CHI - MSN

$134 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 3/31. 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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Everything you should know

Cheapest round-trip
$179
American Airlines
Tue 2/24Tue 3/3
ORD - MSN • Non-stop
Cheapest non-stop
$179
American Airlines
Wed 2/18Wed 2/25
ORD - MSN • Non-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 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
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

Tue, Feb 24 - Tue, Mar 3
American Airlines Logo
10:24 pm - 11:26 pm
ORD
-
MSN
1h 02mnonstop
American Airlines Logo
3:47 pm - 4:55 pm
MSN
-
ORD
1h 08mnonstop
$179American Airlines
Sat, Mar 14 - Sat, Mar 21
American Airlines Logo
8:15 am - 9:22 am
ORD
-
MSN
1h 07mnonstop
American Airlines Logo
8:22 pm - 9:30 pm
MSN
-
ORD
1h 08mnonstop
$181American Airlines
Thu, Feb 12 - Mon, Feb 16
American Airlines Logo
8:05 am - 9:11 am
ORD
-
MSN
1h 06mnonstop
American Airlines Logo
8:24 pm - 9:31 pm
MSN
-
ORD
1h 07mnonstop
$209American Airlines
Fri, Feb 20 - Tue, Feb 24
United Airlines Logo
6:00 pm - 6:58 pm
ORD
-
MSN
0h 58mnonstop
United Airlines Logo
6:30 am - 7:42 am
MSN
-
ORD
1h 12mnonstop
$239United Airlines
Tue, Feb 10 - Sat, Feb 14
United Airlines Logo
4:50 pm - 5:47 pm
ORD
-
MSN
0h 57mnonstop
United Airlines Logo
12:57 pm - 2:08 pm
MSN
-
ORD
1h 11mnonstop
$269United Airlines
Thu, Feb 12 - Mon, Feb 16
United Airlines Logo
1:00 pm - 2:07 pm
ORD
-
MSN
1h 07mnonstop
United Airlines Logo
6:30 am - 7:42 am
MSN
-
ORD
1h 12mnonstop
$334United Airlines
Fri, Feb 20 - Tue, Feb 24
United Airlines Logo
1:55 pm - 2:57 pm
ORD
-
MSN
1h 02mnonstop
United Airlines Logo
4:23 pm - 9:38 am
MSN
-
ORD
17h 15m
1 stop
$378United Airlines
Mon, May 11 - Thu, May 28
United Airlines Logo
8:15 pm - 2:16 pm
ORD
-
MSN
18h 01m
1 stop
United Airlines Logo
8:15 am - 9:25 am
MSN
-
ORD
1h 10mnonstop
$386United Airlines
Tue, Apr 28 - Fri, May 1
American Airlines Logo
1:40 pm - 2:46 pm
ORD
-
MSN
1h 06mnonstop
American Airlines Logo
10:05 am - 11:15 am
MSN
-
ORD
1h 10mnonstop
$407American Airlines
Sat, Feb 14 - Mon, Feb 16
Multiple Airlines Logo
8:15 am - 5:56 pm
ORD
-
MSN
9h 41m
1 stop
Multiple Airlines Logo
6:55 pm - 10:01 pm
MSN
-
ORD
27h 06m
1 stop
$511Multiple 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.

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

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

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 $436 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 Saturday, 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.
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 seasonDecember
Cheapest flight$134
Best time to beat the crowds with an average 42% drop in price.
Most popular time to fly with an average 19% increase in price.
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 $134 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 $203 or less one-way and $438 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 9210 reviews
7.1Entertainment
6.6Food
8.1Crew
7.3Comfort
7.7Boarding
Airline reviews

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

8.0 ExcellentAnonymous, Jan 2026
ORD - TPA
Read more United Airlines reviews

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

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.

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

Information on your arrival and departure airports