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Cheap flights from Chicago to Madison from $125

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 1/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago to Madison

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Madison that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Madison.

Cheap last minute flights

Planning a quick getaway from Chicago to Madison? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Madison, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Madison

Find recent round-trip train or bus tickets from Chicago to Madison.

All round-trip flight deals to Madison

The cheapest plane tickets to Madison found on KAYAK recently.
12:40 pm - 1:46 pmORD-MSN
1h 06mnonstop
3:30 pm - 4:41 pmMSN-ORD
1h 11mnonstop
$249American Airlines
Find Deal
Thu, Jan 9 - Sun, Jan 12
10:11 am - 11:13 amORD-MSN
1h 02mnonstop
10:38 am - 11:50 amMSN-ORD
1h 12mnonstop
$251American Airlines
Find Deal
Sat, Feb 1 - Sat, Feb 8
9:55 am - 11:00 amORD-MSN
1h 05mnonstop
4:52 pm - 5:50 pmMSN-ORD
0h 58mnonstop
$283American Airlines
Find Deal
Thu, Apr 3 - Fri, Apr 4
8:00 am - 5:06 pmORD-MSN
9h 06m1 stop
5:46 pm - 11:20 amMSN-ORD
17h 34m1 stop
Wed, Jan 15 - Wed, Jan 22
6:15 pm - 12:08 pmORD-MSN
17h 53m1 stop
6:40 pm - 9:39 amMSN-ORD
14h 59m1 stop
Thu, Jan 9 - Sun, Jan 12
8:00 am - 5:06 pmORD-MSN
9h 06m1 stop
5:46 pm - 12:39 pmMSN-ORD
18h 53m2 stops
Wed, Jan 15 - Wed, Jan 22
7:10 am - 9:27 pmORD-MSN
14h 17m1 stop
3:53 pm - 5:05 pmMSN-ORD
1h 12mnonstop
$403United Airlines
Find Deal
Sat, Feb 1 - Sat, Feb 8
8:52 am - 10:09 amORD-MSN
1h 17mnonstop
4:00 pm - 9:38 amMSN-ORD
17h 38m1 stop
$407United Airlines
Find Deal
Wed, Jan 15 - Wed, Jan 22
10:50 am - 11:54 amORD-MSN
1h 04mnonstop
4:26 pm - 9:38 amMSN-ORD
17h 12m1 stop
$441United Airlines
Find Deal
Thu, Jan 9 - Sun, Jan 12
8:20 pm - 9:28 pmORD-MSN
1h 08mnonstop
3:20 pm - 9:34 amMSN-ORD
18h 14m1 stop
$450United Airlines
Find Deal
Thu, Apr 3 - Fri, Apr 4
10:11 am - 11:13 amORD-MSN
1h 02mnonstop
$125American Airlines
Find Deal
Fri, Jan 17
10:50 am - 11:54 amORD-MSN
1h 04mnonstop
$155United Airlines
Find Deal
Tue, Jan 21
10:50 am - 11:54 amORD-MSN
1h 04mnonstop
$189United Airlines
Find Deal
Thu, Jan 16
1:55 pm - 2:56 pmORD-MSN
1h 01mnonstop
$197United Airlines
Find Deal
Sat, Feb 15
8:52 am - 10:09 amORD-MSN
1h 17mnonstop
$200United Airlines
Find Deal
Sat, Jan 18
2:10 pm - 3:15 pmORD-MSN
1h 05mnonstop
$210United Airlines
Find Deal
Sun, Jan 5
1:20 pm - 2:29 pmORD-MSN
1h 09mnonstop
$230American Airlines
Find Deal
Sat, Dec 28
1:40 pm - 8:58 amORD-MSN
19h 18m1 stop
$307Delta
Find Deal
Fri, Jan 17
4:15 pm - 10:18 amORD-MSN
18h 03m1 stop
$318Delta
Find Deal
Sat, Feb 15
8:03 pm - 5:41 pmORD-MSN
21h 38m2 stops
$565Sun Country Air
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Sat, Dec 28
5:13 pm - 6:11 pmORD-MSN
0h 58mnonstop
2:54 pm - 4:05 pmMSN-ORD
1h 11mnonstop
$504American Airlines
Find Deal
Sat, Dec 21 - Sat, Dec 28
1:20 pm - 2:29 pmORD-MSN
1h 09mnonstop
6:00 am - 7:06 amMSN-ORD
1h 06mnonstop
$549American Airlines
Find Deal
Fri, Dec 20 - Sun, Dec 22
6:05 am - 5:41 pmORD-MSN
11h 36m1 stop
4:00 pm - 12:47 amMSN-ORD
8h 47m1 stop
Sun, Dec 22 - Mon, Dec 23
6:05 am - 5:41 pmORD-MSN
11h 36m1 stop
4:00 pm - 9:03 amMSN-ORD
17h 03m2 stops
Sun, Dec 22 - Mon, Dec 23
11:45 am - 1:55 pmORD-MSN
26h 10m3 stops
4:00 pm - 12:47 amMSN-ORD
8h 47m1 stop
Sun, Dec 22 - Mon, Dec 23
11:45 am - 1:55 pmORD-MSN
26h 10m3 stops
4:00 pm - 9:03 amMSN-ORD
17h 03m2 stops
Sun, Dec 22 - Mon, Dec 23
8:30 am - 5:11 pmORD-MSN
8h 41m1 stop
12:30 pm - 12:47 amMSN-ORD
12h 17m1 stop
Sat, Dec 21 - Sat, Dec 28
9:40 pm - 1:37 pmORD-MSN
15h 57m1 stop
12:15 pm - 1:28 pmMSN-ORD
1h 13mnonstop
$1,009United Airlines
Find Deal
Sat, Dec 21 - Sat, Dec 28
3:35 pm - 4:40 pmORD-MSN
1h 05mnonstop
2:45 pm - 11:59 pmMSN-ORD
9h 14m1 stop
$1,054United Airlines
Find Deal
Fri, Dec 20 - Sun, Dec 22
2:10 pm - 3:15 pmORD-MSN
1h 05mnonstop
8:21 am - 9:30 pmMSN-ORD
13h 09m1 stop
$1,078United Airlines
Find Deal
Sun, Dec 22 - Mon, Dec 23
12:40 pm - 1:46 pmORD-MSN
1h 06mnonstop
3:30 pm - 4:41 pmMSN-ORD
1h 11mnonstop
$249American Airlines
Find Deal
Thu, Jan 9 - Sun, Jan 12
10:11 am - 11:13 amORD-MSN
1h 02mnonstop
10:38 am - 11:50 amMSN-ORD
1h 12mnonstop
$251American Airlines
Find Deal
Sat, Feb 1 - Sat, Feb 8
9:55 am - 11:00 amORD-MSN
1h 05mnonstop
4:52 pm - 5:50 pmMSN-ORD
0h 58mnonstop
$283American Airlines
Find Deal
Thu, Apr 3 - Fri, Apr 4
10:50 am - 11:54 amORD-MSN
1h 04mnonstop
6:30 am - 7:43 amMSN-ORD
1h 13mnonstop
$510United Airlines
Find Deal
Sun, Feb 2 - Sun, Feb 9

