OMA - MDW

$98 Find Cheap Flights from Omaha to Chicago Midway Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$246
Typical prices: $286-$418
Southwest
Sun 12/9Thu 12/13
OMA - MDW • 1 stop
Cheapest non-stop
$255
Typical prices: $287-$419
Southwest
Tue 11/20Fri 11/23
OMA - MDW • Non-stop
Nonstop flights
You can fly direct with Southwest. Average duration is 1h 28m
Direct flights
+1
Direct flights
+1
Avoid delays
Most punctual • 86% on-time
Best time • Fewest delays
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 12 weeks in advance save around 52% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 18% price drop
Most popular
Good to know
+1
Good to know
+1
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We hope you love your trip to Chicago Midway Airport!
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Booking Insights
Flight Deals

Cheap Flights from Omaha to Midway (OMA-MDW)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Omaha to Midway

Wed, Dec 9 - Sun, Dec 13
Southwest Logo
1:35 pm - 9:30 pmOMA  Omaha Eppley Airfield-MDW Chicago Midway
7h 55m1 stop Denver Intl
Southwest Logo
9:15 pm - 11:00 pmMDW  Chicago Midway-OMA Omaha Eppley Airfield
1h 45mnonstop
$246Southwest
Thu, Dec 10 - Sun, Dec 13
Southwest Logo
5:50 am - 7:20 amOMA  Omaha Eppley Airfield-MDW Chicago Midway
1h 30mnonstop
Southwest Logo
12:25 pm - 6:00 pmMDW  Chicago Midway-OMA Omaha Eppley Airfield
5h 35m1 stop Washington, D.C. Reagan-National
$246Southwest
Thu, Dec 3 - Sun, Dec 6
Southwest Logo
5:50 am - 7:20 amOMA  Omaha Eppley Airfield-MDW Chicago Midway
1h 30mnonstop
Southwest Logo
5:15 am - 2:50 pmMDW  Chicago Midway-OMA Omaha Eppley Airfield
9h 35m1 stop Phoenix Sky Harbor Intl
$246Southwest
Fri, Dec 11 - Sat, Jan 9
Southwest Logo
5:30 am - 7:05 amOMA  Omaha Eppley Airfield-MDW Chicago Midway
1h 35mnonstop
Southwest Logo
6:30 am - 1:50 pmMDW  Chicago Midway-OMA Omaha Eppley Airfield
7h 20m1 stop Denver Intl
$246Southwest
Sat, Nov 21 - Sun, Nov 22
Southwest Logo
10:35 am - 12:00 pmOMA  Omaha Eppley Airfield-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
11:00 am - 6:00 pmMDW  Chicago Midway-OMA Omaha Eppley Airfield
7h 00m1 stop Washington, D.C. Reagan-National
$246Southwest
Sat, Jan 16 - Mon, Jan 18
Southwest Logo
1:10 pm - 2:35 pmOMA  Omaha Eppley Airfield-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
9:55 am - 4:30 pmMDW  Chicago Midway-OMA Omaha Eppley Airfield
6h 35m1 stop Denver Intl
$247Southwest
Wed, Dec 9 - Wed, Dec 16
Southwest Logo
10:25 am - 5:20 pmOMA  Omaha Eppley Airfield-MDW Chicago Midway
6h 55m1 stop Phoenix Sky Harbor Intl
Southwest Logo
10:05 am - 11:35 amMDW  Chicago Midway-OMA Omaha Eppley Airfield
1h 30mnonstop
$247Southwest
Tue, Jan 12 - Thu, Jan 14
Southwest Logo
6:30 am - 12:20 pmOMA  Omaha Eppley Airfield-MDW Chicago Midway
5h 50m1 stop Denver Intl
Southwest Logo
7:35 pm - 9:10 pmMDW  Chicago Midway-OMA Omaha Eppley Airfield
1h 35mnonstop
$247Southwest
Wed, Feb 10 - Sat, Feb 13
Delta Logo
12:35 pm - 4:53 pmOMA  Omaha Eppley Airfield-MDW Chicago Midway
4h 18m1 stop Minneapolis St Paul
Delta Logo
5:35 pm - 9:06 pmMDW  Chicago Midway-OMA Omaha Eppley Airfield
3h 31m1 stop Minneapolis St Paul
$257Delta
Sat, Dec 12 - Mon, Dec 14
Delta Logo
8:10 am - 11:59 amOMA  Omaha Eppley Airfield-MDW Chicago Midway
3h 49m1 stop Minneapolis St Paul
Delta Logo
5:30 pm - 11:18 pmMDW  Chicago Midway-OMA Omaha Eppley Airfield
5h 48m1 stop Minneapolis St Paul
$267Delta
Booking Insights

Price, demand and travel trends for Omaha to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Omaha to Chicago Midway Airport?

Round-trip flights from Omaha to Chicago Midway Airport typically range from $286 to $418. The lowest price found in the past 5 days was $246, on Southwest.

What's the cheapest day of the week to fly from Omaha to Chicago Midway Airport?

Based on deals KAYAK users found in the last 12 months, Saturday is the cheapest day of the week to fly from Omaha to Chicago Midway Airport. It’s 24% cheaper than the average day, while Friday is the most expensive, with prices 9% higher.

What’s the cheapest month to fly from Omaha to Chicago Midway Airport?

•January and April are the cheapest months to fly from Omaha to Chicago Midway Airport at $276 round-trip.
•May ($388) and June ($376) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 40% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Omaha to Chicago Midway Airport the cheapest?

Flights from Omaha to Chicago Midway Airport are cheapest 12 weeks before departure. Booking in this window typically costs about 52% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Key details for Omaha to Chicago Midway Airport flights

Low season

January

Cheapest flight

$98
Beat the crowds with an average 49% drop in travelers.
The most popular month to fly with an average 73% increase in travelers.
One-way flight from Omaha to Chicago Midway Airport

When to book flights from Omaha to Midway

Are your dates flexible? Find out the best times to travel from Omaha to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Omaha to Chicago Midway Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Omaha to Chicago Midway Airport?

    These are the earliest and latest flight times available from Omaha to Chicago Midway Airport:

    • Earliest: departs at 5:05 am and lands at 6:33 am
    • Latest: departs at 6:20 pm and lands at 7:48 pm.

    The flight takes about 1h 28m.

  • What cabin classes can I book on flights from Omaha to Chicago Midway Airport?

    Only Economy Class is available on flights from Omaha to Chicago Midway Airport.

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

    A nonstop flight from Omaha to Chicago Midway Airport takes 1h 28m, covering 422 miles.

  • Do I need a passport to fly from Omaha to Chicago Midway Airport?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Omaha to Chicago Midway Airport flight?

    Round-trip flights from Omaha to Chicago Midway Airport range from $286 to $418, with an average of $337 over the past 12 months. Anything below $286 counts as a good deal.

  • How expensive are last-minute Omaha to Chicago Midway Airport flights?

    Last-minute fares on this route (booked within two weeks of departure) run 68% above the $337 route average. Book 12 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Omaha to Chicago Midway Airport?

    On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $337 round-trip, compared to $396 via a layover through Minneapolis St Paul (MSP).

  • How does on-time performance compare across airlines flying from Omaha to Chicago Midway Airport?

    Southwest is the only airline operating Omaha to Chicago Midway Airport flights. 86% of its flights are on time.

  • What is the standard checked-bag allowance on flights from Omaha to Chicago Midway Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Omaha to Chicago Midway Airport?

    The Airbus A319 family is used most often on this route, operated mainly by United Airlines and American Airlines. Other aircraft seen on the route include Boeing 737 MAX 8 variants.

  • How are flight departures from Omaha to Chicago Midway Airport spread across the day?

    Morning is the busiest departure period on Omaha to Chicago Midway Airport flights, with 67% of flights leaving in that window. Afternoon departures account for 33%, evening flights for 0%, and night flights for 0%.

  • Have flight prices from Omaha to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $242 to $1,229. That means the highest observed fare was about 5x higher than the lowest one.

  • How are flight prices from Omaha to Chicago Midway Airport looking right now?

    One-way fares from Omaha to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $104, which is 65% below the typical average for this route.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates averaging $84 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • Which airports can I use when flying from Omaha to Chicago Midway Airport?

    Flights from Omaha to Chicago Midway Airport usually depart from Omaha Eppley Airfield (OMA) and arrive at Chicago Midway (MDW).

  • What time of day has the fewest delays on flights from Omaha to Chicago Midway Airport?

    Night flights have the fewest delays on this route, while evening departures tend to have the most.

  • At what point is a flight considered delayed from Omaha to Chicago Midway Airport?

    A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Omaha to Chicago Midway Airport route, 14% of flights were delayed in the past 3 months, with delays averaging 1h 42m.

  • Which airports do connecting flights from Omaha to Chicago Midway Airport pass through?

    Most connecting flights from Omaha to Chicago Midway Airport pass through Minneapolis St Paul (MSP), which handles 100% of one-stop traffic on this route.

  • Can I save money by using flexible dates for flights from Omaha to Chicago Midway Airport?

    Yes. Flexible dates can save you up to 31% on flights from Omaha to Chicago Midway Airport. Saturday is the cheapest departure day at $257 round-trip on average, while Friday is the most expensive at $368, a difference of $111.

    Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • What airlines fly from Omaha to Chicago Midway Airport?

    Only Southwest operates flights between Omaha and Chicago Midway Airport.

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Omaha to Chicago Midway Airport flights?

    Among airlines operating Omaha to Chicago Midway Airport flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Omaha to Chicago Midway Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Omaha to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Saturday departure and avoid flying on Friday. On this route, Saturday flights average $257, about $111 less than Friday fares (30% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 12 weeks before you fly. On this route, that window historically saves about 52% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Omaha to Chicago Midway Airport trip for January. Fares historically average $276 round-trip in that month - typically $112 less than the most expensive month, which is May (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel Chicago Midway Airport

Prefer to fly direct from Omaha to Chicago Midway Airport?

 
Find which airlines fly direct from Omaha Eppley Airfield Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Omaha Eppley Airfield to Chicago Midway

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Thursday

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Friday

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Saturday

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Sunday

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See more direct flights

Direct returns

Chicago Midway to Omaha Eppley Airfield

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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See more direct flights

More options for your flight from Omaha to Midway

Complete your trip to Chicago with a hotel stay or car rental