CHI - MSN

$146 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 7/3. 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
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
$239
American Airlines
Tue 6/2Tue 6/9
ORD - MSN • Non-stop
Cheapest one-way
$146
Typical prices: $309-$351
Multiple Airlines
Fri 7/3
ORD - MSN • 2 stops
Advice from real travelers
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
Cheapest • from $239 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 1h 08m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 82% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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, Jun 2 - Tue, Jun 9
American Airlines Logo
12:45 pm - 1:51 pm
ORD
-
MSN
1h 06mnonstop
American Airlines Logo
8:37 am - 10:00 am
MSN
-
ORD
1h 23mnonstop
$239American Airlines
Thu, Jun 11 - Thu, Jun 18
American Airlines Logo
10:00 pm - 11:10 pm
ORD
-
MSN
1h 10mnonstop
American Airlines Logo
6:34 am - 8:00 am
MSN
-
ORD
1h 26mnonstop
$240American Airlines
Mon, Sep 7 - Thu, Sep 17
American Airlines Logo
9:15 pm - 10:19 pm
ORD
-
MSN
1h 04mnonstop
American Airlines Logo
8:18 pm - 9:30 pm
MSN
-
ORD
1h 12mnonstop
$241American Airlines
Mon, May 18 - Sat, May 23
American Airlines Logo
12:36 pm - 1:48 pm
ORD
-
MSN
1h 12mnonstop
American Airlines Logo
11:29 am - 12:42 pm
MSN
-
ORD
1h 13mnonstop
$254American Airlines
Thu, May 28 - Sat, May 30
United Airlines Logo
1:55 pm - 2:57 pm
ORD
-
MSN
1h 02mnonstop
United Airlines Logo
5:00 am - 6:16 am
MSN
-
ORD
1h 16mnonstop
$309United Airlines
Sat, May 16 - Tue, May 19
United Airlines Logo
12:40 pm - 1:44 pm
ORD
-
MSN
1h 04mnonstop
United Airlines Logo
8:10 am - 9:18 am
MSN
-
ORD
1h 08mnonstop
$324United Airlines
Sun, Jul 12 - Tue, Jul 14
United Airlines Logo
8:10 pm - 9:22 pm
ORD
-
MSN
1h 12mnonstop
United Airlines Logo
6:30 am - 7:40 am
MSN
-
ORD
1h 10mnonstop
$338United Airlines
Thu, Jul 9 - Tue, Jul 14
Delta Logo
9:49 am - 5:59 pm
MDW
-
MSN
8h 10m
1 stop
Delta Logo
6:00 am - 1:09 pm
MSN
-
MDW
7h 09m
1 stop
$583Delta
Thu, Jul 9 - Tue, Jul 14
Delta Logo
1:18 pm - 11:00 pm
MDW
-
MSN
9h 42m
2 stops
Delta Logo
8:52 am - 6:18 pm
MSN
-
MDW
9h 26m
1 stop
$588Delta
Mon, May 18 - Wed, May 20
Delta Logo
7:13 pm - 8:26 am
MDW
-
MSN
13h 13m
1 stop
Delta Logo
7:00 am - 6:33 pm
MSN
-
MDW
11h 33m
1 stop
$1,309Delta
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 June.

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 $449 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 Tuesday is the most expensive. Flying from Madison back to Chicago, the best deals are generally found on Saturday, 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 January, where tickets cost $0 (return) on average. On the other hand, the most expensive months are March and November, where the average cost of round-trip tickets is $431 and $368 respectively.

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$146
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly with an average 23% 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 $146 for a one-way ticket and $239 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 175 (Enhanced Winglets) 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 $254 or less one-way and $524 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 9680 reviews
6.6Food
8.1Crew
7.1Entertainment
7.3Comfort
7.7Boarding
Airline reviews

A long delay. Don't travel late in the day.

8.0 ExcellentTimothy, Apr 2026
ORD - CID
Read more United Airlines reviews

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

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

Information on your arrival and departure airports