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Cheap flights from Chicago Midway Airport to Madison from $180

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 9/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Madison

Cheap round-trip flights

Multiple Airlines Logo
2:32 pm - 9:08 amMDW-MSN
18h 36m2 stops
Multiple Airlines Logo
9:48 am - 12:44 pmMSN-MDW
26h 56m1 stop
$291Multiple Airlines
Find Deal
Tue, Sep 30 - Sat, Oct 4
Multiple Airlines Logo
1:56 pm - 9:08 amMDW-MSN
19h 12m2 stops
Multiple Airlines Logo
8:00 pm - 11:30 amMSN-MDW
15h 30m1 stop
$361Multiple Airlines
Find Deal
Tue, Oct 28 - Thu, Oct 30
Multiple Airlines Logo
10:51 am - 7:14 pmMDW-MSN
32h 23m2 stops
Multiple Airlines Logo
9:48 am - 12:44 pmMSN-MDW
26h 56m1 stop
$369Multiple Airlines
Find Deal
Sat, Sep 27 - Sat, Oct 4
Multiple Airlines Logo
12:14 pm - 9:08 amMDW-MSN
20h 54m2 stops
Multiple Airlines Logo
8:00 pm - 11:30 amMSN-MDW
15h 30m1 stop
$432Multiple Airlines
Find Deal
Fri, Nov 7 - Sun, Nov 9
Multiple Airlines Logo
5:15 pm - 9:08 amMDW-MSN
15h 53m2 stops
Multiple Airlines Logo
7:59 pm - 3:53 pmMSN-MDW
19h 54m1 stop
$444Multiple Airlines
Find Deal
Fri, Oct 3 - Sun, Oct 5
Frontier Logo
12:30 pm - 7:15 pmMDW-MSN
6h 45m1 stop
Frontier Logo
8:00 pm - 11:30 amMSN-MDW
15h 30m1 stop
$511Frontier
Find Deal
Fri, Nov 7 - Sun, Nov 9
Delta Logo
9:20 am - 10:08 pmMDW-MSN
12h 48m1 stop
Delta Logo
10:55 am - 6:08 pmMSN-MDW
7h 13m1 stop
$560Delta
Find Deal
Sat, Mar 14 - Tue, Mar 17
Delta Logo
9:30 am - 10:08 pmMDW-MSN
12h 38m2 stops
Delta Logo
6:15 am - 6:08 pmMSN-MDW
11h 53m1 stop
$565Delta
Find Deal
Sat, Mar 14 - Tue, Mar 17
Delta Logo
2:00 pm - 10:08 pmMDW-MSN
8h 08m1 stop
Delta Logo
6:15 am - 6:08 pmMSN-MDW
11h 53m1 stop
$572Delta
Find Deal
Sat, Mar 14 - Tue, Mar 17
Frontier Logo
10:31 am - 7:14 pmMDW-MSN
8h 43m1 stop
Frontier Logo
7:59 pm - 11:20 pmMSN-MDW
27h 21m2 stops
$654Frontier
Find Deal
Mon, Oct 13 - Mon, Oct 20

Delta flights from Chicago Midway Airport to Madison

Our best Delta deals on Chicago Midway Airport to Madison flight tickets
Delta
Mar 14
MDW9:20 amChicago Midway
12h 48m
1 stop
MSN10:08 pmMadison Truax Field
Mar 17
MSN10:55 amMadison Truax Field
7h 13m
1 stop
MDW6:08 pmChicago Midway
$560
Find similar
Delta
Mar 14
MDW9:30 amChicago Midway
12h 38m
2 stops
MSN10:08 pmMadison Truax Field
Mar 17
MSN6:15 amMadison Truax Field
11h 53m
1 stop
MDW6:08 pmChicago Midway
$565
Find similar
Delta
Mar 14
MDW2:00 pmChicago Midway
8h 08m
1 stop
MSN10:08 pmMadison Truax Field
Mar 17
MSN6:15 amMadison Truax Field
11h 53m
1 stop
MDW6:08 pmChicago Midway
$572
Find similar

Frontier flights from Chicago Midway Airport to Madison

Our best Frontier deals on Chicago Midway Airport to Madison flight tickets
Frontier
Nov 7
MDW12:30 pmChicago Midway
6h 45m
1 stop
MSN7:15 pmMadison Truax Field
Nov 9
MSN8:00 pmMadison Truax Field
15h 30m
1 stop
MDW11:30 amChicago Midway
$511
Find similar
Frontier
Oct 13
MDW10:31 amChicago Midway
8h 43m
1 stop
MSN7:14 pmMadison Truax Field
Oct 20
MSN7:59 pmMadison Truax Field
27h 21m
2 stops
MDW11:20 pmChicago Midway
$654
Find similar

momondo Fare Finder

 
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 September 17, 2025.
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

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Tue 9/30

2:32 pm-9:08 am

2 stops18h 36m

Madison Truax Field

Sat 10/4

9:48 am-12:44 pm

1 stop26h 56m

$291

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Tue 10/28

1:56 pm-9:08 am

2 stops19h 12m

Madison Truax Field

Thu 10/30

8:00 pm-11:30 am

1 stop15h 30m

$361

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Sat 9/27

10:51 am-7:14 pm

2 stops32h 23m

Madison Truax Field

Sat 10/4

9:48 am-12:44 pm

1 stop26h 56m

$369

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Fri 11/7

12:14 pm-9:08 am

2 stops20h 54m

Madison Truax Field

Sun 11/9

8:00 pm-11:30 am

1 stop15h 30m

$432

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Fri 10/3

5:15 pm-9:08 am

2 stops15h 53m

Madison Truax Field

Sun 10/5

7:59 pm-3:53 pm

1 stop19h 54m

$444

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Fri 11/7

12:30 pm-7:15 pm

1 stop6h 45m

Madison Truax Field

Sun 11/9

8:00 pm-11:30 am

1 stop15h 30m

$511

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Sat 3/14

9:20 am-10:08 pm

1 stop12h 48m

Madison Truax Field

Tue 3/17

10:55 am-6:08 pm

1 stop7h 13m

$560

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Sat 3/14

9:30 am-10:08 pm

2 stops12h 38m

Madison Truax Field

Tue 3/17

6:15 am-6:08 pm

1 stop11h 53m

$565

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Sat 3/14

2:00 pm-10:08 pm

1 stop8h 08m

Madison Truax Field

Tue 3/17

6:15 am-6:08 pm

1 stop11h 53m

$572

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Mon 10/13

10:31 am-7:14 pm

1 stop8h 43m

Madison Truax Field

Mon 10/20

7:59 pm-11:20 pm

2 stops27h 21m

$654

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 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 Sunday as prices are generally higher than usual. According to our data, the average ticket price to Madison on Sunday is $391.

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 at noon. momondo users have found flights departing from Chicago Midway Airport to Madison at noon for as low as $246. 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 evening when prices are around $312.

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

Direct flights

None
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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  • 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 6h 45m.

  • 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
Portage
Fitchburg
Sun Prairie
Cambridge
Oxford
Windsor
Evansville

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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