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.

$191 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.

6:00 pm - 1:33 pmMSN Madison Truax Field-MDW Chicago Midway

19h 33m2 stops Orlando Atlanta Hartsfield-Jackson

8:42 pm - 9:50 amMDW Chicago Midway-MSN Madison Truax Field

13h 08m1 stop Orlando

$564Multiple Airlines

Sun, Nov 22 - Mon, Nov 30

6:00 pm - 7:47 pmMSN Madison Truax Field-MDW Chicago Midway

25h 47m1 stop Orlando

8:42 pm - 9:50 amMDW Chicago Midway-MSN Madison Truax Field

13h 08m1 stop Orlando

$581Multiple Airlines

Sun, Nov 22 - Mon, Nov 30

7:59 am - 11:47 amMSN Madison Truax Field-MDW Chicago Midway

3h 48m1 stop Minneapolis St Paul

12:27 pm - 7:06 pmMDW Chicago Midway-MSN Madison Truax Field

6h 39m1 stop Minneapolis St Paul

$1,163Delta

Tue, Oct 13 - Tue, Oct 27

6:00 am - 11:47 amMSN Madison Truax Field-MDW Chicago Midway

5h 47m1 stop Minneapolis St Paul

10:12 am - 2:11 pmMDW Chicago Midway-MSN Madison Truax Field

3h 59m1 stop Minneapolis St Paul

$1,183Delta

Sun, Oct 11 - Sat, Oct 17

10:53 am - 4:47 pmMSN Madison Truax Field-MDW Chicago Midway

5h 54m1 stop Minneapolis St Paul

10:12 am - 2:11 pmMDW Chicago Midway-MSN Madison Truax Field

3h 59m1 stop Minneapolis St Paul

$1,333Delta

Fri, Oct 16 - Sun, Oct 18

10:59 am - 5:24 pmMSN Madison Truax Field-MDW Chicago Midway

6h 25m1 stop Minneapolis St Paul

6:20 pm - 10:08 pmMDW Chicago Midway-MSN Madison Truax Field

3h 48m1 stop Minneapolis St Paul

$1,383Delta

Sat, Dec 19 - Tue, Dec 29

1:26 pm - 6:01 pmMSN Madison Truax Field-MDW Chicago Midway

4h 35m1 stop Detroit Metropolitan Wayne County

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

6h 37m1 stop Minneapolis St Paul

$1,408Delta

Tue, Dec 8 - Thu, Dec 10

2:47 pm - 6:19 pmMSN Madison Truax Field-MDW Chicago Midway

3h 32m1 stop Minneapolis St Paul

9:59 am - 2:07 pmMDW Chicago Midway-MSN Madison Truax Field

4h 08m1 stop Minneapolis St Paul

$1,443Delta

Tue, Sep 29 - Sat, Oct 3

12:00 pm - 6:19 pmMSN Madison Truax Field-MDW Chicago Midway

6h 19m1 stop Minneapolis St Paul

9:59 am - 2:07 pmMDW Chicago Midway-MSN Madison Truax Field

4h 08m1 stop Minneapolis St Paul

$1,463Delta

Sun, Sep 27 - Thu, Oct 1

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

5h 20m1 stop Minneapolis St Paul

1:31 pm - 5:35 pmMDW Chicago Midway-MSN Madison Truax Field

4h 04m1 stop Detroit Metropolitan Wayne County

$1,647Delta

Sat, Nov 21 - Sun, Nov 29

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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

Oct 11

MSN7:59 amMadison Truax Field

3h 48m

1 stop

MDW11:47 amChicago Midway

Oct 17

MDW12:27 pmChicago Midway

6h 39m

1 stop

MSN7:06 pmMadison Truax Field

$1,143

Delta

Oct 13

MSN7:59 amMadison Truax Field

3h 48m

1 stop

MDW11:47 amChicago Midway

Oct 27

MDW12:27 pmChicago Midway

6h 39m

1 stop

MSN7:06 pmMadison Truax Field

$1,163

Delta

Oct 9

MSN6:00 amMadison Truax Field

5h 47m

1 stop

MDW11:47 amChicago Midway

Oct 16

MDW10:03 amChicago Midway

4h 08m

1 stop

MSN2:11 pmMadison Truax Field

$1,183

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

Sun 11/22

6:00 pm-1:33 pm

2 stops19h 33m

Chicago Midway

Mon 11/30

8:42 pm-9:50 am

1 stop13h 08m

$564

MadisonChicago

MSN Madison Truax Field - MDW Chicago Midway

MSNMDW

Madison Truax Field

Sun 11/22

6:00 pm-7:47 pm

1 stop25h 47m

Chicago Midway

Mon 11/30

8:42 pm-9:50 am

1 stop13h 08m

$581

MadisonChicago

MSN Madison Truax Field - MDW Chicago Midway

MSNMDW

Madison Truax Field

Tue 10/13

7:59 am-11:47 am

1 stop3h 48m

Chicago Midway

Tue 10/27

12:27 pm-7:06 pm

1 stop6h 39m

$1,163

MadisonChicago

MSN Madison Truax Field - MDW Chicago Midway

MSNMDW

Madison Truax Field

Sun 10/11

6:00 am-11:47 am

1 stop5h 47m

Chicago Midway

Sat 10/17

10:12 am-2:11 pm

1 stop3h 59m

$1,183

MadisonChicago

MSN Madison Truax Field - MDW Chicago Midway

MSNMDW

Madison Truax Field

Fri 10/16

10:53 am-4:47 pm

1 stop5h 54m

Chicago Midway

Sun 10/18

10:12 am-2:11 pm

1 stop3h 59m

$1,333

MadisonChicago

MSN Madison Truax Field - MDW Chicago Midway

MSNMDW

Madison Truax Field

Sat 12/19

10:59 am-5:24 pm

1 stop6h 25m

Chicago Midway

Tue 12/29

6:20 pm-10:08 pm

1 stop3h 48m

$1,383

MadisonChicago

MSN Madison Truax Field - MDW Chicago Midway

MSNMDW

Madison Truax Field

Tue 12/8

1:26 pm-6:01 pm

1 stop4h 35m

Chicago Midway

Thu 12/10

12:39 pm-7:16 pm

1 stop6h 37m

$1,408

Quickest round-trip

MadisonChicago

MSN Madison Truax Field - MDW Chicago Midway

MSNMDW

Madison Truax Field

Tue 9/29

2:47 pm-6:19 pm

1 stop3h 32m

Chicago Midway

Sat 10/3

9:59 am-2:07 pm

1 stop4h 08m

$1,443

MadisonChicago

MSN Madison Truax Field - MDW Chicago Midway

MSNMDW

Madison Truax Field

Sun 9/27

12:00 pm-6:19 pm

1 stop6h 19m

Chicago Midway

Thu 10/1

9:59 am-2:07 pm

1 stop4h 08m

$1,463

MadisonChicago

MSN Madison Truax Field - MDW Chicago Midway

MSNMDW

Madison Truax Field

Sat 11/21

6:30 am-11:50 am

1 stop5h 20m

Chicago Midway

Sun 11/29

1:31 pm-5:35 pm

1 stop4h 04m

$1,647

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted 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

Best Price Found	$191
Fastest flight time	3h 32m
Direct flights	None

The best one-way flight to Chicago Midway Airport from Madison in the past 72 hours is $191. The best round-trip flight deal from Madison to Chicago Midway Airport found on momondo in the last 72 hours is $564.

The fastest flight from Madison to Chicago Midway Airport takes 3h 32m

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 32m.
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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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.