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Cheap flights from Medford to Chicago from $152

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 1/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Alaska Airlines Logo
1:20 pm - 11:37 pm
MFR
-
ORD
8h 17m1 stop
Alaska Airlines Logo
6:06 pm - 11:56 pm
ORD
-
MFR
7h 50m1 stop
$300Alaska Airlines
sáb., ene. 24 - mié., ene. 28
Alaska Airlines Logo
5:09 am - 11:37 pm
MFR
-
ORD
16h 28m2 stops
Alaska Airlines Logo
8:00 am - 4:08 pm
ORD
-
MFR
10h 08m2 stops
$303Alaska Airlines
mar., ene. 13 - sáb., ene. 17
Alaska Airlines Logo
5:42 pm - 2:38 pm
MFR
-
ORD
18h 56m1 stop
Alaska Airlines Logo
6:06 pm - 11:56 pm
ORD
-
MFR
7h 50m1 stop
$304Alaska Airlines
jue., ene. 22 - lun., ene. 26
Delta Logo
5:05 am - 5:26 pm
MFR
-
ORD
10h 21m2 stops
Delta Logo
7:30 am - 1:28 pm
ORD
-
MFR
7h 58m1 stop
$306Delta
mar., ene. 13 - sáb., ene. 17
Alaska Airlines Logo
1:22 pm - 11:50 pm
MFR
-
ORD
8h 28m1 stop
Alaska Airlines Logo
8:00 am - 4:08 pm
ORD
-
MFR
10h 08m2 stops
$307Alaska Airlines
sáb., ene. 24 - mié., ene. 28
Alaska Airlines Logo
5:42 pm - 11:50 pm
MFR
-
ORD
28h 08m1 stop
Alaska Airlines Logo
6:06 pm - 4:08 pm
ORD
-
MFR
24h 02m2 stops
$309Alaska Airlines
jue., ene. 22 - lun., ene. 26
Alaska Airlines Logo
3:45 pm - 2:38 pm
MFR
-
ORD
20h 53m2 stops
Alaska Airlines Logo
6:06 pm - 11:57 am
ORD
-
MFR
19h 51m2 stops
$314Alaska Airlines
jue., ene. 22 - lun., ene. 26
Delta Logo
5:05 am - 5:55 pm
MFR
-
MDW
10h 50m2 stops
Delta Logo
1:49 pm - 10:59 pm
MDW
-
MFR
11h 10m2 stops
$331Delta
jue., ene. 22 - lun., ene. 26
Alaska Airlines Logo
12:39 pm - 11:50 pm
MFR
-
ORD
9h 11m2 stops
Alaska Airlines Logo
8:00 am - 4:08 pm
ORD
-
MFR
10h 08m2 stops
$333Alaska Airlines
sáb., ene. 24 - mié., ene. 28
Alaska Airlines Logo
5:05 am - 1:07 pm
MFR
-
ORD
6h 02m1 stop
Alaska Airlines Logo
6:50 pm - 11:12 am
ORD
-
MFR
18h 22m1 stop
$534Alaska Airlines
vie., mar. 20 - lun., mar. 23

Alaska Airlines flights from Medford to Chicago

Our best Alaska Airlines deals on Medford to Chicago flight tickets
Alaska Airlines
Jan 24
MFR1:20 pmMedford
8h 17m
1 stop
ORD11:37 pmChicago O'Hare Intl
Jan 28
ORD6:06 pmChicago O'Hare Intl
7h 50m
1 stop
MFR11:56 pmMedford
$300
Find similar
Alaska Airlines
Jan 13
MFR5:09 amMedford
16h 28m
2 stops
ORD11:37 pmChicago O'Hare Intl
Jan 17
ORD8:00 amChicago O'Hare Intl
10h 08m
2 stops
MFR4:08 pmMedford
$303
Find similar
Alaska Airlines
Jan 22
MFR5:42 pmMedford
18h 56m
1 stop
ORD2:38 pmChicago O'Hare Intl
Jan 26
ORD6:06 pmChicago O'Hare Intl
7h 50m
1 stop
MFR11:56 pmMedford
$304
Find similar

Delta flights from Medford to Chicago

Our best Delta deals on Medford to Chicago flight tickets
Delta
Jan 13
MFR5:05 amMedford
10h 21m
2 stops
ORD5:26 pmChicago O'Hare Intl
Jan 17
ORD7:30 amChicago O'Hare Intl
7h 58m
1 stop
MFR1:28 pmMedford
$306
Find similar
Delta
Jan 22
MFR5:05 amMedford
10h 50m
2 stops
MDW5:55 pmChicago Midway
Jan 26
MDW1:49 pmChicago Midway
11h 10m
2 stops
MFR10:59 pmMedford
$331
Find similar
Delta
Dec 16
MFR12:41 pmMedford
6h 40m
1 stop
ORD9:21 pmChicago O'Hare Intl
Dec 17
ORD5:40 pmChicago O'Hare Intl
7h 22m
1 stop
MFR11:02 pmMedford
$469
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 diciembre 15, 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

sáb. 1/24

1:20 pm-11:37 pm

1 stop8h 17m

Chicago O'Hare Intl

mié. 1/28

6:06 pm-11:56 pm

1 stop7h 50m

$300

MedfordChicago

MFR - ORD

MFRORD

Medford

mar. 1/13

5:09 am-11:37 pm

2 stops16h 28m

Chicago O'Hare Intl

sáb. 1/17

8:00 am-4:08 pm

2 stops10h 08m

$303

MedfordChicago

MFR - ORD

MFRORD

Medford

jue. 1/22

5:42 pm-2:38 pm

1 stop18h 56m

Chicago O'Hare Intl

lun. 1/26

6:06 pm-11:56 pm

1 stop7h 50m

$304

MedfordChicago

MFR - ORD

MFRORD

Medford

mar. 1/13

5:05 am-5:26 pm

2 stops10h 21m

Chicago O'Hare Intl

sáb. 1/17

7:30 am-1:28 pm

1 stop7h 58m

$306

MedfordChicago

MFR - ORD

MFRORD

Medford

sáb. 1/24

1:22 pm-11:50 pm

1 stop8h 28m

Chicago O'Hare Intl

mié. 1/28

8:00 am-4:08 pm

2 stops10h 08m

$307

MedfordChicago

MFR - ORD

MFRORD

Medford

jue. 1/22

5:42 pm-11:50 pm

1 stop28h 08m

Chicago O'Hare Intl

lun. 1/26

6:06 pm-4:08 pm

2 stops24h 02m

$309

MedfordChicago

MFR - ORD

MFRORD

Medford

jue. 1/22

3:45 pm-2:38 pm

2 stops20h 53m

Chicago O'Hare Intl

lun. 1/26

6:06 pm-11:57 am

2 stops19h 51m

$314

MedfordChicago

MFR - MDW

MFRMDW

Medford

jue. 1/22

5:05 am-5:55 pm

2 stops10h 50m

Chicago Midway

lun. 1/26

1:49 pm-10:59 pm

2 stops11h 10m

$331

MedfordChicago

MFR - ORD

MFRORD

Medford

sáb. 1/24

12:39 pm-11:50 pm

2 stops9h 11m

Chicago O'Hare Intl

mié. 1/28

8:00 am-4:08 pm

2 stops10h 08m

$333

MedfordChicago

MFR - ORD

MFRORD

Medford

vie. 3/20

5:05 am-1:07 pm

1 stop6h 02m

Chicago O'Hare Intl

lun. 3/23

6:50 pm-11:12 am

1 stop18h 22m

$534

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 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.

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?

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
2,819 reviews
Search Hawaiian Airlines flights
DeltaPriceFrom $273Free CancellationRating
7.9
8,008 reviews
Search Delta flights
United AirlinesPriceFrom $304Free CancellationRating
7.4
9,093 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $306Free CancellationRating
8.0
11,453 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
Valparaiso
Schererville
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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mié. 1/14
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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