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$55+ Cheap flights from Omaha (OMA) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
OMA — MDW
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find flight deals from Omaha to Midway

Cheapest flights from Omaha to Midway
Explore the most affordable flight options available from Omaha to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Trip.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/711:29 amOMA - MDW
1 stop10h 39mFrontier
Mon 11/1012:30 pmMDW - OMA
1 stop7h 36mFrontier
Deal found 10/28$220
This Booking.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/137:46 pmOMA - MDW
1 stop15h 44mFrontier
Mon 11/1712:30 pmMDW - OMA
1 stop7h 36mFrontier
Deal found 10/29$233
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/33:40 pmOMA - MDW
Nonstop1h 30mSouthwest
Mon 12/88:25 pmMDW - OMA
Nonstop1h 30mSouthwest
Deal found 10/27$237
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/226:10 pmOMA - MDW
Nonstop1h 25mSouthwest
Mon 11/246:25 pmMDW - OMA
Nonstop1h 35mSouthwest
Deal found 10/27$243
This Priceline deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3111:40 amOMA - MDW
1 stop10h 05mFrontier
Sun 11/212:30 pmMDW - OMA
1 stop6h 21mFrontier
Deal found 10/28$248
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/34:10 pmOMA - MDW
2 stops6h 25mSouthwest
Thu 12/48:25 pmMDW - OMA
Nonstop1h 30mSouthwest
Deal found 10/28$252
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1310:30 amOMA - MDW
Nonstop1h 25mSouthwest
Tue 12/165:15 pmMDW - OMA
1 stop4h 30mSouthwest
Deal found 10/29$257

Cheap flight deals from Omaha to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Omaha (OMA) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$233
(Booking.com)

One-way from

$55
(Priceline)

Popular in

August

Cheapest in

January

Average price

$297

Good round-trip deal

$318 or less

Good one-way deal

$174 or less
Provider with most accurate pricing for Omaha Eppley Airfield-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Omaha Eppley Airfield-Chicago Midway flights.
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From Omaha Eppley Airfield to Chicago Midway
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One-way flight from Omaha Eppley Airfield to Chicago Midway
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Highest demand for flights based on searches. 6% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Omaha Eppley Airfield to Chicago Midway.
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Price to beat on a one-way flight from Omaha Eppley Airfield to Chicago Midway.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Omaha to Midway 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, Cheapflights users made 2,558,603 searches. Data last updated October 30, 2025.
Use the filters below to find and compare flights from Omaha to Chicago Midway Airport that are best for you.

Fly from

Omaha

Fly to

Midway

Route

Depart

Return

Price

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Tue 12/30

7:55 pm-9:25 pm

Nonstop1h 30m

Chicago Midway

Wed 12/31

8:25 pm-9:55 pm

Nonstop1h 30m

$237

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Wed 2/18

5:50 am-7:20 am

Nonstop1h 30m

Chicago Midway

Wed 2/18

7:45 pm-9:20 pm

Nonstop1h 35m

$237

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Wed 2/18

5:50 am-7:20 am

Nonstop1h 30m

Chicago Midway

Thu 2/19

8:30 pm-10:00 pm

Nonstop1h 30m

$237

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Thu 12/4

3:40 pm-5:10 pm

Nonstop1h 30m

Chicago Midway

Sat 12/6

12:30 pm-2:00 pm

Nonstop1h 30m

$237

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Sat 11/22

6:10 pm-7:35 pm

Nonstop1h 25m

Chicago Midway

Mon 11/24

8:00 am-9:35 am

Nonstop1h 35m

$243

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Wed 12/3

3:40 pm-5:10 pm

Nonstop1h 30m

Chicago Midway

Thu 12/4

6:20 am-11:45 am

1 stop5h 25m

$247

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Thu 2/19

5:20 am-10:20 am

1 stop5h 00m

Chicago Midway

Thu 2/19

8:30 pm-10:00 pm

Nonstop1h 30m

$247

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Wed 12/3

6:00 am-12:45 pm

2 stops6h 45m

Chicago Midway

Mon 12/8

8:35 am-10:05 am

Nonstop1h 30m

$252

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Thu 11/27

5:50 am-7:25 am

Nonstop1h 35m

$105

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Sat 2/14

3:35 pm-5:00 pm

Nonstop1h 25m

$115

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 18 results
1
2

Compare providers for flights from Omaha to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Omaha to Midway in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Omaha-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Omaha-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Omaha-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Omaha-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Omaha-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Omaha to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Omaha with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Omaha to Chicago Midway Airport

What is the cheapest month to book a flight from Omaha to Chicago Midway Airport?

Currently, November is the cheapest month in which you can book a flight from Omaha to Chicago Midway Airport (average of $98). Flying from Omaha to Chicago Midway Airport in August is currently the most expensive (average of $400). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from OMA to MDW?

Find hourly flight availability from Omaha to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 19% on flights from Omaha to Chicago Midway Airport by exploring options for tickets in the evening.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated October 30, 2025.
See what other customers who have flown with Southwest from Omaha to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,243 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Omaha to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Omaha to Chicago Midway?

    For a flight from Omaha to Chicago Midway, you will be flying from Eppley Airfield. Omaha Eppley Airfield (OMA) is just 3.9 mi from the center of the city. Eppley Airfield is the only Omaha airport and it handles 0 outbound flights to Chicago Midway per day. 1 airline has flights to Chicago Midway from Omaha Eppley Airfield on a regular basis.

  • How long is the flight from Omaha to Chicago Midway Airport?

    There are many flights that can get you from Omaha to Chicago Midway Airport in 1h 30m. Fly via Southwest to get the fastest option. The distance between Omaha and Chicago Midway Airport is about 422 mi. All flights are typically nonstop.

  • What is the cheapest airline to fly from Omaha to Chicago Midway Airport round-trip?

    According to our current data, Southwest ($207), offers the cheapest pricing from Omaha to Chicago Midway Airport. You may be able to fly from Omaha to Chicago Midway Airport for 30% less than the average price by searching for this airline.

  • What are the cheapest flights from Omaha to Chicago Midway Airport?

    Looking for the cheapest flight from Omaha to Chicago Midway Airport? While on average our users pay $362, our data indicates the cheapest price to be $136. The most popular route (Omaha Eppley Airfield - Chicago Midway), is priced around $202.

  • Can I find deals for flights from Omaha to Midway that include hotel bookings?

    Yes. In addition to deals on Omaha to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Omaha to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Omaha to Midway.

  • Can I find deals for business class flights from Omaha to Midway?

    Yes. Cheapflights offers flight deals from Omaha to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Omaha to Chicago Midway Airport?

    Currently, November is the cheapest month in which you can book a flight from Omaha to Chicago Midway Airport (average of $98). Flying from Omaha to Chicago Midway Airport in August is currently the most expensive (average of $400). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Alternative routes for Omaha to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Omaha to Midway

Discover the top airline that operate flights from Omaha to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$207Average$288FlexibilityNo cancel feeOn-time63%

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