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O'Hare Intl

$93+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — ORD
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$179
(United Airlines)

One-way from

$93
(Kiwi.com)

Popular in

September

Cheapest in

June

Average price

$440

Good round-trip deal

$309 or less

Good one-way deal

$201 or less
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. 12% potential increase in price ($41 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($13 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 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 September 17, 2025.

This American Airlines deal was found by Cheapflights users on 9/16. 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 10/108:25 pmMSN - ORD
Nonstop1h 05mAmerican Airlines
Sat 10/112:56 pmORD - MSN
Nonstop1h 03mAmerican Airlines
Deal found 9/16$179
This American Airlines deal was found by Cheapflights users on 9/15. 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 12/105:00 amMSN - ORD
Nonstop1h 09mAmerican Airlines
Sat 12/133:02 pmORD - MSN
Nonstop1h 07mAmerican Airlines
Deal found 9/15$182
This United Airlines deal was found by Cheapflights users on 9/16. 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 10/26:30 amMSN - ORD
Nonstop1h 07mUnited Airlines
Wed 10/88:52 amORD - MSN
Nonstop1h 03mUnited Airlines
Deal found 9/16$184
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/28:18 pmMSN - ORD
Nonstop1h 09mAmerican Airlines
Mon 10/68:59 amORD - MSN
Nonstop1h 16mAmerican Airlines
Deal found 9/17$189
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Mon 10/206:30 amMSN - ORD
Nonstop1h 07mUnited Airlines
Sun 10/268:51 amORD - MSN
Nonstop1h 09mUnited Airlines
Deal found 9/16$194
This American Airlines deal was found by Cheapflights users on 9/17. 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 9/236:41 pmMSN - ORD
Nonstop1h 11mAmerican Airlines
Thu 10/28:47 amORD - MSN
Nonstop1h 12mAmerican Airlines
Deal found 9/17$199
This United Airlines deal was found by Cheapflights users on 9/17. 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 10/15:20 amMSN - ORD
Nonstop1h 07mUnited Airlines
Sun 10/58:52 amORD - MSN
Nonstop1h 03mUnited Airlines
Deal found 9/17$213
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/98:25 pmMSN - ORD
Nonstop1h 05mAmerican Airlines
Thu 10/168:59 amORD - MSN
Nonstop1h 16mAmerican Airlines
Deal found 9/15$224
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Sat 9/205:00 amMSN - ORD
Nonstop1h 00mAmerican Airlines
Mon 10/208:59 amORD - MSN
Nonstop1h 16mAmerican Airlines
Deal found 9/14$225
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Fri 9/1910:16 amMSN - ORD
Nonstop1h 08mAmerican Airlines
Mon 10/2012:40 pmORD - MSN
Nonstop1h 04mAmerican Airlines
Deal found 9/14$244
This United Airlines deal was found by Cheapflights users on 9/17. 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 10/26:30 amMSN - ORD
Nonstop1h 07mUnited Airlines
Mon 10/610:35 amORD - MSN
Nonstop1h 10mUnited Airlines
Deal found 9/17$249
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/164:29 pmMSN - ORD
Nonstop1h 11mAmerican Airlines
Sun 10/198:59 amORD - MSN
Nonstop1h 16mAmerican Airlines
Deal found 9/15$257

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 September 17, 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

Fri 10/17

6:30 am-7:37 am

Nonstop1h 07m

Chicago O'Hare Intl

Sun 10/19

12:50 pm-1:50 pm

Nonstop1h 00m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Tue 11/11

4:34 pm-5:51 pm

Nonstop1h 17m

Chicago O'Hare Intl

Sun 11/16

8:15 am-9:18 am

Nonstop1h 03m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sun 10/12

5:45 pm-6:55 pm

Nonstop1h 10m

Chicago O'Hare Intl

Sun 10/19

8:52 am-9:55 am

Nonstop1h 03m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 10/8

6:00 am-7:05 am

Nonstop1h 05m

Chicago O'Hare Intl

Sun 10/12

8:59 am-10:15 am

Nonstop1h 16m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 10/2

6:30 am-7:37 am

Nonstop1h 07m

Chicago O'Hare Intl

Wed 10/8

8:52 am-9:55 am

Nonstop1h 03m

$184

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sun 10/5

8:18 pm-9:27 pm

Nonstop1h 09m

Chicago O'Hare Intl

Mon 10/13

10:31 pm-11:36 pm

Nonstop1h 05m

$184

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 10/2

8:18 pm-9:27 pm

Nonstop1h 09m

Chicago O'Hare Intl

Mon 10/6

8:59 am-10:15 am

Nonstop1h 16m

$189

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 10/4

3:48 pm-5:00 pm

Nonstop1h 12m

Chicago O'Hare Intl

Sun 10/5

8:52 am-9:55 am

Nonstop1h 03m

$189

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 12/27

8:15 am-9:36 am

Nonstop1h 21m

Chicago O'Hare Intl

Sat 1/3

5:55 pm-7:05 pm

Nonstop1h 10m

$189

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Mon 10/20

6:30 am-7:37 am

Nonstop1h 07m

Chicago O'Hare Intl

Sun 10/26

8:51 am-10:00 am

Nonstop1h 09m

$194

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 21 results
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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, August is the cheapest month in which you can book a flight from Madison to Chicago O'Hare Intl Airport (average of $245). Flying from Madison to Chicago O'Hare Intl Airport 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 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 September 17, 2025.

It’s typically best to fly out from Madison to Chicago O'Hare Intl Airport in the morning. Doing so could potentially save you 10% 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 September 14, 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 September 17, 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
8,926 reviews

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Food

6.6

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
8,926 reviews
United Airlines
7.4
Good
8,926 reviews

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Food

6.6

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!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,926 reviews

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Food

6.6

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 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 39 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 07m. 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 $184, 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 (89%), Copa Airlines (88%) or Japan Airlines (79%) 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 $776, our data indicates the cheapest price to be $130. 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, August is the cheapest month in which you can book a flight from Madison to Chicago O'Hare Intl Airport (average of $245). Flying from Madison to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport?

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

Browse thousands of different options on Cheapflights for your next trip

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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$184Average$280FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$219Average$290FlexibilityNo cancel feeOn-time69%

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