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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 8/7. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Medford to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
3:40 pm - 5:42 am
MFR
-
ORD
12h 02m
1 stop
Multiple Airlines Logo
1:02 pm - 8:32 am
ORD
-
MFR
21h 30m
1 stop
$349Multiple Airlines
Mon, Sep 14 - Thu, Sep 24
Multiple Airlines Logo
9:17 pm - 5:37 am
MFR
-
ORD
30h 20m
1 stop
Multiple Airlines Logo
7:15 am - 2:48 pm
ORD
-
MFR
9h 33m
1 stop
$369Multiple Airlines
Mon, Aug 10 - Mon, Aug 17
Multiple Airlines Logo
3:40 pm - 5:42 am
MFR
-
ORD
12h 02m
1 stop
Multiple Airlines Logo
11:06 am - 8:32 am
ORD
-
MFR
23h 26m
2 stops
$370Multiple Airlines
Mon, Sep 14 - Wed, Sep 23
Multiple Airlines Logo
9:17 pm - 8:53 pm
MFR
-
ORD
21h 36m
2 stops
Multiple Airlines Logo
8:11 pm - 10:18 am
ORD
-
MFR
16h 07m
1 stop
$384Multiple Airlines
Mon, Aug 17 - Thu, Aug 20
Multiple Airlines Logo
9:11 pm - 5:37 am
MFR
-
ORD
30h 26m
1 stop
Multiple Airlines Logo
7:15 am - 2:46 pm
ORD
-
MFR
9h 31m
1 stop
$387Multiple Airlines
Fri, Jul 24 - Fri, Jul 31
Alaska Airlines Logo
6:11 am - 7:37 pm
MFR
-
ORD
11h 26m
1 stop
Alaska Airlines Logo
8:20 pm - 9:54 am
ORD
-
MFR
15h 34m
1 stop
$393Alaska Airlines
Sat, Jul 4 - Thu, Jul 9
Delta Logo
5:55 am - 6:37 pm
MFR
-
MDW
10h 42m
2 stops
Delta Logo
9:30 am - 4:43 pm
MDW
-
MFR
9h 13m
2 stops
$423Delta
Tue, Oct 27 - Mon, Nov 2
Delta Logo
5:55 am - 6:37 pm
MFR
-
MDW
10h 42m
2 stops
Delta Logo
9:30 am - 4:43 pm
MDW
-
MFR
9h 13m
2 stops
$443Delta
Tue, Oct 27 - Mon, Nov 2
Delta Logo
6:05 am - 6:33 pm
MFR
-
MDW
10h 28m
2 stops
Delta Logo
1:47 pm - 11:55 pm
MDW
-
MFR
12h 08m
2 stops
$476Delta
Thu, Sep 24 - Mon, Sep 28
Delta Logo
6:05 am - 6:33 pm
MFR
-
MDW
10h 28m
2 stops
Delta Logo
1:47 pm - 11:55 pm
MDW
-
MFR
12h 08m
2 stops
$496Delta
Thu, Sep 24 - Mon, Sep 28

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Delta flights from Medford to Chicago

Our best Delta deals on Medford to Chicago flight tickets
Delta
Jun 23
MFR12:25 pmMedford
9h 14m
1 stop
ORD11:39 pmChicago O'Hare Intl
Jun 28
ORD6:55 amChicago O'Hare Intl
8h 06m
1 stop
MFR1:01 pmMedford
$413
Delta
Sep 24
MFR1:31 pmMedford
6h 16m
1 stop
ORD9:47 pmChicago O'Hare Intl
Sep 28
ORD7:45 amChicago O'Hare Intl
11h 02m
2 stops
MFR4:47 pmMedford
$418
Delta
Sep 24
MFR6:05 amMedford
12h 17m
2 stops
ORD8:22 pmChicago O'Hare Intl
Sep 28
ORD2:05 pmChicago O'Hare Intl
11h 09m
2 stops
MFR11:14 pmMedford
$423

