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Madison

$85+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MSN
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$179
(American Airlines)

One-way from

$118
(Frontier)

Popular in

April

Cheapest in

September

Average price

$276

Good one-way deal

$309 or less
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. 40% potential increase in price ($238 potential increase over avg. RT price).
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Cheapest flight prices on average. 12% potential price decrease ($41 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 August 14, 2025.

This United Airlines deal was found by Cheapflights users on 8/12. 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 9/98:45 amORD - MSN
Nonstop1h 03mUnited Airlines
Tue 9/1610:50 amMSN - ORD
Nonstop1h 07mUnited Airlines
Deal found 8/12$179
This American Airlines deal was found by Cheapflights users on 8/13. 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 10/259:29 amORD - MSN
Nonstop1h 15mAmerican Airlines
Wed 10/296:00 amMSN - ORD
Nonstop1h 05mAmerican Airlines
Deal found 8/13$180
This American Airlines deal was found by Cheapflights users on 8/12. 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 8/278:17 amORD - MSN
Nonstop1h 01mAmerican Airlines
Sun 8/313:55 pmMSN - ORD
Nonstop1h 07mAmerican Airlines
Deal found 8/12$189
This United Airlines deal was found by Cheapflights users on 8/13. 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 11/712:55 pmORD - MSN
Nonstop0h 56mUnited Airlines
Sun 11/98:25 amMSN - ORD
Nonstop1h 11mUnited Airlines
Deal found 8/13$192
This American Airlines deal was found by Cheapflights users on 8/14. 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 8/212:20 pmORD - MSN
Nonstop1h 04mAmerican Airlines
Sun 8/248:14 pmMSN - ORD
Nonstop1h 05mAmerican Airlines
Deal found 8/14$209
This American Airlines deal was found by Cheapflights users on 8/13. 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 8/238:17 amORD - MSN
Nonstop1h 01mAmerican Airlines
Sun 9/146:40 pmMSN - ORD
Nonstop1h 09mAmerican Airlines
Deal found 8/13$224
This American Airlines deal was found by Cheapflights users on 8/11. 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.
Wed 8/2011:50 amORD - MSN
Nonstop1h 01mAmerican Airlines
Wed 8/276:44 pmMSN - ORD
Nonstop1h 05mAmerican Airlines
Deal found 8/11$239
This United Airlines deal was found by Cheapflights users on 8/13. 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 8/209:06 amORD - MSN
Nonstop1h 09mUnited Airlines
Wed 8/276:30 amMSN - ORD
Nonstop1h 07mUnited Airlines
Deal found 8/13$259
This Trip.com deal was found by Cheapflights users on 8/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/199:06 amORD - MSN
Nonstop1h 09mUnited Airlines
Tue 8/266:30 amMSN - ORD
Nonstop1h 07mUnited Airlines
Deal found 8/12$263
This United Airlines deal was found by Cheapflights users on 8/14. 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 8/299:20 pmORD - MSN
Nonstop1h 03mUnited Airlines
Tue 9/23:58 pmMSN - ORD
Nonstop1h 07mUnited Airlines
Deal found 8/14$289
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Fri 8/1512:00 pmORD - MSN
Nonstop0h 59mAmerican Airlines
Sat 8/168:14 pmMSN - ORD
Nonstop1h 05mAmerican Airlines
Deal found 8/13$290

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 August 14, 2025.
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

Tue 9/9

8:45 am-9:48 am

Nonstop1h 03m

Madison Truax Field

Tue 9/16

10:50 am-11:57 am

Nonstop1h 07m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sun 9/14

8:47 am-9:59 am

Nonstop1h 12m

Madison Truax Field

Wed 9/24

8:00 am-9:09 am

Nonstop1h 09m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Wed 9/3

6:44 pm-7:56 pm

Nonstop1h 12m

Madison Truax Field

Wed 9/10

5:00 am-6:00 am

Nonstop1h 00m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 9/11

12:45 pm-1:49 pm

Nonstop1h 04m

Madison Truax Field

Sun 9/14

8:15 am-9:22 am

Nonstop1h 07m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Tue 9/9

5:05 pm-6:11 pm

Nonstop1h 06m

Madison Truax Field

Tue 9/16

6:41 pm-7:52 pm

Nonstop1h 11m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sat 10/18

10:23 am-11:25 am

Nonstop1h 02m

Madison Truax Field

Mon 10/20

8:25 pm-9:30 pm

Nonstop1h 05m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 9/11

8:47 am-9:59 am

Nonstop1h 12m

Madison Truax Field

Sun 9/14

6:40 pm-7:49 pm

Nonstop1h 09m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Wed 9/10

8:38 am-9:43 am

Nonstop1h 05m

Madison Truax Field

Wed 9/17

5:00 am-6:00 am

Nonstop1h 00m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sat 9/27

7:59 am-9:05 am

Nonstop1h 06m

Madison Truax Field

Sat 10/4

5:00 am-6:00 am

Nonstop1h 00m

$180

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sat 10/25

9:29 am-10:44 am

Nonstop1h 15m

Madison Truax Field

Wed 10/29

8:25 am-9:30 am

Nonstop1h 05m

$180

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 20 results
1
2

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, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Madison (average of $338). Flying from Chicago O'Hare Intl Airport to Madison in March is currently the most expensive (average of $422). 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 August 14, 2025.

It’s optimal to fly from Chicago O'Hare Intl Airport to Madison at noon. By choosing this option you can save up to 28% on the cost of your flight, compared to a flight in the morning.

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 August 10, 2025.

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

Weekly flight availability from Chicago O'Hare Intl Airport to Madison

Explore weekly flight availability from O'Hare Intl to Madison. 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 August 14, 2025.

The most flights from ORD to MSN are scheduled on a Thursday (44 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 on average).

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 August 14, 2025.
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
8,916 reviews

Crew

8.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,916 reviews
United Airlines
7.4
Good
8,916 reviews

Crew

8.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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 28 flights from Chicago O'Hare Intl to Truax Field per day from 1 airline.

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

    According to our current data, United Airlines ($179), 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 Republic Airways (86%), GoJet (83%) or Copa Airlines (76%) 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 $247. On average you can expect to pay $309. 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, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Madison (average of $338). Flying from Chicago O'Hare Intl Airport to Madison in March is currently the most expensive (average of $422). 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$275FlexibilityNo cancel feeOn-time69%

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