$69 Cheap Flights from Omaha (OMA) to Chicago (MDW)

View $69 flight on Mon, Sep 29, 2025Opens in a new window

Popular airlines from Eppley Field Airport (OMA) to Chicago Midway Airport (MDW)

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Cheap Flights from Omaha to Chicago (OMA-MDW)

Prices were available within the past 7 days and start at $69 for one-way flights and $137 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Mon, Aug 4 - Thu, Aug 7
OMA
Omaha
MDW
Chicago
$137 Roundtrip, found 5 hours ago
$137
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Mon, Aug 4 from Omaha to Chicago, returning Thu, Aug 7, priced at $137 found 5 hours ago
Southwest Airlines
Mon, Aug 4 - Thu, Aug 7
OMA
Omaha
MDW
Chicago
$147 Roundtrip, found 5 hours ago
$147
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Mon, Aug 4 from Omaha to Chicago, returning Thu, Aug 7, priced at $147 found 5 hours ago
Southwest Airlines
Tue, Sep 9 - Thu, Sep 11
OMA
Omaha
MDW
Chicago
$152 Roundtrip, found 6 hours ago
$152
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Tue, Sep 9 from Omaha to Chicago, returning Thu, Sep 11, priced at $152 found 6 hours ago
Southwest Airlines
Tue, Sep 9 - Thu, Sep 11
OMA
Omaha
MDW
Chicago
$157 Roundtrip, found 6 hours ago
$157
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Tue, Sep 9 from Omaha to Chicago, returning Thu, Sep 11, priced at $157 found 6 hours ago
Delta
Tue, Sep 9 - Thu, Sep 11
OMA
Omaha
MDW
Chicago
$157 Roundtrip, found 6 hours ago
$157
Roundtrip
found 6 hours ago
Select Delta flight, departing Tue, Sep 9 from Omaha to Chicago, returning Thu, Sep 11, priced at $157 found 6 hours ago
Southwest Airlines
Tue, Sep 9 - Thu, Sep 11
OMA
Omaha
MDW
Chicago
$162 Roundtrip, found 6 hours ago
$162
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Tue, Sep 9 from Omaha to Chicago, returning Thu, Sep 11, priced at $162 found 6 hours ago
Southwest Airlines
Thu, Sep 18 - Wed, Sep 24
OMA
Omaha
MDW
Chicago
$167 Roundtrip, found 11 hours ago
$167
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Thu, Sep 18 from Omaha to Chicago, returning Wed, Sep 24, priced at $167 found 11 hours ago
Southwest Airlines
Mon, Aug 4 - Thu, Aug 7
OMA
Omaha
MDW
Chicago
$167 Roundtrip, found 5 hours ago
$167
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Mon, Aug 4 from Omaha to Chicago, returning Thu, Aug 7, priced at $167 found 5 hours ago
Southwest Airlines
Thu, Sep 4 - Sat, Sep 6
OMA
Omaha
MDW
Chicago
$168 Roundtrip, found 4 hours ago
$168
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Thu, Sep 4 from Omaha to Chicago, returning Sat, Sep 6, priced at $168 found 4 hours ago
Frontier Airlines
Thu, Aug 14 - Fri, Aug 22
OMA
Omaha
MDW
Chicago
$228 Roundtrip, found 5 days ago
$228
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Aug 14 from Omaha to Chicago, returning Fri, Aug 22, priced at $228 found 5 days ago

Find the cheapest month to fly from Omaha (OMA) to Chicago (MDW)

February is typically the cheapest month to fly

From $115 - $636 per traveler.

Graph displaying average flight prices per month

Flights from Omaha (OMA) to Chicago (MDW)
Origin airport
Eppley Field
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$137
Distance
423 mi
Average flight time
1 hour 25 mins

Omaha to Chicago Flights

The cheapest times to fly from Omaha 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 Omaha to Chicago are during the month of August. You can find some of the cheapest flights from Omaha to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Omaha to Chicago

Sunday is one of the best days to book for cheap flights from Omaha 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 Omaha 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 Omaha to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $69 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 Omaha 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 Omaha 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.

