MSN - CHI

$142 Find Cheap Flights from Madison to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Madison to Chicago departing on 7/3. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Madison to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Madison to Chicago, as well as popular online travel agencies
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41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$239
Typical prices: $661-$463
United Airlines
Tue 5/26Sun 5/31
MSN - ORD • Non-stop
Cheapest one-way
$142
Typical prices: $216-$658
Multiple Airlines
Fri 7/3
MSN - ORD • 2 stops
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American's Basic Economy is budget-friendly with carry-on.
United's Priority Boarding secures overhead bin space.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $239 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 1h 14m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
When to travel
Cheapest • 5% price drop
Most popular
Good to know
Good to know
+1
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Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Madison to Chicago (MSN-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Madison to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Madison to Chicago

Tue, May 26 - Sun, May 31
United Airlines Logo
8:10 am - 9:20 am
MSN
-
ORD
1h 10mnonstop
United Airlines Logo
9:53 pm - 11:05 pm
ORD
-
MSN
1h 12mnonstop
$239United Airlines
Thu, May 21 - Sun, May 24
American Airlines Logo
3:03 pm - 4:17 pm
MSN
-
ORD
1h 14mnonstop
American Airlines Logo
6:40 am - 7:49 am
ORD
-
MSN
1h 09mnonstop
$241American Airlines
Thu, May 21 - Sun, May 24
American Airlines Logo
3:03 pm - 4:17 pm
MSN
-
ORD
1h 14mnonstop
American Airlines Logo
6:47 pm - 11:59 pm
ORD
-
MSN
5h 12m
1 stop
$250American Airlines
Mon, May 18 - Mon, May 25
American Airlines Logo
8:24 pm - 9:40 pm
MSN
-
ORD
1h 16mnonstop
American Airlines Logo
6:40 am - 7:49 am
ORD
-
MSN
1h 09mnonstop
$254American Airlines
Tue, May 12 - Sat, May 16
American Airlines Logo
8:24 pm - 9:40 pm
MSN
-
ORD
1h 16mnonstop
American Airlines Logo
8:40 am - 9:48 am
ORD
-
MSN
1h 08mnonstop
$269American Airlines
Tue, Jun 30 - Sat, Jul 4
United Airlines Logo
9:40 am - 10:56 am
MSN
-
ORD
1h 16mnonstop
United Airlines Logo
7:42 am - 8:55 am
ORD
-
MSN
1h 13mnonstop
$309United Airlines
Sun, Aug 2 - Sat, Aug 15
American Airlines Logo
5:00 am - 6:15 am
MSN
-
ORD
1h 15mnonstop
American Airlines Logo
4:48 pm - 11:57 pm
ORD
-
MSN
7h 09m
1 stop
$319American Airlines
Mon, Aug 17 - Tue, Sep 1
Multiple Airlines Logo
6:50 pm - 7:55 pm
MSN
-
ORD
25h 05m
2 stops
Multiple Airlines Logo
5:30 pm - 5:25 pm
ORD
-
MSN
23h 55m
1 stop
$326Multiple Airlines
Thu, Jun 11 - Fri, Jun 12
American Airlines Logo
6:42 pm - 8:09 pm
MSN
-
ORD
1h 27mnonstop
American Airlines Logo
6:40 am - 7:45 am
ORD
-
MSN
1h 05mnonstop
$327American Airlines
Tue, May 12 - Sat, May 16
United Airlines Logo
8:10 am - 9:18 am
MSN
-
ORD
1h 08mnonstop
United Airlines Logo
6:00 pm - 7:07 pm
ORD
-
MSN
1h 07mnonstop
$339United Airlines
Booking Insights

KAYAK's insights & trends for Madison to Chicago flights

Get data-powered insights and trends into flights from Madison to Chicago to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Madison to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Madison to Chicago departing in May.

What is the cheapest Madison to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Madison to Chicago costs $290 on the route between Madison (MSN) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

What’s the cheapest day of the week to fly from Madison to Chicago?

The average price of all round-trip flights from Madison to Chicago clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Madison to Chicago, look for departures on Saturdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Chicago, Friday is the cheapest day to fly and Tuesday is the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Madison to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Madison to Chicago is January, where tickets cost $179 (return) on average. On the other hand, the most expensive months are July and August, where the average cost of round-trip tickets is $238 and $226 respectively.

Expert advice

Expert advice for your flight from Madison to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Good to know

Low seasonMarch
Cheapest flight$142
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 2% increase in price.
Flight from Madison to Chicago O'Hare Airport

When to book flights from Madison to Chicago

Are your dates flexible? Find out the best times to travel from Madison to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Madison to Chicago

  • What is the cheapest flight from Madison to Chicago?

    In the last 3 days, the lowest price for a flight from Madison to Chicago was $142 for a one-way ticket and $239 for a round-trip.

  • Do I need a passport to fly between Madison and Chicago?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airlines offer Wi-Fi service onboard planes from Madison to Chicago?

    American Airlines, Delta, United Airlines, Lufthansa, and Iberia offer inflight Wi-Fi service on the Madison to Chicago flight route.

  • Which aircraft models fly most regularly from Madison to Chicago?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Madison to Chicago flight route.

  • Which airline alliances offer flights from Madison to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between Madison and Chicago, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Madison to Chicago?

    There are nonstop flights from Madison to Chicago on a daily basis.

  • How does KAYAK find such low prices on flights from Madison to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Madison to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Madison to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Madison is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Madison to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Madison with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Madison to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Madison up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Madison to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $238 or less one-way and $378 or less round-trip.

Prefer to fly direct from Madison to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Madison Truax Field to Chicago.
Find which airlines fly direct from Madison Truax Field Airport to Chicago, which days they fly and book direct flights.

Direct departures

Madison Truax Field to Chicago

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Direct returns

Chicago to Madison Truax Field

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Reviews of the top airline flying from Madison to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Madison to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Madison to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9680 reviews
8.1Crew
7.1Entertainment
7.7Boarding
7.3Comfort
6.6Food
Airline reviews

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

8.0 ExcellentWendi, Apr 2026
MSP - ORD
Read more United Airlines reviews

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

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

Information on your arrival and departure airports