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.

$203 Cheap Flights from Madison to Chicago Midway Airport in 2026

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.

9:02 am - 1:20 pm

MSN

MDW

4h 18m

1 stop

5:31 pm - 9:23 pm

MDW

MSN

3h 52m

1 stop

$1,223Delta

Wed, Sep 30 - Wed, Nov 4

9:02 am - 1:20 pm

MSN

MDW

4h 18m

1 stop

10:01 am - 2:11 pm

MDW

MSN

4h 10m

1 stop

$1,223Delta

Wed, Sep 30 - Wed, Nov 4

2:47 pm - 6:19 pm

MSN

MDW

3h 32m

1 stop

9:59 am - 2:07 pm

MDW

MSN

4h 08m

1 stop

$1,223Delta

Wed, Sep 9 - Wed, Sep 16

9:02 am - 1:20 pm

MSN

MDW

4h 18m

1 stop

2:00 pm - 5:57 pm

MDW

MSN

3h 57m

1 stop

$1,223Delta

Wed, Sep 9 - Wed, Sep 16

7:59 am - 11:47 am

MSN

MDW

3h 48m

1 stop

10:01 am - 2:11 pm

MDW

MSN

4h 10m

1 stop

$1,233Delta

Wed, Oct 21 - Sun, Nov 1

12:00 pm - 6:19 pm

MSN

MDW

6h 19m

1 stop

9:59 am - 2:07 pm

MDW

MSN

4h 08m

1 stop

$1,233Delta

Fri, Sep 18 - Sat, Sep 19

2:47 pm - 6:19 pm

MSN

MDW

3h 32m

1 stop

9:59 am - 2:07 pm

MDW

MSN

4h 08m

1 stop

$1,233Delta

Thu, Sep 17 - Sat, Sep 19

12:00 pm - 6:19 pm

MSN

MDW

6h 19m

1 stop

2:00 pm - 5:57 pm

MDW

MSN

3h 57m

1 stop

$1,243Delta

Thu, Sep 10 - Thu, Sep 17

12:10 pm - 6:01 pm

MSN

MDW

5h 51m

1 stop

1:51 pm - 5:48 pm

MDW

MSN

3h 57m

1 stop

$1,243Delta

Wed, Aug 26 - Fri, Aug 28

12:10 pm - 6:01 pm

MSN

MDW

5h 51m

1 stop

1:51 pm - 5:48 pm

MDW

MSN

3h 57m

1 stop

$1,243Delta

Mon, Aug 24 - Mon, Aug 31

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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

Sep 9

MSN2:47 pmMadison Truax Field

3h 32m

1 stop

MDW6:19 pmChicago Midway

Sep 16

MDW9:59 amChicago Midway

4h 08m

1 stop

MSN2:07 pmMadison Truax Field

$1,223

Delta

Sep 17

MSN2:47 pmMadison Truax Field

3h 32m

1 stop

MDW6:19 pmChicago Midway

Sep 19

MDW9:59 amChicago Midway

4h 08m

1 stop

MSN2:07 pmMadison Truax Field

$1,233

Delta

Aug 24

MSN12:10 pmMadison Truax Field

5h 51m

1 stop

MDW6:01 pmChicago Midway

Aug 31

MDW1:51 pmChicago Midway

3h 57m

1 stop

MSN5:48 pmMadison Truax Field

$1,243

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 - MDW

MSNMDW

Madison Truax Field

Wed 9/30

9:02 am-1:20 pm

1 stop4h 18m

Chicago Midway

Wed 11/4

5:31 pm-9:23 pm

1 stop3h 52m

$1,223

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Wed 9/30

9:02 am-1:20 pm

1 stop4h 18m

Chicago Midway

Wed 11/4

10:01 am-2:11 pm

1 stop4h 10m

$1,223

Quickest round-trip

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Wed 9/9

2:47 pm-6:19 pm

1 stop3h 32m

Chicago Midway

Wed 9/16

9:59 am-2:07 pm

1 stop4h 08m

$1,223

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Wed 9/9

9:02 am-1:20 pm

1 stop4h 18m

Chicago Midway

Wed 9/16

2:00 pm-5:57 pm

1 stop3h 57m

$1,223

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Wed 10/21

7:59 am-11:47 am

1 stop3h 48m

Chicago Midway

Sun 11/1

10:01 am-2:11 pm

1 stop4h 10m

$1,233

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Fri 9/18

12:00 pm-6:19 pm

1 stop6h 19m

Chicago Midway

Sat 9/19

9:59 am-2:07 pm

1 stop4h 08m

$1,233

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Thu 9/17

2:47 pm-6:19 pm

1 stop3h 32m

Chicago Midway

Sat 9/19

9:59 am-2:07 pm

1 stop4h 08m

$1,233

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Thu 9/10

12:00 pm-6:19 pm

1 stop6h 19m

Chicago Midway

Thu 9/17

2:00 pm-5:57 pm

1 stop3h 57m

$1,243

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Wed 8/26

12:10 pm-6:01 pm

1 stop5h 51m

Chicago Midway

Fri 8/28

1:51 pm-5:48 pm

1 stop3h 57m

$1,243

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Mon 8/24

12:10 pm-6:01 pm

1 stop5h 51m

Chicago Midway

Mon 8/31

1:51 pm-5:48 pm

1 stop3h 57m

$1,243

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 and Frontier are the most popular carriers 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

Fastest flight time	3h 48m
Direct flights	None

The fastest flight from Madison to Chicago Midway Airport takes 3h 48m

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 3h 48m.
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.