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Cheap flights from Chicago Midway Airport to Madison from $172

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Madison departing on 9/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago Midway Airport to Madison

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:05 am - 7:10 pm
MDW
-
MSN
13h 05m
2 stops
Frontier Logo
7:55 pm - 11:07 am
MSN
-
MDW
39h 12m
2 stops
$640Frontier
Thu, Jul 9 - Sun, Jul 12
Delta Logo
1:51 pm - 11:00 pm
MDW
-
MSN
9h 09m
1 stop
Delta Logo
6:05 am - 1:10 pm
MSN
-
MDW
7h 05m
1 stop
$1,110Delta
Mon, Aug 10 - Mon, Aug 24

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Customize your flight search to find flights from Chicago Midway Airport to Madison that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated June 16, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Madison that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Thu 7/9

6:05 am-7:10 pm

2 stops13h 05m

Madison Truax Field

Sun 7/12

7:55 pm-11:07 am

2 stops39h 12m

$640
Quickest round-trip

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Mon 8/10

1:51 pm-11:00 pm

1 stop9h 09m

Madison Truax Field

Mon 8/24

6:05 am-1:10 pm

1 stop7h 05m

$1,110
Cheapest one-way

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Tue 9/15

7:25 am-9:53 am

2 stops26h 28m

$172

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Tue 9/15

12:03 pm-9:53 am

3 stops21h 50m

$204

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Fri 7/31

6:05 am-9:47 am

3 stops27h 42m

$223

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Fri 7/31

12:11 pm-9:47 am

2 stops21h 36m

$228

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Sun 7/12

6:05 am-8:25 am

2 stops26h 20m

$234

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Tue 7/14

12:11 pm-9:47 am

2 stops21h 36m

$260

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Tue 7/14

12:11 pm-9:47 am

3 stops21h 36m

$279
Quickest one-way

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Sat 7/18

6:05 am-7:15 pm

2 stops13h 10m

$294

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
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See travel insights to Madison from

How to get the cheapest flight ticket from Chicago Midway Airport to Madison

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Madison?

The cheapest day to depart from Chicago Midway Airport to Madison is on a Friday when prices can be found for as low as $239. Be sure to avoid booking your departure on a Tuesday as prices are generally higher than usual. According to our data, the average ticket price to Madison on Tuesday is $542.

What is the cheapest time of day to depart on your flight to Madison?

According to our data, the cheapest time of day to fly to Madison is in the evening. momondo users have found flights departing from Chicago Midway Airport to Madison in the evening for as low as $413. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Madison is in the afternoon when prices are around $460.

When to book flights from Chicago Midway Airport to Madison

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Madison according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Madison (MDW to MSN) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Madison

Fastest flight time

4h 10m

Direct flights

None
The fastest flight from Chicago Midway Airport to Madison takes 4h 10m
There are no direct flights from Chicago Midway Airport to Madison. There are no popular flight routes from Chicago Midway Airport to Madison.
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Frequently asked questions about flying from Chicago Midway Airport to Madison

  • How far is Chicago Midway to Madison Truax Field by plane?

    A flight from Chicago Midway to Madison Truax Field will travel around 122.5 mi. In terms of flight time, this usually takes a little over 4h 10m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Madison Truax Field Airport?

    Prices for flights from Chicago Midway Airport to Madison Truax Field Airport refresh daily.

  • How old do you have to be to fly from Chicago Midway Airport to Madison Truax Field Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Madison Truax Field Airport.

  • What documentation or ID do you need to fly to Madison Truax Field Airport?

    The travel and health documents required for your trip to Madison Truax Field Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Madison Truax Field Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Wisconsin Dells
Baraboo
Middleton
Fitchburg
Sun Prairie
Portage
Windsor
Evansville
Cambridge
Oxford

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Madison?

Finding the right flight to Madison from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Madison quick and easy, saving you time and money.

Can I find flights from Chicago to Madison with flexible booking policies on momondo?

All flight searches from Chicago to Madison on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Madison?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Madison from Chicago.

I’m not ready to book a flight from Chicago to Madison right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Madison from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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