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$149+ Cheap flights from Madison (MSN) to Chicago (CHI)

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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — CHI
Jun 29 — Jul 61
Mon 6/29
Mon 7/6
1 adult, Economy
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Cheap flight deals from Madison to Chicago

Cheapest flights from Madison to Chicago
Explore the most affordable flight options available from Madison to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 30, 2026.

This United Airlines deal was found by Cheapflights users on 5/28. 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 7/28:10 am
MSN
-
ORD
Nonstop1h 10m
United Airlines
Mon 7/67:45 pm
ORD
-
MSN
Nonstop1h 12m
United Airlines
Deal found 5/28$239
This American Airlines deal was found by Cheapflights users on 5/27. 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 6/2412:08 pm
MSN
-
ORD
Nonstop1h 13m
American Airlines
Wed 7/111:30 pm
ORD
-
MSN
Nonstop1h 10m
American Airlines
Deal found 5/27$240
This United Airlines deal was found by Cheapflights users on 5/29. 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 6/133:56 pm
MSN
-
ORD
Nonstop1h 09m
United Airlines
Sat 8/221:55 pm
ORD
-
MSN
Nonstop1h 04m
United Airlines
Deal found 5/29$254
This American Airlines deal was found by Cheapflights users on 5/25. 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 6/92:42 pm
MSN
-
ORD
Nonstop1h 12m
American Airlines
Sat 6/1312:30 pm
ORD
-
MSN
Nonstop1h 05m
American Airlines
Deal found 5/25$269
This American Airlines deal was found by Cheapflights users on 5/26. 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 6/26:44 pm
MSN
-
ORD
Nonstop1h 21m
American Airlines
Thu 6/1111:30 pm
ORD
-
MSN
Nonstop1h 10m
American Airlines
Deal found 5/26$284
This American Airlines deal was found by Cheapflights users on 5/25. 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 5/296:44 pm
MSN
-
ORD
Nonstop1h 21m
American Airlines
Mon 6/19:55 pm
ORD
-
MSN
Nonstop1h 11m
American Airlines
Deal found 5/25$293
This United Airlines deal was found by Cheapflights users on 5/28. 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 6/56:30 am
MSN
-
ORD
Nonstop1h 10m
United Airlines
Mon 6/89:53 pm
ORD
-
MSN
Nonstop1h 12m
United Airlines
Deal found 5/28$299
This United Airlines deal was found by Cheapflights users on 5/27. 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 8/293:55 pm
MSN
-
ORD
Nonstop1h 16m
United Airlines
Tue 9/112:40 pm
ORD
-
MSN
Nonstop1h 02m
United Airlines
Deal found 5/27$309
This United Airlines deal was found by Cheapflights users on 5/27. 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 6/188:05 am
MSN
-
ORD
Nonstop1h 10m
United Airlines
Sun 6/217:58 pm
ORD
-
MSN
Nonstop1h 09m
United Airlines
Deal found 5/27$310
This United Airlines deal was found by Cheapflights users on 5/30. 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.
Tue 7/1412:30 pm
MSN
-
ORD
Nonstop1h 12m
United Airlines
Tue 7/2110:00 pm
ORD
-
MSN
Nonstop1h 12m
United Airlines
Deal found 5/30$311
This American Airlines deal was found by Cheapflights users on 5/26. 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.
Sun 5/318:19 am
MSN
-
ORD
Nonstop1h 24m
American Airlines
Sat 8/11:00 pm
ORD
-
MSN
Nonstop1h 08m
American Airlines
Deal found 5/26$319
This United Airlines deal was found by Cheapflights users on 5/29. 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 6/156:30 am
MSN
-
ORD
Nonstop1h 10m
United Airlines
Thu 6/2510:00 pm
ORD
-
MSN
Nonstop1h 12m
United Airlines
Deal found 5/29$324

Find flight deals from Madison to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Chicago (CHI). 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 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$239
(American Airlines)

One-way from

$149
(Kiwi.com)

Popular in

April

Cheapest in

November

Average price

$344

Good round-trip deal

$380 or less

Good one-way deal

$262 or less
Provider with most accurate pricing for Madison Truax Field-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Chicago (CHI) flights.
Search Deals
From Madison Truax Field to Chicago (CHI)
Search Deals
One-way flight from Madison Truax Field to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 32% potential increase in price ($132 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 13% potential price decrease ($35 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 Madison Truax Field to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Madison Truax Field to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Chicago 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 30, 2026.
Use the filters below to find and compare flights from Madison to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 6/25

