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Cheap flights from Medford to Chicago from $153

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 9/28. 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
1 adult, Economy, 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.
Multiple Airlines Logo
9:22 am - 5:38 am
MFR
-
ORD
18h 16m
1 stop
Multiple Airlines Logo
8:55 pm - 2:50 pm
ORD
-
MFR
19h 55m
1 stop
$387Multiple Airlines
Thu, Sep 24 - Sun, Sep 27
Multiple Airlines Logo
9:22 am - 12:45 am
MFR
-
ORD
13h 23m
2 stops
Multiple Airlines Logo
8:55 pm - 2:50 pm
ORD
-
MFR
19h 55m
1 stop
$393Multiple Airlines
Thu, Sep 24 - Sun, Sep 27
Alaska Airlines Logo
7:00 am - 7:21 pm
MFR
-
ORD
10h 21m
1 stop
Alaska Airlines Logo
3:43 pm - 11:59 pm
ORD
-
MFR
10h 16m
1 stop
$405Alaska Airlines
Sat, Aug 29 - Sat, Sep 5
Alaska Airlines Logo
5:59 am - 4:50 pm
MFR
-
ORD
8h 51m
1 stop
Alaska Airlines Logo
2:21 pm - 8:37 pm
ORD
-
MFR
8h 16m
1 stop
$407Alaska Airlines
Tue, Oct 27 - Sat, Oct 31
Alaska Airlines Logo
6:58 pm - 6:20 am
MFR
-
ORD
9h 22m
1 stop
Alaska Airlines Logo
6:00 am - 12:57 pm
ORD
-
MFR
8h 57m
1 stop
$407Alaska Airlines
Tue, Sep 15 - Sat, Sep 19
Delta Logo
6:15 am - 5:00 pm
MFR
-
ORD
8h 45m
1 stop
Delta Logo
2:30 pm - 10:33 pm
ORD
-
MFR
10h 03m
2 stops
$412Delta
Sat, Aug 29 - Sat, Sep 5
Delta Logo
6:15 am - 5:00 pm
MFR
-
ORD
8h 45m
1 stop
Delta Logo
7:00 am - 12:53 pm
ORD
-
MFR
7h 53m
1 stop
$415Delta
Wed, Sep 2 - Sun, Sep 6
United Airlines Logo
5:00 am - 1:29 pm
MFR
-
ORD
6h 29m
1 stop
United Airlines Logo
3:56 pm - 9:08 pm
ORD
-
MFR
7h 12m
1 stop
$415United Airlines
Wed, Sep 2 - Sun, Sep 6
United Airlines Logo
2:07 pm - 11:05 pm
MFR
-
ORD
6h 58m
1 stop
United Airlines Logo
6:07 am - 11:55 am
ORD
-
MFR
7h 48m
1 stop
$427United Airlines
Wed, Sep 23 - Sun, Sep 27
American Airlines Logo
3:40 pm - 12:28 am
MFR
-
ORD
6h 48m
1 stop
American Airlines Logo
5:00 am - 12:47 pm
ORD
-
MFR
9h 47m
1 stop
$466American Airlines
Wed, Aug 26 - Wed, Sep 2

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Alaska Airlines flights from Medford to Chicago

Our best Alaska Airlines deals on Medford to Chicago flight tickets
Alaska Airlines
Aug 29
MFR7:00 amMedford
10h 21m
1 stop
ORD7:21 pmChicago O'Hare Intl
Sep 5
ORD3:43 pmChicago O'Hare Intl
10h 16m
1 stop
MFR11:59 pmMedford
$405
Alaska Airlines
Sep 15
MFR6:58 pmMedford
9h 22m
1 stop
ORD6:20 amChicago O'Hare Intl
Sep 19
ORD6:00 amChicago O'Hare Intl
8h 57m
1 stop
MFR12:57 pmMedford
$407
Alaska Airlines
Oct 27
MFR10:33 amMedford
17h 07m
1 stop
ORD5:40 amChicago O'Hare Intl
Nov 2
ORD7:56 pmChicago O'Hare Intl
20h 10m
1 stop
MFR2:06 pmMedford
$425

