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.

$179 Cheap Flights from Madison to Chicago Midway Airport in 2026/27

Find the cheapest flights from Madison to Chicago

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

10:40 am - 7:30 pmMSN Madison Truax Field-MDW Chicago Midway

32h 50m3 stops Fort Myers SW Florida Intl Minneapolis St Paul Orlando

6:43 am - 2:00 pmMDW Chicago Midway-MSN Madison Truax Field

31h 17m3 stops Atlanta Hartsfield-Jackson Los Angeles Phoenix Sky Harbor Intl

$852Multiple Airlines

Thu, Dec 17 - Thu, Dec 24

6:30 am - 11:50 amMSN Madison Truax Field-MDW Chicago Midway

5h 20m1 stop Minneapolis St Paul

5:29 pm - 9:17 pmMDW Chicago Midway-MSN Madison Truax Field

3h 48m1 stop Minneapolis St Paul

$1,220Delta

Sun, Nov 15 - Sun, Nov 22

10:59 am - 4:39 pmMSN Madison Truax Field-MDW Chicago Midway

5h 40m1 stop Minneapolis St Paul

5:29 pm - 9:17 pmMDW Chicago Midway-MSN Madison Truax Field

3h 48m1 stop Minneapolis St Paul

$1,370Delta

Sun, Nov 22 - Sun, Nov 29

10:59 am - 4:39 pmMSN Madison Truax Field-MDW Chicago Midway

5h 40m1 stop Minneapolis St Paul

5:29 pm - 9:17 pmMDW Chicago Midway-MSN Madison Truax Field

3h 48m1 stop Minneapolis St Paul

$1,422Delta

Fri, Nov 20 - Sun, Nov 22

10:59 am - 4:50 pmMSN Madison Truax Field-MDW Chicago Midway

5h 51m1 stop Minneapolis St Paul

12:39 pm - 7:16 pmMDW Chicago Midway-MSN Madison Truax Field

6h 37m1 stop Minneapolis St Paul

$1,453Delta

Fri, Dec 4 - Sun, Dec 6

10:59 am - 4:50 pmMSN Madison Truax Field-MDW Chicago Midway

5h 51m1 stop Minneapolis St Paul

12:39 pm - 7:16 pmMDW Chicago Midway-MSN Madison Truax Field

6h 37m1 stop Minneapolis St Paul

$1,453Delta

Sat, Dec 12 - Sun, Dec 13

10:59 am - 4:50 pmMSN Madison Truax Field-MDW Chicago Midway

5h 51m1 stop Minneapolis St Paul

5:30 pm - 9:29 pmMDW Chicago Midway-MSN Madison Truax Field

3h 59m1 stop Minneapolis St Paul

$1,453Delta

Fri, Dec 11 - Sat, Dec 12

6:30 am - 11:50 amMSN Madison Truax Field-MDW Chicago Midway

5h 20m1 stop Minneapolis St Paul

10:34 am - 1:50 pmMDW Chicago Midway-MSN Madison Truax Field

3h 16m1 stop Minneapolis St Paul

$1,643Delta

Sun, Nov 15 - Mon, Nov 16

10:49 am - 4:39 pmMSN Madison Truax Field-MDW Chicago Midway

5h 50m1 stop Minneapolis St Paul

10:34 am - 1:50 pmMDW Chicago Midway-MSN Madison Truax Field

3h 16m1 stop Minneapolis St Paul

$1,643Delta

Sat, Nov 14 - Wed, Nov 18

Cheap last minute flights

Enter your travel dates to find the best prices.

