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Cheap flights from Medford to Chicago from $187

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 8/22. 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.
United Airlines Logo
2:00 pm - 11:38 pm
MFR
-
ORD
7h 38m
1 stop
United Airlines Logo
6:25 am - 11:48 am
ORD
-
MFR
7h 23m
1 stop
$304United Airlines
Tue, Mar 24 - Tue, Mar 31
Hawaiian Airlines Logo
1:22 pm - 11:59 pm
MFR
-
ORD
8h 37m
1 stop
Hawaiian Airlines Logo
6:00 am - 12:45 pm
ORD
-
MFR
8h 45m
1 stop
$308Hawaiian Airlines
Mon, Apr 13 - Mon, Apr 20
United Airlines Logo
12:50 pm - 9:20 pm
MFR
-
ORD
6h 30m
1 stop
United Airlines Logo
6:25 am - 11:49 am
ORD
-
MFR
7h 24m
1 stop
$323United Airlines
Thu, Apr 16 - Sun, Apr 26
United Airlines Logo
2:12 pm - 12:59 am
MFR
-
ORD
8h 47m
2 stops
United Airlines Logo
6:25 am - 11:49 am
ORD
-
MFR
7h 24m
1 stop
$324United Airlines
Thu, Apr 16 - Sun, Apr 26
Delta Logo
6:10 am - 4:39 pm
MFR
-
ORD
8h 29m
1 stop
Delta Logo
2:09 pm - 11:20 pm
ORD
-
MFR
11h 11m
2 stops
$328Delta
Mon, Apr 13 - Mon, Apr 20
Alaska Airlines Logo
1:26 pm - 10:59 pm
MFR
-
ORD
7h 33m
1 stop
Alaska Airlines Logo
9:00 am - 10:21 pm
ORD
-
MFR
15h 21m
1 stop
$340Alaska Airlines
Wed, May 13 - Mon, May 18
Delta Logo
6:00 am - 9:34 pm
MFR
-
ORD
13h 34m
2 stops
Delta Logo
1:19 pm - 10:50 pm
ORD
-
MFR
11h 31m
2 stops
$348Delta
Wed, Mar 25 - Wed, Apr 1
Alaska Airlines Logo
12:31 pm - 1:13 pm
MFR
-
ORD
22h 42m
1 stop
Alaska Airlines Logo
7:24 pm - 12:45 pm
ORD
-
MFR
19h 21m
1 stop
$361Alaska Airlines
Tue, Mar 24 - Tue, Mar 31
Alaska Airlines Logo
1:22 pm - 6:39 am
MFR
-
ORD
15h 17m
1 stop
Alaska Airlines Logo
7:24 pm - 12:45 pm
ORD
-
MFR
19h 21m
1 stop
$363Alaska Airlines
Sat, Mar 28 - Tue, Mar 31
Alaska Airlines Logo
7:50 pm - 6:39 am
MFR
-
ORD
8h 49m
1 stop
Alaska Airlines Logo
2:09 pm - 10:36 pm
ORD
-
MFR
10h 27m
1 stop
$365Alaska Airlines
Thu, Mar 26 - Thu, Apr 2

United Airlines flights from Medford to Chicago

Our best United Airlines deals on Medford to Chicago flight tickets
United Airlines
Mar 24
MFR2:00 pmMedford
7h 38m
1 stop
ORD11:38 pmChicago O'Hare Intl
Mar 31
ORD6:25 amChicago O'Hare Intl
7h 23m
1 stop
MFR11:48 amMedford
$304
United Airlines
Apr 16
MFR12:50 pmMedford
6h 30m
1 stop
ORD9:20 pmChicago O'Hare Intl
Apr 26
ORD6:25 amChicago O'Hare Intl
7h 24m
1 stop
MFR11:49 amMedford
$323
United Airlines
Apr 16
MFR2:12 pmMedford
8h 47m
2 stops
ORD12:59 amChicago O'Hare Intl
Apr 26
ORD6:25 amChicago O'Hare Intl
7h 24m
1 stop
MFR11:49 amMedford
$324

Alaska Airlines flights from Medford to Chicago

Our best Alaska Airlines deals on Medford to Chicago flight tickets
Alaska Airlines
May 13
MFR1:26 pmMedford
7h 33m
1 stop
ORD10:59 pmChicago O'Hare Intl
May 18
ORD9:00 amChicago O'Hare Intl
15h 21m
1 stop
MFR10:21 pmMedford
$340
Alaska Airlines
Mar 24
MFR12:31 pmMedford
22h 42m
1 stop
ORD1:13 pmChicago O'Hare Intl
Mar 31
ORD7:24 pmChicago O'Hare Intl
19h 21m
1 stop
MFR12:45 pmMedford
$361
Alaska Airlines
Mar 28
MFR1:22 pmMedford
15h 17m
1 stop
ORD6:39 amChicago O'Hare Intl
Mar 31
ORD7:24 pmChicago O'Hare Intl
19h 21m
1 stop
MFR12:45 pmMedford
$363

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 February 28, 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

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 3/24

2:00 pm-11:38 pm

1 stop7h 38m

Chicago O'Hare Intl

Tue 3/31

6:25 am-11:48 am

1 stop7h 23m

$304

MedfordChicago

MFR - ORD

MFRORD

Medford

Mon 4/13

1:22 pm-11:59 pm

1 stop8h 37m

Chicago O'Hare Intl

Mon 4/20

6:00 am-12:45 pm

1 stop8h 45m

$308

MedfordChicago

MFR - ORD

MFRORD

Medford

Thu 4/16

12:50 pm-9:20 pm

1 stop6h 30m

Chicago O'Hare Intl

Sun 4/26

6:25 am-11:49 am

1 stop7h 24m

$323

MedfordChicago

MFR - ORD

MFRORD

Medford

Thu 4/16

2:12 pm-12:59 am

2 stops8h 47m

Chicago O'Hare Intl

Sun 4/26

6:25 am-11:49 am

1 stop7h 24m

$324

MedfordChicago

MFR - ORD

MFRORD

Medford

Mon 4/13

6:10 am-4:39 pm

1 stop8h 29m

Chicago O'Hare Intl

Mon 4/20

2:09 pm-11:20 pm

2 stops11h 11m

$328

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 5/13

1:26 pm-10:59 pm

1 stop7h 33m

Chicago O'Hare Intl

Mon 5/18

9:00 am-10:21 pm

1 stop15h 21m

$340

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 3/25

6:00 am-9:34 pm

2 stops13h 34m

Chicago O'Hare Intl

Wed 4/1

1:19 pm-10:50 pm

2 stops11h 31m

$348

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 3/24

12:31 pm-1:13 pm

1 stop22h 42m

Chicago O'Hare Intl

Tue 3/31

7:24 pm-12:45 pm

1 stop19h 21m

$361

MedfordChicago

MFR - ORD

MFRORD

Medford

Sat 3/28

1:22 pm-6:39 am

1 stop15h 17m

Chicago O'Hare Intl

Tue 3/31

7:24 pm-12:45 pm

1 stop19h 21m

$363

MedfordChicago

MFR - ORD

MFRORD

Medford

Thu 3/26

7:50 pm-6:39 am

1 stop8h 49m

Chicago O'Hare Intl

Thu 4/2

2:09 pm-10:36 pm

1 stop10h 27m

$365

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 cheapest month to fly to Chicago?

The month of October is, on average, the cheapest month to fly to Chicago from Medford, with most prices found around $296. If you’re not able to fly to Chicago in October, then September is your next best option. Flight prices from Medford to Chicago during September average around $338.

Can stopping save me money on Medford to Chicago flights?

You could potentially save up to 67% 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 February 2026, prices for Medford to Chicago flights are approximately 6% 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

Fastest flight time

6h 48m

Direct flights

None
The fastest flight from Medford to Chicago takes 6h 48m
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 6h 48m, 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
2,837 reviews
Search Hawaiian Airlines flights
DeltaPriceFrom $273Free CancellationRating
7.9
8,244 reviews
Search Delta flights
United AirlinesPriceFrom $302Free CancellationRating
7.4
9,362 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $308Free CancellationRating
8.0
11,966 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
Munster
Crown Point
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