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$95+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MSN
Jan 25 — Feb 11
Sat 1/25
Sat 2/1
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 January 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$193
(American Airlines)

One-way from

$95
(American Airlines)

Popular in

March

Cheapest in

August

Average price

$311
Provider with most accurate pricing for Chicago (CHI)-Madison Truax Field flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Madison Truax Field flights.
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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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High demand for flights, 13% potential price rise
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Best time to find cheap flights, 3% potential price drop
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Average for round-trip flights in January 2025
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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 January 20, 2025.

This American Airlines deal was found by Cheapflights users on 1/20. 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 2/1910:16 amORD - MSN
Nonstop0h 59mAmerican Airlines
Wed 2/264:12 pmMSN - ORD
Nonstop0h 59mAmerican Airlines
Deal found 1/20$193
This United Airlines deal was found by Cheapflights users on 1/20. 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.
Sun 3/163:35 pmORD - MSN
Nonstop0h 59mUnited Airlines
Sun 3/232:25 pmMSN - ORD
Nonstop1h 05mUnited Airlines
Deal found 1/20$249
This Mytrip deal was found by Cheapflights users on 1/20. 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.
Fri 2/75:50 amORD - MSN
3 stops27h 18mMultiple Airlines
Sun 2/97:10 pmMSN - ORD
1 stop14h 29mMultiple Airlines
Deal found 1/20$431
This Delta deal was found by Cheapflights users on 1/18. 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.
Sat 2/85:45 amORD - MSN
1 stop15h 47mDelta
Sun 2/91:00 pmMSN - ORD
1 stop10h 49mDelta
Deal found 1/18$705
This Delta deal was found by Cheapflights users on 1/18. 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.
Sat 2/811:25 amMDW - MSN
1 stop11h 12mDelta
Sun 2/96:35 amMSN - MDW
1 stop11h 08mDelta
Deal found 1/18$740

Find flights from Chicago to Madison within your budget

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 January 20, 2025.

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ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Wed 2/19

10:16 am-11:15 am

Nonstop0h 59m

Madison Truax Field

Wed 2/26

4:12 pm-5:11 pm

Nonstop0h 59m

$193

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sun 3/16

3:35 pm-4:34 pm

Nonstop0h 59m

Madison Truax Field

Sun 3/23

2:25 pm-3:30 pm

Nonstop1h 05m

$249

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 2/20

5:45 am-6:21 pm

1 stop12h 36m

Madison Truax Field

Wed 2/26

9:48 am-6:18 pm

1 stop8h 30m

$418

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Thu 3/6

4:45 pm-12:56 pm

2 stops44h 11m

Madison Truax Field

Thu 3/13

2:04 pm-12:17 am

1 stop10h 13m

$472

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sat 2/8

5:45 am-9:32 pm

1 stop15h 47m

Madison Truax Field

Sun 2/9

1:00 pm-11:49 pm

1 stop10h 49m

$705

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Sat 2/8

11:25 am-10:37 pm

1 stop11h 12m

Madison Truax Field

Sun 2/9

6:35 am-5:43 pm

1 stop11h 08m

$740

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Wed 2/19

10:16 am-11:15 am

Nonstop0h 59m

$95

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Mon 2/17

8:05 pm-9:11 pm

Nonstop1h 06m

$155

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 2/7

5:50 am-9:08 am

3 stops27h 18m

$196

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sat 2/22

4:15 pm-10:18 am

1 stop18h 03m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 11 results
1
2

Compare providers for flights from Chicago 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 Chicago to Madison in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

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

Travel insights for flights from Chicago to Madison

Get recent, data-driven insights about flights from Chicago to Madison including ideal travel times, pricing trends, and more.

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 June is currently the most expensive (average of $423). 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 January 20, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Madison in the evening. If you’re flexible enough to do this you can expect to save up to 34% on your trip compared to booking a flight in the morning.

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 January 20, 2025.

The most flights from CHI to MSN are scheduled on a Monday (33 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (20 on average).

Rainfall in Madison by month

Plan your trip to Madison by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Madison ranges from 1.2 - 4.5 inches per month. June is typically the wettest month, when rainfall can reach 4.5 in. January is typically the driest time to visit Madison when rainfall is around 1.2 in.

Temperature in Madison by month

Plan your trip to Madison by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Madison, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 71.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 19.4 F).

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 20, 2025.
To help decide which airline to fly from Chicago to Madison, see what other customers have to say about American Airlines, United Airlines and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,521 reviews

Crew

8.6

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,521 reviews
Delta
8.0
Very good
8,521 reviews

Crew

8.6

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines
7.4
Good
8,982 reviews
Delta
8.0
Very good
8,521 reviews

Crew

8.6

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,521 reviews

Crew

8.6

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Sun Country Air
7.0
Good
386 reviews
Delta
8.0
Very good
8,521 reviews

Crew

8.6

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 28 inbound flights from Chicago per day from 2 airlines. 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 $193. Other airlines that can offer you cheap pricing are United Airlines, from $249, and Delta, from $705. You may be able to fly from Chicago to Madison for 31% less than the average price by searching for these airlines.

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

    $95 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on United Airlines and Delta, with prices starting from $155 and $227, 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 Republic Airways (83%), Air Wisconsin (77%) or Japan Airlines (77%) 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 $274 for a flight from Chicago to Madison. The cheapest flight overall is $154 while the most popular route, (Chicago O'Hare Intl - Madison Truax Field) is currently priced at $189.

  • 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 June is currently the most expensive (average of $423). 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?

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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 2 airlines flying from Chicago to Madison

Discover the top 2 airlines 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 January 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$169Average$284FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$226Average$279FlexibilityNo cancel feeOn-time71%
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