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Cheap flights from Medford to Chicago from $144

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 4/9. 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.
United Airlines Logo
2:12 pm - 12:59 am
MFR
-
ORD
8h 47m
1 stop
United Airlines Logo
6:25 am - 11:48 am
ORD
-
MFR
7h 23m
1 stop
$237United Airlines
Tue, Mar 31 - Sat, Apr 4
Alaska Airlines Logo
1:10 pm - 11:59 pm
MFR
-
ORD
8h 49m
1 stop
Alaska Airlines Logo
7:00 am - 1:02 pm
ORD
-
MFR
8h 02m
1 stop
$242Alaska Airlines
Mon, Mar 9 - Wed, Mar 11
Alaska Airlines Logo
6:45 pm - 12:01 pm
MFR
-
ORD
15h 16m
1 stop
Alaska Airlines Logo
3:07 pm - 12:33 pm
ORD
-
MFR
23h 26m
1 stop
$262Alaska Airlines
Wed, Mar 4 - Sun, Mar 8
Alaska Airlines Logo
5:44 pm - 1:11 pm
MFR
-
ORD
17h 27m
2 stops
Alaska Airlines Logo
7:00 am - 1:02 pm
ORD
-
MFR
8h 02m
1 stop
$275Alaska Airlines
Mon, Mar 9 - Wed, Mar 11
Alaska Airlines Logo
6:45 pm - 12:01 pm
MFR
-
ORD
15h 16m
1 stop
Alaska Airlines Logo
3:07 pm - 12:33 pm
ORD
-
MFR
23h 26m
1 stop
$287Alaska Airlines
Wed, Mar 4 - Sun, Mar 8
Delta Logo
6:00 am - 6:00 pm
MFR
-
ORD
10h 00m
2 stops
Delta Logo
7:20 am - 4:35 pm
ORD
-
MFR
11h 15m
2 stops
$312Delta
Mon, Mar 9 - Wed, Mar 11
Multiple Airlines Logo
9:16 pm - 5:31 am
MFR
-
ORD
30h 15m
1 stop
Multiple Airlines Logo
8:53 pm - 8:41 pm
ORD
-
MFR
25h 48m
1 stop
$314Multiple Airlines
Mon, Jun 1 - Sat, Jun 13
Alaska Airlines Logo
7:40 am - 11:56 pm
MFR
-
ORD
14h 16m
2 stops
Alaska Airlines Logo
3:07 pm - 12:33 pm
ORD
-
MFR
23h 26m
1 stop
$330Alaska Airlines
Wed, Mar 4 - Sun, Mar 8
Delta Logo
6:00 am - 6:05 pm
MFR
-
ORD
10h 05m
2 stops
Delta Logo
6:15 am - 4:36 pm
ORD
-
MFR
12h 21m
2 stops
$332Delta
Tue, Mar 31 - Sat, Apr 4
United Airlines Logo
12:50 pm - 9:20 pm
MFR
-
ORD
6h 30m
1 stop
United Airlines Logo
3:45 pm - 11:14 pm
ORD
-
MFR
9h 29m
1 stop
$333United Airlines
Fri, Apr 10 - Mon, Apr 13

United Airlines flights from Medford to Chicago

Our best United Airlines deals on Medford to Chicago flight tickets
United Airlines
Mar 31
MFR2:12 pmMedford
8h 47m
1 stop
ORD12:59 amChicago O'Hare Intl
Apr 4
ORD6:25 amChicago O'Hare Intl
7h 23m
1 stop
MFR11:48 amMedford
$237
United Airlines
Apr 10
MFR12:50 pmMedford
6h 30m
1 stop
ORD9:20 pmChicago O'Hare Intl
Apr 13
ORD3:45 pmChicago O'Hare Intl
9h 29m
1 stop
MFR11:14 pmMedford
$333
United Airlines
Apr 10
MFR2:12 pmMedford
8h 47m
2 stops
ORD12:59 amChicago O'Hare Intl
Apr 13
ORD3:45 pmChicago O'Hare Intl
9h 29m
1 stop
MFR11:14 pmMedford
$381

