$227+ Cheap flights from Medford (MFR) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/23. Fares are subject to change and may not be available on all flights or dates of travel.
MFR — CHI
Nov 1 — Nov 81
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Medford to Chicago
Cheapest
Best
Last-minute
One-way
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 October 2, 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 October 2, 2026.
This Expedia deal was found by Cheapflights users on 9/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/282:50 pm -
1 stop20h 28m
Wed 11/42:07 pm -
2 stops11h 36m
Deal found 9/29![Alaska Airlines logo]()
$423
This Kiwi.com deal was found by Cheapflights users on 9/26. 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.
Sun 12/69:26 pm -
1 stop29h 35m
Wed 12/166:21 am -
1 stop29h 40m
Deal found 9/26![Multiple Airlines logo]()
$428
This Orbitz deal was found by Cheapflights users on 9/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/97:03 am -
2 stops14h 56m
Wed 12/169:00 am -
1 stop10h 18m
Deal found 9/28![Alaska Airlines logo]()
$433
This Delta deal was found by Cheapflights users on 9/28. 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.
Wed 12/91:31 pm -
1 stop6h 25m
Wed 12/165:55 pm -
1 stop7h 41m
Deal found 9/28![Delta logo]()
$443
This Delta deal was found by Cheapflights users on 9/26. 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.
Tue 12/86:10 am -
2 stops8h 33m
Wed 12/165:55 pm -
1 stop7h 41m
Deal found 9/26![Delta logo]()
$448
This Delta deal was found by Cheapflights users on 9/29. 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 10/286:11 am -
2 stops13h 54m
Wed 11/41:55 pm -
2 stops10h 04m
Deal found 9/29![Delta logo]()
$454
This Delta deal was found by Cheapflights users on 9/26. 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.
Tue 12/812:31 pm -
1 stop9h 26m
Sat 12/196:00 am -
1 stop9h 10m
Deal found 9/26![Delta logo]()
$462
This Delta deal was found by Cheapflights users on 9/29. 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 11/2412:30 pm -
1 stop9h 29m
Sat 11/286:40 am -
1 stop8h 11m
Deal found 9/29![Delta logo]()
$463
This Orbitz deal was found by Cheapflights users on 9/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/11:28 pm -
1 stop8h 31m
Thu 12/106:00 am -
2 stops18h 11m
Deal found 9/28![Alaska Airlines logo]()
$466
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 October 2, 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 October 2, 2026.
This United Airlines deal was found by Cheapflights users on 9/29. 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 10/282:06 pm -
1 stop7h 21m
Wed 11/412:42 pm -
1 stop7h 27m
Deal found 9/29![United Airlines logo]()
$443
This Delta deal was found by Cheapflights users on 9/28. 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.
Wed 12/91:31 pm -
1 stop6h 25m
Wed 12/165:55 pm -
1 stop7h 41m
Deal found 9/28![Delta logo]()
$443
This Orbitz deal was found by Cheapflights users on 9/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/11:28 pm -
1 stop8h 31m
Thu 12/106:00 am -
2 stops18h 11m
Deal found 9/28![Alaska Airlines logo]()
$466
This Delta deal was found by Cheapflights users on 9/29. 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 10/286:11 am -
2 stops13h 54m
Wed 11/41:55 pm -
2 stops10h 04m
Deal found 9/29![Delta logo]()
$454
This Delta deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/96:10 am -
1 stop8h 40m
Sat 12/196:00 am -
1 stop9h 10m
Deal found 9/26![Delta logo]()
$462
This Alaska Airlines deal was found by Cheapflights users on 9/30. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2610:33 am -
1 stop11h 26m
Sat 11/77:00 am -
1 stop9h 36m
Deal found 9/30![Alaska Airlines logo]()
$516
This Delta deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1212:31 pm -
1 stop9h 26m
Thu 12/177:25 am -
1 stop6h 26m
Deal found 9/26![Delta logo]()
$500
This Delta deal was found by Cheapflights users on 9/27. 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.