Alaska Airlines flights from Medford to Chicago

Our best Alaska Airlines deals on Medford to Chicago flight tickets
Alaska Airlines
Jul 4
MFR6:11 amMedford
11h 26m
1 stop
ORD7:37 pmChicago O'Hare Intl
Jul 9
ORD8:20 pmChicago O'Hare Intl
15h 34m
1 stop
MFR9:54 amMedford
$393
Alaska Airlines
Sep 9
MFR7:00 amMedford
10h 21m
1 stop
ORD7:21 pmChicago O'Hare Intl
Sep 12
ORD1:03 pmChicago O'Hare Intl
7h 18m
1 stop
MFR6:21 pmMedford
$413
Alaska Airlines
Jul 1
MFR7:50 pmMedford
8h 30m
1 stop
ORD6:20 amChicago O'Hare Intl
Jul 5
ORD7:20 amChicago O'Hare Intl
6h 33m
1 stop
MFR11:53 amMedford
$426

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 June 20, 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

Mon 9/14

3:40 pm-5:42 am

1 stop12h 02m

Chicago O'Hare Intl

Thu 9/24

1:02 pm-8:32 am

1 stop21h 30m

$349

MedfordChicago

MFR - ORD

MFRORD

Medford

Mon 8/10

9:17 pm-5:37 am

1 stop30h 20m

Chicago O'Hare Intl

Mon 8/17

7:15 am-2:48 pm

1 stop9h 33m

$369

MedfordChicago

MFR - ORD

MFRORD

Medford

Mon 9/14

3:40 pm-5:42 am

1 stop12h 02m

Chicago O'Hare Intl

Wed 9/23

11:06 am-8:32 am

2 stops23h 26m

$370

MedfordChicago

MFR - ORD

MFRORD

Medford

Mon 8/17

9:17 pm-8:53 pm

2 stops21h 36m

Chicago O'Hare Intl

Thu 8/20

8:11 pm-10:18 am

1 stop16h 07m

$384

MedfordChicago

MFR - ORD

MFRORD

Medford

Fri 7/24

9:11 pm-5:37 am

1 stop30h 26m

Chicago O'Hare Intl

Fri 7/31

7:15 am-2:46 pm

1 stop9h 31m

$387

MedfordChicago

MFR - ORD

MFRORD

Medford

Sat 7/4

6:11 am-7:37 pm

1 stop11h 26m

Chicago O'Hare Intl

Thu 7/9

8:20 pm-9:54 am

1 stop15h 34m

$393
Quickest round-trip

MedfordChicago

MFR - MDW

MFRMDW

Medford

Tue 10/27

5:55 am-6:37 pm

2 stops10h 42m

Chicago Midway

Mon 11/2

9:30 am-4:43 pm

2 stops9h 13m

$423

MedfordChicago

MFR - MDW

MFRMDW

Medford

Tue 10/27

5:55 am-6:37 pm

2 stops10h 42m

Chicago Midway

Mon 11/2

9:30 am-4:43 pm

2 stops9h 13m

$443

MedfordChicago

MFR - MDW

MFRMDW

Medford

Thu 9/24

6:05 am-6:33 pm

2 stops10h 28m

Chicago Midway

Mon 9/28

1:47 pm-11:55 pm

2 stops12h 08m

$476

MedfordChicago

MFR - MDW

MFRMDW

Medford

Thu 9/24

6:05 am-6:33 pm

2 stops10h 28m

Chicago Midway

Mon 9/28

1:47 pm-11:55 pm

2 stops12h 08m

$496

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 September is, on average, the cheapest month to fly to Chicago from Medford, with most prices found around $96. If you’re not able to fly to Chicago in September, then October is your next best option. Flight prices from Medford to Chicago during October average around $211.

Can stopping save me money on Medford to Chicago flights?

You could potentially save up to 31% 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 22m

Direct flights

None
The fastest flight from Medford to Chicago takes 6h 22m
There are no direct flights from Medford to Chicago. There are no popular flight routes from Medford to Chicago.
Search flight deals

Frequently asked questions about flying from Medford to Chicago

  • 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 22m, 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 $273Free CancellationRating
7.8
8,420 reviews
Search Delta flights
United AirlinesPriceFrom $302Free CancellationRating
7.4
9,865 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $308Free CancellationRating
7.9
12,549 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
Portage
Saint Joseph
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