CHI - MSN

$179 Find Cheap Flights from Chicago to Madison

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Madison departing on 7/8. 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
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Flights 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, Jul 8 - Tue, Jul 15
United Airlines Logo
12:45 pm - 1:54 pmORD-MSN
1h 09mnonstop
United Airlines Logo
8:10 am - 9:20 amMSN-ORD
1h 10mnonstop
$179United Airlines
Find Deal
Thu, Sep 11 - Sat, Sep 13
American Airlines Logo
8:47 am - 9:59 amORD-MSN
1h 12mnonstop
American Airlines Logo
7:58 am - 9:07 amMSN-ORD
1h 09mnonstop
$181American Airlines
Find Deal
Wed, Jun 25 - Wed, Jul 2
American Airlines Logo
8:16 am - 9:20 amORD-MSN
1h 04mnonstop
American Airlines Logo
1:27 pm - 2:29 pmMSN-ORD
1h 02mnonstop
$184American Airlines
Find Deal
Tue, Jun 24 - Sat, Jun 28
American Airlines Logo
8:16 am - 9:20 amORD-MSN
1h 04mnonstop
American Airlines Logo
1:27 pm - 2:29 pmMSN-ORD
1h 02mnonstop
$229American Airlines
Find Deal
Sat, Jul 26 - Sat, Aug 2
United Airlines Logo
9:20 pm - 10:30 pmORD-MSN
1h 10mnonstop
United Airlines Logo
6:40 am - 7:48 amMSN-ORD
1h 08mnonstop
$239United Airlines
Find Deal
Thu, Sep 11 - Sat, Sep 13
United Airlines Logo
8:45 am - 9:48 amORD-MSN
1h 03mnonstop
United Airlines Logo
2:31 pm - 3:42 pmMSN-ORD
1h 11mnonstop
$240United Airlines
Find Deal
Fri, Jul 25 - Fri, Aug 1
American Airlines Logo
9:03 am - 10:15 amORD-MSN
1h 12mnonstop
American Airlines Logo
8:27 pm - 9:30 pmMSN-ORD
1h 03mnonstop
$271American Airlines
Find Deal
Thu, Jun 26 - Mon, Jun 30
American Airlines Logo
8:16 am - 9:20 amORD-MSN
1h 04mnonstop
American Airlines Logo
8:16 pm - 9:19 pmMSN-ORD
1h 03mnonstop
$281American Airlines
Find Deal
Fri, Jul 25 - Fri, Aug 1
American Airlines Logo
6:25 pm - 11:50 pmORD-MSN
5h 25m1 stop
American Airlines Logo
8:27 pm - 9:30 pmMSN-ORD
1h 03mnonstop
$288American Airlines
Find Deal
Fri, Oct 3 - Sun, Oct 5
Frontier Logo
10:41 am - 7:29 pmORD-MSN
8h 48m1 stop
Frontier Logo
8:14 pm - 9:36 amMSN-ORD
13h 22m1 stop
$351Frontier
Find Deal
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.

Read more about American Airlinesby Harriet Baskas
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.

Read more about United Airlinesby Stefanie Waldek
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
Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Madison.

Our data shows that the cheapest route for a return flight from Chicago to Madison cost $184 and was between Chicago O'Hare Intl Airport (ORD) and Madison (MSN). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $184.

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 Wednesday is the most expensive. Flying from Madison back to Chicago, the best deals are generally found on Wednesday, with Monday being the most expensive.

Find deals

Good to know

Low seasonDecember
High seasonMay
Cheapest flight$179
Best time to beat the crowds with an average 39% drop in price.
Most popular time to fly with an average 40% 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 $204 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 Embraer 170 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 $283 or less round-trip.

Prefer to fly direct from Chicago to Madison?

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
See more direct flights

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 8790 reviews
6.6Food
7.7Boarding
7.3Comfort
7.0Entertainment
8.1Crew
Airline reviews

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

6.0 GoodAndrea, May 2025ORD - ATL
Read more United Airlines reviews

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.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

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

Information on your arrival and departure airports

Madison (MSN)

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