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CHI - MSN

$100 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 5/21. 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
0 bags
Thu 6/13
Thu 6/20

Search 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
In the last 7 days travelers have searched 42,566,405 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Chicago to Madison (CHI-MSN)

 
These are the cheapest deals for flights from Chicago to Madison currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. 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

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to Madison.

Recent one-way flight deals from Chicago to Madison

Only flying one-way? Below are some of the best one-way flight deals from Chicago to Madison found on KAYAK recently.

Recent last minute flight deals from Chicago to Madison

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Chicago to Madison.

Recent direct flight deals from Chicago to Madison

The latest deals for direct flights from Chicago to Madison so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Chicago to Madison

Find recent round-trip train or bus tickets from Chicago to Madison.

All round-trip flight deals to Madison

The cheapest plane tickets to Madison found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
5:16 pm - 6:09 pmORD-MSN
0h 53mnonstop
8:00 am - 9:00 amMSN-ORD
1h 00mnonstop
$249American Airlines
Find Deal
Wed, Aug 7 - Fri, Aug 9
9:09 am - 10:14 amORD-MSN
1h 05mnonstop
6:30 am - 7:31 amMSN-ORD
1h 01mnonstop
$279United Airlines
Find Deal
Tue, Aug 27 - Sat, Aug 31
9:20 pm - 10:22 pmORD-MSN
1h 02mnonstop
6:20 am - 7:23 amMSN-ORD
1h 03mnonstop
$299United Airlines
Find Deal
Wed, Jun 12 - Wed, Jun 19
5:13 pm - 6:06 pmORD-MSN
0h 53mnonstop
6:36 pm - 7:33 pmMSN-ORD
0h 57mnonstop
$317American Airlines
Find Deal
Mon, Jul 22 - Sun, Jul 28
8:50 am - 9:06 pmORD-MSN
12h 16m1 stop
6:30 am - 7:31 amMSN-ORD
1h 01mnonstop
$357United Airlines
Find Deal
Tue, Aug 27 - Sat, Aug 31
8:50 am - 9:06 pmORD-MSN
12h 16m1 stop
5:30 pm - 6:38 pmMSN-ORD
1h 08mnonstop
$371United Airlines
Find Deal
Tue, Aug 27 - Sat, Aug 31
5:04 am - 10:22 pmORD-MSN
17h 18m1 stop
6:20 am - 7:23 amMSN-ORD
1h 03mnonstop
$381United Airlines
Find Deal
Wed, Jun 12 - Wed, Jun 19
11:59 am - 9:14 pmMDW-MSN
9h 15m1 stop
6:00 am - 6:06 pmMSN-MDW
12h 06m1 stop
$394Delta
Find Deal
Tue, Aug 27 - Sat, Aug 31
5:16 am - 10:29 pmORD-MSN
17h 13m1 stop
6:32 am - 7:35 amMSN-ORD
1h 03mnonstop
$425United Airlines
Find Deal
Wed, Aug 7 - Fri, Aug 9
5:59 pm - 8:43 amMDW-MSN
14h 44m1 stop
5:25 pm - 8:44 amMSN-MDW
15h 19m1 stop
$435Delta
Find Deal
Tue, Aug 27 - Sat, Aug 31
5:36 pm - 8:30 amORD-MSN
14h 54m1 stop
Tue, May 21
1:10 pm - 2:03 pmORD-MSN
0h 53mnonstop
$110American Airlines
Find Deal
Sat, Sep 28
9:35 am - 8:30 amORD-MSN
22h 55m3 stops
Tue, May 21
7:00 am - 8:30 amORD-MSN
25h 30m2 stops
Tue, May 21
11:04 am - 12:02 pmORD-MSN
0h 58mnonstop
$140American Airlines
Find Deal
Sat, Jun 15
5:04 am - 10:22 pmORD-MSN
17h 18m1 stop
$238United Airlines
Find Deal
Sat, Jun 15
8:42 pm - 9:46 pmORD-MSN
1h 04mnonstop
$255American Airlines
Find Deal
Tue, May 21
9:45 am - 3:50 pmORD-MSN
6h 05m1 stop
$257American Airlines
Find Deal
Wed, Jul 17
6:11 pm - 1:38 pmORD-MSN
19h 27m3 stops
$484United Airlines
Find Deal
Sat, Sep 28
6:11 pm - 1:38 pmORD-MSN
19h 27m3 stops
$529United Airlines
Find Deal
Wed, Oct 9
2:10 pm - 3:10 pmORD-MSN
1h 00mnonstop
6:20 am - 7:23 amMSN-ORD
1h 03mnonstop
$434United Airlines
Find Deal
Wed, May 15 - Fri, May 31
5:00 am - 8:48 pmORD-MSN
15h 48m1 stop
5:20 pm - 6:26 pmMSN-ORD
1h 06mnonstop
$478United Airlines
Find Deal
Wed, May 15 - Fri, May 31
3:20 pm - 10:23 pmORD-MSN
7h 03m1 stop
10:45 am - 5:26 pmMSN-ORD
6h 41m1 stop
$554American Airlines
Find Deal
Wed, May 15 - Fri, May 31
5:16 pm - 6:09 pmORD-MSN
0h 53mnonstop
8:00 am - 9:00 amMSN-ORD
1h 00mnonstop
$249American Airlines
Find Deal
Wed, Aug 7 - Fri, Aug 9
9:20 pm - 10:22 pmORD-MSN
1h 02mnonstop
6:20 am - 7:23 amMSN-ORD
1h 03mnonstop
$299United Airlines
Find Deal
Wed, Jun 12 - Wed, Jun 19
5:13 pm - 6:06 pmORD-MSN
0h 53mnonstop
6:36 pm - 7:33 pmMSN-ORD
0h 57mnonstop
$317American Airlines
Find Deal
Mon, Jul 22 - Sun, Jul 28
10:16 am - 11:17 amORD-MSN
1h 01mnonstop
6:30 am - 7:29 amMSN-ORD
0h 59mnonstop
$509American Airlines
Find Deal
Mon, May 20 - Thu, May 23
12:00 am - 2:35 amChicago O'Hare Intl-
Monona Madison (Dutch Mill)
2h 35mnonstop
4:15 pm - 7:15 pmMonona Madison (Dutch Mill)-
Chicago O'Hare Intl
3h 00mnonstop
$77Bus
Find Deal
Sun, May 19 - Thu, May 23
8:00 pm - 10:50 pmChicago O'Hare Intl-
Madison University of Wisconsin
2h 50mnonstop
1:30 am - 4:45 amMadison University of Wisconsin-
Chicago O'Hare Intl
3h 15mnonstop
$77Bus
Find Deal
Wed, Jun 12 - Tue, Jun 18
8:00 pm - 10:50 pmChicago O'Hare Intl-
Madison University of Wisconsin
2h 50mnonstop
1:30 am - 4:40 amMadison University of Wisconsin-
Chicago O'Hare Intl
3h 10mnonstop
$77Bus
Find Deal
Mon, May 20 - Wed, May 22
12:00 am - 2:50 amChicago O'Hare Intl-
Madison University of Wisconsin
2h 50mnonstop
1:30 am - 4:45 amMadison University of Wisconsin-
Chicago O'Hare Intl
3h 15mnonstop
$77Bus
Find Deal
Sun, May 19 - Wed, May 22
4:00 pm - 6:50 pmChicago O'Hare Intl-
Madison University of Wisconsin
2h 50mnonstop
10:00 am - 1:15 pmMadison University of Wisconsin-
Chicago O'Hare Intl
3h 15mnonstop
$77Bus
Find Deal
Mon, May 20 - Thu, May 23
6:00 pm - 8:35 pmChicago O'Hare Intl-
Monona Madison (Dutch Mill)
2h 35mnonstop
1:15 pm - 4:25 pmMonona Madison (Dutch Mill)-
Chicago O'Hare Intl
3h 10mnonstop
$77Bus
Find Deal
Mon, May 20 - Thu, May 23
9:00 pm - 11:50 pmChicago O'Hare Intl-
Madison University of Wisconsin
2h 50mnonstop
10:00 am - 1:25 pmMadison University of Wisconsin-
Chicago O'Hare Intl
3h 25mnonstop
$77Bus
Find Deal
Wed, Jun 12 - Wed, Jun 19
12:00 am - 2:50 amChicago O'Hare Intl-
Madison University of Wisconsin
2h 50mnonstop
2:30 pm - 5:55 pmMadison University of Wisconsin-
Chicago O'Hare Intl
3h 25mnonstop
$77Bus
Find Deal
Sun, May 19 - Thu, May 23
10:00 pm - 12:35 amChicago O'Hare Intl-
Monona Madison (Dutch Mill)
2h 35mnonstop
2:45 am - 5:50 amMonona Madison (Dutch Mill)-
Chicago O'Hare Intl
3h 05mnonstop
$77Bus
Find Deal
Mon, May 20 - Wed, May 22
12:00 am - 2:50 amChicago O'Hare Intl-
Madison University of Wisconsin
2h 50mnonstop
1:30 am - 4:45 amMadison University of Wisconsin-
Chicago O'Hare Intl
3h 15mnonstop
$77Bus
Find Deal
Tue, Jun 11 - Tue, Jun 18

