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$119+ Cheap flights from Omaha (OMA) to Chicago (CHI)

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 7/28. Fares are subject to change and may not be available on all flights or dates of travel.
OMA — CHI
Jul 21 — Jul 281
Tue 7/21
Tue 7/28
1 adult, Economy
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Cheapflights Tip: The best prices from Omaha Eppley Airfield to Chicago are usually found in August or April, booked 71 days in advance, depart on a Friday or Thursday and return on a Saturday

Cheap flight deals from Omaha to Chicago

Cheapest flights from Omaha to Chicago
Explore the most affordable flight options available from Omaha to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 21, 2026.

This Southwest deal was found by Cheapflights users on 6/20. 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.
Fri 7/2412:20 pm
OMA
-
MDW
1 stop7h 55m
Southwest
Tue 7/2811:50 am
MDW
-
OMA
2 stops10h 50m
Southwest
Deal found 6/20$312
This United Airlines deal was found by Cheapflights users on 6/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/17:55 am
OMA
-
ORD
Nonstop1h 50m
United Airlines
Fri 8/73:47 pm
ORD
-
OMA
Nonstop1h 41m
United Airlines
Deal found 6/20$312
This Southwest deal was found by Cheapflights users on 6/18. 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.
Tue 7/213:50 pm
OMA
-
MDW
Nonstop1h 25m
Southwest
Fri 7/2411:00 am
MDW
-
OMA
2 stops10h 25m
Southwest
Deal found 6/18$313
This Booking.com deal was found by Cheapflights users on 6/17. 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.
Fri 9/258:41 pm
OMA
-
ORD
1 stop24h 54m
Frontier
Sun 9/2711:06 am
ORD
-
OMA
1 stop8h 40m
Frontier
Deal found 6/17$313
This Southwest deal was found by Cheapflights users on 6/17. 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 8/66:20 pm
OMA
-
MDW
Nonstop1h 25m
Southwest
Mon 8/109:20 am
MDW
-
OMA
2 stops11h 40m
Southwest
Deal found 6/17$314
This Southwest deal was found by Cheapflights users on 6/21. 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 8/66:20 pm
OMA
-
MDW
Nonstop1h 25m
Southwest
Sun 8/97:55 am
MDW
-
OMA
1 stop7h 00m
Southwest
Deal found 6/21$315
This American Airlines deal was found by Cheapflights users on 6/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:05 pm
OMA
-
ORD
1 stop7h 13m
American Airlines
Sun 8/2311:45 am
ORD
-
OMA
Nonstop1h 39m
American Airlines
Deal found 6/21$315
This Southwest deal was found by Cheapflights users on 6/20. 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 8/267:30 am
OMA
-
MDW
2 stops8h 30m
Southwest
Sun 8/301:30 pm
MDW
-
OMA
2 stops9h 25m
Southwest
Deal found 6/20$317
This American Airlines deal was found by Cheapflights users on 6/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:26 pm
OMA
-
ORD
Nonstop2h 12m
American Airlines
Sat 7/1810:29 pm
ORD
-
OMA
Nonstop1h 37m
American Airlines
Deal found 6/18$317
This Southwest deal was found by Cheapflights users on 6/17. 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 7/225:00 am
OMA
-
MDW
1 stop7h 45m
Southwest
Wed 7/224:40 pm
MDW
-
OMA
1 stop6h 00m
Southwest
Deal found 6/17$318
This Delta deal was found by Cheapflights users on 6/18. 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.
Tue 10/276:20 am
OMA
-
ORD
1 stop5h 22m
Delta
Sun 11/86:00 am
ORD
-
OMA
1 stop4h 17m
Delta
Deal found 6/18$318
This Southwest deal was found by Cheapflights users on 6/18. 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 7/83:50 pm
OMA
-
MDW
Nonstop1h 25m
Southwest
Mon 7/136:00 pm
MDW
-
OMA
1 stop5h 05m
Southwest
Deal found 6/18$319

Find flight deals from Omaha to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Omaha (OMA) to Chicago (CHI). 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 June 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$312
(Southwest)

One-way from

$119
(Southwest)

Popular in

May

Cheapest in

August

Average price

$359

Good round-trip deal

$337 or less

Good one-way deal

$179 or less
Provider with most accurate pricing for Omaha Eppley Airfield-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Omaha Eppley Airfield-Chicago (CHI) flights.
Search Deals
From Omaha Eppley Airfield to Chicago (CHI)
Search Deals
One-way flight from Omaha Eppley Airfield to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
Price to beat on a round-trip flight from Omaha Eppley Airfield to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Omaha Eppley Airfield to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Omaha to Chicago 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 June 21, 2026.
Use the filters below to find and compare flights from Omaha to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Sat 8/1

