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Cheap flights from Medford to Chicago from $158

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 2/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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
6:45 pm - 12:01 pm
MFR
-
ORD
15h 16m1 stop
Hawaiian Airlines Logo
7:00 am - 6:05 pm
ORD
-
MFR
13h 05m1 stop
$245Hawaiian Airlines
Wed, Feb 18 - Wed, Feb 25
Alaska Airlines Logo
5:42 pm - 2:38 pm
MFR
-
ORD
18h 56m1 stop
Alaska Airlines Logo
8:00 am - 5:02 pm
ORD
-
MFR
11h 02m1 stop
$261Alaska Airlines
Mon, Feb 2 - Mon, Feb 9
Alaska Airlines Logo
5:42 pm - 5:10 pm
MFR
-
ORD
21h 28m1 stop
Alaska Airlines Logo
6:06 pm - 11:57 am
ORD
-
MFR
19h 51m2 stops
$275Alaska Airlines
Mon, Feb 2 - Mon, Feb 9
Alaska Airlines Logo
3:45 pm - 2:38 pm
MFR
-
ORD
20h 53m2 stops
Alaska Airlines Logo
8:00 am - 10:49 pm
ORD
-
MFR
16h 49m2 stops
$289Alaska Airlines
Mon, Feb 2 - Mon, Feb 9
Alaska Airlines Logo
1:22 pm - 11:50 pm
MFR
-
ORD
8h 28m1 stop
Alaska Airlines Logo
3:35 pm - 11:56 pm
ORD
-
MFR
10h 21m1 stop
$305Alaska Airlines
Sat, Jan 24 - Wed, Jan 28
Alaska Airlines Logo
5:45 am - 2:11 pm
MFR
-
ORD
6h 26m1 stop
Alaska Airlines Logo
8:20 am - 6:05 pm
ORD
-
MFR
11h 45m2 stops
$312Alaska Airlines
Wed, Feb 18 - Wed, Feb 25
Alaska Airlines Logo
5:44 pm - 11:56 pm
MFR
-
ORD
28h 12m1 stop
Alaska Airlines Logo
7:00 am - 6:05 pm
ORD
-
MFR
13h 05m1 stop
$315Alaska Airlines
Fri, Feb 13 - Sun, Feb 15
Delta Logo
5:20 pm - 9:53 am
MFR
-
MDW
14h 33m2 stops
Delta Logo
9:33 am - 4:40 pm
MDW
-
MFR
9h 07m2 stops
$316Delta
Mon, Feb 2 - Mon, Feb 9
Delta Logo
6:55 am - 9:30 pm
MFR
-
ORD
12h 35m2 stops
Delta Logo
7:40 am - 2:36 pm
ORD
-
MFR
8h 56m1 stop
$321Delta
Fri, Feb 13 - Sun, Feb 15
Delta Logo
5:55 am - 6:40 pm
MFR
-
MDW
10h 45m2 stops
Delta Logo
1:49 pm - 11:12 pm
MDW
-
MFR
11h 23m2 stops
$399Delta
Wed, Feb 18 - Wed, Feb 25

Alaska Airlines flights from Medford to Chicago

Our best Alaska Airlines deals on Medford to Chicago flight tickets
Alaska Airlines
Feb 2
MFR5:42 pmMedford
18h 56m
1 stop
ORD2:38 pmChicago O'Hare Intl
Feb 9
ORD8:00 amChicago O'Hare Intl
11h 02m
1 stop
MFR5:02 pmMedford
$261
Find similar
Alaska Airlines
Feb 2
MFR5:42 pmMedford
21h 28m
1 stop
ORD5:10 pmChicago O'Hare Intl
Feb 9
ORD6:06 pmChicago O'Hare Intl
19h 51m
2 stops
MFR11:57 amMedford
$275
Find similar
Alaska Airlines
Feb 2
MFR3:45 pmMedford
20h 53m
2 stops
ORD2:38 pmChicago O'Hare Intl
Feb 9
ORD8:00 amChicago O'Hare Intl
16h 49m
2 stops
MFR10:49 pmMedford
$289
Find similar

United Airlines flights from Medford to Chicago

Our best United Airlines deals on Medford to Chicago flight tickets
United Airlines
Jun 9
MFR2:03 pmMedford
8h 55m
2 stops
ORD12:58 amChicago O'Hare Intl
Jun 10
ORD6:02 amChicago O'Hare Intl
7h 32m
1 stop
MFR11:34 amMedford
$374
Find similar
United Airlines
Jan 17
MFR12:55 pmMedford
6h 20m
1 stop
ORD9:15 pmChicago O'Hare Intl
Jan 24
ORD11:05 amChicago O'Hare Intl
8h 47m
1 stop
MFR5:52 pmMedford
$419
Find similar
United Airlines
Jun 17
MFR2:03 pmMedford
8h 55m
2 stops
ORD12:58 amChicago O'Hare Intl
Jun 24
ORD4:17 pmChicago O'Hare Intl
8h 52m
1 stop
MFR11:09 pmMedford
$464
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 January 6, 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

Wed 2/18

6:45 pm-12:01 pm

1 stop15h 16m

Chicago O'Hare Intl

Wed 2/25

7:00 am-6:05 pm

1 stop13h 05m

$245

MedfordChicago

MFR - ORD

MFRORD

Medford

Mon 2/2

5:42 pm-2:38 pm

1 stop18h 56m

Chicago O'Hare Intl

Mon 2/9

8:00 am-5:02 pm

1 stop11h 02m

$261

MedfordChicago

MFR - ORD

MFRORD

Medford

Mon 2/2

5:42 pm-5:10 pm

1 stop21h 28m

Chicago O'Hare Intl

Mon 2/9

6:06 pm-11:57 am

2 stops19h 51m

$275

MedfordChicago

MFR - ORD

MFRORD

Medford

Mon 2/2

3:45 pm-2:38 pm

2 stops20h 53m

Chicago O'Hare Intl

Mon 2/9

8:00 am-10:49 pm

2 stops16h 49m

$289

MedfordChicago

MFR - ORD

MFRORD

Medford

Sat 1/24

1:22 pm-11:50 pm

1 stop8h 28m

Chicago O'Hare Intl

Wed 1/28

3:35 pm-11:56 pm

1 stop10h 21m

$305

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 2/18

5:45 am-2:11 pm

1 stop6h 26m

Chicago O'Hare Intl

Wed 2/25

8:20 am-6:05 pm

2 stops11h 45m

$312

MedfordChicago

MFR - ORD

MFRORD

Medford

Fri 2/13

5:44 pm-11:56 pm

1 stop28h 12m

Chicago O'Hare Intl

Sun 2/15

7:00 am-6:05 pm

1 stop13h 05m

$315

MedfordChicago

MFR - MDW

MFRMDW

Medford

Mon 2/2

5:20 pm-9:53 am

2 stops14h 33m

Chicago Midway

Mon 2/9

9:33 am-4:40 pm

2 stops9h 07m

$316

MedfordChicago

MFR - ORD

MFRORD

Medford

Fri 2/13

6:55 am-9:30 pm

2 stops12h 35m

Chicago O'Hare Intl

Sun 2/15

7:40 am-2:36 pm

1 stop8h 56m

$321

MedfordChicago

MFR - MDW

MFRMDW

Medford

Wed 2/18

5:55 am-6:40 pm

2 stops10h 45m

Chicago Midway

Wed 2/25

1:49 pm-11:12 pm

2 stops11h 23m

$399

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 50% 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 January 2026, prices for Medford to Chicago flights are approximately 18% 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

7h 14m

Direct flights

None
The fastest flight from Medford to Chicago takes 7h 14m
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 7h 14m, 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
2,825 reviews
Search Hawaiian Airlines flights
DeltaPriceFrom $273Free CancellationRating
7.9
8,018 reviews
Search Delta flights
United AirlinesPriceFrom $304Free CancellationRating
7.4
9,134 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $308Free CancellationRating
8.0
11,651 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