Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Medford to Chicago from $233

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 11/25. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Medford to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 6:45 pmMFR-ORD
10h 45m2 stops
Delta Logo
5:40 pm - 11:02 pmORD-MFR
7h 22m1 stop
$238Delta
Find Deal
Tue, Dec 9 - Wed, Dec 10
Delta Logo
6:00 am - 6:45 pmMFR-ORD
10h 45m2 stops
Delta Logo
7:20 am - 4:43 pmORD-MFR
11h 23m2 stops
$243Delta
Find Deal
Tue, Dec 9 - Wed, Dec 10
Delta Logo
12:41 pm - 9:21 pmMFR-ORD
6h 40m1 stop
Delta Logo
5:40 pm - 11:02 pmORD-MFR
7h 22m1 stop
$250Delta
Find Deal
Tue, Dec 9 - Wed, Dec 10
Hawaiian Airlines Logo
1:30 pm - 10:30 pmMFR-ORD
7h 00m1 stop
Hawaiian Airlines Logo
8:00 am - 1:16 pmORD-MFR
7h 16m1 stop
$279Hawaiian Airlines
Find Deal
Tue, Dec 9 - Wed, Dec 10
Delta Logo
6:00 am - 9:21 pmMFR-ORD
13h 21m2 stops
Delta Logo
5:40 pm - 11:02 pmORD-MFR
7h 22m1 stop
$284Delta
Find Deal
Tue, Dec 9 - Wed, Dec 10
Delta Logo
6:00 am - 5:15 pmMFR-ORD
9h 15m1 stop
Delta Logo
5:40 pm - 11:02 pmORD-MFR
7h 22m1 stop
$285Delta
Find Deal
Fri, Dec 12 - Wed, Dec 17
Delta Logo
6:00 am - 6:45 pmMFR-ORD
10h 45m2 stops
Delta Logo
7:20 am - 4:43 pmORD-MFR
11h 23m2 stops
$289Delta
Find Deal
Tue, Dec 9 - Wed, Dec 10
Alaska Airlines Logo
5:45 pm - 11:56 pmMFR-ORD
28h 11m1 stop
Alaska Airlines Logo
7:00 am - 1:02 pmORD-MFR
8h 02m1 stop
$291Alaska Airlines
Find Deal
Sun, Mar 1 - Tue, Mar 3
Delta Logo
5:20 pm - 11:55 pmMFR-ORD
28h 35m1 stop
Delta Logo
10:35 am - 11:06 pmORD-MFR
14h 31m2 stops
$297Delta
Find Deal
Sun, Mar 1 - Tue, Mar 3
American Airlines Logo
3:00 pm - 12:31 amMFR-ORD
7h 31m1 stop
American Airlines Logo
12:10 pm - 8:11 pmORD-MFR
10h 01m1 stop
$320American Airlines
Find Deal
Mon, Dec 8 - Thu, Dec 11

Delta flights from Medford to Chicago

Our best Delta deals on Medford to Chicago flight tickets
Delta
Dec 9
MFR6:00 amMedford
10h 45m
2 stops
ORD6:45 pmChicago O'Hare Intl
Dec 10
ORD5:40 pmChicago O'Hare Intl
7h 22m
1 stop
MFR11:02 pmMedford
$238
Find similar
Delta
Dec 9
MFR6:00 amMedford
10h 45m
2 stops
ORD6:45 pmChicago O'Hare Intl
Dec 10
ORD7:20 amChicago O'Hare Intl
11h 23m
2 stops
MFR4:43 pmMedford
$243
Find similar
Delta
Dec 9
MFR12:41 pmMedford
6h 40m
1 stop
ORD9:21 pmChicago O'Hare Intl
Dec 10
ORD5:40 pmChicago O'Hare Intl
7h 22m
1 stop
MFR11:02 pmMedford
$250
Find similar

Alaska Airlines flights from Medford to Chicago

Our best Alaska Airlines deals on Medford to Chicago flight tickets
Alaska Airlines
Mar 1
MFR5:45 pmMedford
28h 11m
1 stop
ORD11:56 pmChicago O'Hare Intl
Mar 3
ORD7:00 amChicago O'Hare Intl
8h 02m
1 stop
MFR1:02 pmMedford
$291
Find similar
Alaska Airlines
Mar 1
MFR7:40 amMedford
14h 16m
2 stops
ORD11:56 pmChicago O'Hare Intl
Mar 3
ORD7:00 amChicago O'Hare Intl
10h 58m
2 stops
MFR3:58 pmMedford
$334
Find similar
Alaska Airlines
Dec 12
MFR8:20 amMedford
12h 10m
2 stops
ORD10:30 pmChicago O'Hare Intl
Dec 17
ORD10:00 amChicago O'Hare Intl
9h 03m
1 stop
MFR5:03 pmMedford
$337
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 19, 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

6:00 am-6:45 pm

2 stops10h 45m

Chicago O'Hare Intl

Wed 12/10

5:40 pm-11:02 pm

1 stop7h 22m

$238

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 12/9

6:00 am-6:45 pm

2 stops10h 45m

Chicago O'Hare Intl

Wed 12/10

7:20 am-4:43 pm

2 stops11h 23m

$243

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 12/9

12:41 pm-9:21 pm

1 stop6h 40m

Chicago O'Hare Intl

Wed 12/10

5:40 pm-11:02 pm

1 stop7h 22m

$250

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 12/9

1:30 pm-10:30 pm

1 stop7h 00m

Chicago O'Hare Intl

Wed 12/10

8:00 am-1:16 pm

1 stop7h 16m

$279

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 12/9

6:00 am-9:21 pm

2 stops13h 21m

Chicago O'Hare Intl

Wed 12/10

5:40 pm-11:02 pm

1 stop7h 22m

$284

MedfordChicago

MFR - ORD

MFRORD

Medford

Fri 12/12

6:00 am-5:15 pm

1 stop9h 15m

Chicago O'Hare Intl

Wed 12/17

5:40 pm-11:02 pm

1 stop7h 22m

$285

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 12/9

6:00 am-6:45 pm

2 stops10h 45m

Chicago O'Hare Intl

Wed 12/10

7:20 am-4:43 pm

2 stops11h 23m

$289

MedfordChicago

MFR - ORD

MFRORD

Medford

Sun 3/1

5:45 pm-11:56 pm

1 stop28h 11m

Chicago O'Hare Intl

Tue 3/3

7:00 am-1:02 pm

1 stop8h 02m

$291

MedfordChicago

MFR - ORD

MFRORD

Medford

Sun 3/1

5:20 pm-11:55 pm

1 stop28h 35m

Chicago O'Hare Intl

Tue 3/3

10:35 am-11:06 pm

2 stops14h 31m

$297

MedfordChicago

MFR - ORD

MFRORD

Medford

Mon 12/8

3:00 pm-12:31 am

1 stop7h 31m

Chicago O'Hare Intl

Thu 12/11

12:10 pm-8:11 pm

1 stop10h 01m

$320

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

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 46% 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

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 40m, 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
2,809 reviews
Search Hawaiian Airlines flights
United AirlinesPriceFrom $304Free CancellationRating
7.4
9,020 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $306Free CancellationRating
8.0
11,319 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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 12/19
Fri 12/26
By creating a price alert you accept our terms of use and privacy policy.

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