Which airport is the most popular layover for flights between Medford and Chicago?

Portland (PDX) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

What airlines fly to Chicago?

Alaska Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago from Medford according to our data. Alaska Airlines is the first choice among our users, with 45% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Which layover airport has the shortest connection time from Medford to Chicago?

Portland (PDX) has the shortest average layover time for this route: 1h 04m.

Which layover airport has the shortest travel time from Medford to Chicago?

Flights connecting via Portland (PDX) have the shortest average one-way travel time: 5h 54m.

What is the cheapest airline that flies from Medford to Chicago?

Hawaiian Airlines, American Airlines, and United Airlines are the most popular carriers operating from Medford to Chicago

Which layover airport offers the lowest fares from Medford to Chicago?

Flights via Portland (PDX) offer the lowest average round-trip price of $416.

When did momondo last update prices for flights from Medford Airport to Chicago?

Prices for flights from Medford Airport to Chicago refresh daily.

How many operators does momondo search for flights from Medford Airport to Chicago?

There are 4 operators available for flights from Medford Airport to Chicago as of August 2025.

How old do you have to be to fly from Medford Airport to Chicago?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Medford Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$128 Cheap Flights from Medford to Chicago (MFR-CHI) in 2025

Q: What is the typical price of a round-trip flight between Medford and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from $422 to $503. The lowest price recently found on this route was $279.

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Find the cheapest flights from Medford to Chicago (MFR-CHI)

Round-trip

One-way

Last minute

Cheap round-trip flights

2:40 pm - 12:27 amMFR-ORD

7h 47m1 stop

7:34 am - 1:28 pmORD-MFR

7h 54m1 stop

$279American Airlines

Find Deal

Tue, Sep 9 - Sat, Sep 13

3:46 pm - 5:00 amMFR-ORD

11h 14m1 stop

6:20 am - 11:25 amORD-MFR

7h 05m1 stop

$287Alaska Airlines

Find Deal

Fri, Sep 12 - Mon, Sep 15

1:32 pm - 12:03 amMFR-ORD

8h 31m1 stop

6:20 am - 11:25 amORD-MFR

7h 05m1 stop

$306Hawaiian Airlines

Find Deal

Tue, Sep 9 - Sat, Sep 13

12:02 pm - 8:50 pmMFR-ORD

6h 48m1 stop

6:00 am - 11:16 amORD-MFR

7h 16m1 stop

$308Hawaiian Airlines

Find Deal

Wed, Oct 8 - Sat, Oct 11

12:39 pm - 12:03 amMFR-ORD

9h 24m2 stops

6:20 am - 11:25 amORD-MFR

7h 05m1 stop

$312Alaska Airlines

Find Deal

Tue, Sep 9 - Sat, Sep 13

4:52 pm - 10:42 amMFR-ORD

15h 50m2 stops

1:03 pm - 8:43 amORD-MFR

21h 40m1 stop

$331

Find Deal

Fri, Sep 12 - Sun, Sep 14

8:53 am - 12:03 amMFR-ORD

13h 10m2 stops

5:45 pm - 12:33 amORD-MFR

8h 48m1 stop

$342Alaska Airlines

Find Deal

Tue, Sep 9 - Sat, Sep 13

2:40 pm - 12:27 amMFR-ORD

7h 47m1 stop

7:34 am - 1:28 pmORD-MFR

7h 54m1 stop

$343American Airlines

Find Deal

Thu, Sep 11 - Sun, Sep 14

6:00 am - 5:30 pmMFR-ORD

9h 30m2 stops

7:45 am - 4:50 pmORD-MFR

11h 05m2 stops

$500Delta

Find Deal

Thu, Sep 4 - Sat, Sep 6

5:15 am - 5:37 pmMFR-MDW

10h 22m2 stops

9:30 am - 4:50 pmMDW-MFR

9h 20m2 stops

$582Delta

Find Deal

Sun, Aug 31 - Thu, Sep 4

Alaska Airlines flights from Medford to Chicago

Our best Alaska Airlines deals on Medford to Chicago flight tickets

Alaska Airlines

Sep 12

MFR3:46 pmMedford

11h 14m

1 stop

ORD5:00 amChicago O'Hare Intl

Sep 15

ORD6:20 amChicago O'Hare Intl

7h 05m

1 stop

MFR11:25 amMedford

$287

Find similar

Alaska Airlines

Sep 9

MFR12:39 pmMedford

9h 24m

2 stops

ORD12:03 amChicago O'Hare Intl

Sep 13

ORD6:20 amChicago O'Hare Intl

7h 05m

1 stop

MFR11:25 amMedford

$312

Find similar

Alaska Airlines

Sep 9

MFR8:53 amMedford

13h 10m

2 stops

ORD12:03 amChicago O'Hare Intl

Sep 13

ORD5:45 pmChicago O'Hare Intl

8h 48m

1 stop

MFR12:33 amMedford

$342

Find similar

American Airlines flights from Medford to Chicago

Our best American Airlines deals on Medford to Chicago flight tickets

American Airlines

Sep 9

MFR2:40 pmMedford

7h 47m

1 stop

ORD12:27 amChicago O'Hare Intl

Sep 13

ORD7:34 amChicago O'Hare Intl

7h 54m

1 stop

MFR1:28 pmMedford

$279

Find similar

American Airlines

Sep 11

MFR2:40 pmMedford

7h 47m

1 stop

ORD12:27 amChicago O'Hare Intl

Sep 14

ORD7:34 amChicago O'Hare Intl

7h 54m

1 stop

MFR1:28 pmMedford

$343

Find similar

Fly from

Fly to

Route

Depart

Return

Price

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 9/9

2:40 pm-12:27 am

1 stop7h 47m

Chicago O'Hare Intl

Sat 9/13

7:34 am-1:28 pm

1 stop7h 54m

$279

MedfordChicago

MFR - ORD

MFRORD

Medford

Fri 9/12

3:46 pm-5:00 am

1 stop11h 14m

Chicago O'Hare Intl

Mon 9/15

6:20 am-11:25 am

1 stop7h 05m

$287

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 9/9

1:32 pm-12:03 am

1 stop8h 31m

Chicago O'Hare Intl

Sat 9/13

6:20 am-11:25 am

1 stop7h 05m

$306

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 10/8

12:02 pm-8:50 pm

1 stop6h 48m

Chicago O'Hare Intl

Sat 10/11

6:00 am-11:16 am

1 stop7h 16m

$308

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 9/9

12:39 pm-12:03 am

2 stops9h 24m

Chicago O'Hare Intl

Sat 9/13

6:20 am-11:25 am

1 stop7h 05m

$312

MedfordChicago

MFR - ORD

MFRORD

Medford

Fri 9/12

4:52 pm-10:42 am

2 stops15h 50m

Chicago O'Hare Intl

Sun 9/14

1:03 pm-8:43 am

1 stop21h 40m

$331

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 9/9

8:53 am-12:03 am

2 stops13h 10m

Chicago O'Hare Intl

Sat 9/13

5:45 pm-12:33 am

1 stop8h 48m

$342

MedfordChicago

MFR - ORD

MFRORD

Medford

Thu 9/11

2:40 pm-12:27 am

1 stop7h 47m

Chicago O'Hare Intl

Sun 9/14

7:34 am-1:28 pm

1 stop7h 54m

$343

MedfordChicago

MFR - ORD

MFRORD

Medford

Thu 9/4

6:00 am-5:30 pm

2 stops9h 30m

Chicago O'Hare Intl

Sat 9/6

7:45 am-4:50 pm

2 stops11h 05m

$500

MedfordChicago

MFR - MDW

MFRMDW

Medford

Sun 8/31

5:15 am-5:37 pm

2 stops10h 22m

Chicago Midway

Thu 9/4

9:30 am-4:50 pm

2 stops9h 20m

$582

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Medford to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Layovers

What is the typical price of a round-trip flight between Medford and Chicago?

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Medford, with most prices found around $345. If you’re not able to fly to Chicago in February, then October is your next best option. Flight prices from Medford to Chicago during October average around $360.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Sunday when prices can be found for as low as $384. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Medford to Chicago for around $646.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Medford to Chicago during this time can be as low as $481. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $618.

How have Medford to Chicago flight prices changed over time?

As of August 2025, prices for Medford to Chicago flights are approximately 10% more expensive when compared to flights at the same time last year.

When to book flights from Medford to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Medford to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Medford to Chicago (MFR to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Medford to Chicago

Best Price Found	$128
Fastest flight time	5h 55m
Direct flights	None
Airports in Chicago	2 airports

The best one-way flight to Chicago from Medford in the past 72 hours is $128. The best round-trip flight deal from Medford to Chicago found on momondo in the last 72 hours is $279.

The fastest flight from Medford to Chicago takes 5h 55m

There are no direct flights from Medford to Chicago. Popular non-direct routes for this connection are Medford Airport - Chicago O'Hare Intl Airport and Medford Airport - Chicago Midway Airport.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

How far is Medford to Chicago by plane?
Medford and Chicago are 1792.9 mi apart from one another. Flights usually cover this in 5h 55m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Medford Airport to Chicago?
Prices for flights from Medford Airport to Chicago refresh daily.
How many operators does momondo search for flights from Medford Airport to Chicago?
There are 4 operators available for flights from Medford Airport to Chicago as of August 2025.
How old do you have to be to fly from Medford Airport to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Medford Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular airline from Medford to Chicago?
Based on momondo bookings for flights between Medford and Chicago, the leading airline is Alaska Airlines, making up 41% of the total bookings. Other popular airlines include United Airlines with 32% and Delta with 27%.

Best airlines flying from Medford to Chicago

Compare and see reviews for airlines that fly from Medford to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Hawaiian Airlines	PriceFrom $258	Free Cancellation	Rating 7.8 2,665 reviews	Search Hawaiian Airlines flights
Delta	PriceFrom $283	Free Cancellation	Rating 8.0 7,981 reviews	Search Delta flights
Alaska Airlines	PriceFrom $300	Free Cancellation	Rating 8.0 10,000 reviews	Search Alaska Airlines flights
United Airlines	PriceFrom $304	Free Cancellation	Rating 7.4 8,925 reviews	Search United Airlines flights

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Hammond

Benton Harbor

Saint Joseph

Lansing

Portage

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Medford to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Medford.

Can I find flights from Medford to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Medford on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Medford to Chicago?

momondo helps you find the best flight between Medford and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Medford to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Medford and alert you when they change.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Flights to Denverfrom $63

Cheap flights from Medford to Chicago from $128

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Medford to Chicago departing on 9/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

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Find the cheapest flights from Medford to Chicago (MFR-CHI)

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Alaska Airlines flights from Medford to Chicago

Our best Alaska Airlines deals on Medford to Chicago flight tickets

American Airlines flights from Medford to Chicago

Our best American Airlines deals on Medford to Chicago flight tickets

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

See travel insights to Chicago from

How to get the cheapest flight ticket from Medford to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Medford and Chicago?

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Medford, with most prices found around $345. If you’re not able to fly to Chicago in February, then October is your next best option. Flight prices from Medford to Chicago during October average around $360.

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Medford to Chicago during this time can be as low as $481. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $618.

How have Medford to Chicago flight prices changed over time?

As of August 2025, prices for Medford to Chicago flights are approximately 10% more expensive when compared to flights at the same time last year.

What is the cheapest airline that flies from Medford to Chicago?

Hawaiian Airlines, American Airlines, and United Airlines are the most popular carriers operating from Medford to Chicago

What airlines fly to Chicago?

Which airport is the most popular layover for flights between Medford and Chicago?

Portland (PDX) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Medford to Chicago?

Flights via Portland (PDX) offer the lowest average round-trip price of $416.

Which layover airport has the shortest travel time from Medford to Chicago?

Flights connecting via Portland (PDX) have the shortest average one-way travel time: 5h 54m.

Which layover airport has the shortest connection time from Medford to Chicago?

Portland (PDX) has the shortest average layover time for this route: 1h 04m.

When to book flights from Medford to Chicago

Cheap Medford to Chicago (MFR to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Medford to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is Medford to Chicago by plane?

When did momondo last update prices for flights from Medford Airport to Chicago?

How many operators does momondo search for flights from Medford Airport to Chicago?

How old do you have to be to fly from Medford Airport to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular airline from Medford to Chicago?

Best airlines flying from Medford to Chicago

Compare and see reviews for airlines that fly from Medford to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Medford to Chicago?

Can I find flights from Medford to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Medford to Chicago?

I’m not ready to book a flight from Medford to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago