 pm
MFR
- ORD
1 stop29h 36m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$201
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:01 am
MFR
- MDW
2 stops10h 24m
Delta
Deal found 5/6![Delta logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/109:11 pm
MFR
- MDW
2 stops44h 10m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:49 am
MFR
- MDW
2 stops9h 12m
Delta
Deal found 5/6![Delta logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/129:33 pm
MFR
- MDW
3 stops46h 35m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/219:31 pm
MFR
- MDW
3 stops35h 41m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$255
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 May 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $372 (Kiwi.com) |
One-way from | $130 (Kiwi.com) |
Popular in | January |
Cheapest in | October |
Average price | $443 |
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 May 7, 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
Wed 6/3
12:21 pm-11:55 pm
1 stop9h 34m
Chicago O'Hare Intl
Wed 6/10
7:45 am-4:44 pm
2 stops10h 59m
$390
Quickest round-trip
MedfordChicago
MFR - ORD
MFRORD
Medford
Wed 7/15
2:11 pm-10:59 pm
1 stop6h 48m
Chicago O'Hare Intl
Wed 7/22
6:10 am-12:04 pm
1 stop7h 54m
$413
MedfordChicago
MFR - ORD
MFRORD
Medford
Sat 7/25
6:01 am-4:43 pm
1 stop8h 42m
Chicago O'Hare Intl
Wed 8/5
7:00 am-12:58 pm
1 stop7h 58m
$413
MedfordChicago
MFR - ORD
MFRORD
Medford
Fri 5/29
6:15 am-4:49 pm
1 stop8h 34m
Chicago O'Hare Intl
Fri 6/5
3:47 pm-11:42 pm
2 stops9h 55m
$420
MedfordChicago
MFR - ORD
MFRORD
Medford
Tue 7/14
6:01 am-9:48 pm
2 stops13h 47m
Chicago O'Hare Intl
Wed 7/22
7:45 am-4:47 pm
2 stops11h 02m
$423
MedfordChicago
MFR - ORD
MFRORD
Medford
Thu 6/4
12:21 pm-11:55 pm
1 stop9h 34m
Chicago O'Hare Intl
Thu 6/11
5:55 pm-11:12 pm
1 stop7h 17m
$442
MedfordChicago
MFR - ORD
MFRORD
Medford
Thu 6/25
7:35 pm-5:00 am
1 stop7h 25m
Chicago O'Hare Intl
Fri 7/3
5:42 pm-12:04 am
1 stop8h 22m
$445
MedfordChicago
MFR - ORD
MFRORD
Medford
Thu 7/9
6:01 am-6:57 pm
2 stops10h 56m
Chicago O'Hare Intl
Sat 7/18
5:55 pm-11:11 pm
1 stop7h 16m
$445
MedfordChicago
MFR - ORD
MFRORD
Medford
Tue 10/27
6:05 am-5:57 pm
2 stops9h 52m
Chicago O'Hare Intl
Mon 11/2
7:30 am-12:36 pm
1 stop7h 06m
$445
MedfordChicago
MFR - MDW
MFRMDW
Medford
Sat 5/23
5:15 am-5:56 pm
2 stops10h 41m
Chicago Midway
Fri 5/29
1:59 pm-11:55 pm
2 stops11h 56m
$455
Showing 1-10 of 39 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 May.
| 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 June is currently the most expensive (average of $389). 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 May 7, 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.
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.8
Entertainment
7.0
Food
7.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.8
Entertainment
7.0
Food
7.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.8
Entertainment
7.0
Food
7.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.8
Entertainment
7.0
Food
7.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Related info for your journey
Find useful and relevant information for your journey from 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
Lansing
Merrillville
Hammond
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 7, 2026.
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Medford and Chicago flights
Browse other Medford and Chicago flight options. Last updated on May 7, 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 May 7, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Medford to Chicago
Discover the top 4 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 May 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$258 | Average$363 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$273 | Average$439 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$302 | Average$421 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$308 | Average$417 | FlexibilityNo cancel fee | On-time75% |