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Cheap flights from Medford to Chicago from $215

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 12/1. 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.
Alaska Airlines Logo
5:45 am - 2:39 pmMFR-ORD
6h 54m1 stop
Alaska Airlines Logo
10:00 am - 5:03 pmORD-MFR
9h 03m1 stop
$464Alaska Airlines
Find Deal
Tue, Dec 9 - Sat, Dec 13
Delta Logo
6:00 am - 4:57 pmMFR-ORD
8h 57m2 stops
Delta Logo
7:20 am - 12:01 pmORD-MFR
6h 41m1 stop
$470Delta
Find Deal
Tue, Dec 9 - Sat, Dec 13
Delta Logo
6:00 am - 6:45 pmMFR-ORD
10h 45m2 stops
Delta Logo
8:55 am - 4:43 pmORD-MFR
9h 48m2 stops
$475Delta
Find Deal
Tue, Dec 9 - Wed, Dec 10
Delta Logo
6:00 am - 6:18 pmMFR-MDW
10h 18m2 stops
Delta Logo
9:34 am - 4:43 pmMDW-MFR
9h 09m2 stops
$475Delta
Find Deal
Sat, Dec 6 - Tue, Dec 9
Alaska Airlines Logo
3:47 pm - 1:09 pmMFR-ORD
19h 22m1 stop
Alaska Airlines Logo
3:37 pm - 12:56 pmORD-MFR
23h 19m1 stop
$486Alaska Airlines
Find Deal
Tue, Dec 23 - Wed, Dec 31
Alaska Airlines Logo
5:43 pm - 6:21 amMFR-ORD
10h 38m1 stop
Alaska Airlines Logo
6:00 am - 3:29 pmORD-MFR
11h 29m2 stops
$504Alaska Airlines
Find Deal
Wed, Dec 10 - Sun, Dec 14
Alaska Airlines Logo
12:30 pm - 11:10 pmMFR-ORD
8h 40m1 stop
Alaska Airlines Logo
6:50 pm - 11:12 amORD-MFR
18h 22m1 stop
$506Alaska Airlines
Find Deal
Fri, Mar 20 - Mon, Mar 23
Alaska Airlines Logo
12:39 pm - 11:59 pmMFR-ORD
9h 20m2 stops
Alaska Airlines Logo
6:00 am - 3:29 pmORD-MFR
11h 29m2 stops
$510Alaska Airlines
Find Deal
Wed, Dec 10 - Sun, Dec 14
Multiple Airlines Logo
11:24 am - 12:39 pmMFR-ORD
23h 15m2 stops
Multiple Airlines Logo
9:14 pm - 9:06 pmORD-MFR
25h 52m3 stops
$511Multiple Airlines
Find Deal
Tue, Dec 9 - Sat, Dec 13
Alaska Airlines Logo
12:30 pm - 1:59 pmMFR-ORD
23h 29m1 stop
Alaska Airlines Logo
6:50 pm - 11:12 amORD-MFR
18h 22m1 stop
$518Alaska Airlines
Find Deal
Fri, Mar 20 - Mon, Mar 23

Delta flights from Medford to Chicago

Our best Delta deals on Medford to Chicago flight tickets
Delta
Nov 27
MFR6:00 amMedford
9h 21m
1 stop
ORD5:21 pmChicago O'Hare Intl
Dec 3
ORD7:20 amChicago O'Hare Intl
6h 41m
1 stop
MFR12:01 pmMedford
$419
Find similar
Delta
Nov 27
MFR5:00 amMedford
11h 52m
2 stops
ORD6:52 pmChicago O'Hare Intl
Dec 3
ORD7:20 amChicago O'Hare Intl
6h 41m
1 stop
MFR12:01 pmMedford
$424
Find similar
Delta
Dec 9
MFR6:00 amMedford
8h 57m
2 stops
ORD4:57 pmChicago O'Hare Intl
Dec 13
ORD7:20 amChicago O'Hare Intl
6h 41m
1 stop
MFR12:01 pmMedford
$470
Find similar

American Airlines flights from Medford to Chicago

Our best American Airlines deals on Medford to Chicago flight tickets
American Airlines
Mar 20
MFR5:15 amMedford
8h 39m
2 stops
ORD3:54 pmChicago O'Hare Intl
Mar 23
ORD4:10 pmChicago O'Hare Intl
8h 49m
2 stops
MFR10:59 pmMedford
$1,332
Find similar
American Airlines
Mar 20
MFR5:15 amMedford
8h 39m
2 stops
ORD3:54 pmChicago O'Hare Intl
Mar 23
ORD4:10 pmChicago O'Hare Intl
8h 49m
2 stops
MFR10:59 pmMedford
$1,396
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 November 26, 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

Tue 12/9

5:45 am-2:39 pm

1 stop6h 54m

Chicago O'Hare Intl

Sat 12/13

10:00 am-5:03 pm

1 stop9h 03m

$464

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 12/9

6:00 am-4:57 pm

2 stops8h 57m

Chicago O'Hare Intl

Sat 12/13

7:20 am-12:01 pm

1 stop6h 41m

$470

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 12/9

6:00 am-6:45 pm

2 stops10h 45m

Chicago O'Hare Intl

Wed 12/10

8:55 am-4:43 pm

2 stops9h 48m

$475

MedfordChicago

MFR - MDW

MFRMDW

Medford

Sat 12/6

6:00 am-6:18 pm

2 stops10h 18m

Chicago Midway

Tue 12/9

9:34 am-4:43 pm

2 stops9h 09m

$475

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 12/23

3:47 pm-1:09 pm

1 stop19h 22m

Chicago O'Hare Intl

Wed 12/31

3:37 pm-12:56 pm

1 stop23h 19m

$486

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 12/10

5:43 pm-6:21 am

1 stop10h 38m

Chicago O'Hare Intl

Sun 12/14

6:00 am-3:29 pm

2 stops11h 29m

$504

MedfordChicago

MFR - ORD

MFRORD

Medford

Fri 3/20

12:30 pm-11:10 pm

1 stop8h 40m

Chicago O'Hare Intl

Mon 3/23

6:50 pm-11:12 am

1 stop18h 22m

$506

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 12/10

12:39 pm-11:59 pm

2 stops9h 20m

Chicago O'Hare Intl

Sun 12/14

6:00 am-3:29 pm

2 stops11h 29m

$510

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 12/9

11:24 am-12:39 pm

2 stops23h 15m

Chicago O'Hare Intl

Sat 12/13

9:14 pm-9:06 pm

3 stops25h 52m

$511

MedfordChicago

MFR - ORD

MFRORD

Medford

Fri 3/20

12:30 pm-1:59 pm

1 stop23h 29m

Chicago O'Hare Intl

Mon 3/23

6:50 pm-11:12 am

1 stop18h 22m

$518

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?

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.

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 42% 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 November 2025, prices for Medford to Chicago flights are approximately 78% 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

5h 55m

Direct flights

None
The fastest flight from Medford to Chicago takes 5h 55m
There are no direct flights from Medford to Chicago. There are no popular flight routes from Medford to Chicago.
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  • 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?

  • 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
2,814 reviews
Search Hawaiian Airlines flights
United AirlinesPriceFrom $304Free CancellationRating
7.4
9,046 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $306Free CancellationRating
8.0
11,357 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