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$134+ Cheap flights from O'Hare Intl (ORD) to Madison (MSN)

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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MSN
Feb 6 — Feb 131
Fri 2/6
Fri 2/13
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Madison

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Madison (MSN). 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 January 7, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$179
(American Airlines)

One-way from

$134
(American Airlines)

Popular in

April

Cheapest in

December

Good one-way deal

$294 or less
Provider with most accurate pricing for Chicago O'Hare Intl-Madison Truax Field flight deals.
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Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Madison Truax Field flights.
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From Chicago O'Hare Intl to Madison Truax Field
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One-way flight from Chicago O'Hare Intl to Madison Truax Field
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Highest demand for flights based on searches. 35% potential increase in price ($210 potential increase over avg. RT price).
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Cheapest flight prices on average. 12% potential price decrease ($43 potential savings vs. average RT price).
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Price to beat on a one-way flight from Chicago O'Hare Intl to Madison Truax Field.
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Find flight deals from O'Hare Intl to Madison

Cheapest flights from O'Hare Intl to Madison
Explore the most affordable flight options available from O'Hare Intl to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 7, 2026.

This American Airlines deal was found by Cheapflights users on 1/7. 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 1/299:45 amORD - MSN
Nonstop1h 10mAmerican Airlines
Sun 2/11:16 pmMSN - ORD
Nonstop1h 13mAmerican Airlines
Deal found 1/7$179
This American Airlines deal was found by Cheapflights users on 1/6. 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 1/213:49 pmORD - MSN
Nonstop1h 03mAmerican Airlines
Sun 1/257:30 amMSN - ORD
Nonstop1h 19mAmerican Airlines
Deal found 1/6$209
This American Airlines deal was found by Cheapflights users on 1/7. 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 1/159:45 amORD - MSN
Nonstop1h 10mAmerican Airlines
Sun 1/1811:25 amMSN - ORD
Nonstop1h 19mAmerican Airlines
Deal found 1/7$239
This United Airlines deal was found by Cheapflights users on 1/5. 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.
Tue 1/204:50 pmORD - MSN
Nonstop0h 57mUnited Airlines
Sat 1/2412:32 pmMSN - ORD
Nonstop1h 21mUnited Airlines
Deal found 1/5$269
This United Airlines deal was found by Cheapflights users on 1/5. 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.
Sat 1/106:10 pmORD - MSN
Nonstop0h 57mUnited Airlines
Mon 1/122:56 pmMSN - ORD
Nonstop1h 21mUnited Airlines
Deal found 1/5$270
This American Airlines deal was found by Cheapflights users on 1/6. 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 1/179:45 amORD - MSN
Nonstop1h 10mAmerican Airlines
Wed 1/215:22 pmMSN - ORD
Nonstop1h 22mAmerican Airlines
Deal found 1/6$320
This United Airlines deal was found by Cheapflights users on 1/6. 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 1/96:10 pmORD - MSN
Nonstop0h 57mUnited Airlines
Sun 1/1112:32 pmMSN - ORD
Nonstop1h 21mUnited Airlines
Deal found 1/6$339
This United Airlines deal was found by Cheapflights users on 1/6. 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.
Tue 2/33:35 pmORD - MSN
Nonstop1h 09mUnited Airlines
Tue 2/108:15 amMSN - ORD
1 stop11h 36mUnited Airlines
Deal found 1/6$360

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Madison 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 January 7, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Madison that are best for you.

