CHI - MSN

$132 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 1/13. 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, 0 bags

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
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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
$179
American Airlines
Fri 1/9Sun 1/11
ORD - MSN • Non-stop
Cheapest one-way
$132
Typical prices: $201-$274
Multiple Airlines
Tue 1/13
ORD - MSN • 1 stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
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 routes
ORD-MSN
Cheapest
ORD-MSN
Most popular
Insights
Insights
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Insights
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!
Flight Deals
Booking Insights
Expert advice
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

Fri, Jan 9 - Sun, Jan 11
American Airlines Logo
5:40 pm - 6:44 pm
ORD
-
MSN
1h 04mnonstop
American Airlines Logo
5:22 pm - 6:44 pm
MSN
-
ORD
1h 22mnonstop
$179American Airlines
Wed, Dec 31 - Sat, Jan 3
American Airlines Logo
4:50 pm - 5:55 pm
ORD
-
MSN
1h 05mnonstop
American Airlines Logo
8:10 pm - 9:30 pm
MSN
-
ORD
1h 20mnonstop
$209American Airlines
Fri, Dec 26 - Sat, Jan 3
American Airlines Logo
8:12 am - 9:30 am
ORD
-
MSN
1h 18mnonstop
American Airlines Logo
8:10 pm - 9:30 pm
MSN
-
ORD
1h 20mnonstop
$224American Airlines
Tue, Apr 7 - Sat, Apr 11
United Airlines Logo
7:35 pm - 8:47 pm
ORD
-
MSN
1h 12mnonstop
United Airlines Logo
8:30 am - 9:37 am
MSN
-
ORD
1h 07mnonstop
$239United Airlines
Mon, Dec 29 - Sun, Jan 4
American Airlines Logo
8:12 am - 9:30 am
ORD
-
MSN
1h 18mnonstop
American Airlines Logo
9:30 pm - 10:47 pm
MSN
-
ORD
1h 17mnonstop
$249American Airlines
Thu, Apr 16 - Mon, Apr 20
American Airlines Logo
2:50 pm - 3:53 pm
ORD
-
MSN
1h 03mnonstop
American Airlines Logo
6:49 pm - 7:50 pm
MSN
-
ORD
1h 01mnonstop
$261American Airlines
Sun, Jan 11 - Sun, Jan 18
Multiple Airlines Logo
7:21 pm - 11:12 am
ORD
-
MSN
15h 51m1 stop
Multiple Airlines Logo
6:40 pm - 9:43 am
MSN
-
ORD
15h 03m1 stop
$276Multiple Airlines
Sun, Jan 11 - Sun, Jan 18
Multiple Airlines Logo
7:21 pm - 11:12 am
ORD
-
MSN
15h 51m1 stop
Multiple Airlines Logo
6:40 pm - 1:57 pm
MSN
-
ORD
43h 17m2 stops
$316Multiple Airlines
Tue, Jan 13 - Tue, Jan 20
United Airlines Logo
7:00 am - 9:20 pm
ORD
-
MSN
14h 20m1 stop
United Airlines Logo
5:25 pm - 6:46 pm
MSN
-
ORD
1h 21mnonstop
$375United Airlines
Tue, Jan 13 - Fri, Jan 16
United Airlines Logo
8:57 am - 10:10 am
ORD
-
MSN
1h 13mnonstop
United Airlines Logo
4:20 pm - 9:44 am
MSN
-
ORD
17h 24m1 stop
$378United Airlines
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 $179 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 Monday is the most expensive. Flying from Madison back to Chicago, the best deals are generally found on Friday, with Monday being the most expensive.

Expert advice

Expert advice for your flight from Chicago to Madison

 
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.
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

Good to know

Low seasonDecember
Cheapest flight$132
Best time to beat the crowds with an average 53% drop in price.
Most popular time to fly and prices are also 18% 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 $132 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?

    Star Alliance is the only airline alliance operating flights between Chicago and Madison.

  • 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 $294 or less one-way.

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 9092 reviews
8.1Crew
7.7Boarding
7.3Comfort
6.6Food
7.1Entertainment
Airline reviews

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

8.0 Excellentt, Dec 2025
ORD - RSW
Read more United Airlines reviews

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

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

Information on your arrival and departure airports