Trip.com
>
Flights
>
Flights to United States
>
Flights to Illinois
>
Flights to Chicago
Hotels in Chicago
>
Flights from Medford to Chicago

What to know about flights from Medford to Chicago?

The approximate distance between Medford and Chicago is 2,885.36 km. According to Trip.com data, travel demand hits its peak in December.

Cheapest one-way
US$190
Delta Air Lines Delta Air Lines MFR-CHI 9h 14m · 1 stop Mon, Oct 26
Book Now
Cheapest round-trip
US$352
Delta Air Lines Delta Air Lines MFR-CHI 8h 42m · 2 stops Tue, Oct 20 - Wed, Oct 21
Book Now
Recommended airlines
Delta Air Lines Delta Air LinesCheapest· From US$190 Hawaiian Airlines Hawaiian AirlinesMost booked
When to fly
October
Cheapest
December
Peak season
Route details
2,885.36 km
Flight distance

Explore the cheapest one-way and round-trip flights from Medford to Chicago over the next 90 days, with one-way fares from US$190 and round-trip from US$352. Based on Trip.com's latest 7-day flight data.

    • Cheapest
      MFR 12:20
      9h 14m
      1 stop
      ORD 23:34
      Medford - Chicago | Mon, Oct 26 | Delta Air Lines
      US$190 US$596
      68% off
      68% off
      US$596 US$190
    • MFR 13:22
      9h 13m
      1 stop
      ORD 00:35
      Medford - Chicago | Wed, Oct 21 | American Airlines
      US$274 US$596
      54% off
      54% off
      US$596 US$274
    • MFR 13:28
      8h 6m
      1 stop
      ORD 23:34
      Medford - Chicago | Wed, Nov 25 | American Airlines
      US$276 US$596
      54% off
      54% off
      US$596 US$276
    • MFR 13:00
      8h 59m
      1 stop
      ORD 23:59
      Medford - Chicago | Wed, Nov 25 | United Airlines
      US$281
      53% off
      US$596 US$281
    • MFR 05:16
      7h 17m
      1 stop
      ORD 14:33
      Medford - Chicago | Thu, Oct 29 | American Airlines
      US$281
      53% off
      US$596 US$281
    • MFR 12:20
      9h 34m
      1 stop
      ORD 23:54
      Medford - Chicago | Sat, Oct 31 | Delta Air Lines
      US$284
      52% off
      US$596 US$284
    • MFR 12:20
      9h 14m
      1 stop
      ORD 23:34
      Medford - Chicago | Wed, Oct 21 | Delta Air Lines
      US$285
      52% off
      US$596 US$285
    • MFR 06:11
      8h 42m
      1 stop
      ORD 16:53
      Medford - Chicago | Thu, Oct 29 | Delta Air Lines
      US$291
      51% off
      US$596 US$291
    • MFR 13:59
      8h
      1 stop
      ORD 23:59
      Medford - Chicago | Thu, Nov 26 | Delta Air Lines
      US$291
      51% off
      US$596 US$291
    • MFR 13:00
      17h 25m
      1 stop
      CHI 14:00
      Medford - Chicago | Mon, Oct 19 | Normal Airline
      More cheap flights
      More cheap flights
    • MFR 06:11
      8h 42m
      1 stop
      ORD 16:53
      Medford - Chicago | Tue, Oct 20 | Delta Air Lines
      ORD 06:35
      8h 5m
      1 stop
      MFR 12:40
      Chicago - Medford | Wed, Oct 21 | Delta Air Lines
      US$352 US$724
      51% off
      51% off
      US$724 US$352
    • MFR 08:17
      8h 36m
      1 stop
      ORD 18:53
      Medford - Chicago | Sat, Oct 31 | Alaska Airlines
      ORD 18:35
      7h 24m
      1 stop
      MFR 23:59
      Chicago - Medford | Mon, Nov 2 | Alaska Airlines
      US$414 US$724
      43% off
      43% off
      US$724 US$414
    • MFR 18:37
      9h 3m
      1 stop
      ORD 05:40
      Medford - Chicago | Sat, Oct 24 | Alaska Airlines
      ORD 07:00
      7h 46m
      1 stop
      MFR 12:46
      Chicago - Medford | Sat, Oct 31 | Alaska Airlines
      US$445 US$724
      39% off
      39% off
      US$724 US$445
    • MFR 06:04
      8h 43m
      1 stop
      ORD 16:47
      Medford - Chicago | Sat, Nov 14 | Delta Air Lines
      ORD 06:40
      8h 11m
      1 stop
      MFR 12:51
      Chicago - Medford | Wed, Nov 18 | Delta Air Lines
      US$455
      37% off
      US$724 US$455
    • MFR 06:10
      8h 40m
      1 stop
      ORD 16:50
      Medford - Chicago | Tue, Dec 8 | Delta Air Lines
      ORD 06:40
      8h 11m
      1 stop
      MFR 12:51
      Chicago - Medford | Wed, Dec 16 | Delta Air Lines
      US$456
      37% off
      US$724 US$456
    • MFR 13:20
      6h 45m
      1 stop
      ORD 22:05
      Medford - Chicago | Sat, Nov 7 | Delta Air Lines
      ORD 07:35
      6h 10m
      1 stop
      MFR 11:45
      Chicago - Medford | Tue, Nov 10 | Delta Air Lines
      US$456
      37% off
      US$724 US$456
    • MFR 13:00
      7h 46m
      1 stop
      ORD 22:46
      Medford - Chicago | Sat, Oct 31 | United Airlines
      ORD 07:20
      9h 28m
      1 stop
      MFR 14:48
      Chicago - Medford | Mon, Nov 2 | Alaska Airlines
      US$459
      37% off
      US$724 US$459
    • MFR 13:28
      8h 6m
      1 stop
      ORD 23:34
      Medford - Chicago | Fri, Nov 20 | American Airlines
      ORD 05:00
      9h 58m
      1 stop
      MFR 12:58
      Chicago - Medford | Tue, Nov 24 | American Airlines
      US$483
      33% off
      US$724 US$483
    • MFR 05:16
      7h 17m
      1 stop
      ORD 14:33
      Medford - Chicago | Sat, Oct 24 | American Airlines
      ORD 05:00
      9h 52m
      1 stop
      MFR 12:52
      Chicago - Medford | Sat, Oct 31 | American Airlines
      US$489
      32% off
      US$724 US$489
    • MFR 13:00
      17h 25m
      1 stop
      CHI 14:00
      Medford - Chicago | Mon, Oct 19 | Normal Airline
      CHI 15:00
      6h
      Nonstop
      MFR 16:00
      Chicago - Medford | Wed, Oct 21 | Normal Airline
      More cheap flights
      More cheap flights

