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$185+ 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 11/25. Fares are subject to change and may not be available on all flights or dates of travel.
MFR — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find 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 October 30, 2025.

This KAYAK deal was found by Cheapflights users on 10/30. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/195:10 amMFR - ORD
1 stop5h 59mAlaska Airlines
Sun 11/236:00 amORD - MFR
1 stop7h 18mAlaska Airlines
Deal found 10/30$413
This Delta deal was found by Cheapflights users on 10/30. 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 11/196:00 amMFR - ORD
2 stops10h 45mDelta
Sun 11/236:13 pmORD - MFR
1 stop7h 19mDelta
Deal found 10/30$439
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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.
Sat 11/1512:30 pmMFR - ORD
1 stop9h 29mAlaska Airlines
Wed 11/192:54 pmORD - MFR
1 stop23h 55mAlaska Airlines
Deal found 10/30$456
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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.
Fri 11/143:45 pmMFR - ORD
2 stops12h 37mAlaska Airlines
Tue 11/188:00 amORD - MFR
1 stop7h 55mAlaska Airlines
Deal found 10/30$519
This Delta deal was found by Cheapflights users on 10/30. 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 11/196:00 amMFR - MDW
2 stops10h 18mDelta
Sun 11/239:34 amMDW - MFR
2 stops9h 09mDelta
Deal found 10/30$522
This Delta deal was found by Cheapflights users on 10/30. 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.
Fri 11/146:00 amMFR - ORD
2 stops13h 25mDelta
Tue 11/188:55 amORD - MFR
2 stops9h 48mDelta
Deal found 10/30$535
This Delta deal was found by Cheapflights users on 10/30. 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.
Fri 11/145:00 amMFR - MDW
2 stops11h 08mDelta
Tue 11/181:15 pmMDW - MFR
2 stops12h 17mDelta
Deal found 10/30$535
This Delta deal was found by Cheapflights users on 10/29. 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.
Thu 11/136:00 amMFR - ORD
1 stop9h 18mDelta
Mon 11/176:13 pmORD - MFR
1 stop7h 19mDelta
Deal found 10/29$563
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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.
Thu 11/1312:39 pmMFR - ORD
2 stops15h 43mAlaska Airlines
Mon 11/176:00 amORD - MFR
2 stops11h 33mAlaska Airlines
Deal found 10/29$573
This Delta deal was found by Cheapflights users on 10/29. 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.
Thu 11/136:00 amMFR - MDW
2 stops10h 18mDelta
Mon 11/171:47 pmMDW - MFR
2 stops12h 09mDelta
Deal found 10/29$595
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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 12/225:07 amMFR - ORD
1 stop21h 55mAlaska Airlines
Sun 12/287:00 amORD - MFR
1 stop10h 10mAlaska Airlines
Deal found 10/30$638
This Delta deal was found by Cheapflights users on 10/29. 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 11/256:00 amMFR - MDW
2 stops10h 18mDelta
Sun 11/301:15 pmMDW - MFR
2 stops12h 41mDelta
Deal found 10/29$1,059

Cheap 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 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$321
(Delta)

One-way from

$185
(Alaska Airlines)

Popular in

April

Cheapest in

September

Average price

$399
Provider with most accurate pricing for Medford-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Medford-Chicago (CHI) flights.
Search Deals
From Medford to Chicago (CHI)
Search Deals
One-way flight from Medford to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 30, 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

Sun 3/1

11:24 am-11:44 pm

1 stop10h 20m

Chicago O'Hare Intl

Tue 3/3

7:15 am-12:40 pm

1 stop7h 25m

$321

MedfordChicago

MFR - MDW

MFRMDW

Medford

Sun 3/1

6:05 am-6:34 pm

2 stops10h 29m

Chicago Midway

Tue 3/3

9:30 am-4:44 pm

2 stops9h 14m

$394

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 11/19

5:10 am-1:09 pm

1 stop5h 59m

Chicago O'Hare Intl

Sun 11/23

6:00 am-11:18 am

1 stop7h 18m

$413

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 11/19

6:00 am-6:45 pm

2 stops10h 45m

Chicago O'Hare Intl

Sun 11/23

6:13 pm-11:32 pm

1 stop7h 19m

$439

MedfordChicago

MFR - ORD

MFRORD

Medford

Sat 11/15

12:30 pm-11:59 pm

1 stop9h 29m

Chicago O'Hare Intl

Wed 11/19

2:54 pm-12:49 pm

1 stop23h 55m

$456

MedfordChicago

MFR - ORD

MFRORD

Medford

Fri 11/14

3:45 pm-6:22 am

2 stops12h 37m

Chicago O'Hare Intl

Tue 11/18

8:00 am-1:55 pm

1 stop7h 55m

$519

MedfordChicago

MFR - MDW

MFRMDW

Medford

Wed 11/19

6:00 am-6:18 pm

2 stops10h 18m

Chicago Midway

Sun 11/23

9:34 am-4:43 pm

2 stops9h 09m

$522

MedfordChicago

MFR - MDW

MFRMDW

Medford

Fri 11/14

5:00 am-6:08 pm

2 stops11h 08m

Chicago Midway

Tue 11/18

1:15 pm-11:32 pm

2 stops12h 17m

$535

MedfordChicago

MFR - MDW

MFRMDW

Medford

Thu 11/13

6:00 am-6:18 pm

2 stops10h 18m

Chicago Midway

Mon 11/17

1:47 pm-11:56 pm

2 stops12h 09m

$595

MedfordChicago

MFR - MDW

MFRMDW

Medford

Tue 11/25

6:00 am-6:18 pm

2 stops10h 18m

Chicago Midway

Sun 11/30

1:15 pm-11:56 pm

2 stops12h 41m

$1,059

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 14 results
1
2

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.
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, January is the cheapest month in which you can book a flight from Medford to Chicago (average of $247). Flying from Medford to Chicago in December is currently the most expensive (average of $767). 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 October 30, 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.
Alaska Airlines
8.0
Very good
11,214 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,214 reviews
Alaska Airlines
8.0
Very good
11,214 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Delta
7.9
Good
7,993 reviews
Alaska Airlines
8.0
Very good
11,214 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
8,998 reviews
Alaska Airlines
8.0
Very good
11,214 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

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 can get you from Medford to Chicago in just under 10h 20m. Your travel time can differ by up to . There are 1777 mi between Medford and Chicago.

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

    Currently priced at $258, Hawaiian Airlines will fly you from Medford to Chicago and back. In addition to Hawaiian Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Delta and United Airlines - these airlines can fly you to your destination from $298 and $304, respectively. Hawaiian Airlines is priced at 44% lower than the current average price of a flight leaving 3 months from now.

  • 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, January is the cheapest month in which you can book a flight from Medford to Chicago (average of $247). Flying from Medford to Chicago in December is currently the most expensive (average of $767). 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
Merrillville
Lansing
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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$258Average$363FlexibilityNo cancel feeOn-time85%
DeltaCheapest$298Average$385FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$304Average$421FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$305Average$416FlexibilityNo cancel feeOn-time75%

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