$115 Cheap Flights from Eugene (EUG) to Chicago (MDW)

View $115 flight on Sat, Dec 6, 2025Opens in a new window

Popular airlines from Mahlon Sweet Field Airport (EUG) to Chicago Midway Airport (MDW)

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Cheap Flights from Eugene to Chicago (EUG-MDW)

Prices were available within the past 7 days and start at $115 for one-way flights and $219 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Sat, Dec 6 - Fri, Dec 12
EUG
Eugene
MDW
Chicago
$219 Roundtrip, found 5 days ago
$219
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Dec 6 from Eugene to Chicago, returning Fri, Dec 12, priced at $219 found 5 days ago
Southwest Airlines
Wed, Oct 22 - Sat, Oct 25
EUG
Eugene
MDW
Chicago
$243 Roundtrip, found 5 days ago
$243
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Oct 22 from Eugene to Chicago, returning Sat, Oct 25, priced at $243 found 5 days ago
Southwest Airlines
Wed, Oct 22 - Sat, Oct 25
EUG
Eugene
MDW
Chicago
$248 Roundtrip, found 5 days ago
$248
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Oct 22 from Eugene to Chicago, returning Sat, Oct 25, priced at $248 found 5 days ago
Southwest Airlines
Wed, Oct 22 - Sat, Oct 25
EUG
Eugene
MDW
Chicago
$262 Roundtrip, found 5 days ago
$262
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Oct 22 from Eugene to Chicago, returning Sat, Oct 25, priced at $262 found 5 days ago
Southwest Airlines
Wed, Oct 22 - Sat, Oct 25
EUG
Eugene
MDW
Chicago
$267 Roundtrip, found 5 days ago
$267
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Oct 22 from Eugene to Chicago, returning Sat, Oct 25, priced at $267 found 5 days ago
Southwest Airlines
Wed, Oct 22 - Tue, Oct 28
EUG
Eugene
MDW
Chicago
$277 Roundtrip, found 1 day ago
$277
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Oct 22 from Eugene to Chicago, returning Tue, Oct 28, priced at $277 found 1 day ago
Southwest Airlines
Wed, Oct 22 - Tue, Oct 28
EUG
Eugene
MDW
Chicago
$282 Roundtrip, found 5 hours ago
$282
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Wed, Oct 22 from Eugene to Chicago, returning Tue, Oct 28, priced at $282 found 5 hours ago
Southwest Airlines
Sat, Dec 6 - Fri, Dec 12
EUG
Eugene
MDW
Chicago
$286 Roundtrip, found 5 days ago
$286
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Dec 6 from Eugene to Chicago, returning Fri, Dec 12, priced at $286 found 5 days ago
Southwest Airlines
Wed, Oct 22 - Tue, Oct 28
EUG
Eugene
MDW
Chicago
$287 Roundtrip, found 5 hours ago
$287
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Wed, Oct 22 from Eugene to Chicago, returning Tue, Oct 28, priced at $287 found 5 hours ago
Delta
Tue, Feb 3 - Wed, Feb 4
EUG
Eugene
MDW
Chicago
$287 Roundtrip, found 6 days ago
$287
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Feb 3 from Eugene to Chicago, returning Wed, Feb 4, priced at $287 found 6 days ago

Frequently asked questions

How much does a flight from Mahlon Sweet Field Airport (EUG) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight from $115 or cheap return flight from $219 from Mahlon Sweet Field Airport (EUG) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Mahlon Sweet Field Airport (EUG) to Midway Intl. Airport (MDW)?
December is the most affordable month to fly from EUG to MDW. Planning your trip for the off-season is often the key to finding better fares.
What is the cheapest airline that flies from Mahlon Sweet Field Airport (EUG) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare different airlines, departure times and fares all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to find the carrier with the cheapest EUG to MDW flight.
How many flights per day from Mahlon Sweet Field Airport (EUG) to Midway Intl. Airport (MDW)?
You'll need to hop on a flight with a layover if you're traveling from Mahlon Sweet Field Airport (EUG) to Midway Intl. Airport (MDW). Direct flights don't operate daily on this route. However, just filter your search to include one or two stops to find the best option for your trip.
What day of the week has the most flights from EUG to MDW?
Generally you'll find the most flight options available on a Friday. Tuesdays are often the quietest.* But this can change based on the time of year, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Mahlon Sweet Field Airport (EUG) to Midway Intl. Airport (MDW)?
Book a flight from Mahlon Sweet Field Airport (EUG) to Midway Intl. Airport (MDW) that takes off before 3 PM to reduce the likelihood of delays. Departures after this time have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Mahlon Sweet Field Airport (EUG) to Midway Intl. Airport (MDW) last-minute?
Waiting until right before your break to book a ticket from EUG to MDW generally means paying more. Although you may find some last-minute offers, they're not always guaranteed. Be flexible with your itinerary for the best chance of getting a bargain.
Is it cheaper to book an EUG to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking an EUG to MDW flight and hotel package with Expedia could result in significant savings. Better yet, having everything in one place will take the hassle out of travel planning. Simply secure your flights and select from our wide range of stays, then customize your trip with extras like car rentals and activities.
Can I cancel or change the date of my flight from Mahlon Sweet Field Airport (EUG) to Midway Intl. Airport (MDW)?
Generally, it's possible to cancel or reschedule your EUG to MDW flight. However, for bookings made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Travel information

Origin airport
Eugene
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$219
Distance
1786 mi

Book with confidence

Book with confidence

Eugene to Chicago Flights

The cheapest times to fly from Eugene to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Eugene to Chicago are during the month of December. You can find some of the cheapest flights from Eugene to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Eugene to Chicago

Sunday is one of the best days to book for cheap flights from Eugene to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Eugene to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Eugene to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $115 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Eugene to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Eugene to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Eugene to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.