8:10 am-9:20 am

Nonstop1h 10m

Chicago O'Hare Intl

Thu 7/2

10:00 pm-11:12 pm

Nonstop1h 12m

$239

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sun 8/16

5:00 am-6:12 am

Nonstop1h 12m

Chicago O'Hare Intl

Sat 8/29

9:26 pm-10:35 pm

Nonstop1h 09m

$239

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 6/24

10:40 am-11:57 am

Nonstop1h 17m

Chicago O'Hare Intl

Wed 7/1

5:45 pm-6:57 pm

Nonstop1h 12m

$239

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 7/2

6:44 am-8:01 am

Nonstop1h 17m

Chicago O'Hare Intl

Mon 7/6

11:00 pm-12:10 am

Nonstop1h 10m

$239

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 7/2

10:43 am-11:56 am

Nonstop1h 13m

Chicago O'Hare Intl

Mon 7/6

5:45 pm-6:57 pm

Nonstop1h 12m

$239

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 7/3

5:00 am-6:17 am

Nonstop1h 17m

Chicago O'Hare Intl

Sun 7/5

7:45 pm-8:57 pm

Nonstop1h 12m

$239
Quickest round-trip

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 6/13

3:56 pm-5:05 pm

Nonstop1h 09m

Chicago O'Hare Intl

Sat 8/22

1:55 pm-2:59 pm

Nonstop1h 04m

$254

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Tue 6/9

2:42 pm-3:54 pm

Nonstop1h 12m

Chicago O'Hare Intl

Sat 6/13

12:30 pm-1:35 pm

Nonstop1h 05m

$269

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 6/11

8:05 am-9:15 am

Nonstop1h 10m

Chicago O'Hare Intl

Sun 6/14

9:53 pm-11:05 pm

Nonstop1h 12m

$269

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sun 8/2

5:00 am-6:17 am

Nonstop1h 17m

Chicago O'Hare Intl

Sat 8/15

1:55 pm-2:59 pm

Nonstop1h 04m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/25

Showing 1-10 of 28 resultsSorted by cheapest first
1
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3

Compare providers for flights from Madison to Chicago

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

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

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

Currently, January is the cheapest month in which you can book a flight from Madison to Chicago (average of $179). Flying from Madison to Chicago in June is currently the most expensive (average of $397). 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 CHI?

Find hourly flight availability from Madison to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 30, 2026.

A simple way to save on the total cost of your ticket is to fly from Madison to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 18% on your trip compared to booking a flight in the evening.

Weekly flight availability from Madison to Chicago

Explore weekly flight availability from Madison to Chicago. 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 30, 2026.

The most flights from MSN to CHI are scheduled on a Saturday (48 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (9 on average).

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

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

Use this chart to determine the cheapest time to fly round-trip from Madison to Chicago. Price data was last updated on May 23, 2026.

Travelers seeking maximum savings on their Madison to Chicago 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 Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated May 30, 2026.
See what other customers who have flown with United Airlines from Madison to Chicago have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,766 reviews

Crew

8.1

Boarding

7.7

Entertainment

7.1

Food

6.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
United Airlines
7.4
Good
9,766 reviews
United Airlines
7.4
Good
9,766 reviews

Crew

8.1

Boarding

7.7

Entertainment

7.1

Food

6.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

Related info for your journey

Find useful and relevant information for your journey from Madison to Chicago. 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?

    For a flight from Madison to Chicago, you will be flying from Truax Field. Madison Truax Field (MSN) is just 5.4 mi from the center of the city. Truax Field is the only Madison airport and it handles 29 outbound flights to Chicago per day. 2 airlines have flights to Chicago from Madison Truax Field on a regular basis.

  • How long is the flight from Madison to Chicago?

    There are many flights that can get you from Madison to Chicago in 1h 10m. Fly via United Airlines or American Airlines to get the fastest option. Airlines will cover a distance of 108 mi. All flights are typically nonstop.

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

    According to our current data, American Airlines ($179), and United Airlines ($179) offers the cheapest pricing from Madison to Chicago. American Airlines is priced at 36% lower than the current average price of a flight leaving 3 months from now.

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

    No one likes to see their flight delayed. When booking a flight from Madison to Chicago consider choosing Japan Airlines (83%), Envoy Air (83%) or Republic Airways (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?

    Looking for the cheapest flight from Madison to Chicago? While on average our users pay $544, our data indicates the cheapest price to be $199. The most popular route (Madison Truax Field - Chicago O'Hare Intl), is priced around $239.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Madison to Chicago 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?

    Currently, January is the cheapest month in which you can book a flight from Madison to Chicago (average of $179). Flying from Madison to Chicago in June is currently the most expensive (average of $397). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Top 2 airlines flying from Madison to Chicago

Discover the top 2 airlines that operate flights from Madison to Chicago. 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 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$231FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$290FlexibilityNo cancel feeOn-time69%

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