American Airlines flights from Medford to Chicago

Our best American Airlines deals on Medford to Chicago flight tickets
American Airlines
Aug 26
MFR3:40 pmMedford
6h 48m
1 stop
ORD12:28 amChicago O'Hare Intl
Sep 2
ORD5:00 amChicago O'Hare Intl
9h 47m
1 stop
MFR12:47 pmMedford
$466
American Airlines
Aug 25
MFR5:20 amMedford
7h 02m
1 stop
ORD2:22 pmChicago O'Hare Intl
Aug 30
ORD6:59 amChicago O'Hare Intl
7h 58m
1 stop
MFR12:57 pmMedford
$486
American Airlines
Aug 19
MFR5:20 amMedford
8h 45m
1 stop
ORD4:05 pmChicago O'Hare Intl
Aug 26
ORD1:59 pmChicago O'Hare Intl
7h 21m
1 stop
MFR7:20 pmMedford
$525

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 August 2, 2026.
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

Cheapest round-trip

MedfordChicago

MFR - ORD

MFRORD

Medford

Thu 9/24

9:22 am-5:38 am

1 stop18h 16m

Chicago O'Hare Intl

Sun 9/27

8:55 pm-2:50 pm

1 stop19h 55m

$387

MedfordChicago

MFR - ORD

MFRORD

Medford

Thu 9/24

9:22 am-12:45 am

2 stops13h 23m

Chicago O'Hare Intl

Sun 9/27

8:55 pm-2:50 pm

1 stop19h 55m

$393

MedfordChicago

MFR - ORD

MFRORD

Medford

Sat 8/29

7:00 am-7:21 pm

1 stop10h 21m

Chicago O'Hare Intl

Sat 9/5

3:43 pm-11:59 pm

1 stop10h 16m

$405

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 10/27

5:59 am-4:50 pm

1 stop8h 51m

Chicago O'Hare Intl

Sat 10/31

2:21 pm-8:37 pm

1 stop8h 16m

$407

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 9/15

6:58 pm-6:20 am

1 stop9h 22m

Chicago O'Hare Intl

Sat 9/19

6:00 am-12:57 pm

1 stop8h 57m

$407

MedfordChicago

MFR - ORD

MFRORD

Medford

Sat 8/29

6:15 am-5:00 pm

1 stop8h 45m

Chicago O'Hare Intl

Sat 9/5

2:30 pm-10:33 pm

2 stops10h 03m

$412

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 9/2

6:15 am-5:00 pm

1 stop8h 45m

Chicago O'Hare Intl

Sun 9/6

7:00 am-12:53 pm

1 stop7h 53m

$415
Quickest round-trip

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 9/2

5:00 am-1:29 pm

1 stop6h 29m

Chicago O'Hare Intl

Sun 9/6

3:56 pm-9:08 pm

1 stop7h 12m

$415

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 9/23

2:07 pm-11:05 pm

1 stop6h 58m

Chicago O'Hare Intl

Sun 9/27

6:07 am-11:55 am

1 stop7h 48m

$427

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 8/26

3:40 pm-12:28 am

1 stop6h 48m

Chicago O'Hare Intl

Wed 9/2

5:00 am-12:47 pm

1 stop9h 47m

$466

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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?

Prices are currently low for flights on this route.

Typical prices usually range from $441 to $475.
The lowest price recently found on this route was $387.

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 $379. If you’re not able to fly to Chicago in September, then November is your next best option. Flight prices from Medford to Chicago during November average around $418.

What is the cheapest Medford to Chicago flight route?

Fly from Medford to Chicago O'Hare Intl for the best Medford - Chicago flight prices

What cabin class options are available on Medford to Chicago flights?

There is only 1 cabin class available to choose from on Medford to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Medford to Chicago flights?

You could potentially save up to 14% on your flight if you consider stops on a Medford to Chicago flight.

How have Medford to Chicago flight prices changed over time?

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

Fastest flight time

8h 45m

Direct flights

None
The fastest flight from Medford to Chicago takes 8h 45m
There are no direct flights from Medford to Chicago. There are no popular flight routes from Medford to Chicago.
Search flight deals

Frequently asked questions about flying from Medford to Chicago

  • How far is Medford to Chicago by plane?

    Medford and Chicago are 1792.9 mi apart from one another. Flights usually cover this in 8h 45m, 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
DeltaPriceFrom $273Free CancellationRating
7.8
8,493 reviews
Search Delta flights
United AirlinesPriceFrom $302Free CancellationRating
7.4
10,061 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $306Free CancellationRating
7.9
12,749 reviews
Search Alaska Airlines flights

  • United Airlines Flights From Medford to Chicago

    The lowest priced United Airlines flight from Medford to Chicago from the last 72 hours was $302. Generally, United Airlines has 2 flights on this route every week with an average price of $421. United Airlines is rated 7.4/10 by our users.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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