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Cheap flights from Madison to Chicago 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 Madison to Chicago 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 Madison to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Madison to Chicago 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 Madison to Chicago.

Cheap last minute flights

Planning a quick getaway from Madison to Chicago? 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 Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Madison to Chicago

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

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
6:27 pm - 7:35 pmMSN-ORD
1h 08mnonstop
5:07 pm - 6:08 pmORD-MSN
1h 01mnonstop
$249American Airlines
Find Deal
Thu, Jan 30 - Mon, Feb 3
3:53 pm - 5:05 pmMSN-ORD
1h 12mnonstop
3:45 pm - 4:48 pmORD-MSN
1h 03mnonstop
$309United Airlines
Find Deal
Thu, Jan 30 - Mon, Feb 3
6:19 am - 7:32 amMSN-ORD
1h 13mnonstop
10:50 am - 11:54 amORD-MSN
1h 04mnonstop
$384United Airlines
Find Deal
Wed, Jan 1 - Tue, Jan 7
6:35 am - 9:15 pmMSN-ORD
14h 40m2 stops
10:10 am - 10:37 pmORD-MSN
12h 27m1 stop
$387Delta
Find Deal
Thu, Jan 30 - Mon, Feb 3
8:12 am - 9:25 amMSN-ORD
1h 13mnonstop
5:50 pm - 1:17 pmORD-MSN
19h 27m1 stop
$407United Airlines
Find Deal
Thu, Jan 30 - Mon, Feb 3
6:35 am - 3:30 pmMSN-ORD
8h 55m1 stop
10:10 am - 5:36 pmORD-MSN
7h 26m1 stop
$409Delta
Find Deal
Thu, Jan 30 - Mon, Feb 3
8:12 am - 9:25 amMSN-ORD
1h 13mnonstop
8:05 pm - 2:07 pmORD-MSN
18h 02m1 stop
$412United Airlines
Find Deal
Thu, Jan 30 - Sun, Feb 2
4:26 pm - 9:38 amMSN-ORD
17h 12m1 stop
8:00 pm - 9:03 pmORD-MSN
1h 03mnonstop
$416United Airlines
Find Deal
Sat, Jan 11 - Sun, Jan 26
6:00 am - 7:11 amMSN-ORD
1h 11mnonstop
8:40 pm - 10:00 pmORD-MSN
1h 20mnonstop
$419American Airlines
Find Deal
Tue, Dec 31 - Thu, Jan 2
6:35 am - 9:15 pmMSN-ORD
14h 40m2 stops
10:10 am - 5:40 pmORD-MSN
7h 30m1 stop
$441Delta
Find Deal
Thu, Jan 30 - Sun, Feb 2
3:30 pm - 4:41 pmMSN-ORD
1h 11mnonstop
$125American Airlines
Find Deal
Fri, Jan 17
12:40 pm - 1:52 pmMSN-ORD
1h 12mnonstop
$155United Airlines
Find Deal
Wed, Jan 15
12:40 pm - 1:52 pmMSN-ORD
1h 12mnonstop
$189United Airlines
Find Deal
Sun, Jan 19
6:30 am - 7:37 amMSN-ORD
1h 07mnonstop
$200United Airlines
Find Deal
Fri, Feb 14
12:33 pm - 1:44 pmMSN-ORD
1h 11mnonstop
$230American Airlines
Find Deal
Sun, Dec 29
5:45 am - 10:27 pmMSN-MDW
16h 42m1 stop
$347Delta
Find Deal
Wed, Mar 19
6:00 am - 2:15 pmMSN-MDW
8h 15m1 stop
$366Delta
Find Deal
Thu, Mar 20
2:44 pm - 12:23 amMSN-ORD
9h 39m1 stop
$431United Airlines
Find Deal
Thu, Mar 20
6:35 am - 9:15 pmMSN-ORD
14h 40m2 stops
$452Delta
Find Deal
Sat, Jan 18
6:40 pm - 6:38 pmMSN-ORD
23h 58m2 stops
$580Sun Country Air
Find Deal
Sun, Dec 29
12:33 pm - 1:44 pmMSN-ORD
1h 11mnonstop
12:40 pm - 1:46 pmORD-MSN
1h 06mnonstop
$429American Airlines
Find Deal
Sun, Dec 22 - Mon, Jan 13
2:54 pm - 4:05 pmMSN-ORD
1h 11mnonstop
4:40 pm - 5:38 pmORD-MSN
0h 58mnonstop
$504American Airlines
Find Deal
Mon, Dec 23 - Sun, Dec 29
5:00 am - 6:13 amMSN-ORD
1h 13mnonstop
4:08 pm - 1:17 pmORD-MSN
21h 09m1 stop
$531United Airlines
Find Deal
Sun, Dec 22 - Mon, Jan 13
12:33 pm - 1:44 pmMSN-ORD
1h 11mnonstop
10:05 am - 11:12 amORD-MSN
1h 07mnonstop
$549American Airlines
Find Deal
Sat, Dec 21 - Mon, Dec 23
4:00 pm - 12:47 amMSN-ORD
8h 47m1 stop
6:05 am - 5:41 pmORD-MSN
11h 36m1 stop
Mon, Dec 23 - Sun, Dec 29
4:00 pm - 12:47 amMSN-ORD
8h 47m1 stop
8:03 pm - 3:05 pmORD-MSN
19h 02m2 stops
Mon, Dec 23 - Sun, Dec 29
4:00 pm - 12:47 amMSN-ORD
8h 47m1 stop
8:03 pm - 3:05 pmORD-MSN
19h 02m3 stops
Mon, Dec 23 - Sun, Dec 29
12:15 pm - 1:28 pmMSN-ORD
1h 13mnonstop
9:40 pm - 1:37 pmORD-MSN
15h 57m1 stop
$814United Airlines
Find Deal
Sat, Dec 21 - Mon, Dec 23
4:00 pm - 9:03 amMSN-ORD
17h 03m2 stops
8:03 pm - 3:05 pmORD-MSN
19h 02m3 stops
Mon, Dec 23 - Sun, Dec 29
8:21 am - 11:10 pmMSN-ORD
14h 49m1 stop
2:10 pm - 3:15 pmORD-MSN
1h 05mnonstop
$1,054United Airlines
Find Deal
Mon, Dec 23 - Sun, Dec 29
6:27 pm - 7:35 pmMSN-ORD
1h 08mnonstop
5:07 pm - 6:08 pmORD-MSN
1h 01mnonstop
$249American Airlines
Find Deal
Thu, Jan 30 - Mon, Feb 3
3:53 pm - 5:05 pmMSN-ORD
1h 12mnonstop
3:45 pm - 4:48 pmORD-MSN
1h 03mnonstop
$309United Airlines
Find Deal
Thu, Jan 30 - Mon, Feb 3
6:19 am - 7:32 amMSN-ORD
1h 13mnonstop
10:50 am - 11:54 amORD-MSN
1h 04mnonstop
$384United Airlines
Find Deal
Wed, Jan 1 - Tue, Jan 7
6:00 am - 7:11 amMSN-ORD
1h 11mnonstop
8:40 pm - 10:00 pmORD-MSN
1h 20mnonstop
$419American Airlines
Find Deal
Tue, Dec 31 - Thu, Jan 2
6:03 pm - 7:12 pmMSN-ORD
1h 09mnonstop
8:40 pm - 10:00 pmORD-MSN
1h 20mnonstop
$459American Airlines
Find Deal
Sun, Dec 29 - Mon, Dec 30

American Airlines flights from Madison to Chicago

Our best American Airlines deals on Madison to Chicago flight tickets
American Airlines
Jan 30
MSN6:27 pmMadison Truax Field
1h 08m
ORD7:35 pmChicago O'Hare Intl
Feb 3
ORD5:07 pmChicago O'Hare Intl
1h 01m
MSN6:08 pmMadison Truax Field
American Airlines
Dec 31
MSN6:00 amMadison Truax Field
1h 11m
ORD7:11 amChicago O'Hare Intl
Jan 2
ORD8:40 pmChicago O'Hare Intl
1h 20m
MSN10:00 pmMadison Truax Field
American Airlines
Dec 22
MSN12:33 pmMadison Truax Field
1h 11m
ORD1:44 pmChicago O'Hare Intl
Jan 13
ORD12:40 pmChicago O'Hare Intl
1h 06m
MSN1:46 pmMadison Truax Field

United Airlines flights from Madison to Chicago

Our best United Airlines deals on Madison to Chicago flight tickets
United Airlines
Jan 30
MSN3:53 pmMadison Truax Field
1h 12m
ORD5:05 pmChicago O'Hare Intl
Feb 3
ORD3:45 pmChicago O'Hare Intl
1h 03m
MSN4:48 pmMadison Truax Field
United Airlines
Jan 1
MSN6:19 amMadison Truax Field
1h 13m
ORD7:32 amChicago O'Hare Intl
Jan 7
ORD10:50 amChicago O'Hare Intl
1h 04m
MSN11:54 amMadison Truax Field
United Airlines
Jan 30
MSN8:12 amMadison Truax Field
1h 13m
ORD9:25 amChicago O'Hare Intl
Feb 3
ORD5:50 pmChicago O'Hare Intl
19h 27m
1 stop
MSN1:17 pmMadison Truax Field

See travel insights to Chicago from

How to get the cheapest flight ticket from Madison to Chicago

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 Chicago?

The cheapest day to depart on your flight to Chicago is on a Monday when prices can be found for as low as $278. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Madison to Chicago for around $456.

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

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Madison to Chicago during this time can be as low as $226. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $408.

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

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

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

There are 4 cabin classes available to choose from on Madison Truax Field to Chicago 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 Madison to Chicago flights?

You could potentially save up to 177% on your flight if you consider stops on a Madison to Chicago flight.

How have Madison to Chicago flight prices changed over time?

As of December 2024, prices for Madison to Chicago flights are approximately 84% more expensive when compared to flights at the same time last year.

When to book flights from Madison to Chicago

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

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

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

Best Price Found

$125

Fastest flight time

1h 07m

Direct flights

Mon, Wed, Thu, Fri and Sat

Airports in Chicago

2 airports
The best one-way flight to Chicago from Madison in the past 72 hours is $125. The best round-trip flight deal from Madison to Chicago found on momondo in the last 72 hours is $249.
The fastest flight from Madison to Chicago takes 1h 07m
Direct flights go from Madison to Chicago on Monday, Wednesday, Thursday, Friday and Saturday. Airlines offering direct flights are: United Airlines and American Airlines.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

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

    Madison Truax Field and Chicago are 122.4 mi apart from one another. In terms of flight time, this usually takes a little over 1h 07m.

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

    Prices for flights from Madison Truax Field Airport to Chicago were last updated today.

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

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

    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.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

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


Best airlines flying from Madison to Chicago

Compare and see reviews for airlines that fly from Madison to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $176Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $178Free CancellationRating
7.4
9,055 reviews
Search United Airlines flights
  • United Airlines Flights From Madison to Chicago

    Across 16 United Airlines flights from Madison to Chicago this week, the average price was $304, with the best United Airlines deals starting from $178 round-trip. 9,059 users have rated United Airlines on momondo, with an average score of 7.4/10.

  • American Airlines Flights From Madison to Chicago

    Another popular option for Madison to Chicago flights is American Airlines (7.2/10, 10,000 ratings). American Airlines flies from Madison to Chicago around 7 times per week, with deals starting from $176 round-trip and rising to an average price of around $278.


Why use momondo?

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

Finding the right flight to Chicago from Madison is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

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

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?

Of course. momondo tracks the price of Madison to Chicago 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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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago