Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Madison to Chicago from $90

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 12/23. 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

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
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.

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
12:40 pm - 1:46 pmORD-MSN
1h 06mnonstop
$179American Airlines
Find Deal
Mon, Jan 13 - Thu, Jan 16
6:15 am - 7:22 amMSN-ORD
1h 07mnonstop
9:30 pm - 10:30 pmORD-MSN
1h 00mnonstop
$198United Airlines
Find Deal
Tue, Mar 11 - Tue, Mar 11
5:00 am - 6:13 amMSN-ORD
1h 13mnonstop
3:35 pm - 4:40 pmORD-MSN
1h 05mnonstop
$214United Airlines
Find Deal
Mon, Dec 23 - Mon, Dec 30
5:30 am - 6:33 amMSN-ORD
1h 03mnonstop
5:07 pm - 6:00 pmORD-MSN
0h 53mnonstop
$240American Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
12:33 pm - 1:46 pmMSN-ORD
1h 13mnonstop
5:07 pm - 6:00 pmORD-MSN
0h 53mnonstop
$244American Airlines
Find Deal
Wed, Dec 11 - Sun, Dec 15
5:54 pm - 11:57 pmMSN-ORD
6h 03m1 stop
8:55 am - 9:53 amORD-MSN
0h 58mnonstop
$249United Airlines
Find Deal
Tue, Apr 15 - Wed, Apr 30
12:15 pm - 1:28 pmMSN-ORD
1h 13mnonstop
8:00 pm - 9:03 pmORD-MSN
1h 03mnonstop
$274United Airlines
Find Deal
Sun, Dec 22 - Mon, Jan 13
5:53 pm - 6:55 pmMSN-ORD
1h 02mnonstop
10:05 am - 11:08 amORD-MSN
1h 03mnonstop
$279American Airlines
Find Deal
Mon, Dec 9 - Fri, Dec 13
5:30 am - 6:33 amMSN-ORD
1h 03mnonstop
3:45 pm - 4:38 pmORD-MSN
0h 53mnonstop
$281American Airlines
Find Deal
Tue, Dec 10 - Sat, Dec 14
1:05 pm - 4:08 pmMSN-ORD
27h 03m3 stops
5:35 am - 5:51 pmORD-MSN
12h 16m1 stop
Mon, Jan 13 - Thu, Jan 16
6:20 am - 7:33 amMSN-ORD
1h 13mnonstop
$90United Airlines
Find Deal
Mon, Dec 23
3:53 pm - 5:05 pmMSN-ORD
1h 12mnonstop
$109United Airlines
Find Deal
Fri, Feb 7
6:20 am - 7:33 amMSN-ORD
1h 13mnonstop
$120United Airlines
Find Deal
Mon, Dec 23
12:33 pm - 1:46 pmMSN-ORD
1h 13mnonstop
$125American Airlines
Find Deal
Mon, Dec 16
2:45 pm - 11:11 pmMSN-ORD
8h 26m1 stop
Mon, Dec 16
2:45 pm - 8:15 pmMSN-ORD
29h 30m3 stops
Mon, Dec 16
11:29 am - 12:39 pmMSN-ORD
1h 10mnonstop
$206American Airlines
Find Deal
Thu, Nov 28
4:00 pm - 9:03 amMSN-ORD
17h 03m2 stops
$368Sun Country Air
Find Deal
Mon, Dec 23
10:56 am - 4:52 pmMSN-ORD
5h 56m1 stop
$448Delta
Find Deal
Fri, Nov 29
10:56 am - 4:31 pmMSN-ORD
5h 35m2 stops
$453Delta
Find Deal
Thu, Nov 28
2:38 pm - 3:38 pmMSN-ORD
1h 00mnonstop
10:05 am - 11:06 amORD-MSN
1h 01mnonstop
$359American Airlines
Find Deal
Sun, Nov 24 - Wed, Dec 11
10:42 am - 11:55 amMSN-ORD
1h 13mnonstop
8:00 pm - 9:03 pmORD-MSN
1h 03mnonstop
$378United Airlines
Find Deal
Sat, Nov 23 - Mon, Feb 10
6:00 am - 1:11 pmMSN-ORD
7h 11m1 stop
1:55 pm - 2:49 pmORD-MSN
0h 54mnonstop
$434United Airlines
Find Deal
Sun, Nov 24 - Wed, Dec 11
2:38 pm - 3:38 pmMSN-ORD
1h 00mnonstop
8:57 pm - 9:59 pmORD-MSN
1h 02mnonstop
$479American Airlines
Find Deal
Sun, Nov 24 - Tue, Nov 26
6:30 am - 7:34 amMSN-ORD
1h 04mnonstop
8:05 pm - 1:17 pmORD-MSN
17h 12m1 stop
$483United Airlines
Find Deal
Sat, Nov 23 - Mon, Feb 10
5:38 pm - 6:51 pmMSN-ORD
1h 13mnonstop
3:45 pm - 10:55 pmORD-MSN
7h 10m1 stop
$489United Airlines
Find Deal
Sun, Nov 24 - Tue, Nov 26
6:00 am - 2:34 pmMSN-ORD
8h 34m1 stop
2:30 pm - 8:58 pmORD-MSN
6h 28m1 stop
$493United Airlines
Find Deal
Sun, Nov 24 - Wed, Dec 11
6:00 am - 2:34 pmMSN-ORD
8h 34m1 stop
2:36 pm - 10:55 pmORD-MSN
8h 19m1 stop
$498United Airlines
Find Deal
Sun, Nov 24 - Tue, Nov 26
2:35 pm - 11:38 pmMSN-ORD
9h 03m1 stop
11:51 am - 5:30 pmORD-MSN
29h 39m3 stops
Sun, Nov 24 - Tue, Nov 26
6:16 pm - 9:27 amMSN-ORD
15h 11m1 stop
7:05 am - 5:31 pmORD-MSN
10h 26m1 stop
$1,410Delta
Find Deal
Tue, Nov 26 - Sun, Dec 1
6:27 pm - 7:35 pmMSN-ORD
1h 08mnonstop
12:40 pm - 1:46 pmORD-MSN
1h 06mnonstop
$179American Airlines
Find Deal
Mon, Jan 13 - Thu, Jan 16
6:15 am - 7:22 amMSN-ORD
1h 07mnonstop
9:30 pm - 10:30 pmORD-MSN
1h 00mnonstop
$198United Airlines
Find Deal
Tue, Mar 11 - Tue, Mar 11
5:00 am - 6:13 amMSN-ORD
1h 13mnonstop
3:35 pm - 4:40 pmORD-MSN
1h 05mnonstop
$214United Airlines
Find Deal
Mon, Dec 23 - Mon, Dec 30
5:30 am - 6:33 amMSN-ORD
1h 03mnonstop
5:07 pm - 6:00 pmORD-MSN
0h 53mnonstop
$240American Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
12:33 pm - 1:46 pmMSN-ORD
1h 13mnonstop
5:07 pm - 6:00 pmORD-MSN
0h 53mnonstop
$244American Airlines
Find Deal
Wed, Dec 11 - Sun, Dec 15
12:15 pm - 1:28 pmMSN-ORD
1h 13mnonstop
8:00 pm - 9:03 pmORD-MSN
1h 03mnonstop
$274United Airlines
Find Deal
Sun, Dec 22 - Mon, Jan 13
5:53 pm - 6:55 pmMSN-ORD
1h 02mnonstop
10:05 am - 11:08 amORD-MSN
1h 03mnonstop
$279American Airlines
Find Deal
Mon, Dec 9 - Fri, Dec 13
5:30 am - 6:33 amMSN-ORD
1h 03mnonstop
3:45 pm - 4:38 pmORD-MSN
0h 53mnonstop
$281American Airlines
Find Deal
Tue, Dec 10 - Sat, Dec 14
7:00 am - 8:04 amMSN-ORD
1h 04mnonstop
7:45 pm - 8:49 pmORD-MSN
1h 04mnonstop
$309United Airlines
Find Deal
Tue, Dec 3 - Fri, Dec 6
7:00 am - 8:04 amMSN-ORD
1h 04mnonstop
6:10 pm - 7:12 pmORD-MSN
1h 02mnonstop
$369United Airlines
Find Deal
Thu, Dec 5 - Mon, Dec 9