3:35 pm-4:55 pm

Nonstop1h 20m

Chicago Midway

Sat 8/8

10:15 am-11:45 am

Nonstop1h 30m

$318

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Thu 10/29

6:20 am-11:42 am

1 stop5h 22m

Chicago O'Hare Intl

Sat 10/31

3:50 pm-7:44 pm

1 stop3h 54m

$319

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Thu 8/6

6:20 pm-7:45 pm

Nonstop1h 25m

Chicago Midway

Mon 8/10

3:20 pm-10:00 pm

2 stops6h 40m

$320

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Thu 9/3

5:35 am-7:00 am

Nonstop1h 25m

Chicago Midway

Tue 9/8

4:40 pm-10:05 pm

1 stop5h 25m

$326

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Tue 10/27

1:08 pm-2:46 pm

Nonstop1h 38m

Chicago O'Hare Intl

Wed 10/28

7:52 pm-9:29 pm

Nonstop1h 37m

$329

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Wed 7/8

5:40 pm-9:52 pm

1 stop4h 12m

Chicago O'Hare Intl

Thu 7/9

8:27 am-11:57 am

1 stop3h 30m

$329

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Fri 7/24

6:40 pm-8:34 pm

Nonstop1h 54m

Chicago O'Hare Intl

Mon 7/27

6:00 pm-7:49 pm

Nonstop1h 49m

$337

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Fri 7/17

7:55 am-9:45 am

Nonstop1h 50m

Chicago O'Hare Intl

Sun 7/19

8:40 am-10:27 am

Nonstop1h 47m

$337

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Fri 8/28

6:20 pm-7:45 pm

Nonstop1h 25m

Chicago Midway

Sun 8/30

8:40 pm-10:10 pm

Nonstop1h 30m

$337

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Sat 8/1

5:50 pm-9:52 pm

1 stop4h 02m

Chicago O'Hare Intl

Sat 8/8

6:00 pm-10:58 pm

1 stop4h 58m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/20

Showing 1-10 of 58 resultsSorted by cheapest first
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6

Compare providers for flights from Omaha to Chicago

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 Chicago in June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
Trip.comPrice Accuracy1 starTrust 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 flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Omaha-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Omaha-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Omaha-Chicago 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 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 Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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

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

Currently, February is the cheapest month in which you can book a flight from Omaha to Chicago (average of $80). Flying from Omaha to Chicago in June is currently the most expensive (average of $275). 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 CHI?

Find hourly flight availability from Omaha to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 21, 2026.

One of the essential ways to save on airfare from Omaha to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 26% on airfare.

Weekly flight availability from Omaha to Chicago

Explore weekly flight availability from Omaha to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 21, 2026.

The most flights from OMA to CHI are scheduled on a Sunday (48 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (26 on average).

How much does it cost to fly round-trip from Omaha to Chicago?

How often are flights from Omaha to Chicago delayed?

About 12% of weekly flights between Omaha and Chicago have experienced delays in the past year, with the average delay time being 118 minutes.

What is the most punctual flight time for Omaha to Chicago flights?

Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Omaha to Chicago flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 10% of flights being delayed.

How far ahead should I book a flight from Omaha to Chicago?

Booking 70 days in advance of your planned departure date is, on average, the best time to get cheap flights from Omaha to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest day to fly from Omaha to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Omaha to Chicago. Price data was last updated on June 20, 2026.

Travelers seeking maximum savings on their Omaha to Chicago flight should consider departing on Monday evenings when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated June 21, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Omaha to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,242 reviews

Overall

7.9

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

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
7.9
Good
4,242 reviews
Southwest
7.9
Good
4,242 reviews

Overall

7.9

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

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
9,868 reviews
Southwest
7.9
Good
4,242 reviews

Overall

7.9

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,723 reviews
Southwest
7.9
Good
4,242 reviews

Overall

7.9

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

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 Chicago. 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?

    Located just 3.9 mi from the city center, Omaha Eppley Airfield is the airport most travelers will use when flying to Chicago from Omaha. Booking flights from Eppley Airfield (OMA) to Chicago should be relatively easy as there are 38 daily outbound flights to Chicago from 3 different airlines.

  • How long is the flight from Omaha to Chicago?

    Airlines like Southwest, Delta, and United Airlines fly from Omaha to Chicago in about 1h 20m. The time it takes to get you to your destination can typically vary by up to 4h 02m. Omaha and Chicago are separated by a distance of 422 mi. This flight may include one or multiple stops.

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

    According to our current data, American Airlines ($137), United Airlines ($203), and Southwest ($227) offers the cheapest pricing from Omaha to Chicago. American Airlines is currently priced 56% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Omaha to Chicago one-way?

    $88 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Southwest and United Airlines, with prices starting from $99 and $114, respectively.

  • What are the most popular routes from Omaha to Chicago?

    While some choose either Omaha Eppley Airfield - Chicago Midway or Omaha Eppley Airfield - Chicago Greater Rockford, Omaha Eppley Airfield - Chicago O'Hare Intl is the most popular route from Omaha to Chicago.

  • What are the most reliable airlines from Omaha to Chicago?

    Consider Republic Airways (92%), Japan Airlines (89%) or ANA (85%) when booking your flight. These represent the most reliable airlines when flying from Omaha to Chicago.

  • What are the cheapest flights from Omaha to Chicago?

    Looking at all options, your cheapest flight can be booked for $167. While the most popular route (Omaha Eppley Airfield - Chicago O'Hare Intl) can be booked for $255 on average, our data indicates $729 when flying from Omaha to Chicago.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Omaha to Chicago 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?

    Currently, February is the cheapest month in which you can book a flight from Omaha to Chicago (average of $80). Flying from Omaha to Chicago in June is currently the most expensive (average of $275). 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?

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

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Top 3 airlines flying from Omaha to Chicago

Discover the top 3 airlines that operate flights from Omaha to Chicago. 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 June 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$137Average$300FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$203Average$361FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$227Average$317FlexibilityNo cancel feeOn-time63%

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