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$115+ 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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheap 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 July 3, 2025.

Round-trip from

$179
(United Airlines)

One-way from

$115
(FlightHub)

Popular in

November

Cheapest in

June

Average price

$479

Good round-trip deal

$327 or less

Good one-way deal

$234 or less
From Madison Truax Field to Chicago (CHI)
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One-way flight from Madison Truax Field to Chicago (CHI)
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Highest demand for flights based on searches. 23% potential increase in price ($107 potential increase over avg. RT price).
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Cheapest flight prices on average. 10% potential price decrease ($33 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 Madison Truax Field to Chicago (CHI).
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Price to beat on a one-way flight from Madison Truax Field to Chicago (CHI).
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Find 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 July 3, 2025.

This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/296:40 amMSN - ORD
Nonstop1h 08mUnited Airlines
Tue 8/52:00 pmORD - MSN
Nonstop1h 03mUnited Airlines
Deal found 7/1$179
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/166:44 pmMSN - ORD
Nonstop1h 05mAmerican Airlines
Sat 8/2312:00 pmORD - MSN
Nonstop0h 59mAmerican Airlines
Deal found 7/2$180
This FlightHub deal was found by Cheapflights users on 7/3. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/287:59 pmMSN - ORD
1 stop14h 38mFrontier
Sun 9/710:42 amORD - MSN
1 stop8h 32mFrontier
Deal found 7/3$412
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.
Wed 7/2310:19 amMSN - ORD
1 stop10h 09mMultiple Airlines
Tue 7/294:36 pmORD - MSN
1 stop17h 03mMultiple Airlines
Deal found 7/2$415

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

Fly from

Madison

Fly to

Chicago

Route

Depart

Return

Price

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Tue 7/29

6:40 am-7:48 am

Nonstop1h 08m

Chicago O'Hare Intl

Tue 8/5

2:00 pm-3:03 pm

Nonstop1h 03m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 8/16

6:44 pm-7:49 pm

Nonstop1h 05m

Chicago O'Hare Intl

Sat 8/23

12:00 pm-12:59 pm

Nonstop0h 59m

$180

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 8/28

7:59 pm-10:37 am

1 stop14h 38m

Chicago O'Hare Intl

Sun 9/7

10:42 am-7:14 pm

1 stop8h 32m

$412

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 7/23

10:19 am-8:28 pm

1 stop10h 09m

Chicago O'Hare Intl

Tue 7/29

4:36 pm-9:39 am

1 stop17h 03m

$415

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sun 10/5

7:59 pm-9:36 am

1 stop13h 37m

$115

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sun 10/5

8:18 pm-9:27 pm

Nonstop1h 09m

$192

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 8/30

10:19 am-10:22 pm

1 stop12h 03m

$209

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Mon 10/6

5:50 pm-9:41 am

1 stop15h 51m

$260

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Sat 8/16

9:25 am-12:28 pm

1 stop3h 03m

$572

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

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, August is the cheapest month in which you can book a flight from Madison to Chicago (average of $245). Flying from Madison to Chicago 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 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 July 3, 2025.

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 14% on your trip compared to booking a flight in the evening.

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 October 20, 2024.

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.

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 July 3, 2025.

The most flights from MSN to CHI are scheduled on a Thursday (44 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (7 on average).

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 July 3, 2025.
See what other customers who have flown with Delta, United Airlines, and American 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.
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 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 23 outbound flights to Chicago per day. 2 airlines have flights to Chicago from Madison Truax Field on a regular basis.

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

    According to our current data, United Airlines ($179), American Airlines ($180), and Frontier ($412) offers the cheapest pricing from Madison to Chicago. United Airlines is priced at 47% lower than the current average price of a flight leaving 3 months from now.

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

    One-way options have recently been found by users for as low as $115 on Frontier. Other airlines that offer cheap prices include American Airlines from $192 and United Airlines from $260 one-way.

  • 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 Piedmont Airlines (94%), Copa Airlines (89%) or Avianca (89%) 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 $1,278, our data indicates the cheapest price to be $178. The most popular route (Madison Truax Field - Chicago O'Hare Intl), is priced around $179.

  • 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, August is the cheapest month in which you can book a flight from Madison to Chicago (average of $245). Flying from Madison to Chicago 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 Madison?

Book flights to Madison if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$296FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$184Average$286FlexibilityNo cancel feeOn-time71%

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