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Cheap flights from Medford to Chicago from $232

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 11/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Medford to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Hawaiian Airlines Logo
5:05 am - 1:04 pmMFR-ORD
5h 59m1 stop
Hawaiian Airlines Logo
10:00 am - 3:00 pmORD-MFR
7h 00m1 stop
$283Hawaiian Airlines
Find Deal
Sun, Mar 1 - Tue, Mar 3
Alaska Airlines Logo
3:40 pm - 11:59 pmMFR-ORD
6h 19m1 stop
Alaska Airlines Logo
2:05 pm - 12:09 amORD-MFR
12h 04m2 stops
$308Alaska Airlines
Find Deal
Sun, Mar 1 - Tue, Mar 3
Delta Logo
5:21 pm - 11:44 pmMFR-ORD
28h 23m1 stop
Delta Logo
7:15 am - 12:40 pmORD-MFR
7h 25m1 stop
$313Delta
Find Deal
Sun, Mar 1 - Tue, Mar 3
Delta Logo
5:21 pm - 11:44 pmMFR-ORD
28h 23m1 stop
Delta Logo
7:00 am - 4:44 pmORD-MFR
11h 44m2 stops
$318Delta
Find Deal
Sun, Mar 1 - Tue, Mar 3
Alaska Airlines Logo
5:42 pm - 11:55 pmMFR-ORD
28h 13m1 stop
Alaska Airlines Logo
6:06 pm - 11:56 pmORD-MFR
7h 50m1 stop
$321Alaska Airlines
Find Deal
Fri, Jan 16 - Tue, Jan 20
Delta Logo
11:24 am - 11:44 pmMFR-ORD
10h 20m1 stop
Delta Logo
1:35 pm - 11:09 pmORD-MFR
11h 34m2 stops
$326Delta
Find Deal
Sun, Mar 1 - Tue, Mar 3
Alaska Airlines Logo
5:42 pm - 2:38 pmMFR-ORD
18h 56m1 stop
Alaska Airlines Logo
9:00 am - 11:56 pmORD-MFR
16h 56m2 stops
$343Alaska Airlines
Find Deal
Fri, Jan 16 - Tue, Jan 20
Delta Logo
6:05 am - 6:46 pmMFR-ORD
10h 41m2 stops
Delta Logo
10:35 am - 11:09 pmORD-MFR
14h 34m2 stops
$351Delta
Find Deal
Sun, Mar 1 - Tue, Mar 3
Delta Logo
6:05 am - 6:34 pmMFR-MDW
10h 29m2 stops
Delta Logo
1:00 pm - 11:09 pmMDW-MFR
12h 09m2 stops
$381Delta
Find Deal
Sun, Mar 1 - Tue, Mar 3
Delta Logo
6:05 am - 6:46 pmMFR-ORD
10h 41m2 stops
Delta Logo
7:00 am - 4:44 pmORD-MFR
11h 44m2 stops
$394Delta
Find Deal
Sun, Mar 1 - Tue, Mar 3

Alaska Airlines flights from Medford to Chicago

Our best Alaska Airlines deals on Medford to Chicago flight tickets
Alaska Airlines
Mar 1
MFR3:40 pmMedford
6h 19m
1 stop
ORD11:59 pmChicago O'Hare Intl
Mar 3
ORD2:05 pmChicago O'Hare Intl
12h 04m
2 stops
MFR12:09 amMedford
$308
Find similar
Alaska Airlines
Jan 16
MFR5:42 pmMedford
28h 13m
1 stop
ORD11:55 pmChicago O'Hare Intl
Jan 20
ORD6:06 pmChicago O'Hare Intl
7h 50m
1 stop
MFR11:56 pmMedford
$321
Find similar
Alaska Airlines
Jan 16
MFR5:42 pmMedford
18h 56m
1 stop
ORD2:38 pmChicago O'Hare Intl
Jan 20
ORD9:00 amChicago O'Hare Intl
16h 56m
2 stops
MFR11:56 pmMedford
$343
Find similar

