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Madison

$146+ 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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MSN
Jun 11 — Jun 181
Thu 6/11
Thu 6/18
1 adult, Economy
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Cheap 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 May 12, 2026.

This American Airlines deal was found by Cheapflights users on 5/11. 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.
Fri 6/511:30 pm
ORD
-
MSN
Nonstop1h 10m
American Airlines
Fri 6/126:42 pm
MSN
-
ORD
Nonstop1h 27m
American Airlines
Deal found 5/11$239
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Thu 6/41:07 pm
ORD
-
MSN
Nonstop1h 05m
American Airlines
Sun 6/76:42 pm
MSN
-
ORD
Nonstop1h 27m
American Airlines
Deal found 5/12$240
This American Airlines deal was found by Cheapflights users on 5/7. 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 6/410:05 pm
ORD
-
MSN
Nonstop1h 10m
American Airlines
Thu 6/115:00 am
MSN
-
ORD
Nonstop1h 15m
American Airlines
Deal found 5/7$249
This United Airlines deal was found by Cheapflights users on 5/9. 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 11/247:50 pm
ORD
-
MSN
Nonstop1h 04m
United Airlines
Sat 11/285:00 am
MSN
-
ORD
Nonstop1h 17m
United Airlines
Deal found 5/9$282
This American Airlines deal was found by Cheapflights users on 5/10. 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 5/2012:36 pm
ORD
-
MSN
Nonstop1h 12m
American Airlines
Wed 5/275:00 am
MSN
-
ORD
Nonstop1h 09m
American Airlines
Deal found 5/10$284
This American Airlines deal was found by Cheapflights users on 5/11. 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.
Thu 6/256:47 pm
ORD
-
MSN
1 stop5h 12m
American Airlines
Thu 7/25:00 am
MSN
-
ORD
Nonstop1h 15m
American Airlines
Deal found 5/11$305
This United Airlines deal was found by Cheapflights users on 5/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/97:50 pm
ORD
-
MSN
Nonstop1h 04m
United Airlines
Sat 12/1210:45 am
MSN
-
ORD
Nonstop1h 04m
United Airlines
Deal found 5/11$309
This American Airlines deal was found by Cheapflights users on 5/7. 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 5/2810:28 am
ORD
-
MSN
Nonstop1h 08m
American Airlines
Sun 5/315:00 am
MSN
-
ORD
Nonstop1h 09m
American Airlines
Deal found 5/7$312
This American Airlines deal was found by Cheapflights users on 5/10. 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 11/2411:40 am
ORD
-
MSN
Nonstop1h 04m
American Airlines
Sat 11/285:00 am
MSN
-
ORD
Nonstop1h 15m
American Airlines
Deal found 5/10$324
This American Airlines deal was found by Cheapflights users on 5/11. 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.
Mon 6/291:07 pm
ORD
-
MSN
Nonstop1h 05m
American Airlines
Wed 7/16:34 am
MSN
-
ORD
Nonstop1h 26m
American Airlines
Deal found 5/11$327
This Lucky2Go deal was found by Cheapflights users on 5/7. 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 Lucky2Go is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
MDW
-
MSN
2 stops13h 14m
Frontier
Sun 5/317:59 pm
MSN
-
MDW
2 stops26h 03m
Frontier
Deal found 5/7$339
This Kiwi.com deal was found by Cheapflights users on 5/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/154:52 pm
MDW
-
MSN
1 stop26h 23m
Multiple Airlines
Mon 5/186:50 pm
MSN
-
MDW
2 stops16h 19m
Multiple Airlines
Deal found 5/11$1,096

Find 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 May 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$239
(American Airlines)

One-way from

$146
(Kiwi.com)

Popular in

April

Cheapest in

December

Average price

$482

Good round-trip deal

$460 or less

Good one-way deal

$354 or less
Provider with most accurate pricing for Chicago (CHI)-Madison Truax Field flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Madison Truax Field flights.
Search Deals
From Chicago (CHI) to Madison Truax Field
Search Deals
One-way flight from Chicago (CHI) to Madison Truax Field
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($124 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Madison Truax Field.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Madison Truax Field.
Search Deals

