MFR - CHI

$149 Find Cheap Flights from Medford to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Medford to Chicago departing on 5/16. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Medford to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Medford to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$277
Typical prices: $471-$809
Alaska Airlines
Sat 4/18Tue 4/21
MFR - ORD • 1 stop
Cheapest one-way
$154
Delta
Sat 5/16
MFR - MDW • 2 stops
Top airlines
Cheapest • from $277 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Medford and Chicago. You'll need at least 1 connection.
Insights
Insights
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Insights
Top layover airports
Cheapest • Avg $363 (round-trip)
Shortest trip • 6h 05m (one-way)
Insights
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Top routes
Cheapest
Most popular
Insights
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Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Medford to Chicago (MFR-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Medford to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Medford to Chicago

Sat, Apr 18 - Tue, Apr 21
Alaska Airlines Logo
7:40 am - 7:02 pm
MFR
-
ORD
9h 22m
1 stop
Alaska Airlines Logo
6:00 am - 12:45 pm
ORD
-
MFR
8h 45m
1 stop
$277Alaska Airlines
Wed, Apr 15 - Sat, Apr 18
Delta Logo
12:28 pm - 9:18 pm
MFR
-
ORD
6h 50m
1 stop
Delta Logo
7:35 am - 11:47 am
ORD
-
MFR
6h 12m
1 stop
$297Delta
Sat, Apr 18 - Tue, Apr 21
Alaska Airlines Logo
7:40 am - 7:02 pm
MFR
-
ORD
9h 22m
1 stop
Alaska Airlines Logo
6:00 am - 12:45 pm
ORD
-
MFR
8h 45m
1 stop
$300Alaska Airlines
Thu, Apr 23 - 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
$301United Airlines
Wed, Apr 15 - Sat, Apr 18
Delta Logo
6:10 am - 9:18 pm
MFR
-
ORD
13h 08m
2 stops
Delta Logo
7:35 am - 11:47 am
ORD
-
MFR
6h 12m
1 stop
$302Delta
Sat, Apr 18 - Tue, Apr 21
Alaska Airlines Logo
5:45 am - 3:13 pm
MFR
-
ORD
7h 28m
1 stop
Alaska Airlines Logo
6:00 am - 12:45 pm
ORD
-
MFR
8h 45m
1 stop
$323Alaska Airlines
Thu, May 7 - Sun, May 10
United Airlines Logo
2:07 pm - 12:34 am
MFR
-
ORD
8h 27m
2 stops
United Airlines Logo
7:00 am - 1:01 pm
ORD
-
MFR
8h 01m
1 stop
$324United Airlines
Wed, Apr 22 - Sun, May 3
Alaska Airlines Logo
5:36 pm - 6:40 am
MFR
-
ORD
11h 04m
1 stop
Alaska Airlines Logo
8:48 pm - 12:52 pm
ORD
-
MFR
18h 04m
1 stop
$338Alaska Airlines
Thu, Apr 16 - Sun, Apr 19
United Airlines Logo
12:50 pm - 10:54 pm
MFR
-
ORD
8h 04m
1 stop
United Airlines Logo
6:25 am - 11:49 am
ORD
-
MFR
7h 24m
1 stop
$343United Airlines
Wed, Apr 22 - Tue, Apr 28
Alaska Airlines Logo
5:36 pm - 6:40 am
MFR
-
ORD
11h 04m
1 stop
Alaska Airlines Logo
8:50 am - 7:04 pm
ORD
-
MFR
12h 14m
2 stops
$345Alaska Airlines
Booking Insights

KAYAK's insights & trends for Medford to Chicago flights

Get data-powered insights and trends into flights from Medford to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Medford to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Medford to Chicago costs $1,162 on the route between Medford (MFR) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

Good to know

Low seasonOctober
Cheapest flight$154
Best time to beat the crowds with an average 41% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Medford to Chicago Midway Airport

When to book flights from Medford to Chicago

Are your dates flexible? Find out the best times to travel from Medford to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Medford to Chicago

  • What is the cheapest flight from Medford to Chicago?

    In the last 3 days, the lowest price for a flight from Medford to Chicago was $154 for a one-way ticket and $277 for a round-trip.

  • Do I need a passport to fly between Medford and Chicago?

    A passport is not required to fly from Medford to Chicago.

  • Which aircraft models fly most regularly from Medford to Chicago?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Medford to Chicago?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Medford and Chicago, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Medford to Chicago, Alaska Airlines or United Airlines?

    The two airlines most popular with KAYAK users for flights from Medford to Chicago are Alaska Airlines and United Airlines. With an average price for the route of $448 and an overall rating of 7.9, Alaska Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of $606 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Medford to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Medford to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Medford to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Medford is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Medford to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Medford with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Medford to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Medford up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Medford to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Medford to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Medford to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
Alaska AirlinesOverall score based on 12052 reviews
7.0Entertainment
7.8Comfort
8.1Boarding
8.5Crew
7.1Food
Airline reviews

Never got on because first part of trip was cancelled and we have no idea when we will get rebooked…

2.0 MediocreAnonymous, Mar 2026
PDX - SEA
Read more Alaska Airlines reviews

Never got on because first part of trip was cancelled and we have no idea when we will get rebooked…

There was an issue with the plane and it was late getting in. This caused me to miss my connecting flight from PDX to BOI. I had to ask if they would provide me with a food voucher and they did but didn’t seem to concerned about my delay.

Wonderful as always! Pleasant staff, smooth ride, and timely departure.

I'm not sure if you are going to ask me about the check in process. I could not get my boarding pass, so I had to stop at the American desk before security. I also had a difficult time downloading the app with the confirmation code for the two flights.

Everything ran like it should. Staff was professional. Looking forward to flying with them again.

Boarding much smoother than previous United flights! The flight attendant helped monitor putting bags in overhead bins. On united no help resulted in bins in first class being filled before I boarded for first class. I had to search further down into economy. Then got stuck unable to return to my seat. People were putting backpacks that needed to go under seats in bins. It was a mess. This flight was a refreshing improvement. United also had so many categories of preboarding that first class could not board early. The pilot talked to us directly instead of using the intercom before flight.

Liked the attention and speed when getting wheelchair..........Was assured by phone that my needs would be taken care of and they were with my name.

The planes were in very nice condition. Comfortable enough leg room. I had a very quick connection on my return home I made it just fine and so did my luggage!!

Everything was fine. The snacks are a little on the tiny side.

Most of it was good. The flights were on time. The staff were helpful and friendly. I had a short time connecting flights and they let me deplane first and I made the connection. On the outbound from DTW to SEA I was seated in the middle of two very large people. I am petite and even with my arms crossed they were both hanging over into my seat touching me. The meal had way too much pepper and spice, my lips were burning. Other than those two issues, I was pleased with the service and the trip and will use Alaska Air again.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

Everything you need to know for your flight from Medford to Chicago

Information on your arrival and departure airports