CHI - MSN

$93 Find Cheap Flights from Chicago to Madison

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Madison departing on 11/13. 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

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Madison, 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 Chicago to Madison, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Expert advice
Booking Insights
Flight Deals

Cheap Flights from Chicago to Madison (CHI-MSN)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Madison 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 Chicago to Madison

Sat, Oct 11 - Sun, Oct 12
American Airlines Logo
12:40 pm - 1:44 pmORD-MSN
1h 04mnonstop
American Airlines Logo
8:25 pm - 9:30 pmMSN-ORD
1h 05mnonstop
$179American Airlines
Find Deal
Sat, Oct 11 - Sun, Oct 12
American Airlines Logo
12:40 pm - 1:44 pmORD-MSN
1h 04mnonstop
American Airlines Logo
8:25 pm - 9:30 pmMSN-ORD
1h 05mnonstop
$180American Airlines
Find Deal
Mon, Sep 22 - Mon, Sep 29
United Airlines Logo
10:35 am - 11:44 amORD-MSN
1h 09mnonstop
United Airlines Logo
5:20 am - 6:30 amMSN-ORD
1h 10mnonstop
$199United Airlines
Find Deal
Fri, Nov 7 - Sun, Nov 9
United Airlines Logo
4:50 pm - 5:50 pmORD-MSN
1h 00mnonstop
United Airlines Logo
6:30 am - 7:41 amMSN-ORD
1h 11mnonstop
$204United Airlines
Find Deal
Tue, Sep 30 - Sat, Oct 4
Multiple Airlines Logo
5:46 pm - 9:08 amORD-MSN
15h 22m1 stop
Multiple Airlines Logo
9:48 am - 7:10 amMSN-ORD
21h 22m1 stop
$279Multiple Airlines
Find Deal
Tue, Sep 30 - Sat, Oct 4
Multiple Airlines Logo
2:32 pm - 9:08 amMDW-MSN
18h 36m2 stops
Multiple Airlines Logo
9:48 am - 12:44 pmMSN-MDW
26h 56m1 stop
$291Multiple Airlines
Find Deal
Sun, Sep 28 - Sun, Oct 5
Frontier Logo
6:00 am - 7:14 pmORD-MSN
13h 14m1 stop
Frontier Logo
7:59 pm - 11:59 pmMSN-ORD
28h 00m1 stop
$381Frontier
Find Deal
Sun, Sep 28 - Sun, Oct 5
Frontier Logo
11:36 am - 7:14 pmORD-MSN
31h 38m2 stops
Frontier Logo
7:59 pm - 9:37 amMSN-ORD
13h 38m1 stop
$421Frontier
Find Deal
Sat, Oct 11 - Sun, Oct 12
Delta Logo
1:25 pm - 8:21 pmORD-MSN
6h 56m1 stop
Delta Logo
7:00 am - 4:11 pmMSN-ORD
9h 11m1 stop
$476Delta
Find Deal
Sat, Mar 14 - Tue, Mar 17
Delta Logo
2:00 pm - 10:08 pmMDW-MSN
8h 08m1 stop
Delta Logo
2:40 pm - 8:54 amMSN-MDW
18h 14m1 stop
$572Delta
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
Choose Basic Economy on American for budget travel.
United's Economy Plus offers extra legroom benefits.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
American Airlines
Cheapest • from $179 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
ORD-MSN
Cheapest
ORD-MSN
Most popular
Insights
Insights
Insights
Insights
When to travel
December
Cheapest • 41% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$179
American Airlines
Sat 10/11Sun 10/12
ORD - MSN • Non-stop
Cheapest one-way
$93
Typical prices: $141-257
Frontier
Thu 11/13
ORD - MSN • 1 stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Madison!
Expert advice

Expert advice for your flight from Chicago to Madison

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
American Airlines

Consider Basic Economy for budget travel; check restrictions like Group 9 boarding and no seat assignment.


Use Main Cabin Extra for early boarding and complimentary drinks; ideal for longer flights.

United Airlines

Opt for Economy Plus for extra legroom; up to six inches more than standard economy.


Purchase Priority Boarding to ensure overhead bin space; automatically places you in Zone 2.

Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

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.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek

Stefanie Waldek

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.

Read more
Booking Insights

KAYAK's insights & trends for Chicago to Madison flights

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

What is the cheapest Chicago to Madison flight route?

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

The cheapest return flight from Chicago to Madison costs $239 on the route between Chicago O'Hare Intl Airport (ORD) and Madison (MSN). It is also the most popular route.

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

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

For Chicago to Madison, Friday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Madison back to Chicago, the best deals are generally found on Wednesday, with Monday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Madison, 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 Chicago to Madison is December, where tickets cost $219 (return) on average. On the other hand, the most expensive months are April and May, where the average cost of round-trip tickets is $807 and $524 respectively.

Good to know

Low seasonJune
Cheapest flight$93
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 16% lower on average.
Flight from Chicago O'Hare Airport to Madison

When to book flights from Chicago to Madison

Are your dates flexible? Find out the best times to travel from Chicago to Madison 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 Chicago to Madison

  • What is the cheapest flight from Chicago to Madison?

    In the last 3 days, the lowest price for a flight from Chicago to Madison was $93 for a one-way ticket and $179 for a round-trip.

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

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

  • Which airports will I be using when flying from Chicago to Madison?

    When flying out of Chicago you will be using one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be landing at Madison Truax Field.

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

    Only American Airlines offers inflight Wi-Fi service on the Chicago to Madison flight route.

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

    The Canadair (Bombardier) Regional Jet 700 is the aircraft model that flies most regularly on the Chicago to Madison flight route.

  • Which airline alliances offer flights from Chicago to Madison?

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

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

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

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

    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 Chicago to Madison.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Madison from Chicago 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 Chicago to Madison?

    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 Madison with an airline and back to Chicago with another airline.

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

    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 Madison from Chicago 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 Chicago to Madison

  • Looking for a cheap flight? 25% of our users found flights on this route for $218 or less one-way and $298 or less round-trip.

Prefer to fly direct from Chicago to Madison?

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

Direct departures

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

Direct returns

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

Reviews of the top airline flying from Chicago to Madison

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Madison. 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 Chicago to Madison? 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 8929 reviews
7.1Entertainment
7.7Boarding
7.3Comfort
8.1Crew
6.6Food
Airline reviews

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

10.0 ExcellentAnonymous, Aug 2025ORD - MEM
Read more United Airlines reviews

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.