How do I get Price Alerts for flights from Madison to Chicago Midway Airport?

Search flight deals from Madison to Chicago Midway Airport . While viewing offers you’ll have the option to create a Price Alert.

How can I save money on flights from Madison to Chicago Midway Airport with momondo?

Leverage our AI within our “Price Forecast” tool, which predicts if it’s better to book now or wait until prices decrease. You can strategically pick the best days to fly and save money on your trip by using our “Price Calendar” tool. “Explore” shows an overview of how much it costs to fly to anywhere from a selected city or airport. Our “Discover” content is a great option for travel inspiration and money-saving tips, while “Price Alerts” will update you when prices change, so you can book when fares are right.

How does momondo find its flight prices?

We aggregate our prices from over 700+ competitors from airlines to OTAs. We operate in over 30 markets worldwide to show you a wide range of travel options.

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.

$151 Cheap Flights from Madison to Chicago Midway Airport in 2026

1 adult

0 bags

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MSN

MDW

123 mimulti-stop

MDW

MSN

123 mimulti-stop

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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 one-way

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Fri 5/15

6:50 pm-11:04 am

2 stops16h 14m

$151

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Mon 5/18

6:50 pm-11:09 am

2 stops16h 19m

$157

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Mon 5/18

6:50 pm-10:02 pm

3 stops27h 12m

$195

Quickest one-way

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Sat 5/2

6:36 pm-7:41 am

1 stop13h 05m

$198

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Fri 5/15

6:50 pm-10:02 pm

3 stops27h 12m

$217

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Fri 7/24

6:50 pm-10:11 pm

2 stops27h 21m

$221

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Sat 5/2

9:48 am-7:46 am

3 stops45h 58m

$235

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Sat 5/2

9:48 am-10:19 pm

2 stops36h 31m

$258

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Mon 5/4

6:30 pm-12:43 pm

2 stops18h 13m

$650

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Mon 5/4

6:22 pm-8:47 am

1 stop14h 25m

$690

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 55m
Direct flights	None

The fastest flight from Madison to Chicago Midway Airport takes 3h 55m

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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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 55m.
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.

Frequently asked questions about flying from Madison to Chicago Midway Airport

How do I get Price Alerts for flights from Madison to Chicago Midway Airport?
Search flight deals from Madison to Chicago Midway Airport. While viewing offers you’ll have the option to create a Price Alert.
How can I save money on flights from Madison to Chicago Midway Airport with momondo?
Leverage our AI within our “Price Forecast” tool, which predicts if it’s better to book now or wait until prices decrease. You can strategically pick the best days to fly and save money on your trip by using our “Price Calendar” tool. “Explore” shows an overview of how much it costs to fly to anywhere from a selected city or airport. Our “Discover” content is a great option for travel inspiration and money-saving tips, while “Price Alerts” will update you when prices change, so you can book when fares are right.
How does momondo find its flight prices?
We aggregate our prices from over 700+ competitors from airlines to OTAs. We operate in over 30 markets worldwide to show you a wide range of travel options.

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Hammond

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Portage

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Valparaiso

Munster

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Chesterton

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Griffith

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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.