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$129+ 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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
MFR — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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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 September 15, 2025.

Round-trip from

$254
(Delta)

One-way from

$129
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$370
From Medford to Chicago (CHI)
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One-way flight from Medford to Chicago (CHI)
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Highest demand for flights based on searches. 11% potential increase in price ($62 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 15, 2025.

This Delta deal was found by Cheapflights users on 9/13. 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 10/46:15 amMFR - ORD
1 stop9h 05mDelta
Tue 10/76:05 pmORD - MFR
1 stop6h 45mDelta
Deal found 9/13$254
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2910:58 amMFR - ORD
2 stops21h 42mMultiple Airlines
Fri 10/36:15 amORD - MFR
1 stop12h 07mMultiple Airlines
Deal found 9/14$290
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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 10/88:51 amMFR - ORD
1 stop18h 10mAlaska Airlines
Sat 10/116:00 amORD - MFR
1 stop7h 16mAlaska Airlines
Deal found 9/13$298
This United Airlines deal was found by Cheapflights users on 9/13. 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 10/252:13 pmMFR - ORD
1 stop7h 00mUnited Airlines
Wed 10/291:55 pmORD - MFR
1 stop9h 19mUnited Airlines
Deal found 9/13$299
This Delta deal was found by Cheapflights users on 9/14. 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 12/2412:36 pmMFR - ORD
1 stop9h 23mDelta
Wed 12/316:00 amORD - MFR
1 stop8h 57mDelta
Deal found 9/14$335
This Delta deal was found by Cheapflights users on 9/14. 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 12/251:37 pmMFR - ORD
1 stop6h 02mDelta
Wed 12/316:00 amORD - MFR
1 stop8h 57mDelta
Deal found 9/14$337
This Delta deal was found by Cheapflights users on 9/14. 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 12/241:37 pmMFR - ORD
1 stop6h 02mDelta
Sat 1/36:00 amORD - MFR
1 stop19h 08mDelta
Deal found 9/14$347
This Alaska Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/252:41 pmMFR - ORD
1 stop7h 25mAlaska Airlines
Wed 10/298:00 amORD - MFR
2 stops9h 33mAlaska Airlines
Deal found 9/13$356
This Delta deal was found by Cheapflights users on 9/14. 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 12/2712:36 pmMFR - ORD
1 stop9h 23mDelta
Thu 1/16:00 amORD - MFR
1 stop8h 57mDelta
Deal found 9/14$357
This Delta deal was found by Cheapflights users on 9/14. 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 10/105:24 pmMFR - MDW
2 stops14h 16mDelta
Fri 10/171:08 pmMDW - MFR
2 stops11h 42mDelta
Deal found 9/14$682
This Delta deal was found by Cheapflights users on 9/14. 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 9/295:00 pmMFR - MDW
2 stops14h 40mDelta
Fri 10/31:08 pmMDW - MFR
2 stops12h 45mDelta
Deal found 9/14$719
This Delta deal was found by Cheapflights users on 9/14. 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 11/245:23 pmMFR - MDW
2 stops14h 29mDelta
Fri 11/289:41 amMDW - MFR
2 stops11h 24mDelta
Deal found 9/14$826

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 September 15, 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

Sat 10/4

6:15 am-5:20 pm

1 stop9h 05m

Chicago O'Hare Intl

Tue 10/7

6:05 pm-10:50 pm

1 stop6h 45m

$254

MedfordChicago

MFR - ORD

MFRORD

Medford

Sun 3/1

5:05 am-1:04 pm

1 stop5h 59m

Chicago O'Hare Intl

Tue 3/3

7:45 am-3:00 pm

1 stop9h 15m

$291

MedfordChicago

MFR - ORD

MFRORD

Medford

Sun 3/1

3:40 pm-11:59 pm

1 stop6h 19m

Chicago O'Hare Intl

Tue 3/3

7:45 am-3:39 pm

2 stops9h 54m

$297

MedfordChicago

MFR - ORD

MFRORD

Medford

Sat 10/25

2:41 pm-12:06 am

1 stop7h 25m

Chicago O'Hare Intl

Wed 10/29

2:05 pm-7:57 pm

1 stop7h 52m

$298

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 10/8

8:51 am-5:01 am

1 stop18h 10m

Chicago O'Hare Intl

Sat 10/11

6:00 am-11:16 am

1 stop7h 16m

$298

MedfordChicago

MFR - ORD

MFRORD

Medford

Sat 10/25

2:13 pm-11:13 pm

1 stop7h 00m

Chicago O'Hare Intl

Wed 10/29

1:55 pm-9:14 pm

1 stop9h 19m

$299

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 12/24

1:37 pm-9:39 pm

1 stop6h 02m

Chicago O'Hare Intl

Thu 1/1

6:00 am-12:57 pm

1 stop8h 57m

$299

MedfordChicago

MFR - ORD

MFRORD

Medford

Sat 10/25

6:00 am-5:18 pm

1 stop9h 18m

Chicago O'Hare Intl

Wed 10/29

7:50 am-4:44 pm

2 stops10h 54m

$304

MedfordChicago

MFR - MDW

MFRMDW

Medford

Sun 3/1

5:21 pm-8:54 am

2 stops37h 33m

Chicago Midway

Tue 3/3

2:00 pm-11:09 pm

2 stops11h 09m

$562

MedfordChicago

MFR - MDW

MFRMDW

Medford

Fri 10/10

5:24 pm-9:40 am

2 stops14h 16m

Chicago Midway

Fri 10/17

1:08 pm-10:50 pm

2 stops11h 42m

$682

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 31 results
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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, August is the cheapest month in which you can book a flight from Medford to Chicago (average of $245). Flying from Medford to Chicago in March is currently the most expensive (average of $321). 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 September 15, 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
10,000 reviews

Entertainment

7.0

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Delta
8.0
Very good
7,954 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,929 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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, Hawaiian Airlines, and Alaska Airlines can get you from Medford to Chicago in just under 5h 59m. Your travel time can differ by up to 3h 06m. 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 $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 Alaska Airlines and United Airlines - these airlines can fly you to your destination from $300 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, August is the cheapest month in which you can book a flight from Medford to Chicago (average of $245). Flying from Medford to Chicago in March is currently the most expensive (average of $321). 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
Benton Harbor
Porter
Chesterton

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Alternative routes for Medford to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$258Average$363FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$300Average$413FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$304Average$422FlexibilityNo cancel feeOn-time69%
DeltaCheapest$306Average$542FlexibilityNo cancel feeOn-timeN/A

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