Fri 11/61:20 pm -
1 stop6h 45m
Tue 11/103:47 pm -
2 stops10h 08m
Deal found 9/27![Delta logo]()
$506
This Delta deal was found by Cheapflights users on 9/28. 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 10/136:11 am -
2 stops13h 54m
Sat 10/177:35 am -
1 stop6h 05m
Deal found 9/28![Delta logo]()
$550
This Delta deal was found by Cheapflights users on 9/29. 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 10/176:11 am -
2 stops12h 19m
Sat 10/245:48 pm -
1 stop7h 30m
Deal found 9/29![Delta logo]()
$550
Last-minute flights from Medford to ChicagoDiscover last-minute flight deals from Medford to Chicago. Data last updated October 2, 2026 and is based on user searches.
Discover last-minute flight deals from Medford to Chicago. Data last updated October 2, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 9/30. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2610:33 am -
1 stop11h 26m
Sat 11/77:00 am -
1 stop9h 36m
Deal found 9/30![Alaska Airlines logo]()
$516
This Delta deal was found by Cheapflights users on 9/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/261:20 pm -
1 stop6h 45m
Sat 11/711:19 am -
2 stops13h 59m
Deal found 9/30![Delta logo]()
$521
This Alaska Airlines deal was found by Cheapflights users on 9/27. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:10 am -
1 stop6h 08m
Mon 11/26:35 pm -
1 stop16h 59m
Deal found 9/27![Alaska Airlines logo]()
$493
This Delta deal was found by Cheapflights users on 9/27. 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.
Tue 10/275:15 am -
2 stops13h 23m
Mon 11/26:35 am -
1 stop8h 05m
Deal found 9/27![Delta logo]()
$506
This Expedia deal was found by Cheapflights users on 9/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/282:50 pm -
1 stop20h 28m
Wed 11/42:07 pm -
2 stops11h 36m
Deal found 9/29![Alaska Airlines logo]()
$423
This United Airlines deal was found by Cheapflights users on 9/29. 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 10/282:06 pm -
1 stop7h 21m
Wed 11/412:42 pm -
1 stop7h 27m
Deal found 9/29![United Airlines logo]()
$443
This Delta deal was found by Cheapflights users on 9/29. 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 10/286:11 am -
2 stops13h 54m
Wed 11/41:55 pm -
2 stops10h 04m
Deal found 9/29![Delta logo]()
$454
This Expedia deal was found by Cheapflights users on 9/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/304:34 pm -
2 stops11h 06m
Sun 11/17:57 pm -
1 stop20h 51m
Deal found 9/30![Alaska Airlines logo]()
$486
This Alaska Airlines deal was found by Cheapflights users on 9/27. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/63:32 pm -
1 stop25h 27m
Tue 11/103:59 pm -
1 stop10h 00m
Deal found 9/27![Alaska Airlines logo]()
$483
This Delta deal was found by Cheapflights users on 9/29. 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.
Sun 11/86:11 am -
1 stop8h 29m
Wed 11/117:17 pm -
1 stop6h 38m
Deal found 9/29![Delta logo]()
$501
This Delta deal was found by Cheapflights users on 9/29. 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 11/2412:30 pm -
1 stop9h 29m
Sat 11/286:40 am -
1 stop8h 11m
Deal found 9/29![Delta logo]()
$463
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 October 2, 2026.
Search for one-way flight options from Medford to Chicago. Find affordable one-way fares based on user searches. Data last updated October 2, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/29. 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.
Wed 12/234:30 pm -
1 stop18h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Alaska Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 10/124:40 pm -
2 stops24h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Multiple Airlines logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 10/99:52 pm -
2 stops33h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Multiple Airlines logo]()
$253
This Priceline deal was found by Cheapflights users on 9/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/78:17 am -
1 stop8h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Alaska Airlines logo]()
$273
This Delta deal was found by Cheapflights users on 9/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:11 am -
2 stops12h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Delta logo]()
$278
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Thu 12/171:30 pm -
1 stop9h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![American Airlines logo]()
$280
This Delta deal was found by Cheapflights users on 9/27. 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.