Flights from Chicago to Madison - Travel Insights & Trends

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 one-way flights from Chicago to Madison.
Our data shows that the cheapest route for a one-way flight from Chicago to Madison cost $139 and was between Chicago O'Hare Intl Airport and Madison. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $194.

What’s the cheapest day of the week to fly from Chicago to Madison?

The average price of all flights from Chicago to Madison clicked on KAYAK for each day over the last 12 months.
When flying from Chicago to Madison, you should consider leaving on a Sunday and avoid Mondays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Mondays and the most expensive ones on Fridays.

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 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 July, where tickets cost $158 on average. On the other hand, the most expensive months are December and March, where the average cost of tickets is $423 and $368 respectively.

Which airlines provide the cheapest flights from Chicago to Madison?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on American Airlines ($110) and United Airlines ($238). The cheapest round-trip tickets were found on American Airlines ($249) and United Airlines ($279).

Which airlines fly non-stop between Chicago and Madison?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Chicago to Madison.
There are 2 airlines that fly nonstop from Chicago to Madison. They are American Airlines and United Airlines. The cheapest airline for this route is United Airlines, with the best one-way deal found costing $138. On average, the best prices for this route can be found at United Airlines.

How many flights are there between Chicago and Madison per day?

Each day, there are between 16 and 19 nonstop flights that take off from Chicago and land in Madison, with an average flight time of 1h 03m. The most common departure time is 8:00 pm and most flights take off in the afternoon. Each week, there are 120 flights. The most frequent day of departure is Wednesday, when 16% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Chicago and Madison?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 3 cabin class options for the route. These are First, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Chicago to Madison take?

Nonstop flights from Chicago generally make it to Madison in 0h 53m. The flying distance between the two cities is 123 miles.

What’s the earliest departure time from Chicago to Madison?

Early birds can take the earliest flight from Chicago at 9:00 am and will be landing in Madison at 10:05 am.

What’s the latest departure time from Chicago to Madison?

If you prefer to fly at night, the latest flight from Chicago to Madison jets off at 9:20 pm and lands at 10:22 pm.

Good to know

Low season

January

High season

August

Cheapest flight

$100
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 10% lower on average.
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 $100 for a one-way ticket and $249 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 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.

  • Which is the best airline for flights from Chicago to Madison, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Madison are United Airlines and American Airlines. With an average price for the route of $218 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $222 and an overall rating of 7.3.

  • 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.

See more FAQs

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 $278 or less round-trip.

Prefer to fly non-stop from Chicago to Madison?

Find which airlines fly direct from Chicago to Truax Field, which days they fly and book direct flights.

