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$51+ 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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
OMA — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Omaha Eppley Airfield to Chicago are usually found in August or November, booked 90 days in advance, depart on a Thursday or Friday and return on a Thursday

Cheap 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 September 11, 2025.

Round-trip from

$189
(Kiwi.com)

One-way from

$51
(Southwest)

Popular in

March

Cheapest in

August

Average price

$285

Good round-trip deal

$286 or less

Good one-way deal

$154 or less
From Omaha Eppley Airfield to Chicago (CHI)
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One-way flight from Omaha Eppley Airfield to Chicago (CHI)
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Highest demand for flights based on searches. 6% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Omaha Eppley Airfield to Chicago (CHI).
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Price to beat on a one-way flight from Omaha Eppley Airfield to Chicago (CHI).
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Find 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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/137:46 pmOMA - MDW
2 stops21h 29mFrontier
Sun 11/1612:30 pmMDW - OMA
1 stop6h 21mFrontier
Deal found 9/10$189
This United Airlines deal was found by Cheapflights users on 9/11. 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.
Thu 10/91:04 pmOMA - ORD
Nonstop1h 51mUnited Airlines
Thu 10/168:52 amORD - OMA
Nonstop1h 39mUnited Airlines
Deal found 9/11$189
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Fri 10/176:33 pmOMA - ORD
Nonstop1h 47mUnited Airlines
Sun 10/198:52 amORD - OMA
Nonstop1h 39mUnited Airlines
Deal found 9/10$190
This Southwest deal was found by Cheapflights users on 9/10. 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 10/251:25 pmOMA - MDW
1 stop5h 40mSouthwest
Sat 11/18:20 amMDW - OMA
2 stops8h 00mSouthwest
Deal found 9/10$191
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/167:35 pmOMA - ORD
Nonstop1h 44mAmerican Airlines
Mon 10/207:08 amORD - OMA
Nonstop1h 43mAmerican Airlines
Deal found 9/10$191
This Gotogate deal was found by Cheapflights users on 9/10. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/307:46 pmOMA - MDW
1 stop15h 44mFrontier
Mon 11/312:30 pmMDW - OMA
1 stop7h 36mFrontier
Deal found 9/10$192
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Thu 10/236:33 pmOMA - ORD
Nonstop1h 47mUnited Airlines
Sun 10/263:50 pmORD - OMA
Nonstop1h 35mUnited Airlines
Deal found 9/10$193
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Sat 10/117:22 pmOMA - ORD
Nonstop1h 45mAmerican Airlines
Sun 10/197:08 amORD - OMA
Nonstop1h 43mAmerican Airlines
Deal found 9/11$194
This Southwest deal was found by Cheapflights users on 9/11. 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 11/83:05 pmOMA - MDW
Nonstop1h 25mSouthwest
Sun 11/98:00 amMDW - OMA
Nonstop1h 35mSouthwest
Deal found 9/11$195
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/248:59 pmOMA - ORD
1 stop26h 54mMultiple Airlines
Fri 10/314:44 pmORD - OMA
2 stops51h 07mMultiple Airlines
Deal found 9/9$195
This Southwest deal was found by Cheapflights users on 9/11. 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 10/111:20 amOMA - MDW
1 stop8h 10mSouthwest
Sat 10/41:00 pmMDW - OMA
Nonstop1h 30mSouthwest
Deal found 9/11$196
This Southwest deal was found by Cheapflights users on 9/10. 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 9/303:40 pmOMA - ORD
1 stop7h 25mSouthwest
Wed 10/13:10 pmORD - OMA
2 stops6h 50mSouthwest
Deal found 9/10$198

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 September 11, 2025.
Use the filters below to find and compare flights from Omaha to Chicago that are best for you.

Fly from

Omaha

Fly to

Chicago

Route

Depart

Return

Price

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Thu 10/9

1:04 pm-2:55 pm

Nonstop1h 51m

Chicago O'Hare Intl

Thu 10/16

8:52 am-10:31 am

Nonstop1h 39m

$189

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Fri 10/17

6:33 pm-8:20 pm

Nonstop1h 47m

Chicago O'Hare Intl

Sun 10/19

8:52 am-10:31 am

Nonstop1h 39m

$190

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Thu 10/23

3:17 pm-5:04 pm

Nonstop1h 47m

Chicago O'Hare Intl

Mon 10/27

3:50 pm-5:25 pm

Nonstop1h 35m

$193

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Wed 10/1

10:45 am-12:10 pm

Nonstop1h 25m

Chicago Midway

Fri 10/3

9:45 pm-11:15 pm

Nonstop1h 30m

$196

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Wed 10/1

11:20 am-7:30 pm

1 stop8h 10m

Chicago Midway

Sat 10/4

1:00 pm-2:30 pm

Nonstop1h 30m

$196

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Fri 11/14

1:20 pm-6:55 pm

1 stop5h 35m

Chicago Midway

Sun 11/16

8:00 am-9:35 am

Nonstop1h 35m

$200

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Fri 11/7

4:50 pm-9:15 pm

1 stop4h 25m

Chicago Midway

Sun 11/9

8:00 am-9:35 am

Nonstop1h 35m

$200

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Tue 10/7

4:30 pm-10:25 pm

2 stops5h 55m

Chicago Midway

Wed 10/8

7:55 am-2:55 pm

2 stops7h 00m

$204

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Thu 11/20

3:40 pm-5:10 pm

Nonstop1h 30m

Chicago Midway

Mon 11/24

7:00 pm-11:50 pm

1 stop4h 50m

$205

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Wed 11/19

8:00 am-9:45 am

Nonstop1h 45m

Chicago O'Hare Intl

Thu 11/20

8:50 am-10:31 am

Nonstop1h 41m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 48 results
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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

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

Use this chart to determine the optimal time to book a round-trip flight from Omaha to Chicago. Price data was last updated on August 29, 2025.

Booking 89 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 month to book a flight from Omaha to Chicago?

Currently, August is the cheapest month in which you can book a flight from Omaha to Chicago (average of $245). Flying from Omaha to Chicago in March is currently the most expensive (average of $321). 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 September 11, 2025.

One of the essential ways to save on airfare from Omaha to Chicago is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the morning could potentially save you up to 41% on airfare.

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 September 7, 2025.

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

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 September 11, 2025.

The most flights from OMA to CHI are scheduled on a Thursday (44 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (31 on average).

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

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 September 11, 2025.
See what other customers who have flown with Southwest, United Airlines, and American 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
8.0
Very good
4,248 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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 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 United Airlines, Southwest, and American Airlines fly from Omaha to Chicago in about 1h 25m. The time it takes to get you to your destination is usually consistent. Omaha and Chicago are separated by a distance of 422 mi. All flights are typically nonstop.

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

    According to our current data, American Airlines ($129), United Airlines ($191), and Southwest ($192) offers the cheapest pricing from Omaha to Chicago. American Airlines is currently priced 54% below the average price you’ll pay for this route.

  • 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 ANA (87%), Royal Jordanian (83%) or Japan Airlines (80%) 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 $108. While the most popular route (Omaha Eppley Airfield - Chicago O'Hare Intl) can be booked for $101 on average, our data indicates $910 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, August is the cheapest month in which you can book a flight from Omaha to Chicago (average of $245). Flying from Omaha to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$129Average$279FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$191Average$322FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$192Average$279FlexibilityNo cancel feeOn-time63%

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