American Airlines flights from Chicago to Madison

Our best American Airlines deals on Chicago to Madison flight tickets
American Airlines
Jan 9
ORD12:40 pmChicago O'Hare Intl
1h 06m
MSN1:46 pmMadison Truax Field
Jan 12
MSN3:30 pmMadison Truax Field
1h 11m
ORD4:41 pmChicago O'Hare Intl
American Airlines
Feb 1
ORD10:11 amChicago O'Hare Intl
1h 02m
MSN11:13 amMadison Truax Field
Feb 8
MSN10:38 amMadison Truax Field
1h 12m
ORD11:50 amChicago O'Hare Intl
American Airlines
Apr 3
ORD9:55 amChicago O'Hare Intl
1h 05m
MSN11:00 amMadison Truax Field
Apr 4
MSN4:52 pmMadison Truax Field
0h 58m
ORD5:50 pmChicago O'Hare Intl

United Airlines flights from Chicago to Madison

Our best United Airlines deals on Chicago to Madison flight tickets
United Airlines
Feb 1
ORD7:10 amChicago O'Hare Intl
14h 17m
1 stop
MSN9:27 pmMadison Truax Field
Feb 8
MSN3:53 pmMadison Truax Field
1h 12m
ORD5:05 pmChicago O'Hare Intl
United Airlines
Jan 15
ORD8:52 amChicago O'Hare Intl
1h 17m
MSN10:09 amMadison Truax Field
Jan 22
MSN4:00 pmMadison Truax Field
17h 38m
1 stop
ORD9:38 amChicago O'Hare Intl
United Airlines
Jan 9
ORD10:50 amChicago O'Hare Intl
1h 04m
MSN11:54 amMadison Truax Field
Jan 12
MSN4:26 pmMadison Truax Field
17h 12m
1 stop
ORD9:38 amChicago O'Hare Intl

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 day to depart on your flight to Madison?

The cheapest day to depart from Chicago to Madison is on a Monday when prices can be found for as low as $248. Be sure to avoid booking your departure on a Friday as prices are generally higher than usual. According to our data, the average ticket price to Madison on Friday is $288.

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 in the evening. momondo users have found flights departing from Chicago to Madison in the evening for as low as $244. 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 morning when prices are around $368.

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 4 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.

Can stopping save me money on Chicago to Madison flights?

You could potentially save up to 145% on your flight if you consider stops on a Chicago to Madison flight.

How have Chicago to Madison flight prices changed over time?

As of December 2024, prices for Chicago to Madison flights are approximately 139% 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

$125

Fastest flight time

1h 00m

Direct flights

Mon, Tue, Wed, Fri, Sat and Sun

Airports in Madison

1 airport
The best one-way flight to Madison from Chicago in the past 72 hours is $125. The best round-trip flight deal from Chicago to Madison found on momondo in the last 72 hours is $249.
The fastest flight from Chicago to Madison takes 1h 00m
Direct flights go from Chicago to Madison on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. Airlines offering direct flights are: United Airlines and American Airlines.
There is 1 airport near Madison: Madison Truax Field (MSN)

  • 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 1h 02m 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 $169Free CancellationRating
7.4
9,048 reviews
Search United Airlines flights
American AirlinesPriceFrom $176Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
  • United Airlines Flights From Chicago to Madison

    Across 13 United Airlines flights from Chicago to Madison this week, the average price was $339, with the best United Airlines deals starting from $169 round-trip. 9,048 users have rated United Airlines on momondo, with an average score of 7.4/10.

  • American Airlines Flights From Chicago to Madison

    American Airlines is also a popular choice for this route. American Airlines flight deals for Chicago to Madison start from as low as $176 round-trip, depending on your selected dates, with average American Airlines deals seen on momondo around $279. American Airlines operates 7 flights to Madison from Chicago in an average week. Users have rated it 7.2/10 across 10,000 reviews.


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.


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