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Cheap flights from Medford to Chicago from $149

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 12/2. 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

Multiple Airlines Logo
10:58 am - 10:40 amMFR-ORD
21h 42m2 stops
Multiple Airlines Logo
6:15 am - 4:22 pmORD-MFR
12h 07m1 stop
$290Multiple Airlines
Find Deal
Mon, Sep 29 - Fri, Oct 3
Hawaiian Airlines Logo
2:41 pm - 11:59 pmMFR-ORD
7h 18m1 stop
Hawaiian Airlines Logo
6:00 am - 11:16 amORD-MFR
7h 16m1 stop
$298Hawaiian Airlines
Find Deal
Wed, Oct 8 - Sat, Oct 11
United Airlines Logo
1:09 pm - 10:39 pmMFR-ORD
7h 30m1 stop
United Airlines Logo
6:15 am - 12:07 pmORD-MFR
7h 52m1 stop
$299United Airlines
Find Deal
Wed, Oct 15 - Mon, Oct 20
Delta Logo
6:00 am - 5:18 pmMFR-ORD
9h 18m1 stop
Delta Logo
7:50 am - 4:44 pmORD-MFR
10h 54m2 stops
$304Delta
Find Deal
Sat, Oct 25 - Wed, Oct 29
Delta Logo
6:00 am - 9:43 pmMFR-ORD
13h 43m2 stops
Delta Logo
10:30 am - 10:50 pmORD-MFR
14h 20m2 stops
$309Delta
Find Deal
Wed, Oct 29 - Sat, Nov 1
Alaska Airlines Logo
12:40 pm - 5:01 amMFR-ORD
14h 21m1 stop
Alaska Airlines Logo
3:15 pm - 11:16 amORD-MFR
22h 01m1 stop
$320Alaska Airlines
Find Deal
Wed, Oct 8 - Sat, Oct 11
Delta Logo
12:36 pm - 11:59 pmMFR-ORD
9h 23m1 stop
Delta Logo
6:00 am - 12:57 pmORD-MFR
8h 57m1 stop
$335Delta
Find Deal
Wed, Dec 24 - Wed, Dec 31
Delta Logo
1:37 pm - 9:39 pmMFR-ORD
6h 02m1 stop
Delta Logo
6:00 am - 12:57 pmORD-MFR
8h 57m1 stop
$337Delta
Find Deal
Thu, Dec 25 - Wed, Dec 31
Alaska Airlines Logo
3:52 pm - 5:01 amMFR-ORD
11h 09m1 stop
Alaska Airlines Logo
7:59 pm - 2:01 pmORD-MFR
20h 02m1 stop
$342Alaska Airlines
Find Deal
Thu, Oct 16 - Mon, Oct 20
United Airlines Logo
1:09 pm - 11:59 pmMFR-ORD
8h 50m1 stop
United Airlines Logo
6:15 am - 12:07 pmORD-MFR
7h 52m1 stop
$353United Airlines
Find Deal
Thu, Oct 16 - Mon, Oct 20

Hawaiian Airlines flights from Medford to Chicago

Our best Hawaiian Airlines deals on Medford to Chicago flight tickets
Hawaiian Airlines
Oct 8
MFR2:41 pmMedford
7h 18m
1 stop
ORD11:59 pmChicago O'Hare Intl
Oct 11
ORD6:00 amChicago O'Hare Intl
7h 16m
1 stop
MFR11:16 amMedford
$298
Find similar
Hawaiian Airlines
Oct 4
MFR5:00 amMedford
7h 19m
1 stop
ORD2:19 pmChicago O'Hare Intl
Oct 7
ORD6:00 amChicago O'Hare Intl
7h 16m
1 stop
MFR11:16 amMedford
$366
Find similar
Hawaiian Airlines
Nov 24
MFR8:57 pmMedford
7h 31m
1 stop
ORD6:28 amChicago O'Hare Intl
Nov 28
ORD6:00 amChicago O'Hare Intl
7h 18m
1 stop
MFR11:18 amMedford
$380
Find similar

Delta flights from Medford to Chicago

Our best Delta deals on Medford to Chicago flight tickets
Delta
Oct 25
MFR6:00 amMedford
9h 18m
1 stop
ORD5:18 pmChicago O'Hare Intl
Oct 29
ORD7:50 amChicago O'Hare Intl
10h 54m
2 stops
MFR4:44 pmMedford
$304
Find similar
Delta
Oct 29
MFR6:00 amMedford
13h 43m
2 stops
ORD9:43 pmChicago O'Hare Intl
Nov 1
ORD10:30 amChicago O'Hare Intl
14h 20m
2 stops
MFR10:50 pmMedford
$309
Find similar
Delta
Dec 24
MFR12:36 pmMedford
9h 23m
1 stop
ORD11:59 pmChicago O'Hare Intl
Dec 31
ORD6:00 amChicago O'Hare Intl
8h 57m
1 stop
MFR12:57 pmMedford
$335
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 September 16, 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

Mon 9/29

10:58 am-10:40 am

2 stops21h 42m

Chicago O'Hare Intl

Fri 10/3

6:15 am-4:22 pm

1 stop12h 07m

$290

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 10/8

2:41 pm-11:59 pm

1 stop7h 18m

Chicago O'Hare Intl

Sat 10/11

6:00 am-11:16 am

1 stop7h 16m

$298

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 10/15

1:09 pm-10:39 pm

1 stop7h 30m

Chicago O'Hare Intl

Mon 10/20

6:15 am-12:07 pm

1 stop7h 52m

$299

MedfordChicago

MFR - ORD

MFRORD

Medford

Sat 10/25

6:00 am-5:18 pm

1 stop9h 18m

Chicago O'Hare Intl

Wed 10/29

7:50 am-4:44 pm

2 stops10h 54m

$304

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 10/29

6:00 am-9:43 pm

2 stops13h 43m

Chicago O'Hare Intl

Sat 11/1

10:30 am-10:50 pm

2 stops14h 20m

$309

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 10/8

12:40 pm-5:01 am

1 stop14h 21m

Chicago O'Hare Intl

Sat 10/11

3:15 pm-11:16 am

1 stop22h 01m

$320

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 12/24

12:36 pm-11:59 pm

1 stop9h 23m

Chicago O'Hare Intl

Wed 12/31

6:00 am-12:57 pm

1 stop8h 57m

$335

MedfordChicago

MFR - ORD

MFRORD

Medford

Thu 12/25

1:37 pm-9:39 pm

1 stop6h 02m

Chicago O'Hare Intl

Wed 12/31

6:00 am-12:57 pm

1 stop8h 57m

$337

MedfordChicago

MFR - ORD

MFRORD

Medford

Thu 10/16

3:52 pm-5:01 am

1 stop11h 09m

Chicago O'Hare Intl

Mon 10/20

7:59 pm-2:01 pm

1 stop20h 02m

$342

MedfordChicago

MFR - ORD

MFRORD

Medford

Thu 10/16

1:09 pm-11:59 pm

1 stop8h 50m

Chicago O'Hare Intl

Mon 10/20

6:15 am-12:07 pm

1 stop7h 52m

$353

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 February is, on average, the cheapest month to fly to Chicago from Medford, with most prices found around $345. If you’re not able to fly to Chicago in February, then September is your next best option. Flight prices from Medford to Chicago during September average around $370.

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.

How have Medford to Chicago flight prices changed over time?

As of September 2025, prices for Medford to Chicago flights are approximately 14% 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

Direct flights

None
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 02m, 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
2,724 reviews
Search Hawaiian Airlines flights
Alaska AirlinesPriceFrom $300Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $304Free CancellationRating
7.4
8,924 reviews
Search United Airlines flights
DeltaPriceFrom $306Free CancellationRating
7.9
7,957 reviews
Search Delta 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
Lansing
Portage
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