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 6/3. 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

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.

Flights Deals
Expert advice
Useful Info
Flights Deals

Cheap Flights from Chicago to Madison

 
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.

Recent round-trip flight deals from Chicago to Madison

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Madison.
Discover the best prices for you by selecting your travel dates on KAYAK.
American Airlines Logo
10:21 am - 11:19 amORD-MSN
0h 58mnonstop
American Airlines Logo
6:39 pm - 7:49 pmMSN-ORD
1h 10mnonstop
$179American Airlines
Find Deal
Tue, Jun 3 - Sat, Jun 7
American Airlines Logo
10:21 am - 11:19 amORD-MSN
0h 58mnonstop
American Airlines Logo
8:16 pm - 9:19 pmMSN-ORD
1h 03mnonstop
$180American Airlines
Find Deal
Thu, May 29 - Thu, Jun 5
American Airlines Logo
10:21 am - 11:19 amORD-MSN
0h 58mnonstop
American Airlines Logo
8:16 pm - 9:19 pmMSN-ORD
1h 03mnonstop
$181American Airlines
Find Deal
Thu, May 29 - Thu, Jun 5
American Airlines Logo
10:19 pm - 11:26 pmORD-MSN
1h 07mnonstop
American Airlines Logo
6:28 pm - 7:29 pmMSN-ORD
1h 01mnonstop
$184American Airlines
Find Deal
Mon, May 19 - Mon, May 26
American Airlines Logo
10:21 am - 11:19 amORD-MSN
0h 58mnonstop
American Airlines Logo
3:28 pm - 4:29 pmMSN-ORD
1h 01mnonstop
$189American Airlines
Find Deal
Thu, May 15 - Tue, May 20
United Airlines Logo
2:10 pm - 3:17 pmORD-MSN
1h 07mnonstop
United Airlines Logo
6:30 am - 7:33 amMSN-ORD
1h 03mnonstop
$249United Airlines
Find Deal
Wed, May 14 - Sun, May 18
United Airlines Logo
7:10 am - 9:43 pmORD-MSN
14h 33m1 stop
United Airlines Logo
6:30 am - 7:41 amMSN-ORD
1h 11mnonstop
$349United Airlines
Find Deal
Tue, Jun 3 - Sat, Jun 7
United Airlines Logo
12:45 pm - 1:54 pmORD-MSN
1h 09mnonstop
United Airlines Logo
8:33 am - 12:25 amMSN-ORD
15h 52m1 stop
$363United Airlines
Find Deal
Thu, May 29 - Thu, Jun 5
United Airlines Logo
8:20 pm - 9:28 pmORD-MSN
1h 08mnonstop
United Airlines Logo
3:09 pm - 9:41 amMSN-ORD
18h 32m1 stop
$368United Airlines
Find Deal
Mon, May 19 - Mon, May 26
 Logo
6:30 am - 8:01 amORD-MSN
25h 31m1 stop
 Logo
8:46 am - 6:42 amMSN-ORD
21h 56m1 stop
Tue, Jun 3 - Sat, Jun 7
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
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 $250 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 $250.

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.

Good to know

Low seasonDecember
High seasonMay
Cheapest flight$179
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly with an average 18% 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 $203 or less one-way and $312 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 8696 reviews
7.3Comfort
6.6Food
8.1Crew
7.1Entertainment
7.7Boarding
Airline reviews

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

8.0 ExcellentAnonymous, Apr 2025ORD - SFO
Read more United Airlines reviews

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.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

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

Information on your arrival and departure airports

Compare transportation modes for Chicago to Madison

Average priceAverage duration
Flights$4260h 58m
Buses$863h 35m

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