Delta flights from Medford to Chicago

Our best Delta deals on Medford to Chicago flight tickets
Delta
Mar 1
MFR5:21 pmMedford
28h 23m
1 stop
ORD11:44 pmChicago O'Hare Intl
Mar 3
ORD7:15 amChicago O'Hare Intl
7h 25m
1 stop
MFR12:40 pmMedford
$313
Find similar
Delta
Mar 1
MFR5:21 pmMedford
28h 23m
1 stop
ORD11:44 pmChicago O'Hare Intl
Mar 3
ORD7:00 amChicago O'Hare Intl
11h 44m
2 stops
MFR4:44 pmMedford
$318
Find similar
Delta
Mar 1
MFR11:24 amMedford
10h 20m
1 stop
ORD11:44 pmChicago O'Hare Intl
Mar 3
ORD1:35 pmChicago O'Hare Intl
11h 34m
2 stops
MFR11:09 pmMedford
$326
Find similar

momondo 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, momondo users made 832,500 searches. Data last updated October 29, 2025.
Use the filters below to find and compare flights from Medford to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MedfordChicago

MFR - ORD

MFRORD

Medford

Sun 3/1

5:05 am-1:04 pm

1 stop5h 59m

Chicago O'Hare Intl

Tue 3/3

10:00 am-3:00 pm

1 stop7h 00m

$283

MedfordChicago

MFR - ORD

MFRORD

Medford

Sun 3/1

3:40 pm-11:59 pm

1 stop6h 19m

Chicago O'Hare Intl

Tue 3/3

2:05 pm-12:09 am

2 stops12h 04m

$308

MedfordChicago

MFR - ORD

MFRORD

Medford

Sun 3/1

5:21 pm-11:44 pm

1 stop28h 23m

Chicago O'Hare Intl

Tue 3/3

7:15 am-12:40 pm

1 stop7h 25m

$313

MedfordChicago

MFR - ORD

MFRORD

Medford

Sun 3/1

5:21 pm-11:44 pm

1 stop28h 23m

Chicago O'Hare Intl

Tue 3/3

7:00 am-4:44 pm

2 stops11h 44m

$318

MedfordChicago

MFR - ORD

MFRORD

Medford

Fri 1/16

5:42 pm-11:55 pm

1 stop28h 13m

Chicago O'Hare Intl

Tue 1/20

6:06 pm-11:56 pm

1 stop7h 50m

$321

MedfordChicago

MFR - ORD

MFRORD

Medford

Sun 3/1

11:24 am-11:44 pm

1 stop10h 20m

Chicago O'Hare Intl

Tue 3/3

1:35 pm-11:09 pm

2 stops11h 34m

$326

MedfordChicago

MFR - ORD

MFRORD

Medford

Fri 1/16

5:42 pm-2:38 pm

1 stop18h 56m

Chicago O'Hare Intl

Tue 1/20

9:00 am-11:56 pm

2 stops16h 56m

$343

MedfordChicago

MFR - ORD

MFRORD

Medford

Sun 3/1

6:05 am-6:46 pm

2 stops10h 41m

Chicago O'Hare Intl

Tue 3/3

10:35 am-11:09 pm

2 stops14h 34m

$351

MedfordChicago

MFR - MDW

MFRMDW

Medford

Sun 3/1

6:05 am-6:34 pm

2 stops10h 29m

Chicago Midway

Tue 3/3

1:00 pm-11:09 pm

2 stops12h 09m

$381

MedfordChicago

MFR - ORD

MFRORD

Medford

Sun 3/1

6:05 am-6:46 pm

2 stops10h 41m

Chicago O'Hare Intl

Tue 3/3

7:00 am-4:44 pm

2 stops11h 44m

$394

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
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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 September is, on average, the cheapest month to fly to Chicago from Medford, with most prices found around $338. If you’re not able to fly to Chicago in September, then February is your next best option. Flight prices from Medford to Chicago during February average around $365.

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.

Can stopping save me money on Medford to Chicago flights?

You could potentially save up to 46% on your flight if you consider stops on a Medford to Chicago flight.

How have Medford to Chicago flight prices changed over time?

As of October 2025, prices for Medford to Chicago flights are approximately 22% cheaper 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

Direct flights

None
There are no direct flights from Medford to Chicago. There are no popular flight routes from Medford to Chicago.
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 59m, 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?

  • 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?

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 AirlinesPriceFrom $258Free CancellationRating
7.8
2,794 reviews
Search Hawaiian Airlines flights
DeltaPriceFrom $298Free CancellationRating
7.9
7,994 reviews
Search Delta flights
United AirlinesPriceFrom $304Free CancellationRating
7.4
9,001 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $305Free CancellationRating
8.0
11,206 reviews
Search Alaska Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
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.

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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
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport