Chicago

$231+ 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 12/30. Fares are subject to change and may not be available on all flights or dates of travel.
MFR — CHI
Jan 17 — Jan 241
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Cheap flight deals from Medford to Chicago

Cheapest flights from Medford to Chicago
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 December 18, 2025.

This Delta deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” 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 12/2312:36 pmMFR - ORD
1 stop9h 23mDelta
Wed 12/312:15 pmORD - MFR
1 stop8h 59mDelta
Deal found 12/16$667
This United Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” 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 12/235:00 amMFR - ORD
1 stop6h 19mUnited Airlines
Wed 12/318:02 pmORD - MFR
2 stops19h 23mUnited Airlines
Deal found 12/16$818
This United Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” 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 12/235:00 amMFR - ORD
1 stop6h 19mUnited Airlines
Fri 12/267:10 amORD - MFR
1 stop8h 15mUnited Airlines
Deal found 12/16$902
This American Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” 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 12/203:12 pmMFR - ORD
1 stop7h 04mAmerican Airlines
Sat 12/277:06 amORD - MFR
1 stop8h 53mAmerican Airlines
Deal found 12/16$979
This Delta deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” 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 12/2312:36 pmMFR - ORD
1 stop9h 23mDelta
Fri 12/266:00 amORD - MFR
1 stop8h 54mDelta
Deal found 12/17$1,003
This American Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/233:12 pmMFR - ORD
1 stop7h 04mAmerican Airlines
Fri 12/261:15 pmORD - MFR
2 stops9h 05mAmerican Airlines
Deal found 12/17$1,049

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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$296
(Delta)

One-way from

$231
(Kiwi.com)

Popular in

April

Cheapest in

October

Average price

$593
Provider with most accurate pricing for Medford-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Medford-Chicago (CHI) flights.
From Medford to Chicago (CHI)
One-way flight from Medford to Chicago (CHI)
Highest demand for flights based on searches. 11% potential increase in price ($61 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($21 potential savings vs. average RT price).
Average for round-trip flights in December 2025

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 December 18, 2025.
Use the filters below to find and compare flights from Medford to Chicago that are best for you.

Fly from

Medford

Fly to

Chicago

Route

Depart

Return

Price

MedfordChicago

MFR - ORD

MFRORD

Medford

Fri 1/9

6:05 am-5:44 pm

2 stops9h 39m

Chicago O'Hare Intl

Sun 1/11

1:50 pm-10:59 pm

2 stops11h 09m

$296

MedfordChicago

MFR - ORD

MFRORD

Medford

Sat 1/24

1:20 pm-11:37 pm

1 stop8h 17m

Chicago O'Hare Intl

Wed 1/28

6:06 pm-11:56 pm

1 stop7h 50m

$300

MedfordChicago

MFR - ORD

MFRORD

Medford

Fri 1/9

5:42 am-11:50 pm

1 stop16h 08m

Chicago O'Hare Intl

Sun 1/11

9:00 am-12:45 pm

1 stop29h 45m

$312

MedfordChicago

MFR - MDW

MFRMDW

Medford

Fri 1/9

5:05 am-6:32 pm

2 stops11h 27m

Chicago Midway

Sun 1/11

1:49 pm-10:59 pm

2 stops11h 10m

$380

MedfordChicago

MFR - MDW

MFRMDW

Medford

Thu 1/1

5:00 am-5:26 pm

2 stops10h 26m

Chicago Midway

Mon 1/5

1:49 pm-10:57 pm

2 stops11h 08m

$1,790

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 12/30

9:03 pm-11:59 pm

1 stop24h 56m

$231

MedfordChicago

MFR - MDW

MFRMDW

Medford

Tue 12/30

8:09 pm-10:12 pm

3 stops48h 03m

$334

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 12/30

8:09 pm-10:45 pm

3 stops24h 36m

$357

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Medford-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Medford-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.
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

What is the cheapest month to book a flight from Medford to Chicago?

Currently, October is the cheapest month in which you can book a flight from Medford to Chicago (average of $241). Flying from Medford to Chicago in June is currently the most expensive (average of $672). 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 December 18, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Delta, and United 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

Entertainment

7.0

Overall

8.0

Comfort

7.8

Food

7.1

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

Crew

8.5

Entertainment

7.0

Overall

8.0

Comfort

7.8

Food

7.1

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

Crew

8.5

Entertainment

7.0

Overall

8.0

Comfort

7.8

Food

7.1

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

Crew

8.5

Entertainment

7.0

Overall

8.0

Comfort

7.8

Food

7.1

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

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.
  • What airport do you fly from for flights from Medford to Chicago?

    Medford (MFR) is the airport you will fly out of if you book a flight from Medford to Chicago. You should not have trouble finding flights to Chicago from Medford; the airport handles an average of 0 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 4 airlines have flights from the Medford airport to Chicago. It is only a 3.0 mi journey to Medford (MFR) from Medford’s city center.

  • How long is the flight from Medford to Chicago?

    Delta and Alaska Airlines can get you from Medford to Chicago in just under 8h 17m. Your travel time can differ by up to 1h 22m. There are 1777 mi between Medford and Chicago. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Medford to Chicago round-trip?

    Currently priced at $193, Delta will fly you from Medford to Chicago and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Hawaiian Airlines and United Airlines - these airlines can fly you to your destination from $258 and $304, respectively. Delta is priced at 57% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Medford to Chicago one-way?

    One-way options have recently been found by users for as low as $173 on Alaska Airlines. Other airlines that offer cheap prices include Delta from $194 and United Airlines from $234 one-way.

  • Can I find deals for flights from Medford to Chicago that include hotel bookings?

    Yes. In addition to deals on Medford to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Medford to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Medford to Chicago.

  • Can I find deals for business class flights from Medford to Chicago?

    Yes. Cheapflights offers flight deals from Medford to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Medford to Chicago?

    Currently, October is the cheapest month in which you can book a flight from Medford to Chicago (average of $241). Flying from Medford to Chicago in June is currently the most expensive (average of $672). 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$258Average$363FlexibilityNo cancel feeOn-time85%
DeltaCheapest$273Average$372FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$304Average$421FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$306Average$418FlexibilityNo cancel feeOn-time75%

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