Delta flights from Medford to Chicago

Our best Delta deals on Medford to Chicago flight tickets
Delta
Mar 9
MFR6:00 amMedford
10h 00m
2 stops
ORD6:00 pmChicago O'Hare Intl
Mar 11
ORD7:20 amChicago O'Hare Intl
11h 15m
2 stops
MFR4:35 pmMedford
$312
Delta
Mar 31
MFR6:00 amMedford
10h 05m
2 stops
ORD6:05 pmChicago O'Hare Intl
Apr 4
ORD6:15 amChicago O'Hare Intl
12h 21m
2 stops
MFR4:36 pmMedford
$332
Delta
Jun 3
MFR12:21 pmMedford
9h 36m
1 stop
ORD11:57 pmChicago O'Hare Intl
Jun 9
ORD6:00 pmChicago O'Hare Intl
7h 13m
1 stop
MFR11:13 pmMedford
$373

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 February 4, 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

Tue 3/31

2:12 pm-12:59 am

1 stop8h 47m

Chicago O'Hare Intl

Sat 4/4

6:25 am-11:48 am

1 stop7h 23m

$237

MedfordChicago

MFR - ORD

MFRORD

Medford

Mon 3/9

1:10 pm-11:59 pm

1 stop8h 49m

Chicago O'Hare Intl

Wed 3/11

7:00 am-1:02 pm

1 stop8h 02m

$242

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 3/4

6:45 pm-12:01 pm

1 stop15h 16m

Chicago O'Hare Intl

Sun 3/8

3:07 pm-12:33 pm

1 stop23h 26m

$262

MedfordChicago

MFR - ORD

MFRORD

Medford

Mon 3/9

5:44 pm-1:11 pm

2 stops17h 27m

Chicago O'Hare Intl

Wed 3/11

7:00 am-1:02 pm

1 stop8h 02m

$275

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 3/4

6:45 pm-12:01 pm

1 stop15h 16m

Chicago O'Hare Intl

Sun 3/8

3:07 pm-12:33 pm

1 stop23h 26m

$287

MedfordChicago

MFR - ORD

MFRORD

Medford

Mon 3/9

6:00 am-6:00 pm

2 stops10h 00m

Chicago O'Hare Intl

Wed 3/11

7:20 am-4:35 pm

2 stops11h 15m

$312

MedfordChicago

MFR - ORD

MFRORD

Medford

Mon 6/1

9:16 pm-5:31 am

1 stop30h 15m

Chicago O'Hare Intl

Sat 6/13

8:53 pm-8:41 pm

1 stop25h 48m

$314

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 3/4

7:40 am-11:56 pm

2 stops14h 16m

Chicago O'Hare Intl

Sun 3/8

3:07 pm-12:33 pm

1 stop23h 26m

$330

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 3/31

6:00 am-6:05 pm

2 stops10h 05m

Chicago O'Hare Intl

Sat 4/4

6:15 am-4:36 pm

2 stops12h 21m

$332

MedfordChicago

MFR - ORD

MFRORD

Medford

Fri 4/10

12:50 pm-9:20 pm

1 stop6h 30m

Chicago O'Hare Intl

Mon 4/13

3:45 pm-11:14 pm

1 stop9h 29m

$333

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?

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 67% 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 February 2026, prices for Medford to Chicago flights are approximately 6% 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

6h 12m

Direct flights

None
The fastest flight from Medford to Chicago takes 6h 12m
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 12m, 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
DeltaPriceFrom $237Free CancellationRating
7.9
8,138 reviews
Search Delta flights
Hawaiian AirlinesPriceFrom $258Free CancellationRating
7.8
2,831 reviews
Search Hawaiian Airlines flights
Alaska AirlinesPriceFrom $308Free CancellationRating
8.0
11,833 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $308Free CancellationRating
7.4
9,236 reviews
Search United 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