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Cheap flights from Madison to Chicago from $138

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Madison to Chicago departing on 10/27. 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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Frontier Logo
7:59 pm - 11:38 amMSN-MDW
15h 39m2 stops
Frontier Logo
12:30 pm - 7:15 pmMDW-MSN
6h 45m1 stop
$279Frontier
Find Deal
Mon, Oct 27 - Fri, Oct 31
Frontier Logo
6:36 pm - 11:16 amMSN-MDW
16h 40m1 stop
Frontier Logo
12:30 pm - 7:15 pmMDW-MSN
6h 45m1 stop
$287Frontier
Find Deal
Sun, Oct 26 - Thu, Oct 30
Frontier Logo
8:00 pm - 11:38 amMSN-MDW
15h 38m2 stops
Frontier Logo
12:30 pm - 7:15 pmMDW-MSN
6h 45m1 stop
$289Frontier
Find Deal
Mon, Nov 10 - Mon, Nov 17
Frontier Logo
6:36 pm - 11:16 amMSN-MDW
16h 40m1 stop
Frontier Logo
1:37 pm - 7:15 pmMDW-MSN
29h 38m2 stops
$303Frontier
Find Deal
Sun, Oct 26 - Thu, Oct 30
Frontier Logo
6:36 pm - 4:09 pmMSN-MDW
21h 33m2 stops
Frontier Logo
12:30 pm - 7:15 pmMDW-MSN
6h 45m1 stop
$355Frontier
Find Deal
Sun, Oct 26 - Thu, Oct 30
Delta Logo
6:15 am - 1:08 pmMSN-MDW
6h 53m1 stop
Delta Logo
9:20 am - 10:08 pmMDW-MSN
12h 48m1 stop
$416Delta
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Wed, Mar 4 - Sat, Mar 7
Delta Logo
6:15 am - 6:08 pmMSN-MDW
11h 53m1 stop
Delta Logo
9:30 am - 10:08 pmMDW-MSN
12h 38m2 stops
$421Delta
Find Deal
Wed, Mar 4 - Sat, Mar 7
Frontier Logo
8:00 pm - 11:30 amMSN-MDW
15h 30m1 stop
Frontier Logo
6:06 pm - 7:15 pmMDW-MSN
25h 09m2 stops
$455Frontier
Find Deal
Thu, Nov 6 - Sun, Nov 9
Delta Logo
5:55 pm - 12:35 pmMSN-MDW
18h 40m2 stops
Delta Logo
9:30 am - 10:08 pmMDW-MSN
12h 38m2 stops
$534Delta
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Wed, Mar 4 - Sat, Mar 7
Multiple Airlines Logo
3:02 pm - 11:20 amMSN-MDW
20h 18m1 stop
Multiple Airlines Logo
6:00 am - 5:36 pmMDW-MSN
11h 36m2 stops
$750Multiple Airlines
Find Deal
Sun, Mar 22 - Wed, Apr 1

Frontier flights from Madison to Chicago Midway Airport

Our best Frontier deals on Madison to Chicago Midway Airport flight tickets
Frontier
Oct 27
MSN7:59 pmMadison Truax Field
15h 39m
2 stops
MDW11:38 amChicago Midway
Oct 31
MDW12:30 pmChicago Midway
6h 45m
1 stop
MSN7:15 pmMadison Truax Field
$279
Find similar
Frontier
Oct 26
MSN6:36 pmMadison Truax Field
16h 40m
1 stop
MDW11:16 amChicago Midway
Oct 30
MDW12:30 pmChicago Midway
6h 45m
1 stop
MSN7:15 pmMadison Truax Field
$287
Find similar
Frontier
Nov 10
MSN8:00 pmMadison Truax Field
15h 38m
2 stops
MDW11:38 amChicago Midway
Nov 17
MDW12:30 pmChicago Midway
6h 45m
1 stop
MSN7:15 pmMadison Truax Field
$289
Find similar

Delta flights from Madison to Chicago Midway Airport

Our best Delta deals on Madison to Chicago Midway Airport flight tickets
Delta
Mar 4
MSN6:15 amMadison Truax Field
6h 53m
1 stop
MDW1:08 pmChicago Midway
Mar 7
MDW9:20 amChicago Midway
12h 48m
1 stop
MSN10:08 pmMadison Truax Field
$416
Find similar
Delta
Mar 4
MSN6:15 amMadison Truax Field
11h 53m
1 stop
MDW6:08 pmChicago Midway
Mar 7
MDW9:30 amChicago Midway
12h 38m
2 stops
MSN10:08 pmMadison Truax Field
$421
Find similar
Delta
Mar 4
MSN5:55 pmMadison Truax Field
18h 40m
2 stops
MDW12:35 pmChicago Midway
Mar 7
MDW9:30 amChicago Midway
12h 38m
2 stops
MSN10:08 pmMadison Truax Field
$534
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Madison to Chicago Midway Airport 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 October 14, 2025.
Use the filters below to find and compare flights from Madison to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Mon 10/27

7:59 pm-11:38 am

2 stops15h 39m

Chicago Midway

Fri 10/31

12:30 pm-7:15 pm

1 stop6h 45m

$279

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Sun 10/26

6:36 pm-11:16 am

1 stop16h 40m

Chicago Midway

Thu 10/30

12:30 pm-7:15 pm

1 stop6h 45m

$287

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Mon 11/10

8:00 pm-11:38 am

2 stops15h 38m

Chicago Midway

Mon 11/17

12:30 pm-7:15 pm

1 stop6h 45m

$289

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Sun 10/26

6:36 pm-11:16 am

1 stop16h 40m

Chicago Midway

Thu 10/30

1:37 pm-7:15 pm

2 stops29h 38m

$303

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Sun 10/26

6:36 pm-4:09 pm

2 stops21h 33m

Chicago Midway

Thu 10/30

12:30 pm-7:15 pm

1 stop6h 45m

$355

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Wed 3/4

6:15 am-1:08 pm

1 stop6h 53m

Chicago Midway

Sat 3/7

9:20 am-10:08 pm

1 stop12h 48m

$416

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Wed 3/4

6:15 am-6:08 pm

1 stop11h 53m

Chicago Midway

Sat 3/7

9:30 am-10:08 pm

2 stops12h 38m

$421

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Thu 11/6

8:00 pm-11:30 am

1 stop15h 30m

Chicago Midway

Sun 11/9

6:06 pm-7:15 pm

2 stops25h 09m

$455

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Wed 3/4

5:55 pm-12:35 pm

2 stops18h 40m

Chicago Midway

Sat 3/7

9:30 am-10:08 pm

2 stops12h 38m

$534

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Sun 3/22

3:02 pm-11:20 am

1 stop20h 18m

Chicago Midway

Wed 4/1

6:00 am-5:36 pm

2 stops11h 36m

$750

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
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See travel insights to Chicago from

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

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 airline that flies from Madison Truax Field to Chicago Midway?

Frontier is the most popular carrier operating from Madison Truax Field to Chicago Midway

When to book flights from Madison to Chicago Midway Airport

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

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

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

Direct flights

None
There are no direct flights from Madison to Chicago Midway Airport. There are no popular flight routes from Madison to Chicago Midway Airport.
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  • How far is Madison Truax Field to Chicago Midway by plane?

    The straight-line distance from Madison Truax Field to Chicago Midway is 122.5 mi. In terms of flight time, this usually takes a little over 6h 53m.

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

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Madison Truax Field Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find Madison to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Yes. momondo enables you to select and highlight flights to Chicago from Madison with this policy.

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

Once all potential Madison to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes. momondo can track prices for Madison to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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