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MSN - CHI

$115 Find cheap flights from Madison to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Madison to Chicago departing on 6/1. 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
Sun 6/2
Sun 6/9

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Madison to Chicago, 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 Madison to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 43,693,958 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Madison to Chicago 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 and deals for you by selecting your travel dates.
Choose your dates
12:30 pm - 1:30 pmMSN-ORD
1h 00mnonstop
8:19 pm - 9:18 pmORD-MSN
0h 59mnonstop
$229American Airlines
Find Deal
Mon, Jul 1 - Fri, Jul 5
8:00 am - 9:01 amMSN-ORD
1h 01mnonstop
9:50 am - 10:45 amORD-MSN
0h 55mnonstop
$254American Airlines
Find Deal
Sun, Sep 15 - Sat, Sep 21
6:30 pm - 7:29 pmMSN-ORD
0h 59mnonstop
5:02 pm - 6:00 pmORD-MSN
0h 58mnonstop
$273American Airlines
Find Deal
Thu, May 30 - Fri, May 31
8:35 am - 9:46 amMSN-ORD
1h 11mnonstop
9:25 pm - 10:27 pmORD-MSN
1h 02mnonstop
$279United Airlines
Find Deal
Sun, Jun 23 - Mon, Jul 8
5:25 pm - 6:31 pmMSN-ORD
1h 06mnonstop
9:25 pm - 10:27 pmORD-MSN
1h 02mnonstop
$289United Airlines
Find Deal
Wed, Jul 3 - Fri, Jul 5
4:02 pm - 5:08 pmMSN-ORD
1h 06mnonstop
3:41 pm - 4:44 pmORD-MSN
1h 03mnonstop
$299United Airlines
Find Deal
Tue, Jul 2 - Wed, Jul 3
10:55 am - 12:04 pmMSN-ORD
1h 09mnonstop
2:04 pm - 3:06 pmORD-MSN
1h 02mnonstop
$314United Airlines
Find Deal
Sat, Jun 29 - Thu, Jul 4
7:00 am - 9:03 pmMSN-ORD
14h 03m1 stop
10:15 am - 8:24 pmORD-MSN
10h 09m1 stop
$394Delta
Find Deal
Mon, Jul 1 - Thu, Jul 4
6:02 am - 6:31 pmMSN-MDW
12h 29m1 stop
9:29 am - 8:24 pmMDW-MSN
10h 55m1 stop
$413Delta
Find Deal
Mon, Jul 1 - Thu, Jul 4
6:02 am - 6:31 pmMSN-MDW
12h 29m1 stop
9:29 am - 8:24 pmMDW-MSN
10h 55m1 stop
$414Delta
Find Deal
Thu, Jul 4 - Fri, Jul 5

Flights from Madison to Chicago - Travel Insights & Trends

Get data-powered insights and trends into flights from Madison to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Madison to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Madison to Chicago.
Our data shows that the cheapest route for a one-way flight from Madison to Chicago cost $163 and was between Madison and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $268.

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

The average price of all flights from Madison to Chicago clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Chicago on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Friday is the most expensive day to fly from Madison to Chicago. For your return ticket, we recommend flying on a Sunday and avoiding Mondays for the best deals.

What is the cheapest month to fly from Madison to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Madison to Chicago, 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 Madison to Chicago is October, where tickets cost $138 on average. On the other hand, the most expensive months are January and September, where the average cost of tickets is $344 and $274 respectively.

Which airlines provide the cheapest flights from Madison to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the best return deals on flights connecting Madison to Chicago were found on American Airlines ($229) and United Airlines ($279). American Airlines proposed the cheapest one-way flight at $115.

Which airlines fly non-stop between Madison and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Madison to Chicago.
There are 2 airlines that fly nonstop from Madison to Chicago. They are American Airlines and United Airlines. The cheapest airline for this route is United Airlines, with the best one-way deal found costing $111. On average, the best prices for this route can be found at United Airlines.

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

Each day, there are between 13 and 15 nonstop flights that take off from Madison and land in Chicago, with an average flight time of 1h 04m. The most common departure time is 8:00 am and most flights take off in the morning, while the most flights land at Chicago O'Hare Intl Airport. Each week, there are 103 flights. The most frequent day of departure is Wednesday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday.

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

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 4 cabin class options for the route. These are First, Business, 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 Madison to Chicago take?

A direct flight to Chicago will take on average 0h 59m to travel the 123 miles flying distance from Madison.

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

Early birds can take the earliest flight from Madison at 5:35 am and will be landing in Chicago at 6:35 am.

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

If you prefer to fly at night, the latest flight from Madison to Chicago jets off at 6:30 pm and lands at 7:29 pm.

Good to know

Low season

February

High season

May

Cheapest flight

$115
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Madison to Chicago O'Hare Airport

When to book flights from Madison to Chicago

Are your dates flexible? Find out the best times to travel from Madison to Chicago 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 Madison to Chicago

  • What is the cheapest flight from Madison to Chicago?

    In the last 3 days, the lowest price for a flight from Madison to Chicago was $115 for a one-way ticket and $229 for a round-trip.

  • Do I need a passport to fly between Madison and Chicago?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airlines offer Wi-Fi service onboard planes from Madison to Chicago?

    American Airlines, Delta, Finnair, Lufthansa, and JetBlue offer inflight Wi-Fi service on the Madison to Chicago flight route.

  • Which aircraft models fly most regularly from Madison to Chicago?

    The Airbus A320-100/200 is the aircraft model that flies most regularly on the Madison to Chicago flight route.

  • Which airline alliances offer flights from Madison to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between Madison and Chicago, with Star Alliance being the most commonly used for this route.

  • On which days can I fly direct from Madison to Chicago?

    There are nonstop flights from Madison to Chicago on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Madison to Chicago are United Airlines and American Airlines. With an average price for the route of $208 and an overall rating of 7.3, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $239 and an overall rating of 7.3.

  • How does KAYAK find such low prices on flights from Madison to Chicago?

    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 Madison to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Madison to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Madison 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 Madison to Chicago?

    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 Chicago with an airline and back to Madison with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Madison to Chicago?

    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 Chicago from Madison 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 Madison to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $249 or less one-way and $398 or less round-trip.

Prefer to fly non-stop from Madison to Chicago?

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

Nonstop departures

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

Nonstop returns

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
See more direct flights

Top airlines flying from Madison to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Madison to Chicago. 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 Madison to Chicago? 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.
7.3
United AirlinesOverall score based on 11134 reviews
7.1Entertainment
6.7Food
7.7Boarding
8.1Crew
7.2Comfort
Airline reviews

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

8.0 ExcellentMichelle, Apr 2024MBS - ORD
Read more about United Airlines reviews

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Turn on the heat. Flight was way too cold from Arizona to Chicago.

Book cheap flights from Madison to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Madison to Chicago found on KAYAK in the last 72 hours.
6/1Sat
nonstopAmerican Airlines
0h 59mMSN-ORD
$115
6/1Sat
2 stops
21h 45mMSN-ORD
$144
5/11Sat
2 stops
15h 38mMSN-ORD
$159
6/1Sat
1 stop
14h 52mMSN-ORD
$161
6/1Sat
3 stops
28h 39mMSN-ORD
$174
5/11Sat
1 stop
9h 53mMSN-ORD
$190
5/17Fri
nonstopAmerican Airlines
0h 59mMSN-ORD
$205
5/14Tue
nonstopUnited Airlines
1h 07mMSN-ORD
$254
5/11Sat
nonstopUnited Airlines
1h 03mMSN-ORD
$255
9/18Wed
3 stopsWestJet
30h 49mMSN-ORD
$502

Search by stops

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Last minute flights from Madison to Chicago

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 Madison to Chicago that are departing in the next 10 days.
5/5Sun
nonstopAmerican Airlines
0h 59mMSN-ORD
5/24Fri
nonstopAmerican Airlines
0h 58mORD-MSN
$459
5/5Sun
multi-stopAmerican Airlines
5h 17mMSN-ORD
5/24Fri
nonstopAmerican Airlines
0h 58mORD-MSN
$521
5/8Wed
nonstopAmerican Airlines
0h 59mMSN-ORD
5/18Sat
nonstopAmerican Airlines
1h 09mORD-MSN
$524
5/5Sun
multi-stopAmerican Airlines
5h 17mMSN-ORD
5/24Fri
multi-stopAmerican Airlines
7h 03mORD-MSN
$529
5/8Wed
nonstopUnited Airlines
1h 07mMSN-ORD
5/18Sat
multi-stopUnited Airlines
15h 48mORD-MSN
$542
5/4Sat
nonstopUnited Airlines
1h 04mMSN-ORD
5/5Sun
nonstopUnited Airlines
1h 04mORD-MSN
$579
5/4Sat
multi-stopUnited Airlines
10h 35mMSN-ORD
5/5Sun
multi-stopUnited Airlines
21h 04mORD-MSN
$828
5/7Tue
multi-stopDelta
14h 50mMSN-MDW
5/11Sat
multi-stopDelta
18h 24mMDW-MSN
$896
5/7Tue
multi-stopDelta
17h 07mMSN-MDW
5/11Sat
multi-stopDelta
21h 06mMDW-MSN
$1,046
5/7Tue
multi-stopDelta
15h 29mMSN-MDW
5/11Sat
multi-stopDelta
11h 32mMDW-MSN
$1,073

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Madison - Chicago Flights

Departure:

Madison (MSN)United States

Return flight deals:

Chicago - Madison

Cabin classes:

$958
$2,150
$979
$268

Compare transportation modes for Madison to Chicago

Average priceAverage duration
Flights$1,0770h 59m
Buses$772h 58m