Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Madison from $129

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Madison departing on 10/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago to Madison

Cheap round-trip flights

American Airlines Logo
12:40 pm - 1:44 pmORD-MSN
1h 04mnonstop
American Airlines Logo
8:25 pm - 9:30 pmMSN-ORD
1h 05mnonstop
$179American Airlines
Find Deal
Sat, Oct 11 - Sun, Oct 12
American Airlines Logo
12:40 pm - 1:44 pmORD-MSN
1h 04mnonstop
American Airlines Logo
8:25 pm - 9:30 pmMSN-ORD
1h 05mnonstop
$180American Airlines
Find Deal
Sat, Oct 11 - Sun, Oct 12
United Airlines Logo
4:50 pm - 5:50 pmORD-MSN
1h 00mnonstop
United Airlines Logo
6:30 am - 7:41 amMSN-ORD
1h 11mnonstop
$204United Airlines
Find Deal
Fri, Nov 7 - Sun, Nov 9
United Airlines Logo
6:15 pm - 7:21 pmORD-MSN
1h 06mnonstop
United Airlines Logo
8:25 am - 9:36 amMSN-ORD
1h 11mnonstop
$241United Airlines
Find Deal
Fri, Nov 14 - Sat, Nov 22
Multiple Airlines Logo
6:18 pm - 9:08 amORD-MSN
14h 50m1 stop
Multiple Airlines Logo
7:59 pm - 12:12 amMSN-ORD
28h 13m1 stop
$251Multiple Airlines
Find Deal
Fri, Oct 17 - Mon, Oct 27
Multiple Airlines Logo
12:48 pm - 9:08 amORD-MSN
20h 20m2 stops
Multiple Airlines Logo
7:59 pm - 12:12 amMSN-ORD
28h 13m1 stop
$276Multiple Airlines
Find Deal
Fri, Oct 17 - Mon, Oct 27
Frontier Logo
6:00 am - 7:14 pmORD-MSN
13h 14m1 stop
Frontier Logo
7:59 pm - 11:59 pmMSN-ORD
28h 00m1 stop
$381Frontier
Find Deal
Sun, Sep 28 - Sun, Oct 5
Frontier Logo
11:36 am - 7:14 pmORD-MSN
31h 38m2 stops
Frontier Logo
7:59 pm - 9:37 amMSN-ORD
13h 38m1 stop
$421Frontier
Find Deal
Sun, Sep 28 - Sun, Oct 5
Delta Logo
1:25 pm - 8:21 pmORD-MSN
6h 56m1 stop
Delta Logo
7:00 am - 4:11 pmMSN-ORD
9h 11m1 stop
$476Delta
Find Deal
Sat, Oct 11 - Sun, Oct 12
Delta Logo
9:20 am - 10:08 pmMDW-MSN
12h 48m1 stop
Delta Logo
10:55 am - 6:08 pmMSN-MDW
7h 13m1 stop
$560Delta
Find Deal
Sat, Mar 14 - Tue, Mar 17

American Airlines flights from Chicago to Madison

Our best American Airlines deals on Chicago to Madison flight tickets
American Airlines
Oct 11
ORD12:40 pmChicago O'Hare Intl
1h 04m
MSN1:44 pmMadison Truax Field
Oct 12
MSN8:25 pmMadison Truax Field
1h 05m
ORD9:30 pmChicago O'Hare Intl
$179
Find similar
American Airlines
Oct 11
ORD12:40 pmChicago O'Hare Intl
1h 04m
MSN1:44 pmMadison Truax Field
Oct 12
MSN8:25 pmMadison Truax Field
1h 05m
ORD9:30 pmChicago O'Hare Intl
$180
Find similar
American Airlines
Sep 28
ORD8:47 amChicago O'Hare Intl
1h 12m
MSN9:59 amMadison Truax Field
Oct 5
MSN8:18 pmMadison Truax Field
1h 09m
ORD9:27 pmChicago O'Hare Intl
$184
Find similar

Delta flights from Chicago to Madison

Our best Delta deals on Chicago to Madison flight tickets
Delta
Oct 11
ORD1:25 pmChicago O'Hare Intl
6h 56m
1 stop
MSN8:21 pmMadison Truax Field
Oct 12
MSN7:00 amMadison Truax Field
9h 11m
1 stop
ORD4:11 pmChicago O'Hare Intl
$476
Find similar
Delta
Mar 14
MDW9:20 amChicago Midway
12h 48m
1 stop
MSN10:08 pmMadison Truax Field
Mar 17
MSN10:55 amMadison Truax Field
7h 13m
1 stop
MDW6:08 pmChicago Midway
$560
Find similar
Delta
Mar 14
MDW9:30 amChicago Midway
12h 38m
2 stops
MSN10:08 pmMadison Truax Field
Mar 17
MSN6:15 amMadison Truax Field
11h 53m
1 stop
MDW6:08 pmChicago Midway
$565
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Madison that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated September 17, 2025.
Use the filters below to find and compare flights from Chicago to Madison that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sat 10/11

