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O'Hare Intl

$113+ Cheap flights from Madison (MSN) to O'Hare Intl (ORD)

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 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — ORD
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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Cheap flight deals from Madison to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to O'Hare Intl (ORD). 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 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$179
(American Airlines)

One-way from

$113
(Kiwi.com)

Popular in

September

Cheapest in

June

Average price

$334

Good round-trip deal

$296 or less

Good one-way deal

$221 or less
Provider with most accurate pricing for Madison Truax Field-Chicago O'Hare Intl flight deals.
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Provider most trusted by Cheapflights users for Madison Truax Field-Chicago O'Hare Intl flights.
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From Madison Truax Field to Chicago O'Hare Intl
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One-way flight from Madison Truax Field to Chicago O'Hare Intl
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Highest demand for flights based on searches. 7% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Madison Truax Field to Chicago O'Hare Intl.
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Price to beat on a one-way flight from Madison Truax Field to Chicago O'Hare Intl.
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Find flight deals from Madison to O'Hare Intl

Cheapest flights from Madison to O'Hare Intl
Explore the most affordable flight options available from Madison to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 2, 2025.

This American Airlines deal was found by Cheapflights users on 10/31. 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 12/24:32 pmMSN - ORD
Nonstop1h 17mAmerican Airlines
Tue 12/93:02 pmORD - MSN
Nonstop1h 07mAmerican Airlines
Deal found 10/31$179
This American Airlines deal was found by Cheapflights users on 11/1. 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 11/227:00 amMSN - ORD
Nonstop1h 16mAmerican Airlines
Sun 11/238:22 amORD - MSN
Nonstop1h 02mAmerican Airlines
Deal found 11/1$180
This United Airlines deal was found by Cheapflights users on 11/1. 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 11/266:30 amMSN - ORD
Nonstop1h 11mUnited Airlines
Thu 11/271:55 pmORD - MSN
Nonstop0h 59mUnited Airlines
Deal found 11/1$217
This American Airlines deal was found by Cheapflights users on 11/1. 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 12/198:10 pmMSN - ORD
Nonstop1h 20mAmerican Airlines
Mon 12/228:00 amORD - MSN
Nonstop1h 18mAmerican Airlines
Deal found 11/1$231
This United Airlines deal was found by Cheapflights users on 10/31. 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 11/85:38 pmMSN - ORD
Nonstop1h 09mUnited Airlines
Sun 11/98:51 amORD - MSN
Nonstop1h 09mUnited Airlines
Deal found 10/31$239
This United Airlines deal was found by Cheapflights users on 10/30. 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 11/143:58 pmMSN - ORD
Nonstop1h 11mUnited Airlines
Mon 11/1710:35 amORD - MSN
Nonstop1h 08mUnited Airlines
Deal found 10/30$269
This United Airlines deal was found by Cheapflights users on 10/31. 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 11/512:26 pmMSN - ORD
Nonstop1h 15mUnited Airlines
Sat 11/81:55 pmORD - MSN
Nonstop0h 59mUnited Airlines
Deal found 10/31$270
This American Airlines deal was found by Cheapflights users on 10/30. 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 11/121:53 pmMSN - ORD
Nonstop1h 13mAmerican Airlines
Mon 11/1711:40 amORD - MSN
Nonstop1h 04mAmerican Airlines
Deal found 10/30$284
This United Airlines deal was found by Cheapflights users on 11/1. 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 11/72:48 pmMSN - ORD
Nonstop1h 11mUnited Airlines
Mon 11/104:50 pmORD - MSN
Nonstop1h 00mUnited Airlines
Deal found 11/1$289
This American Airlines deal was found by Cheapflights users on 10/30. 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 11/123:37 pmMSN - ORD
1 stop8h 00mAmerican Airlines
Tue 11/188:14 amORD - MSN
Nonstop1h 03mAmerican Airlines
Deal found 10/30$294
This United Airlines deal was found by Cheapflights users on 10/30. 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 11/76:30 amMSN - ORD
Nonstop1h 11mUnited Airlines
Sat 11/86:35 pmORD - MSN
Nonstop1h 06mUnited Airlines
Deal found 10/30$299

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to O'Hare Intl 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 2, 2025.
Use the filters below to find and compare flights from Madison to Chicago O'Hare Intl Airport that are best for you.