Thu 12/176:10 am -
2 stops13h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Delta logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/112:39 pm -
2 stops32h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Multiple Airlines logo]()
$303
This Delta deal was found by Cheapflights users on 9/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:20 pm -
1 stop6h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Delta logo]()
$328
This Delta deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 10/86:11 am -
2 stops13h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Delta logo]()
$333
This United Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/182:16 pm -
1 stop9h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![United Airlines logo]()
$340
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 October 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $423 (Expedia) |
One-way from | $227 (Alaska Airlines) |
Popular in | January |
Cheapest in | December |
Average price | $573 |
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 7,457,451 searches. Data last updated October 2, 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 Medford - ORD Chicago O'Hare Intl
MFRORD
Medford
Wed 12/23
4:30 pm-1:19 pm
1 stop18h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$227
MedfordChicago
MFR Medford - ORD Chicago O'Hare Intl
MFRORD
Medford
Fri 10/9
9:52 pm-9:21 am
2 stops33h 29m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$253
Quickest round-trip
MedfordChicago
MFR Medford - ORD Chicago O'Hare Intl
MFRORD
Medford
Sat 10/10
1:01 pm-9:18 pm
1 stop6h 17m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$273
MedfordChicago
MFR Medford - ORD Chicago O'Hare Intl
MFRORD
Medford
Thu 12/17
1:30 pm-12:59 am
1 stop9h 29m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$280
MedfordChicago
MFR Medford - ORD Chicago O'Hare Intl
MFRORD
Medford
Thu 10/15
1:20 pm-10:05 pm
1 stop6h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$328
MedfordChicago
MFR Medford - ORD Chicago O'Hare Intl
MFRORD
Medford
Mon 10/12
11:03 am-11:32 am
3 stops22h 29m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$400
MedfordChicago
MFR Medford - ORD Chicago O'Hare Intl
MFRORD
Medford
Wed 10/28
2:06 pm-11:27 pm
1 stop7h 21m
Chicago O'Hare Intl
Wed 11/4
12:42 pm-6:09 pm
1 stop7h 27m
$443
MedfordChicago
MFR Medford - ORD Chicago O'Hare Intl
MFRORD
Medford
Wed 12/9
1:31 pm-9:56 pm
1 stop6h 25m
Chicago O'Hare Intl
Wed 12/16
5:55 pm-11:36 pm
1 stop7h 41m
$443
MedfordChicago
MFR Medford - ORD Chicago O'Hare Intl
MFRORD
Medford
Wed 10/28
6:11 am-10:05 pm
2 stops13h 54m
Chicago O'Hare Intl
Wed 11/4
1:55 pm-9:59 pm
2 stops10h 04m
$454
MedfordChicago
MFR Medford - ORD Chicago O'Hare Intl
MFRORD
Medford
Wed 12/9
6:10 am-4:50 pm
1 stop8h 40m
Chicago O'Hare Intl
Sat 12/19
6:00 am-1:10 pm
1 stop9h 10m
$462
Showing 1-10 of 16 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 October.
| 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
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
What is the cheapest month to book a flight from Medford to Chicago?
Currently, November is the cheapest month in which you can book a flight from Medford to Chicago (average of $418). Flying from Medford to Chicago in January is currently the most expensive (average of $674). 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.
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 October 2, 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.
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
7.8
Crew
8.5
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
7.8
Crew
8.5
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
7.8
Crew
8.5
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
7.8
Crew
8.5
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
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Top 4 airlines flying from Medford to Chicago
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$273 | Average$505 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$302 | Average$544 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$368 | Average$489 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$412 | Average$480 | FlexibilityNo cancel fee | On-time71% |