12:40 pm-1:44 pm

Nonstop1h 04m

Madison Truax Field

Sun 10/12

8:25 pm-9:30 pm

Nonstop1h 05m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sat 10/11

12:40 pm-1:44 pm

Nonstop1h 04m

Madison Truax Field

Sun 10/12

8:25 pm-9:30 pm

Nonstop1h 05m

$180

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 11/7

4:50 pm-5:50 pm

Nonstop1h 00m

Madison Truax Field

Sun 11/9

6:30 am-7:41 am

Nonstop1h 11m

$204

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 11/14

6:15 pm-7:21 pm

Nonstop1h 06m

Madison Truax Field

Sat 11/22

8:25 am-9:36 am

Nonstop1h 11m

$241

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 10/17

6:18 pm-9:08 am

1 stop14h 50m

Madison Truax Field

Mon 10/27

7:59 pm-12:12 am

1 stop28h 13m

$251

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 10/17

12:48 pm-9:08 am

2 stops20h 20m

Madison Truax Field

Mon 10/27

7:59 pm-12:12 am

1 stop28h 13m

$276

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sun 9/28

6:00 am-7:14 pm

1 stop13h 14m

Madison Truax Field

Sun 10/5

7:59 pm-11:59 pm

1 stop28h 00m

$381

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sun 9/28

11:36 am-7:14 pm

2 stops31h 38m

Madison Truax Field

Sun 10/5

7:59 pm-9:37 am

1 stop13h 38m

$421

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sat 10/11

1:25 pm-8:21 pm

1 stop6h 56m

Madison Truax Field

Sun 10/12

7:00 am-4:11 pm

1 stop9h 11m

$476

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Sat 3/14

9:20 am-10:08 pm

1 stop12h 48m

Madison Truax Field

Tue 3/17

10:55 am-6:08 pm

1 stop7h 13m

$560

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Madison from

How to get the cheapest flight ticket from Chicago to Madison

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 month to fly to Madison?

The month of December is, on average, the cheapest month to fly to Madison from Chicago, with most prices found around $219. If you’re not able to fly to Madison in December, then July is your next best option. Flight prices from Chicago to Madison during July average around $255.

What is the cheapest day to depart on your flight to Madison?

The cheapest day to depart from Chicago to Madison is on a Friday when prices can be found for as low as $239. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Madison on Sunday is $391.

What is the cheapest time of day to depart on your flight to Madison?

According to our data, the cheapest time of day to fly to Madison is at noon. momondo users have found flights departing from Chicago to Madison at noon for as low as $246. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Madison is in the evening when prices are around $312.

What is the cheapest Chicago to Madison Truax Field flight route?

Fly from Chicago O'Hare Intl to Madison Truax Field for the best Chicago - Madison Truax Field flight prices

What cabin class options are available on Chicago to Madison Truax Field flights?

There are 3 cabin classes available to choose from on Chicago to Madison Truax Field flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Chicago to Madison flight prices changed over time?

As of September 2025, prices for Chicago to Madison flights are approximately 178% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Madison

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Madison according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Madison (CHI to MSN) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Madison

Best Price Found

$218

Fastest flight time

0h 56m

Direct flights

Every day

Airports in Madison

1 airport
The best one-way flight to Madison from Chicago in the past 72 hours is $218. The best round-trip flight deal from Chicago to Madison found on momondo in the last 72 hours is $298.
The fastest flight from Chicago to Madison takes 0h 56m
Direct flights go from Chicago to Madison every day.
There is 1 airport near Madison: Madison Truax Field (MSN)
Search flight deals

  • How far is Chicago to Madison Truax Field by plane?

    Chicago and Madison Truax Field are 122.4 mi apart from one another. Typically, this will take 0h 56m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago to Madison Truax Field Airport?

    Prices for flights from Chicago to Madison Truax Field Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago to Madison Truax Field Airport?

  • How old do you have to be to fly from Chicago to Madison Truax Field 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 Chicago to Madison Truax Field Airport.

  • What documentation or ID do you need to fly to Madison Truax Field Airport?

    The required travel and health documents for your Madison Truax Field Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Madison Truax Field Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Chicago to Madison?

  • What is the most popular airline from Chicago to Madison?

Best airlines flying from Chicago to Madison

Compare and see reviews for airlines that fly from Chicago to Madison with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $199Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights

  • United Airlines Flights From Chicago to Madison

    Across 40 United Airlines flights from Chicago to Madison this week, the average price was $283, with the best United Airlines deals starting from $199 round-trip. 8,926 users have rated United Airlines on momondo, with an average score of 7.4/10.

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Wisconsin Dells
Baraboo
Middleton
Portage
Fitchburg
Sun Prairie
Cambridge
Oxford
Windsor
Evansville

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Madison?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Madison. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Madison with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Madison flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Madison?

momondo helps you find the best flight between Chicago and Madison by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Madison right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Madison flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Madison trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 10/17
Fri 10/24
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States