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.

$390 Cheap Flights from Madison to Chicago Midway Airport in 2025/26

1 adult

0 bags

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Find the cheapest flights from Madison to Chicago

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:20 am - 6:37 pmMSN-MDW

12h 17m1 stop

5:00 pm - 10:19 amMDW-MSN

17h 19m1 stop

$390Delta

Find Deal

Tue, Feb 17 - Sat, Feb 21

4:34 pm - 8:45 pmMSN-MDW

28h 11m2 stops

3:10 pm - 5:28 pmMDW-MSN

26h 18m1 stop

$444Multiple Airlines

Find Deal

Tue, Dec 23 - Tue, Dec 30

4:34 pm - 8:45 pmMSN-MDW

28h 11m2 stops

3:10 pm - 5:28 pmMDW-MSN

26h 18m1 stop

$445Multiple Airlines

Find Deal

Tue, Dec 23 - Tue, Dec 30

6:20 am - 6:37 pmMSN-MDW

12h 17m1 stop

9:34 am - 10:38 pmMDW-MSN

13h 04m2 stops

$465Delta

Find Deal

Tue, Feb 17 - Sat, Feb 21

Delta flights from Madison to Chicago Midway Airport

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

Delta

Feb 17

MSN6:20 amMadison Truax Field

12h 17m

1 stop

MDW6:37 pmChicago Midway

Feb 21

MDW5:00 pmChicago Midway

17h 19m

1 stop

MSN10:19 amMadison Truax Field

$390

Find similar

Delta

Feb 17

MSN6:20 amMadison Truax Field

12h 17m

1 stop

MDW6:37 pmChicago Midway

Feb 21

MDW9:34 amChicago Midway

13h 04m

2 stops

MSN10:38 pmMadison Truax Field

$465

Find similar

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

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Tue 2/17

6:20 am-6:37 pm

1 stop12h 17m

Chicago Midway

Sat 2/21

5:00 pm-10:19 am

1 stop17h 19m

$390

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Tue 12/23

4:34 pm-8:45 pm

2 stops28h 11m

Chicago Midway

Tue 12/30

3:10 pm-5:28 pm

1 stop26h 18m

$444

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Tue 12/23

4:34 pm-8:45 pm

2 stops28h 11m

Chicago Midway

Tue 12/30

3:10 pm-5:28 pm

1 stop26h 18m

$445

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Tue 2/17

6:20 am-6:37 pm

1 stop12h 17m

Chicago Midway

Sat 2/21

9:34 am-10:38 pm

2 stops13h 04m

$465

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Thu 12/4

12:10 pm-2:04 pm

3 stops25h 54m

$629

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	4h 35m
Direct flights	None

The fastest flight from Madison to Chicago Midway Airport takes 4h 35m

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

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 12h 17m.
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.

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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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.