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$55+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
OMA — CHI
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
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Cheapflights Tip: The best prices from Omaha Eppley Airfield to Chicago are usually found in August or January, booked 42 days in advance, depart on a Thursday or Friday and return on a Thursday

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 November 4, 2025.

This Priceline deal was found by Cheapflights users on 11/3. 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 12/52:24 pmOMA - ORD
1 stop9h 48mFrontier
Mon 12/86:11 amORD - OMA
1 stop9h 17mFrontier
Deal found 11/3$210
This Booking.com deal was found by Cheapflights users on 11/2. 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 12/42:24 pmOMA - MDW
1 stop20h 44mFrontier
Mon 12/86:15 amMDW - OMA
1 stop9h 13mFrontier
Deal found 11/2$212
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/42:24 pmOMA - ORD
2 stops19h 52mFrontier
Sun 12/77:00 amORD - OMA
1 stop6h 31mFrontier
Deal found 11/3$213
This Southwest deal was found by Cheapflights users on 11/4. 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 12/96:25 amOMA - MDW
1 stop6h 35mSouthwest
Sat 12/138:20 amMDW - OMA
Nonstop1h 35mSouthwest
Deal found 11/4$223
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/122:24 pmOMA - ORD
1 stop9h 48mFrontier
Sun 12/147:00 amORD - OMA
1 stop6h 31mFrontier
Deal found 11/3$226
This Delta deal was found by Cheapflights users on 11/3. 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 12/1712:24 pmOMA - MDW
1 stop5h 54mDelta
Tue 1/67:16 pmMDW - OMA
1 stop3h 38mDelta
Deal found 11/3$233
This Delta deal was found by Cheapflights users on 11/3. 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 12/179:00 amOMA - ORD
1 stop5h 59mDelta
Tue 1/66:46 pmORD - OMA
1 stop4h 08mDelta
Deal found 11/3$233
This American Airlines deal was found by Cheapflights users on 11/3. 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.
Mon 11/249:17 amOMA - ORD
Nonstop1h 50mAmerican Airlines
Tue 12/210:13 pmORD - OMA
Nonstop1h 46mAmerican Airlines
Deal found 11/3$237
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/112:24 pmOMA - ORD
1 stop9h 48mFrontier
Mon 12/227:38 pmORD - OMA
2 stops24h 09mFrontier
Deal found 11/2$238
This American Airlines deal was found by Cheapflights users on 11/3. 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.
Tue 12/237:18 pmOMA - ORD
Nonstop1h 56mAmerican Airlines
Thu 12/2512:00 pmORD - OMA
Nonstop1h 48mAmerican Airlines
Deal found 11/3$240
This United Airlines deal was found by Cheapflights users on 11/3. 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 12/33:25 pmOMA - ORD
Nonstop1h 40mUnited Airlines
Thu 12/412:45 pmORD - OMA
Nonstop1h 35mUnited Airlines
Deal found 11/3$243
This Delta deal was found by Cheapflights users on 11/3. 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 12/179:00 amOMA - MDW
1 stop4h 10mDelta
Wed 12/3111:48 amMDW - OMA
1 stop5h 14mDelta
Deal found 11/3$245

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 November 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$210
(Priceline)

One-way from

$55
(Priceline)

Popular in

October

Cheapest in

August

Average price

$287

Good round-trip deal

$319 or less

Good one-way deal

$183 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.
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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. 3% potential increase in price ($11 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 November 2025
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 November 4, 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 - MDW

OMAMDW

Omaha Eppley Airfield

Tue 12/9

6:00 am-1:05 pm

2 stops7h 05m

Chicago Midway

Sat 12/13

12:30 pm-2:00 pm

Nonstop1h 30m

$228

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Wed 12/17

12:24 pm-6:18 pm

1 stop5h 54m

Chicago Midway

Tue 1/6

7:16 pm-10:54 pm

1 stop3h 38m

$233

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Wed 12/17

9:00 am-2:59 pm

1 stop5h 59m

Chicago O'Hare Intl

Tue 1/6

6:46 pm-10:54 pm

1 stop4h 08m

$233

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Wed 12/3

11:28 am-1:10 pm

Nonstop1h 42m

Chicago O'Hare Intl

Thu 12/4

8:05 pm-9:47 pm

Nonstop1h 42m

$243

OmahaChicago

OMA - RFD

OMARFD

Omaha Eppley Airfield

Fri 12/5

7:34 pm-12:48 pm

1 stop17h 14m

Chicago Greater Rockford

Mon 12/8

10:38 am-6:44 pm

1 stop8h 06m

$245

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Wed 12/17

9:00 am-1:10 pm

1 stop4h 10m

Chicago Midway

Thu 1/1

11:48 am-5:02 pm

1 stop5h 14m

$245

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Mon 11/24

3:38 pm-11:47 pm

1 stop8h 09m

Chicago O'Hare Intl

Tue 12/2

11:56 am-1:37 pm

Nonstop1h 41m

$247

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Wed 12/10

4:10 pm-10:35 pm

2 stops6h 25m

Chicago Midway

Fri 12/12

9:35 pm-11:05 pm

Nonstop1h 30m

$266

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Wed 1/7

10:55 am-12:20 pm

Nonstop1h 25m

Chicago Midway

Tue 1/13

12:10 pm-6:10 pm

1 stop6h 00m

$267

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Mon 11/24

6:19 am-12:34 pm

1 stop6h 15m

Chicago Midway

Tue 12/2

7:02 pm-11:04 pm

1 stop4h 02m

$267

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 60 results
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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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Omaha-Chicago flight deals on Cheapflights vs. eDreams >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 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 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

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 October 31, 2025.

Booking 42 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, November is the cheapest month in which you can book a flight from Omaha to Chicago (average of $98). Flying from Omaha to Chicago in June is currently the most expensive (average of $251). 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 November 4, 2025.

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 23% 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 November 2, 2025.

Travelers seeking maximum savings on their Omaha to Chicago flight should consider departing on Sunday 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.

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 November 4, 2025.

The most flights from OMA to CHI are scheduled on a Monday (41 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (14 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 November 4, 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
4,237 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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
8,998 reviews
Southwest
8.0
Very good
4,237 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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
11,038 reviews
Southwest
8.0
Very good
4,237 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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
Frontier
5.8
Fair
3,116 reviews
Southwest
8.0
Very good
4,237 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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 29 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 42m. The time it takes to get you to your destination can typically vary by up to 5h 23m. Omaha and Chicago are separated by a distance of 415 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 ($129), United Airlines ($199), and Southwest ($207) offers the cheapest pricing from Omaha to Chicago. American Airlines is currently priced 55% below the average price you’ll pay for this route.

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

    $55 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Southwest and United Airlines, with prices starting from $107 and $107, 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 (100%), ANA (95%) or United Airlines (86%) 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 $158. While the most popular route (Omaha Eppley Airfield - Chicago O'Hare Intl) can be booked for $172 on average, our data indicates $1,620 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, November is the cheapest month in which you can book a flight from Omaha to Chicago (average of $98). Flying from Omaha to Chicago in June is currently the most expensive (average of $251). 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
Porter
Benton Harbor

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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 November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$129Average$287FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$199Average$327FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$207Average$291FlexibilityNo cancel feeOn-time63%

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