Nonstop departures

Chicago to Madison Truax Field

Monday

ANA, Air Canada, Air New Zealand, +10 more

ANA, Air Canada, +11 more

Tuesday

ANA, Air Canada, Air New Zealand, +10 more

ANA, Air Canada, +11 more

Wednesday

ANA, Air Canada, Air New Zealand, +11 more

ANA, Air Canada, +12 more

Thursday

ANA, Air Canada, Air New Zealand, +10 more

ANA, Air Canada, +11 more

Friday

ANA, Air Canada, Air New Zealand, +11 more

ANA, Air Canada, +12 more

Saturday

ANA, Air Canada, Air New Zealand, +10 more

ANA, Air Canada, +11 more

Sunday

ANA, Air Canada, Air New Zealand, +11 more

ANA, Air Canada, +12 more

See more direct flights

Nonstop returns

Madison Truax Field to Chicago

Monday

ANA, Air Canada, Air New Zealand, +10 more

ANA, Air Canada, +11 more

Tuesday

ANA, Air Canada, Air New Zealand, +10 more

ANA, Air Canada, +11 more

Wednesday

ANA, Air Canada, Air New Zealand, +11 more

ANA, Air Canada, +12 more

Thursday

ANA, Air Canada, Air New Zealand, +10 more

ANA, Air Canada, +11 more

Friday

ANA, Air Canada, Air New Zealand, +11 more

ANA, Air Canada, +12 more

Saturday

ANA, Air Canada, Air New Zealand, +10 more

ANA, Air Canada, +11 more

Sunday

ANA, Air Canada, Air New Zealand, +11 more

ANA, Air Canada, +12 more

See more direct flights
See more direct flights

Top airlines 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 10980 reviews
7.2Comfort
8.1Crew
6.7Food
7.7Boarding
7.1Entertainment
Airline reviews

I’ve had a couple flights this week on United that were delayed by an hour or more

4.0 OkayJared R., May 2024ORD - SFO
Read more about United Airlines reviews

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

American cancelled our flight home. Zero option for hotel, alternative transportation and took 3 hours to find our bags so we could take a 3 hour UBER ride home on our dime. Never flying AA again.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Book cheap flights from Chicago to Madison

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Madison found on KAYAK in the last 72 hours.
5/21Tue
1 stop
14h 54mORD-MSN
$100
9/28Sat
nonstopAmerican Airlines
0h 53mORD-MSN
$110
5/21Tue
3 stops
22h 55mORD-MSN
$117
5/21Tue
2 stops
25h 30mORD-MSN
$122
6/15Sat
nonstopAmerican Airlines
0h 58mORD-MSN
$140
6/15Sat
1 stopUnited Airlines
17h 18mORD-MSN
$238
5/21Tue
nonstopAmerican Airlines
1h 04mORD-MSN
$255
7/17Wed
1 stopAmerican Airlines
6h 05mORD-MSN
$257
9/28Sat
3 stopsUnited Airlines
19h 27mORD-MSN
$484
10/9Wed
3 stopsUnited Airlines
19h 27mORD-MSN
$529

Search by stops

Search by airline

Search by price

Last minute flights from Chicago to Madison

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Madison that are departing in the next 10 days.
5/15Wed
nonstopUnited Airlines
1h 00mORD-MSN
5/31Fri
nonstopUnited Airlines
1h 03mMSN-ORD
$434
5/15Wed
multi-stopUnited Airlines
15h 48mORD-MSN
5/31Fri
nonstopUnited Airlines
1h 06mMSN-ORD
$478
5/15Wed
multi-stopAmerican Airlines
7h 03mORD-MSN
5/31Fri
multi-stopAmerican Airlines
6h 41mMSN-ORD
$554

Search by stops

Search by airline

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Flights to Madison

Destination:

Madison (MSN)United States

Return flight deals:

Madison - Chicago

Cabin classes:

$648
$418
$194

Compare transportation modes for Chicago to Madison

Average priceAverage duration
Flights$3620h 53m
Buses$772h 45m