CHI - MSN

$136 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 5/10. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$199
American Airlines
Wed 5/27Wed 6/24
ORD - MSN • Non-stop
Cheapest non-stop
$219
United Airlines
Fri 4/10Fri 4/17
ORD - MSN • Non-stop
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 $219 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with American Airlines and United Airlines. Average duration is 1h 05m
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
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

Wed, May 27 - Wed, Jun 24
American Airlines Logo
10:28 am - 11:36 am
ORD
-
MSN
1h 08mnonstop
American Airlines Logo
8:19 am - 9:43 am
MSN
-
ORD
1h 24mnonstop
$199American Airlines
Fri, Apr 24 - Fri, May 1
American Airlines Logo
8:40 am - 9:48 am
ORD
-
MSN
1h 08mnonstop
American Airlines Logo
8:24 pm - 9:40 pm
MSN
-
ORD
1h 16mnonstop
$200American Airlines
Fri, Apr 10 - Fri, Apr 17
United Airlines Logo
8:15 pm - 9:21 pm
ORD
-
MSN
1h 06mnonstop
United Airlines Logo
8:35 pm - 9:37 pm
MSN
-
ORD
1h 02mnonstop
$219United Airlines
Tue, Mar 31 - Tue, Apr 7
American Airlines Logo
8:02 am - 9:08 am
ORD
-
MSN
1h 06mnonstop
American Airlines Logo
9:18 am - 10:31 am
MSN
-
ORD
1h 13mnonstop
$234American Airlines
Sat, Mar 28 - Sun, Apr 5
American Airlines Logo
6:50 pm - 7:52 pm
ORD
-
MSN
1h 02mnonstop
American Airlines Logo
8:24 pm - 9:31 pm
MSN
-
ORD
1h 07mnonstop
$237American Airlines
Fri, Mar 27 - Sun, Mar 29
United Airlines Logo
9:35 pm - 10:32 pm
ORD
-
MSN
0h 57mnonstop
United Airlines Logo
10:48 am - 12:00 pm
MSN
-
ORD
1h 12mnonstop
$249United Airlines
Fri, Apr 24 - Fri, May 15
Multiple Airlines Logo
6:49 pm - 5:56 pm
MDW
-
MSN
23h 07m
1 stop
Multiple Airlines Logo
6:50 pm - 11:04 am
MSN
-
MDW
16h 14m
2 stops
$471Multiple Airlines
Mon, Mar 30 - Wed, Apr 8
Multiple Airlines Logo
9:51 pm - 5:21 pm
MDW
-
MSN
19h 30m
1 stop
Multiple Airlines Logo
6:36 pm - 11:13 pm
MSN
-
MDW
28h 37m
2 stops
$530Multiple Airlines
Fri, Apr 3 - Tue, Apr 7
Delta Logo
9:30 am - 10:58 pm
MDW
-
MSN
13h 28m
1 stop
Delta Logo
6:00 am - 6:40 pm
MSN
-
MDW
12h 40m
1 stop
$547Delta
Thu, Apr 2 - Tue, Apr 7
Delta Logo
9:30 am - 10:58 pm
MDW
-
MSN
13h 28m
1 stop
Delta Logo
6:00 am - 6:40 pm
MSN
-
MDW
12h 40m
1 stop
$585Delta
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 $193 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$136
Best time to beat the crowds with an average 39% 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 $136 for a one-way ticket and $219 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 $203 or less one-way and $449 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 9427 reviews
7.1Entertainment
7.7Boarding
8.1Crew
7.3Comfort
6.6Food
Airline reviews

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

4.0 OkayDr. Joseph, Feb 2026
ORD - IAH
Read more United Airlines reviews

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

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. :/

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

Information on your arrival and departure airports