 

Frequently asked questions

How much does a flight from Eppley Field Airport (OMA) to Midway Intl. Airport (MDW) cost?
Grab cheap return fares starting at $137 from Eppley Field Airport (OMA) to Midway Intl. Airport (MDW). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines flight leaving OMA on July 29 2025 and touching down at MDW. The price was last updated on July 4 2025 and has not changed since.
What is the cheapest month to fly from OMA to MDW?
The cheapest flights from OMA to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Eppley Field Airport (OMA) to Midway Intl. Airport (MDW)?
You can travel nonstop from Eppley Field Airport (OMA) to Midway Intl. Airport (MDW) on a Southwest Airlines flight.
What is the cheapest airline that flies from OMA to MDW?
Fly from OMA to MDW with Southwest Airlines. This carrier currently has the lowest one-way fare for this route, starting from $69. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from OMA on September 29 2025. Prices were last updated on July 4 2025 and have not changed since.
How many flights per day from Eppley Field Airport (OMA) to Midway Intl. Airport (MDW)?
With, on average, 2 direct flights that operate from Eppley Field Airport (OMA) to Midway Intl. Airport (MDW) every day, you'll be up in the air in no time.
What are the most popular departure times for flights from Eppley Field Airport (OMA) to Midway Intl. Airport (MDW)?
More travelers fly between OMA and MDW at 7 AM than at any other point in the day. Looking to skip the crowds? Travel outside of rush hours and you could save on your ticket as well.
What day of the week has the most flights from OMA to MDW?
Depart on a Wednesday if you're after the largest selection of flights from Eppley Field Airport (OMA) to Midway Intl. Airport (MDW).
What is the earliest flight from Eppley Field Airport (OMA) to Midway Intl. Airport (MDW)?
The first flight of the day taking off from Eppley Field Airport (OMA) is at around 5:35AM UTC-6. Hop on this flight and you'll land at Midway Intl. Airport (MDW) at approximately 7:10AM UTC-6. The total flight duration is 1h 35m.
How long does it take to fly from Eppley Field Airport (OMA) to Midway Intl. Airport (MDW)?
Flights from OMA to MDW have an average travel time of 1 hour and 31 minutes. The total distance between the two is 420 mi.
What airline has the least delays from OMA to MDW?
Southwest Airlines has the best track record for on-time direct flights from Eppley Field Airport (OMA) to Midway Intl. Airport (MDW), with an on-time rating of 85%. Use the Expedia App to see your flight schedule before you take off and get immediate updates about any trip changes.
What is the best time to fly from Eppley Field Airport (OMA) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Eppley Field Airport (OMA) to Midway Intl. Airport (MDW) route, fly before 3 PM. Later flights have a 22% higher chance of cancellation.**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.
What airports do you fly into for Chicago from Eppley Field Airport (OMA)?
Hop on a direct flight from Eppley Field Airport (OMA) to Chicago and touch down at O'Hare Intl. Airport (ORD). Another convenient point of entry into the city is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Eppley Field Airport (OMA) to Midway Intl. Airport (MDW) last-minute?
Booking your flight from OMA to MDW just before your getaway is generally more expensive. But if you're flexible with your schedule, you could land a cheap last-minute fare.
Is it cheaper to book an OMA to MDW flight and hotel package?
You'll generally save money by securing an OMA to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one convenient place. After selecting your ideal flights and accommodations, consider adding extras such as tours, car rentals and activities.
Can I cancel or change the date of my flight from Eppley Field Airport (OMA) to Midway Intl. Airport (MDW)?
In most cases, you can cancel or modify your OMA to MDW flight. However, additional fees may apply, especially if you made your booking more than 24 hours ago. Double-check your itinerary for the airline's rules and fees on flight changes, or if you want further information, visit our Customer Service portal.

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