Displayed flight fares from Medford to Chicago are based on average prices across airlines for the next 3 months, according to the latest Trip.com database.

Which airlines are the most popular for Medford to Chicago flights?

You can choose from 1 airlines that fly from Medford to Chicago, including Hawaiian Airlines, Delta Air Lines has lowest fares on this route.
Hawaiian Airlines logo Hawaiian Airlines
Airlines are determined based on actual purchased flight tickets from Medford to Chicago according to previous 12 months data from Trip.com.

Frequently Asked Questions

  • What are the cheapest flights from Medford to Chicago (MFR-CHI)?

    Based on Trip.com data, Delta Air Lines offers one-way fares as low as US$190 on Cheapest nonstop routes (e.g. MFR to ORD on Mon, Oct 26), while Delta Air Lines offers Cheapest nonstop round-trips from US$352 departing on Tue, Oct 20 and returning on Wed, Oct 21.
  • At the moment, several airlines serve connecting flights from Medford to Chicago, including: Hawaiian Airlines Selected airlines are based on historical data collected from flight bookings made by users on Trip.com within the last 90 days.
  • By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Medford to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.
  • To find best deals on flights from Medford to Chicago, you can use various tools on Trip.com:
    · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Mon, Oct 26, with one-way flights priced at just US$190.
    · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Delta Air Lines.
    · Set up price alerts to easily monitor ticket prices without having to check every day.
    · Check Trip.com flight deals and promo codes frequently.
    · Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around December.
    · Get exclusive promo codes for Trip.com app users.
  • The cheapest months to fly from Medford to Chicago is October, when demand for travel is lower.
  • After crunching the numbers on our October flight calendar, it's currently cheapest to fly from Medford to Chicago on October 26, 2026 with Delta Air Lines, with prices starting at US$190.
  • You can land at any one of the following hubs in Chicago: Chicago Midway International Airport (MDW), O'Hare International Airport (ORD), and Chicago Rockford International Airport (RFD). Flying from Rogue Valley International-Medford Airport to O'Hare International Airport (MFR-ORD) is by far the most common option on this route.
  • The time difference between Chicago and Medford is 2h.
  • Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.
  • Based on Trip.com data for flights departing in the next 30 days, the average one-way fare from Medford to Chicago is US$358. Fares vary by travel date, airline and availability.
  • Based on Trip.com data for travel in the next 30 days, the average round-trip fare from Medford to Chicago is US$674. The final price depends on the outbound and return dates, airline and fare conditions.
  • Enter Medford and Chicago, choose your travel dates and passengers, then compare flights by price, duration and baggage. Select a fare, review the change and cancellation rules, enter traveler details and complete payment to receive your confirmation.

Trip.com Airline Insights on Flights from Medford to Chicago

Which airline offers the cheapest direct flights from Medford to Chicago?

Data is based on the average price of all nonstop flights from Medford to Chicago on Trip.com over the past 12 months.

Based on Trip.com’s data from the past 12 months, Alaska Airlines provides the lowest-priced direct flights from Medford to Chicago, with fares starting at US$307.

US$217
US$307
US$398
US$488
US$578
Alaska Airlines
US$307
Alaska Airlines
United Airlines
US$375
United Airlines
Hawaiian Airlines
US$396
Hawaiian Airlines
Delta Air Lines
US$578
Delta Air Lines

Explore More Popular Flights

Note: Prices shown on this page are the estimated lowest prices found in the last 24 hours and include all taxes and fees.

Book with no extra fees

Prices displayed on this page are all-inclusive (incl. taxes, fuel surcharges, Civil Aviation Development Fund, etc.), and all fees are clearly shown before you pay. Charges for checked baggage, onboard meals, Wi‑Fi, and other optional services are also included where applicable in the flight cards.

Real-time pricing updates

Prices, availability, and travel details on this page have been updated within the last 24 hours, and for many routes are refreshed in real time. The more popular the route, the more accurate and up-to-date the data.

Change & Cancellation Policy

Trip.com shows the change and cancellation rules for each ticket during the booking process, including all related fees and conditions. Please refer to the following scenarios:
Voluntary cancellation/change:
To request a change or cancellation, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and flight segment, and submit your request. Please note that additional charges may apply based on the airline’s fare rules.
Cancellation/change due to a flight schedule change:
If your flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For full details of change and cancellation policies, please refer to the customer support pages.