Fly from

Madison

Fly to

O'Hare Intl

Route

Depart

Return

Price

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sun 11/30

9:30 pm-10:41 pm

Nonstop1h 11m

Chicago O'Hare Intl

Sun 12/7

1:55 pm-2:54 pm

Nonstop0h 59m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 12/17

5:00 am-6:09 am

Nonstop1h 09m

Chicago O'Hare Intl

Wed 12/24

4:39 pm-5:42 pm

Nonstop1h 03m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 1/7

11:29 am-12:40 pm

Nonstop1h 11m

Chicago O'Hare Intl

Wed 1/14

3:49 pm-4:52 pm

Nonstop1h 03m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 11/28

12:18 pm-1:30 pm

Nonstop1h 12m

Chicago O'Hare Intl

Mon 12/1

6:15 pm-7:21 pm

Nonstop1h 06m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 11/22

7:00 am-8:16 am

Nonstop1h 16m

Chicago O'Hare Intl

Sun 11/23

8:22 am-9:24 am

Nonstop1h 02m

$180

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 11/26

6:30 am-7:41 am

Nonstop1h 11m

Chicago O'Hare Intl

Thu 11/27

1:55 pm-2:54 pm

Nonstop0h 59m

$217

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 12/19

10:45 am-12:05 pm

Nonstop1h 20m

Chicago O'Hare Intl

Mon 12/22

3:35 pm-4:45 pm

Nonstop1h 10m

$269

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 11/14

3:58 pm-5:09 pm

Nonstop1h 11m

Chicago O'Hare Intl

Mon 11/17

10:35 am-11:43 am

Nonstop1h 08m

$269

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 11/15

8:25 am-9:36 am

Nonstop1h 11m

Chicago O'Hare Intl

Wed 11/19

7:35 pm-8:35 pm

Nonstop1h 00m

$269

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sun 11/30

9:55 am-11:09 am

Nonstop1h 14m

Chicago O'Hare Intl

Sun 12/7

12:04 pm-1:09 pm

Nonstop1h 05m

$279

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 22 results
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Compare providers for flights from Madison to O'Hare Intl

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

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

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

Currently, February is the cheapest month in which you can book a flight from Madison to Chicago O'Hare Intl Airport (average of $94). Flying from Madison to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $179). 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 MSN to ORD?

Find hourly flight availability from Madison to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 2, 2025.

It’s typically best to fly out from Madison to Chicago O'Hare Intl Airport in the evening. Doing so could potentially save you 12% on the flight price compared to flying in the afternoon, which is usually more expensive.

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

Use this chart to determine the cheapest time to fly round-trip from Madison to O'Hare Intl. Price data was last updated on October 26, 2025.

Travelers seeking maximum savings on their Madison to Chicago O'Hare Intl Airport flight should consider departing on Thursday 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 O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated November 2, 2025.
Get a feel of what it's like to fly with United Airlines and American Airlines from Madison to Chicago O'Hare Intl Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,997 reviews

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
8,997 reviews
United Airlines
7.4
Good
8,997 reviews

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,034 reviews
United Airlines
7.4
Good
8,997 reviews

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

Related info for your journey

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

    If you book a flight to Chicago O'Hare Intl from Madison, you will be flying from 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 21 flights from Truax Field to Chicago O'Hare Intl per day from 2 different airlines.

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

    A quick flight from Madison to Chicago O'Hare Intl Airport can take about 1h 09m. United Airlines provides one of the quickest options available for as low as $179. Airlines will cover a distance of 108 mi. All flights are typically nonstop.

  • What are the cheapest airlines flying from Madison to Chicago O'Hare Intl Airport round-trip?

    Currently priced at $179, American Airlines will fly you from Madison to Chicago O'Hare Intl Airport and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on United Airlines for as low as $219. You may be able to fly from Madison to Chicago O'Hare Intl Airport for 38% less than the average price by searching for these airlines.

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

    No one likes to see their flight delayed. When booking a flight from Madison to Chicago O'Hare Intl Airport consider choosing Avianca (85%), Copa Airlines (85%) or Envoy Air (83%) as they are the most reliable in getting you off to your destination on time.

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

    Looking for the cheapest flight from Madison to Chicago O'Hare Intl Airport? While on average our users pay $916, our data indicates the cheapest price to be $160. The most popular route (Madison Truax Field - Chicago O'Hare Intl), is priced around $179.

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

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

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

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

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

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

    Currently, February is the cheapest month in which you can book a flight from Madison to Chicago O'Hare Intl Airport (average of $94). Flying from Madison to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $179). 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 O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Skokie
Des Plaines
Gurnee
Hoffman Estates
Beloit
Elgin
Oak Brook
Elk Grove Village
Naperville
Racine
Downers Grove
Rockford
Orland Park
Merrillville
Bridgeview
Warrenville
Waukegan
Aurora

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Top 2 airlines flying from Madison to O'Hare Intl

Discover the top 2 airlines that operate flights from Madison to O'Hare Intl. 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 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$259FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$219Average$290FlexibilityNo cancel feeOn-time69%

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