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 May 12, 2026.
Use the filters below to find and compare flights from Chicago to Madison that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 6/5

6:40 am-7:45 am

Nonstop1h 05m

Madison Truax Field

Fri 6/12

6:42 pm-8:09 pm

Nonstop1h 27m

$239

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 6/4

1:07 pm-2:12 pm

Nonstop1h 05m

Madison Truax Field

Sun 6/7

6:42 pm-8:09 pm

Nonstop1h 27m

$240

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 6/25

6:40 am-7:45 am

Nonstop1h 05m

Madison Truax Field

Thu 7/2

5:00 am-6:15 am

Nonstop1h 15m

$240
Quickest round-trip

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 9/17

8:00 am-9:02 am

Nonstop1h 02m

Madison Truax Field

Sun 9/20

5:07 am-6:10 am

Nonstop1h 03m

$309

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 5/28

10:28 am-11:36 am

Nonstop1h 08m

Madison Truax Field

Sun 5/31

5:00 am-6:09 am

Nonstop1h 09m

$312

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Thu 5/28

6:00 am-7:14 pm

2 stops13h 14m

Madison Truax Field

Sun 5/31

7:59 pm-10:02 pm

2 stops26h 03m

$339

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 5/22

9:53 pm-11:05 pm

Nonstop1h 12m

Madison Truax Field

Tue 5/26

3:53 pm-5:05 pm

Nonstop1h 12m

$339

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Tue 5/26

7:00 am-8:06 am

Nonstop1h 06m

Madison Truax Field

Sat 5/30

6:30 am-7:40 am

Nonstop1h 10m

$339

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Tue 9/15

2:03 pm-9:53 am

2 stops19h 50m

Madison Truax Field

Sun 9/20

4:40 pm-8:21 am

1 stop15h 41m

$388

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Wed 5/27

5:04 pm-6:14 pm

Nonstop1h 10m

Madison Truax Field

Fri 5/29

6:30 am-7:51 am

Nonstop1h 21m

$452

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/7

Showing 1-10 of 30 resultsSorted by cheapest first
1
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3

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Madison

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 May 12, 2026.

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 afternoon.

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 May 12, 2026.

The most flights from CHI to MSN are scheduled on a Friday (56 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (43 on average).

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

How often are flights from Chicago to Madison delayed?

About 19% of weekly flights between Chicago and Madison have experienced delays in the past year, with the average delay time being 116 minutes.

What is the most punctual flight time for Chicago to Madison flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Saturday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Madison flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 18% of flights being delayed.

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 May 12, 2026.
See what other customers who have flown with United 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.
United Airlines
7.4
Good
9,701 reviews

Crew

8.1

Comfort

7.3

Boarding

7.7

Food

6.6

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
United Airlines
7.4
Good
9,701 reviews
United Airlines
7.4
Good
9,701 reviews

Crew

8.1

Comfort

7.3

Boarding

7.7

Food

6.6

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.

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 49 inbound flights from Chicago per day from 1 airline. Madison Truax Field is conveniently located just 5.4 mi from Madison’s city center.

  • How long is the flight from Chicago to Madison?

    There are many flights that can get you from Chicago to Madison in 1h 05m. Fly via American Airlines or Frontier to get the fastest option. The distance between Chicago and Madison is about 108 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Chicago to Madison round-trip?

    Cheapflights users have booked flights from Chicago to Madison round-trip from $199. You may be able to fly from Chicago to Madison for 45% less than the average price by searching for this airline.

  • 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 Avianca (100%), Republic Airways (82%) or GoJet (81%) 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 $439 for a flight from Chicago to Madison. The cheapest flight overall is $243 while the most popular route, (Chicago O'Hare Intl - Madison Truax Field) is currently priced at $239.

  • 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.

See more FAQs

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Sun Prairie
Middleton
Baraboo
Fitchburg

Browse thousands of different options on Cheapflights for your next trip

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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 May 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$199Average$462FlexibilityNo cancel feeOn-time69%

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