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$135+ 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 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
MFR — CHI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$256
(Mytrip)

One-way from

$135
(Mytrip)

Popular in

December

Cheapest in

February

Average price

$497
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. 9% potential increase in price ($51 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 31, 2025.

This Mytrip deal was found by Cheapflights users on 7/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/54:52 pmMFR - ORD
1 stop16h 59mMultiple Airlines
Mon 9/86:15 amORD - MFR
1 stop10h 32mMultiple Airlines
Deal found 7/31$256
This Hawaiian Airlines deal was found by Cheapflights users on 7/30. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/91:32 pmMFR - ORD
1 stop6h 35mHawaiian Airlines
Sat 9/136:20 amORD - MFR
1 stop7h 05mHawaiian Airlines
Deal found 7/30$278
This Alaska Airlines deal was found by Cheapflights users on 7/30. 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.
Wed 10/153:52 pmMFR - ORD
1 stop11h 09mAlaska Airlines
Sun 10/196:00 amORD - MFR
1 stop7h 16mAlaska Airlines
Deal found 7/30$283
This Delta deal was found by Cheapflights users on 7/31. 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 9/96:00 amMFR - ORD
2 stops13h 00mDelta
Sat 9/132:25 pmORD - MFR
1 stop9h 03mDelta
Deal found 7/31$284
This American Airlines deal was found by Cheapflights users on 7/31. 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.
Fri 8/221:52 pmMFR - ORD
1 stop6h 51mAmerican Airlines
Sun 8/245:00 amORD - MFR
1 stop10h 10mAmerican Airlines
Deal found 7/31$287
This Delta deal was found by Cheapflights users on 7/30. 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.
Sat 10/116:00 amMFR - MDW
2 stops9h 43mDelta
Sat 10/1811:10 amMDW - MFR
2 stops13h 56mDelta
Deal found 7/30$319

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 July 31, 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 9/5

4:52 pm-11:51 am

1 stop16h 59m

Chicago O'Hare Intl

Mon 9/8

6:15 am-2:47 pm

1 stop10h 32m

$256

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 9/9

1:32 pm-10:07 pm

1 stop6h 35m

Chicago O'Hare Intl

Sat 9/13

6:20 am-11:25 am

1 stop7h 05m

$278

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 10/15

3:52 pm-5:01 am

1 stop11h 09m

Chicago O'Hare Intl

Sun 10/19

6:00 am-11:16 am

1 stop7h 16m

$283

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 9/9

6:00 am-9:00 pm

2 stops13h 00m

Chicago O'Hare Intl

Sat 9/13

2:25 pm-9:28 pm

1 stop9h 03m

$284

MedfordChicago

MFR - ORD

MFRORD

Medford

Fri 8/22

1:52 pm-10:43 pm

1 stop6h 51m

Chicago O'Hare Intl

Sun 8/24

5:00 am-1:10 pm

1 stop10h 10m

$287

MedfordChicago

MFR - MDW

MFRMDW

Medford

Sat 10/11

6:00 am-5:43 pm

2 stops9h 43m

Chicago Midway

Sat 10/18

11:10 am-11:06 pm

2 stops13h 56m

$319

MedfordChicago

MFR - ORD

MFRORD

Medford

Fri 10/10

5:12 pm-5:25 am

1 stop10h 13m

$135

MedfordChicago

MFR - ORD

MFRORD

Medford

Sat 8/30

1:32 pm-11:59 pm

1 stop8h 27m

$139

MedfordChicago

MFR - ORD

MFRORD

Medford

Thu 8/28

1:52 pm-12:35 am

1 stop8h 43m

$144

MedfordChicago

MFR - ORD

MFRORD

Medford

Sat 8/30

5:47 pm-1:09 pm

2 stops17h 22m

$202

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 12 results
1
2

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 July 31, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Delta, and Hawaiian 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

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Hawaiian Airlines
7.8
Good
2,611 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,900 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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.

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

    Currently priced at $278, 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 Delta - these airlines can fly you to your destination from $283 and $284, respectively. Hawaiian Airlines is priced at 41% 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 $139 on Hawaiian Airlines. Other airlines that offer cheap prices include American Airlines from $144 and Alaska Airlines from $202 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, 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
Valparaiso
Chesterton

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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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$258Average$373FlexibilityNo cancel feeOn-time85%
DeltaCheapest$263Average$385FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$300Average$417FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$304Average$422FlexibilityNo cancel feeOn-time69%

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