HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$137+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — CHI
Mar 31 — Apr 71
Mon 3/31
Mon 4/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Madison to Chicago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 March 26, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$227
(American Airlines)

One-way from

$137
(American Airlines)

Good round-trip deal

$379 or less

Good one-way deal

$213 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
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

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 March 26, 2025.

This American Airlines deal was found by Cheapflights users on 3/25. 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.
Sat 5/2410:39 amMSN - ORD
Nonstop1h 07mAmerican Airlines
Wed 5/281:53 pmORD - MSN
Nonstop0h 58mAmerican Airlines
Deal found 3/25$227
This United Airlines deal was found by Cheapflights users on 3/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/221:05 pmMSN - ORD
Nonstop1h 08mUnited Airlines
Mon 4/288:20 pmORD - MSN
Nonstop1h 08mUnited Airlines
Deal found 3/25$272
This Mytrip deal was found by Cheapflights users on 3/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/44:15 pmMSN - ORD
2 stops20h 38mMultiple Airlines
Sun 4/611:42 amORD - MSN
1 stop21h 17mMultiple Airlines
Deal found 3/25$499

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 March 26, 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

Sat 5/24

10:39 am-11:46 am

Nonstop1h 07m

Chicago O'Hare Intl

Wed 5/28

1:53 pm-2:51 pm

Nonstop0h 58m

$227

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Tue 4/22

1:05 pm-2:13 pm

Nonstop1h 08m

Chicago O'Hare Intl

Mon 4/28

8:20 pm-9:28 pm

Nonstop1h 08m

$272

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 5/24

6:25 pm-11:50 am

2 stops17h 25m

Chicago O'Hare Intl

Wed 5/28

7:47 am-4:19 pm

1 stop8h 32m

$596

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 5/15

3:28 pm-4:29 pm

Nonstop1h 01m

$137

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Mon 5/19

6:30 am-7:33 am

Nonstop1h 03m

$149

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 6/27

6:54 pm-8:25 am

1 stop13h 31m

$183

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Mon 3/31

4:10 pm-12:53 pm

2 stops20h 43m

$291

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Fri 5/9

2:00 pm-6:45 pm

1 stop4h 45m

$612

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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, 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 $323). 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 March 26, 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 10% on your trip compared to booking a flight at noon.

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 March 26, 2025.

The most flights from MSN to CHI are scheduled on a Tuesday (38 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Chicago by month

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

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

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

If weather is an important factor for your trip to Chicago, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 March 26, 2025.
To help decide which airline to fly from Madison to Chicago, see what other customers have to say about Delta, United Airlines and American Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,891 reviews

Boarding

8.2

Comfort

8.0

Overall

8.0

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,891 reviews
Delta
8.0
Very good
7,891 reviews

Boarding

8.2

Comfort

8.0

Overall

8.0

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,608 reviews
Delta
8.0
Very good
7,891 reviews

Boarding

8.2

Comfort

8.0

Overall

8.0

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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
7,891 reviews

Boarding

8.2

Comfort

8.0

Overall

8.0

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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 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 22 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, American Airlines ($227), and United Airlines ($272) offers the cheapest pricing from Madison to Chicago.

  • 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 $137 on American Airlines. Other airlines that offer cheap prices include United Airlines from $149 and Delta from $183 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 Republic Airways (86%), Japan Airlines (84%) or Emirates (80%) 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 $1,469, our data indicates the cheapest price to be $143. The most popular route (Madison Truax Field - Chicago O'Hare Intl), is priced around $227.

  • 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 $323). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Madison to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Minneapolis to O'Hare Intl flights
Minneapolis to Midway flights
O'Hare Intl to St. Louis flights
Minneapolis to St. Louis flights
Appleton to O'Hare Intl flights
Milwaukee to O'Hare Intl flights
Duluth to O'Hare Intl flights
O'Hare Intl to Evansville flights
Madison to O'Hare Intl flights
Green Bay to O'Hare Intl flights
Milwaukee to St. Louis flights
Eau Claire to O'Hare Intl flights
O'Hare Intl to Decatur flights
Minneapolis to Rockford flights
Duluth to Midway flights
Madison to St. Louis flights
Minneapolis to Peoria flights
O'Hare Intl to Peoria flights
Minneapolis to Bloomington flights
Appleton to St. Louis flights
Wausau to O'Hare Intl flights
Dubuque to O'Hare Intl flights
Appleton to Midway flights
Minneapolis to Moline flights
Wausau to Midway flights
O'Hare Intl to Moline flights
O'Hare Intl to Springfield flights
La Crosse to O'Hare Intl flights
O'Hare Intl to Champaign flights
Minneapolis to Evansville flights
Green Bay to Midway flights
O'Hare Intl to Burlington flights
Minneapolis to Springfield flights
Minneapolis to Champaign flights
O'Hare Intl to Bloomington flights
Milwaukee to Midway flights
Madison to Midway flights
O'Hare Intl to Paducah flights
Green Bay to St. Louis flights
Escanaba to O'Hare Intl flights
Wausau to St. Louis flights
Minneapolis to Dubuque flights
Ironwood to O'Hare Intl flights
La Crosse to Midway flights
Rhinelander to St. Louis flights
Appleton to Peoria flights
La Crosse to Peoria flights
La Crosse to St. Louis flights

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 March 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$178Average$278FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$302FlexibilityNo cancel feeOn-time69%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.