Fly from

O'Hare Intl

Fly to

Madison

Route

Depart

Return

Price

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Wed 5/6

10:31 pm-11:37 pm

Nonstop1h 06m

Madison Truax Field

Sun 5/10

8:25 pm-9:40 pm

Nonstop1h 15m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 2/20

7:50 pm-8:56 pm

Nonstop1h 06m

Madison Truax Field

Fri 2/27

9:41 am-10:52 am

Nonstop1h 11m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 5/15

8:28 am-9:35 am

Nonstop1h 07m

Madison Truax Field

Mon 8/17

8:26 pm-9:30 pm

Nonstop1h 04m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 2/6

9:45 am-10:55 am

Nonstop1h 10m

Madison Truax Field

Fri 2/13

5:00 am-6:08 am

Nonstop1h 08m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 1/29

9:45 am-10:55 am

Nonstop1h 10m

Madison Truax Field

Sun 2/1

1:16 pm-2:29 pm

Nonstop1h 13m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 1/22

3:49 pm-4:52 pm

Nonstop1h 03m

Madison Truax Field

Mon 1/26

7:20 am-8:39 am

Nonstop1h 19m

$209

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Tue 1/20

4:50 pm-5:47 pm

Nonstop0h 57m

Madison Truax Field

Sat 1/24

12:32 pm-1:53 pm

Nonstop1h 21m

$269

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sun 3/8

6:10 pm-7:11 pm

2 stops25h 01m

$164

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 1/22

8:43 pm-9:08 am

2 stops36h 25m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Wed 3/4

8:30 am-5:56 pm

1 stop9h 26m

$180

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 18 results
1
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Compare providers for flights from O'Hare Intl to Madison

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 O'Hare Intl to Madison in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 Chicago O'Hare Intl Airport-Madison flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago O'Hare Intl Airport-Madison flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Madison flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Madison 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 Chicago O'Hare Intl Airport-Madison 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 O'Hare Intl to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from O'Hare Intl 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 Chicago O'Hare Intl Airport to Madison

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Madison?

Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Madison (average of $178). Flying from Chicago O'Hare Intl Airport to Madison in March is currently the most expensive (average of $384). 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 ORD to MSN?

Find hourly flight availability from O'Hare Intl to Madison. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 7, 2026.

It’s optimal to fly from Chicago O'Hare Intl Airport to Madison in the afternoon. By choosing this option you can save up to 10% on the cost of your flight, compared to a flight in the evening.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Madison?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Madison. Price data was last updated on January 3, 2026.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Madison flight should consider departing on Thursday at noon when fares are most often at their lowest. Wednesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Madison

Get insights into the airlines that provide service to Madison. 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 Madison. Reviews last updated January 7, 2026.
Peruse reviews from past customers who have flown with United Airlines from Chicago O'Hare Intl Airport to Madison to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,138 reviews

Boarding

7.7

Entertainment

7.1

Food

6.6

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.
United Airlines
7.4
Good
9,138 reviews
United Airlines
7.4
Good
9,138 reviews

Boarding

7.7

Entertainment

7.1

Food

6.6

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Madison. 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 into for flights to Madison from Chicago O'Hare Intl?

    If you book a flight to Madison from Chicago O'Hare Intl, you will be flying to Truax Field, which is the city’s only airport. Madison Truax Field (MSN) is located 5.4 mi from the center of Madison. There are 30 flights from Chicago O'Hare Intl to Truax Field per day from 1 airline.

  • How long is the flight from Chicago O'Hare Intl Airport to Madison?

    For as low as $179, American Airlines can have you in Madison from Chicago O'Hare Intl Airport in 1h 06m. The distance from Chicago O'Hare Intl Airport to Madison is about 108 mi. All flights are typically nonstop.

  • What is the cheapest airline to fly from Chicago O'Hare Intl Airport to Madison round-trip?

    According to our current data, United Airlines ($199), offers the cheapest pricing from Chicago O'Hare Intl Airport to Madison.

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Madison?

    No one likes to see their flight delayed. When booking a flight from Chicago O'Hare Intl Airport to Madison consider choosing Envoy Air (73%), United Airlines (64%) or Air Canada (63%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Madison?

    The cheapest flight price from Chicago O'Hare Intl Airport to Madison is $203. On average you can expect to pay $314. The most popular route, (Chicago O'Hare Intl - Madison Truax Field), can usually be booked for $179.

  • Can I find deals for flights from O'Hare Intl to Madison that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Madison flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Madison?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Madison.

  • Can I find deals for business class flights from O'Hare Intl to Madison?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Madison 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 Chicago O'Hare Intl Airport to Madison?

    Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Madison (average of $178). Flying from Chicago O'Hare Intl Airport to Madison in March is currently the most expensive (average of $384). 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 Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

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Top airline flying from O'Hare Intl to Madison

Discover the top airline that operate flights from O'Hare Intl to Madison. 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 January 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$199Average$288FlexibilityNo cancel feeOn-time69%

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