6:00 am - 4:47 pmMSN Madison Truax Field-MDW Chicago Midway

10h 47m1 stop Minneapolis St Paul

12:30 pm - 9:17 pmMDW Chicago Midway-MSN Madison Truax Field

8h 47m1 stop Minneapolis St Paul

$995Delta

Sat, Nov 7 - Wed, Nov 11

6:00 am - 4:47 pmMSN Madison Truax Field-MDW Chicago Midway

10h 47m1 stop Minneapolis St Paul

12:30 pm - 9:17 pmMDW Chicago Midway-MSN Madison Truax Field

8h 47m1 stop Minneapolis St Paul

$997Delta

Sat, Nov 7 - Wed, Nov 11

9:27 am - 6:00 pmMSN Madison Truax Field-MDW Chicago Midway

8h 33m1 stop Detroit Metropolitan Wayne County

10:34 am - 9:17 pmMDW Chicago Midway-MSN Madison Truax Field

10h 43m1 stop Minneapolis St Paul

$1,063Delta

Sat, Nov 7 - Wed, Nov 11

9:27 am - 6:00 pmMSN Madison Truax Field-MDW Chicago Midway

8h 33m1 stop Detroit Metropolitan Wayne County

12:30 pm - 9:17 pmMDW Chicago Midway-MSN Madison Truax Field

8h 47m1 stop Minneapolis St Paul

$1,063Delta

Sat, Nov 7 - Wed, Nov 11

6:00 am - 4:47 pmMSN Madison Truax Field-MDW Chicago Midway

10h 47m1 stop Minneapolis St Paul

12:30 pm - 9:17 pmMDW Chicago Midway-MSN Madison Truax Field

8h 47m1 stop Minneapolis St Paul

$1,064Delta

Sat, Nov 7 - Wed, Nov 11

6:00 am - 4:47 pmMSN Madison Truax Field-MDW Chicago Midway

10h 47m1 stop Minneapolis St Paul

12:30 pm - 9:17 pmMDW Chicago Midway-MSN Madison Truax Field

8h 47m1 stop Minneapolis St Paul

$1,065Delta

Sat, Nov 7 - Wed, Nov 11

6:00 am - 4:47 pmMSN Madison Truax Field-MDW Chicago Midway

10h 47m1 stop Minneapolis St Paul

11:27 am - 10:50 pmMDW Chicago Midway-MSN Madison Truax Field

11h 23m1 stop Atlanta Hartsfield-Jackson

$1,107Delta

Sat, Nov 7 - Thu, Nov 12

6:00 am - 4:47 pmMSN Madison Truax Field-MDW Chicago Midway

10h 47m1 stop Minneapolis St Paul

12:30 pm - 9:17 pmMDW Chicago Midway-MSN Madison Truax Field

8h 47m1 stop Minneapolis St Paul

$1,467Delta

Sat, Nov 7 - Thu, Nov 12

6:00 am - 4:47 pmMSN Madison Truax Field-MDW Chicago Midway

10h 47m1 stop Minneapolis St Paul

5:29 pm - 9:17 pmMDW Chicago Midway-MSN Madison Truax Field

3h 48m1 stop Minneapolis St Paul

$1,642Delta

Sat, Nov 7 - Thu, Nov 12

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Delta flights from Madison to Chicago Midway Airport

Our best Delta deals on Madison to Chicago Midway Airport flight tickets

Delta

Nov 7

MSN6:00 amMadison Truax Field

10h 47m

1 stop

MDW4:47 pmChicago Midway

Nov 11

MDW12:30 pmChicago Midway

8h 47m

1 stop

MSN9:17 pmMadison Truax Field

$995

Delta

Nov 7

MSN6:00 amMadison Truax Field

10h 47m

1 stop

MDW4:47 pmChicago Midway

Nov 11

MDW12:30 pmChicago Midway

8h 47m

1 stop

MSN9:17 pmMadison Truax Field

$997

Delta

Nov 7

MSN9:27 amMadison Truax Field

8h 33m

1 stop

MDW6:00 pmChicago Midway

Nov 11

MDW12:30 pmChicago Midway

8h 47m

1 stop

MSN9:17 pmMadison Truax Field

$1,063

momondo Fare Finder

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

Cheapest round-trip

MadisonChicago

MSN Madison Truax Field - MDW Chicago Midway

MSNMDW

Madison Truax Field

Thu 12/17

10:40 am-7:30 pm

3 stops32h 50m

Chicago Midway

Thu 12/24

6:43 am-2:00 pm

3 stops31h 17m

$852

MadisonChicago

MSN Madison Truax Field - MDW Chicago Midway

MSNMDW

Madison Truax Field

Sun 11/15

6:30 am-11:50 am

1 stop5h 20m

Chicago Midway

Sun 11/22

5:29 pm-9:17 pm

1 stop3h 48m

$1,220

MadisonChicago

MSN Madison Truax Field - MDW Chicago Midway

MSNMDW

Madison Truax Field

Sun 11/22

10:59 am-4:39 pm

1 stop5h 40m

Chicago Midway

Sun 11/29

5:29 pm-9:17 pm

1 stop3h 48m

$1,370

MadisonChicago

MSN Madison Truax Field - MDW Chicago Midway

MSNMDW

Madison Truax Field

Fri 11/20

10:59 am-4:39 pm

1 stop5h 40m

Chicago Midway

Sun 11/22

5:29 pm-9:17 pm

1 stop3h 48m

$1,422

MadisonChicago

MSN Madison Truax Field - MDW Chicago Midway

MSNMDW

Madison Truax Field

Fri 12/4

10:59 am-4:50 pm

1 stop5h 51m

Chicago Midway

Sun 12/6

12:39 pm-7:16 pm

1 stop6h 37m

$1,453

MadisonChicago

MSN Madison Truax Field - MDW Chicago Midway

MSNMDW

Madison Truax Field

Sat 12/12

10:59 am-4:50 pm

1 stop5h 51m

Chicago Midway

Sun 12/13

12:39 pm-7:16 pm

1 stop6h 37m

$1,453

MadisonChicago

MSN Madison Truax Field - MDW Chicago Midway

MSNMDW

Madison Truax Field

Fri 12/11

10:59 am-4:50 pm

1 stop5h 51m

Chicago Midway

Sat 12/12

5:30 pm-9:29 pm

1 stop3h 59m

$1,453

Quickest round-trip

MadisonChicago

MSN Madison Truax Field - MDW Chicago Midway

MSNMDW

Madison Truax Field

Sun 11/15

6:30 am-11:50 am

1 stop5h 20m

Chicago Midway

Mon 11/16

10:34 am-1:50 pm

1 stop3h 16m

$1,643

MadisonChicago

MSN Madison Truax Field - MDW Chicago Midway

MSNMDW

Madison Truax Field

Sat 11/14

10:49 am-4:39 pm

1 stop5h 50m

Chicago Midway

Wed 11/18

10:34 am-1:50 pm

1 stop3h 16m

$1,643

Cheapest one-way

MadisonChicago

MSN Madison Truax Field - MDW Chicago Midway

MSNMDW

Madison Truax Field

Wed 12/16

10:38 am-11:17 pm

2 stops36h 39m

$179

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 resultsSorted by cheapest first

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?

Delta 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

Best Price Found	$179
Fastest flight time	5h 40m
Direct flights	None

The best one-way flight to Chicago Midway Airport from Madison in the past 72 hours is $179. The best round-trip flight deal from Madison to Chicago Midway Airport found on momondo in the last 72 hours is $852.

The fastest flight from Madison to Chicago Midway Airport takes 5h 40m

There are no direct flights from Madison to Chicago Midway Airport. There are no popular flight routes from Madison to Chicago Midway Airport.

Search flight deals

Frequently asked questions about flying from Madison to Chicago Midway Airport

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 5h 40m.
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.

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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.