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$131+ Cheap flights from Chicago (CHI) 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MSN
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheap flight deals from Chicago to Madison

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) 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 July 3, 2025.

Round-trip from

$179
(United Airlines)

One-way from

$131
(Orbitz)

Popular in

April

Cheapest in

December

Average price

$264

Good round-trip deal

$199 or less

Good one-way deal

$309 or less
From Chicago (CHI) to Madison Truax Field
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One-way flight from Chicago (CHI) to Madison Truax Field
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Highest demand for flights based on searches. 37% potential increase in price ($223 potential increase over avg. RT price).
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Cheapest flight prices on average. 13% potential price decrease ($44 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Madison Truax Field.
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Price to beat on a one-way flight from Chicago (CHI) to Madison Truax Field.
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Find flight deals from Chicago to Madison

Cheapest flights from Chicago to Madison
Explore the most affordable flight options available from Chicago to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.

This United Airlines deal was found by Cheapflights users on 7/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2010:35 amORD - MSN
Nonstop1h 09mUnited Airlines
Sun 8/246:30 amMSN - ORD
Nonstop1h 07mUnited Airlines
Deal found 7/2$179
This American Airlines deal was found by Cheapflights users on 7/1. 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.
Thu 7/249:03 amORD - MSN
Nonstop1h 12mAmerican Airlines
Sun 7/278:27 pmMSN - ORD
Nonstop1h 03mAmerican Airlines
Deal found 7/1$180
This Mytrip deal was found by Cheapflights users on 7/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/167:05 amORD - MSN
1 stop10h 40mMultiple Airlines
Sat 8/236:25 pmMSN - ORD
1 stop16h 01mMultiple Airlines
Deal found 7/2$509
This Delta deal was found by Cheapflights users on 7/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/186:20 pmMDW - MSN
1 stop14h 27mDelta
Mon 7/217:00 amMSN - MDW
1 stop11h 40mDelta
Deal found 7/2$815

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago 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 July 3, 2025.
Use the filters below to find and compare flights from Chicago to Madison that are best for you.

Fly from

Chicago

Fly to

Madison

Route

Depart

Return

Price

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Wed 8/20

10:35 am-11:44 am

Nonstop1h 09m

Madison Truax Field

Sun 8/24

6:30 am-7:37 am

Nonstop1h 07m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 7/24

9:03 am-10:15 am

Nonstop1h 12m

Madison Truax Field

Sun 7/27

8:27 pm-9:30 pm

Nonstop1h 03m

$180

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sat 8/16

7:05 am-5:45 pm

1 stop10h 40m

Madison Truax Field

Sat 8/23

6:25 pm-10:26 am

1 stop16h 01m

$509

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 7/24

5:40 am-6:33 pm

1 stop12h 53m

Madison Truax Field

Sun 7/27

7:18 pm-9:41 am

1 stop14h 23m

$733

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Fri 7/18

6:20 pm-8:47 am

1 stop14h 27m

Madison Truax Field

Mon 7/21

7:00 am-6:40 pm

1 stop11h 40m

$815

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Mon 8/25

11:44 am-6:04 pm

1 stop6h 20m

$131

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Mon 9/1

5:12 pm-6:14 pm

Nonstop1h 02m

$192

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 8/1

4:36 pm-9:39 am

1 stop17h 03m

$230

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Fri 8/1

1:11 pm-9:39 am

2 stops20h 28m

$249

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Mon 7/7

12:45 pm-1:54 pm

Nonstop1h 09m

$310

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 11 results
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Best time to book a flight from Chicago to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from Chicago 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 to Madison

What is the cheapest month to book a flight from Chicago to Madison?

Currently, January is the cheapest month in which you can book a flight from Chicago to Madison (average of $338). Flying from Chicago 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 CHI to MSN?

Find hourly flight availability from Chicago 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 July 3, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Madison at noon. If you’re flexible enough to do this you can expect to save up to 26% on your trip compared to booking a flight in the morning.

What is the cheapest day to fly from Chicago to Madison?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Madison. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago 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 to Madison

Explore weekly flight availability from Chicago 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 July 3, 2025.

The most flights from CHI to MSN are scheduled on a Thursday (41 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).

How much does it cost to fly round-trip from Chicago to Madison?

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 July 3, 2025.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Chicago to Madison have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,861 reviews
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Frontier
5.9
Fair
3,286 reviews
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Chicago 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?

    Most people fly into Madison Truax Field (MSN) if they book a flight to Madison from Chicago. On average, Truax Field has 19 inbound flights from Chicago per day from 1 airline. Madison Truax Field is conveniently located just 5.4 mi from Madison’s city center.

  • What are the cheapest airlines flying from Chicago to Madison round-trip?

    Cheapflights users have booked flights from Chicago to Madison round-trip from $179. Other airlines that can offer you cheap pricing are American Airlines, from $180, and Frontier, from $733. You may be able to fly from Chicago to Madison for 51% less than the average price by searching for these airlines.

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

    $131 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on American Airlines and United Airlines, with prices starting from $192 and $310, respectively.

  • What are the most reliable airlines from Chicago to Madison?

    No one likes to see their flight delayed. When booking a flight from Chicago to Madison consider choosing Piedmont Airlines (96%), Republic Airways (89%) or ANA (86%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Madison?

    On average you can expect to pay $408 for a flight from Chicago to Madison. The cheapest flight overall is $179 while the most popular route, (Chicago O'Hare Intl - Madison Truax Field) is currently priced at $179.

  • Can I find deals for flights from Chicago to Madison that include hotel bookings?

    Yes. In addition to deals on Chicago to Madison flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Madison?

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

  • Can I find deals for business class flights from Chicago to Madison?

    Yes. Cheapflights offers flight deals from Chicago 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 to Madison?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Madison (average of $338). Flying from Chicago 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 Chicago?

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

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Alternative routes for Chicago to Madison

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Chicago to Madison

Discover the top airline that operate flights from Chicago 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$276FlexibilityNo cancel feeOn-time69%

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