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Cheap flights from Madison to Chicago from $95

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 3/18. 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 from Madison to Chicago

The cheapest plane tickets from Madison to Chicago found on KAYAK recently.
4:12 pm - 5:11 pmMSN-ORD
0h 59mnonstop
1:12 pm - 2:07 pmORD-MSN
0h 55mnonstop
$219American Airlines
Find Deal
sáb., feb. 15 - jue., feb. 20
6:30 am - 7:43 amMSN-ORD
1h 13mnonstop
10:50 am - 11:54 amORD-MSN
1h 04mnonstop
$249United Airlines
Find Deal
mar., feb. 4 - sáb., feb. 8
5:30 pm - 6:39 pmMSN-ORD
1h 09mnonstop
3:35 pm - 4:44 pmORD-MSN
1h 09mnonstop
$321United Airlines
Find Deal
sáb., abr. 19 - dom., abr. 27
3:53 pm - 5:05 pmMSN-ORD
1h 12mnonstop
8:52 am - 10:09 amORD-MSN
1h 17mnonstop
$359United Airlines
Find Deal
mié., feb. 5 - dom., feb. 9
4:00 pm - 9:38 amMSN-ORD
17h 38m1 stop
10:50 am - 11:54 amORD-MSN
1h 04mnonstop
$398United Airlines
Find Deal
mar., feb. 4 - sáb., feb. 8
6:15 am - 7:22 amMSN-ORD
1h 07mnonstop
12:45 pm - 1:44 pmORD-MSN
0h 59mnonstop
$399United Airlines
Find Deal
sáb., mar. 22 - sáb., mar. 29
6:30 am - 7:33 amMSN-ORD
1h 03mnonstop
9:40 pm - 2:05 pmORD-MSN
16h 25m1 stop
$416United Airlines
Find Deal
vie., may. 16 - sáb., may. 24
3:05 pm - 9:34 amMSN-ORD
18h 29m1 stop
8:05 pm - 9:11 pmORD-MSN
1h 06mnonstop
$432United Airlines
Find Deal
sáb., feb. 15 - jue., feb. 20
6:38 pm - 7:49 pmMSN-ORD
1h 11mnonstop
8:40 pm - 9:50 pmORD-MSN
1h 10mnonstop
$469American Airlines
Find Deal
lun., feb. 3 - lun., feb. 10
6:16 pm - 11:42 amMSN-ORD
17h 26m2 stops
5:45 am - 6:21 pmORD-MSN
12h 36m1 stop
sáb., feb. 15 - jue., feb. 20
6:48 pm - 7:45 pmMSN-ORD
0h 57mnonstop
$95American Airlines
Find Deal
mar., mar. 18
8:00 am - 9:01 amMSN-ORD
1h 01mnonstop
$97American Airlines
Find Deal
mar., abr. 15
2:20 pm - 3:25 pmMSN-ORD
1h 05mnonstop
$125United Airlines
Find Deal
mar., feb. 18
6:27 pm - 7:29 pmMSN-ORD
1h 02mnonstop
$126American Airlines
Find Deal
jue., feb. 20
5:26 pm - 6:35 pmMSN-ORD
1h 09mnonstop
$155United Airlines
Find Deal
dom., feb. 23
8:10 am - 9:10 amMSN-ORD
1h 00mnonstop
$159American Airlines
Find Deal
dom., jul. 20
9:48 am - 10:29 pmMSN-ORD
12h 41m1 stop
sáb., abr. 19
5:48 pm - 8:36 amMSN-MDW
14h 48m1 stop
$257Delta
Find Deal
sáb., jun. 7
2:57 pm - 8:59 amMSN-ORD
18h 02m1 stop
$257Delta
Find Deal
sáb., feb. 22
4:20 pm - 8:13 pmMSN-ORD
27h 53m3 stops
lun., feb. 3
6:40 pm - 9:39 amMSN-ORD
14h 59m1 stop
5:35 am - 6:16 pmORD-MSN
12h 41m1 stop
dom., ene. 26 - dom., feb. 2
6:40 pm - 9:39 amMSN-ORD
14h 59m1 stop
5:35 am - 6:16 pmORD-MSN
12h 41m1 stop
dom., ene. 26 - dom., feb. 2
5:30 am - 6:41 amMSN-ORD
1h 11mnonstop
10:11 am - 11:13 amORD-MSN
1h 02mnonstop
$469American Airlines
Find Deal
dom., ene. 26 - dom., feb. 2
10:38 am - 11:50 amMSN-ORD
1h 12mnonstop
10:11 am - 11:13 amORD-MSN
1h 02mnonstop
$514American Airlines
Find Deal
sáb., ene. 25 - dom., ene. 26
6:30 am - 7:43 amMSN-ORD
1h 13mnonstop
5:50 pm - 2:07 pmORD-MSN
20h 17m1 stop
$532United Airlines
Find Deal
dom., ene. 26 - dom., feb. 2
6:40 pm - 11:34 pmMSN-ORD
28h 54m3 stops
5:35 am - 6:16 pmORD-MSN
12h 41m1 stop
dom., ene. 26 - dom., feb. 2
3:53 pm - 5:05 pmMSN-ORD
1h 12mnonstop
8:05 pm - 2:07 pmORD-MSN
18h 02m1 stop
$592United Airlines
Find Deal
dom., ene. 26 - dom., feb. 2
12:40 pm - 1:52 pmMSN-ORD
1h 12mnonstop
8:05 pm - 2:07 pmORD-MSN
18h 02m1 stop
$612United Airlines
Find Deal
sáb., ene. 25 - dom., ene. 26
9:48 am - 11:32 pmMSN-ORD
13h 44m2 stops
5:35 am - 5:46 pmORD-MSN
12h 11m1 stop
sáb., ene. 25 - dom., ene. 26
4:26 pm - 9:38 amMSN-ORD
17h 12m1 stop
5:50 pm - 2:07 pmORD-MSN
20h 17m1 stop
$772United Airlines
Find Deal
sáb., ene. 25 - dom., ene. 26
4:12 pm - 5:11 pmMSN-ORD
0h 59mnonstop
1:12 pm - 2:07 pmORD-MSN
0h 55mnonstop
$219American Airlines
Find Deal
sáb., feb. 15 - jue., feb. 20
6:30 am - 7:43 amMSN-ORD
1h 13mnonstop
10:50 am - 11:54 amORD-MSN
1h 04mnonstop
$249United Airlines
Find Deal
mar., feb. 4 - sáb., feb. 8
5:30 pm - 6:39 pmMSN-ORD
1h 09mnonstop
3:35 pm - 4:44 pmORD-MSN
1h 09mnonstop
$321United Airlines
Find Deal
sáb., abr. 19 - dom., abr. 27
3:53 pm - 5:05 pmMSN-ORD
1h 12mnonstop
8:52 am - 10:09 amORD-MSN
1h 17mnonstop
$359United Airlines
Find Deal
mié., feb. 5 - dom., feb. 9
6:15 am - 7:22 amMSN-ORD
1h 07mnonstop
12:45 pm - 1:44 pmORD-MSN
0h 59mnonstop
$399United Airlines
Find Deal
sáb., mar. 22 - sáb., mar. 29
6:38 pm - 7:49 pmMSN-ORD
1h 11mnonstop
8:40 pm - 9:50 pmORD-MSN
1h 10mnonstop
$469American Airlines
Find Deal
lun., feb. 3 - lun., feb. 10

American Airlines flights from Madison to Chicago

Our best American Airlines deals on Madison to Chicago flight tickets
American Airlines
Feb 15
MSN4:12 pmMadison Truax Field
0h 59m
ORD5:11 pmChicago O'Hare Intl
Feb 20
ORD1:12 pmChicago O'Hare Intl
0h 55m
MSN2:07 pmMadison Truax Field
American Airlines
Jan 29
MSN5:30 amMadison Truax Field
1h 11m
ORD6:41 amChicago O'Hare Intl
Feb 5
ORD5:07 pmChicago O'Hare Intl
1h 01m
MSN6:08 pmMadison Truax Field
American Airlines
Feb 1
MSN7:10 amMadison Truax Field
7h 05m
1 stop
ORD2:15 pmChicago O'Hare Intl
Feb 8
ORD10:11 amChicago O'Hare Intl
1h 02m
MSN11:13 amMadison Truax Field

United Airlines flights from Madison to Chicago

Our best United Airlines deals on Madison to Chicago flight tickets
United Airlines
Feb 4
MSN6:30 amMadison Truax Field
1h 13m
ORD7:43 amChicago O'Hare Intl
Feb 8
ORD10:50 amChicago O'Hare Intl
1h 04m
MSN11:54 amMadison Truax Field
United Airlines
Apr 19
MSN5:30 pmMadison Truax Field
1h 09m
ORD6:39 pmChicago O'Hare Intl
Apr 27
ORD3:35 pmChicago O'Hare Intl
1h 09m
MSN4:44 pmMadison Truax Field
United Airlines
Feb 5
MSN3:53 pmMadison Truax Field
1h 12m
ORD5:05 pmChicago O'Hare Intl
Feb 9
ORD8:52 amChicago O'Hare Intl
1h 17m
MSN10:09 amMadison 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.

How have Madison to Chicago flight prices changed over time?

As of January 2025, prices for Madison to Chicago flights are approximately 41% 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

$95

Fastest flight time

0h 57m

Direct flights

Mon, Tue, Wed, Thu, Fri and Sun

Airports in Chicago

2 airports
The best one-way flight to Chicago from Madison in the past 72 hours is $95. The best round-trip flight deal from Madison to Chicago found on momondo in the last 72 hours is $219.
The fastest flight from Madison to Chicago takes 0h 57m
Direct flights go from Madison to Chicago on Monday, Tuesday, Wednesday, Thursday, Friday and Sunday. 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 0h 59m.

  • 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 $178Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $178Free CancellationRating
7.4
8,985 reviews
Search United Airlines flights
  • United Airlines Flights From Madison to Chicago

    Across 30 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. 8,984 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 22 times per week, with deals starting from $178 round-trip and rising to an average price of around $278.


Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
New Buffalo
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Munster
Crown Point
Schererville
Monticello
Chesterton
Porter
Griffith
Saint John

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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago