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Cheap flights from Medford to Chicago from $159

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 4/29. 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
5:10 am - 2:08 pm
MFR
-
ORD
6h 58m
1 stop
Alaska Airlines Logo
6:00 am - 12:52 pm
ORD
-
MFR
8h 52m
1 stop
$317Alaska Airlines
Sat, May 2 - Wed, May 6
Delta Logo
6:10 am - 9:18 pm
MFR
-
ORD
13h 08m
2 stops
Delta Logo
6:00 pm - 11:20 pm
ORD
-
MFR
7h 20m
1 stop
$322Delta
Tue, Apr 21 - Tue, Apr 28
United Airlines Logo
2:12 pm - 11:29 pm
MFR
-
ORD
7h 17m
1 stop
United Airlines Logo
6:20 am - 11:47 am
ORD
-
MFR
7h 27m
1 stop
$353United Airlines
Fri, Apr 24 - Sat, May 2
United Airlines Logo
2:12 pm - 12:59 am
MFR
-
ORD
8h 47m
2 stops
United Airlines Logo
6:20 am - 11:47 am
ORD
-
MFR
7h 27m
1 stop
$354United Airlines
Fri, Apr 24 - Sat, May 2
Delta Logo
6:10 am - 9:18 pm
MFR
-
ORD
13h 08m
2 stops
Delta Logo
6:00 pm - 11:20 pm
ORD
-
MFR
7h 20m
1 stop
$358Delta
Sat, Apr 18 - Mon, Apr 20
Alaska Airlines Logo
7:41 pm - 6:40 am
MFR
-
ORD
8h 59m
1 stop
Alaska Airlines Logo
2:10 pm - 10:21 pm
ORD
-
MFR
10h 11m
1 stop
$381Alaska Airlines
Thu, May 7 - Thu, May 14
Alaska Airlines Logo
5:10 am - 11:59 pm
MFR
-
ORD
16h 49m
2 stops
Alaska Airlines Logo
6:00 am - 12:52 pm
ORD
-
MFR
8h 52m
1 stop
$384Alaska Airlines
Sat, May 2 - Wed, May 6
Alaska Airlines Logo
7:35 am - 7:03 pm
MFR
-
ORD
9h 28m
1 stop
Alaska Airlines Logo
3:52 pm - 10:16 pm
ORD
-
MFR
8h 24m
1 stop
$389Alaska Airlines
Fri, Apr 24 - Fri, May 1
United Airlines Logo
2:12 pm - 12:59 am
MFR
-
ORD
8h 47m
2 stops
United Airlines Logo
6:20 am - 11:47 am
ORD
-
MFR
7h 27m
1 stop
$390United Airlines
Fri, Apr 24 - Fri, May 1
Alaska Airlines Logo
5:10 am - 2:08 pm
MFR
-
ORD
6h 58m
1 stop
Alaska Airlines Logo
8:48 pm - 12:01 pm
ORD
-
MFR
17h 13m
2 stops
$394Alaska Airlines
Sat, May 2 - Wed, May 6

Alaska Airlines flights from Medford to Chicago

Our best Alaska Airlines deals on Medford to Chicago flight tickets
Alaska Airlines
May 2
MFR5:10 amMedford
6h 58m
1 stop
ORD2:08 pmChicago O'Hare Intl
May 6
ORD6:00 amChicago O'Hare Intl
8h 52m
1 stop
MFR12:52 pmMedford
$317
Alaska Airlines
May 7
MFR7:41 pmMedford
8h 59m
1 stop
ORD6:40 amChicago O'Hare Intl
May 14
ORD2:10 pmChicago O'Hare Intl
10h 11m
1 stop
MFR10:21 pmMedford
$381
Alaska Airlines
May 2
MFR5:10 amMedford
16h 49m
2 stops
ORD11:59 pmChicago O'Hare Intl
May 6
ORD6:00 amChicago O'Hare Intl
8h 52m
1 stop
MFR12:52 pmMedford
$384

Delta flights from Medford to Chicago

Our best Delta deals on Medford to Chicago flight tickets
Delta
Apr 21
MFR6:10 amMedford
13h 08m
2 stops
ORD9:18 pmChicago O'Hare Intl
Apr 28
ORD6:00 pmChicago O'Hare Intl
7h 20m
1 stop
MFR11:20 pmMedford
$322
Delta
Apr 18
MFR6:10 amMedford
13h 08m
2 stops
ORD9:18 pmChicago O'Hare Intl
Apr 20
ORD6:00 pmChicago O'Hare Intl
7h 20m
1 stop
MFR11:20 pmMedford
$358
Delta
Apr 21
MFR11:14 amMedford
8h 04m
2 stops
ORD9:18 pmChicago O'Hare Intl
Apr 28
ORD2:09 pmChicago O'Hare Intl
11h 11m
2 stops
MFR11:20 pmMedford
$398

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 March 28, 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

Cheapest round-trip

MedfordChicago

MFR - ORD

MFRORD

Medford

Sat 5/2

5:10 am-2:08 pm

1 stop6h 58m

Chicago O'Hare Intl

Wed 5/6

6:00 am-12:52 pm

1 stop8h 52m

$317

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 4/21

6:10 am-9:18 pm

2 stops13h 08m

Chicago O'Hare Intl

Tue 4/28

6:00 pm-11:20 pm

1 stop7h 20m

$322
Quickest round-trip

MedfordChicago

MFR - ORD

MFRORD

Medford

Fri 4/24

2:12 pm-11:29 pm

1 stop7h 17m

Chicago O'Hare Intl

Sat 5/2

6:20 am-11:47 am

1 stop7h 27m

$353

MedfordChicago

MFR - ORD

MFRORD

Medford

Fri 4/24

2:12 pm-12:59 am

2 stops8h 47m

Chicago O'Hare Intl

Sat 5/2

6:20 am-11:47 am

1 stop7h 27m

$354

MedfordChicago

MFR - ORD

MFRORD

Medford

Sat 4/18

6:10 am-9:18 pm

2 stops13h 08m

Chicago O'Hare Intl

Mon 4/20

6:00 pm-11:20 pm

1 stop7h 20m

$358

MedfordChicago

MFR - ORD

MFRORD

Medford

Thu 5/7

7:41 pm-6:40 am

1 stop8h 59m

Chicago O'Hare Intl

Thu 5/14

2:10 pm-10:21 pm

1 stop10h 11m

$381

MedfordChicago

MFR - ORD

MFRORD

Medford

Sat 5/2

5:10 am-11:59 pm

2 stops16h 49m

Chicago O'Hare Intl

Wed 5/6

6:00 am-12:52 pm

1 stop8h 52m

$384

MedfordChicago

MFR - ORD

MFRORD

Medford

Fri 4/24

7:35 am-7:03 pm

1 stop9h 28m

Chicago O'Hare Intl

Fri 5/1

3:52 pm-10:16 pm

1 stop8h 24m

$389

MedfordChicago

MFR - ORD

MFRORD

Medford

Fri 4/24

2:12 pm-12:59 am

2 stops8h 47m

Chicago O'Hare Intl

Fri 5/1

6:20 am-11:47 am

1 stop7h 27m

$390

MedfordChicago

MFR - ORD

MFRORD

Medford

Sat 5/2

5:10 am-2:08 pm

1 stop6h 58m

Chicago O'Hare Intl

Wed 5/6

8:48 pm-12:01 pm

2 stops17h 13m

$394

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?

Can stopping save me money on Medford to Chicago flights?

You could potentially save up to 55% 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

6h 30m

Direct flights

None
The fastest flight from Medford to Chicago takes 6h 30m
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 30m, 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
2,838 reviews
Search Hawaiian Airlines flights
DeltaPriceFrom $273Free CancellationRating
7.9
8,357 reviews
Search Delta flights
United AirlinesPriceFrom $302Free CancellationRating
7.4
9,501 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $308Free CancellationRating
7.9
12,133 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
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