American Airlines flights from Madison to Chicago

Our best American Airlines deals on Madison to Chicago flight tickets
American Airlines
Jan 13
MSN6:27 pmMadison Truax Field
1h 08m
ORD7:35 pmChicago O'Hare Intl
Jan 16
ORD12:40 pmChicago O'Hare Intl
1h 06m
MSN1:46 pmMadison Truax Field
American Airlines
Dec 12
MSN5:30 amMadison Truax Field
1h 03m
ORD6:33 amChicago O'Hare Intl
Dec 15
ORD5:07 pmChicago O'Hare Intl
0h 53m
MSN6:00 pmMadison Truax Field
American Airlines
Dec 11
MSN12:33 pmMadison Truax Field
1h 13m
ORD1:46 pmChicago O'Hare Intl
Dec 15
ORD5:07 pmChicago O'Hare Intl
0h 53m
MSN6:00 pmMadison Truax Field

United Airlines flights from Madison to Chicago

Our best United Airlines deals on Madison to Chicago flight tickets
United Airlines
Mar 11
MSN6:15 amMadison Truax Field
1h 07m
ORD7:22 amChicago O'Hare Intl
Mar 11
ORD9:30 pmChicago O'Hare Intl
1h 00m
MSN10:30 pmMadison Truax Field
United Airlines
Dec 23
MSN5:00 amMadison Truax Field
1h 13m
ORD6:13 amChicago O'Hare Intl
Dec 30
ORD3:35 pmChicago O'Hare Intl
1h 05m
MSN4:40 pmMadison Truax Field
United Airlines
Apr 15
MSN5:54 pmMadison Truax Field
6h 03m
1 stop
ORD11:57 pmChicago O'Hare Intl
Apr 30
ORD8:55 amChicago O'Hare Intl
0h 58m
MSN9:53 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 Friday when prices can be found for as low as $0. 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 in the evening. Flights from Madison to Chicago during this time can be as low as $0. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $458.

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 54% 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 November 2024, prices for Madison to Chicago flights are approximately 52% cheaper 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

$90

Fastest flight time

1h 02m

Direct flights

Mon, Tue, 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 $90. The best round-trip flight deal from Madison to Chicago found on momondo in the last 72 hours is $179.
The fastest flight from Madison to Chicago takes 1h 02m
Direct flights go from Madison to Chicago on Monday, Tuesday, 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 02m.

  • 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
9,172 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 $301, with the best United Airlines deals starting from $178 round-trip. 9,172 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 20 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.


An easier way to manage your Chicago 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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Tue 11/26
Tue 12/3
Email me momondo's favorite deals

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