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Midway

$109+ 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 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
OMA — MDW
Aug 29 — Sep 51
Sat 8/29
Sat 9/5
1 adult, Economy
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Cheap 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 July 30, 2026.

This Southwest deal was found by Cheapflights users on 7/29. 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.
Wed 8/2610:30 am
OMA
-
MDW
Nonstop1h 25m
Southwest
Wed 9/29:00 am
MDW
-
OMA
1 stop5h 20m
Southwest
Deal found 7/29$227
This Southwest deal was found by Cheapflights users on 7/26. 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 9/54:10 pm
OMA
-
MDW
Nonstop1h 35m
Southwest
Wed 9/92:40 pm
MDW
-
OMA
Nonstop1h 25m
Southwest
Deal found 7/26$236
This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:54 am
OMA
-
MDW
1 stop4h 53m
Delta
Wed 10/2812:27 pm
MDW
-
OMA
1 stop4h 53m
Delta
Deal found 7/27$237
This Southwest deal was found by Cheapflights users on 7/28. 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.
Thu 9/246:20 pm
OMA
-
MDW
Nonstop1h 25m
Southwest
Mon 9/289:20 am
MDW
-
OMA
2 stops11h 45m
Southwest
Deal found 7/28$238
This Southwest deal was found by Cheapflights users on 7/27. 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 9/54:10 pm
OMA
-
MDW
Nonstop1h 35m
Southwest
Sun 9/68:45 am
MDW
-
OMA
Nonstop1h 35m
Southwest
Deal found 7/27$241
This Southwest deal was found by Cheapflights users on 7/29. 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.
Mon 9/2112:25 pm
OMA
-
MDW
1 stop7h 10m
Southwest
Wed 9/2312:35 pm
MDW
-
OMA
2 stops9h 35m
Southwest
Deal found 7/29$248
This Southwest deal was found by Cheapflights users on 7/29. 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 9/128:10 am
OMA
-
MDW
2 stops8h 30m
Southwest
Sat 9/197:40 am
MDW
-
OMA
2 stops12h 10m
Southwest
Deal found 7/29$253

Find 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 July 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$227
(Southwest)

One-way from

$109
(Southwest)

Popular in

November

Cheapest in

September

Average price

$337

Good round-trip deal

$349 or less

Good one-way deal

$213 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
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in July 2026
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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 July 30, 2026.
Use the filters below to find and compare flights from Omaha to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Sun 9/27

8:00 am-2:05 pm

1 stop6h 05m

Chicago Midway

Thu 10/1

9:40 am-11:10 am

Nonstop1h 30m

$292

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Mon 9/14

4:50 pm-10:00 pm

1 stop5h 10m

Chicago Midway

Wed 9/16

8:15 am-2:20 pm

2 stops6h 05m

$312

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Sun 9/27

7:45 am-1:50 pm

2 stops6h 05m

Chicago Midway

Wed 9/30

10:10 am-7:25 pm

2 stops9h 15m

$312
Quickest round-trip

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Fri 8/21

1:10 pm-2:35 pm

Nonstop1h 25m

Chicago Midway

Sun 8/23

5:35 pm-7:05 pm

Nonstop1h 30m

$335

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Sat 9/5

4:10 pm-5:45 pm

Nonstop1h 35m

Chicago Midway

Mon 9/7

3:20 pm-10:05 pm

2 stops6h 45m

$413

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Wed 8/12

3:05 pm-4:30 pm

Nonstop1h 25m

Chicago Midway

Thu 8/13

12:05 pm-1:35 pm

Nonstop1h 30m

$449

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Sat 8/15

6:25 am-2:15 pm

1 stop7h 50m

Chicago Midway

Sun 8/16

1:00 pm-2:30 pm

Nonstop1h 30m

$459

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Fri 8/14

7:55 am-9:20 am

Nonstop1h 25m

Chicago Midway

Sun 8/16

5:50 pm-10:00 pm

1 stop4h 10m

$459

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Sun 8/16

7:45 am-1:50 pm

2 stops6h 05m

Chicago Midway

Sun 8/16

5:35 pm-7:05 pm

Nonstop1h 30m

$464
Cheapest one-way

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Sat 9/26

1:45 pm-5:59 pm

1 stop4h 14m

$119

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 20 resultsSorted by cheapest first
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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Omaha-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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, September is the cheapest month in which you can book a flight from Omaha to Chicago Midway Airport (average of $243). Flying from Omaha to Chicago Midway Airport in November is currently the most expensive (average of $508). 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 July 30, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 10% on flights from Omaha to Chicago Midway Airport by exploring options for tickets at noon.

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 July 30, 2026.
See what other customers who have flown with Southwest and United Airlines 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
4,227 reviews

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,227 reviews
Southwest
8.0
Very good
4,227 reviews

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
10,046 reviews
Southwest
8.0
Very good
4,227 reviews

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

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 2 outbound flights to Chicago Midway per day. 2 airlines have 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 6h 05m. Fly via Southwest to get the fastest option. The distance between Omaha and Chicago Midway Airport is about 422 mi.

  • What are the cheapest airlines flying from Omaha to Chicago Midway Airport round-trip?

    According to our current data, Southwest ($227), and United Airlines ($337) offers the cheapest pricing from Omaha to Chicago Midway Airport. You may be able to fly from Omaha to Chicago Midway Airport for 32% less than the average price by searching for these airlines.

  • 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 $339, our data indicates the cheapest price to be $122. The most popular route (Omaha Eppley Airfield - Chicago Midway), is priced around $217.

  • 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, September is the cheapest month in which you can book a flight from Omaha to Chicago Midway Airport (average of $243). Flying from Omaha to Chicago Midway Airport in November is currently the most expensive (average of $508). 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
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

Browse thousands of different options on Cheapflights for your next trip

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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.
Omaha to O'Hare Intl flights
Lincoln to O'Hare Intl flights
Sioux City to O'Hare Intl flights
Omaha to Rockford flights
Lincoln to Midway flights

Top 2 airlines flying from Omaha to Midway

Discover the top 2 airlines 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 July 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$227Average$317FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$337Average$371FlexibilityNo cancel feeOn-time69%

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