Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Madison to Chicago from $107

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 11/14. 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 Madison to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
9:48 am - 11:02 amMSN-ORD
1h 14mnonstop
American Airlines Logo
12:21 pm - 1:26 pmORD-MSN
1h 05mnonstop
$179American Airlines
Find Deal
Tue, Nov 4 - Tue, Nov 11
American Airlines Logo
1:14 pm - 2:27 pmMSN-ORD
1h 13mnonstop
American Airlines Logo
8:15 am - 9:18 amORD-MSN
1h 03mnonstop
$180American Airlines
Find Deal
Thu, Nov 6 - Sun, Nov 9
United Airlines Logo
3:58 pm - 5:09 pmMSN-ORD
1h 11mnonstop
United Airlines Logo
10:35 am - 11:43 amORD-MSN
1h 08mnonstop
$189United Airlines
Find Deal
Tue, Oct 28 - Sat, Nov 1
United Airlines Logo
12:26 pm - 1:38 pmMSN-ORD
1h 12mnonstop
United Airlines Logo
7:35 pm - 8:35 pmORD-MSN
1h 00mnonstop
$199United Airlines
Find Deal
Sat, Oct 25 - Thu, Oct 30
Frontier Logo
8:00 pm - 3:39 pmMSN-ORD
19h 39m1 stop
Frontier Logo
6:00 am - 7:15 pmORD-MSN
13h 15m1 stop
$261Frontier
Find Deal
Mon, Nov 10 - Mon, Nov 17
Multiple Airlines Logo
8:00 pm - 3:39 pmMSN-ORD
19h 39m1 stop
Multiple Airlines Logo
6:30 pm - 9:08 amORD-MSN
38h 38m2 stops
$268Multiple Airlines
Find Deal
Mon, Nov 10 - Mon, Nov 17
Frontier Logo
7:59 pm - 12:12 amMSN-ORD
28h 13m1 stop
Frontier Logo
6:00 am - 7:15 pmORD-MSN
13h 15m1 stop
$272Frontier
Find Deal
Mon, Oct 27 - Fri, Oct 31
Multiple Airlines Logo
7:59 pm - 12:12 amMSN-ORD
28h 13m1 stop
Multiple Airlines Logo
1:55 pm - 9:08 amORD-MSN
19h 13m2 stops
$276Multiple Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
Delta Logo
6:15 am - 1:08 pmMSN-MDW
6h 53m1 stop
Delta Logo
9:20 am - 10:08 pmMDW-MSN
12h 48m1 stop
$416Delta
Find Deal
Wed, Mar 4 - Sat, Mar 7
Delta Logo
6:15 am - 6:08 pmMSN-MDW
11h 53m1 stop
Delta Logo
9:30 am - 10:08 pmMDW-MSN
12h 38m2 stops
$421Delta
Find Deal
Wed, Mar 4 - Sat, Mar 7

American Airlines flights from Madison to Chicago

Our best American Airlines deals on Madison to Chicago flight tickets
American Airlines
Nov 4
MSN9:48 amMadison Truax Field
1h 14m
ORD11:02 amChicago O'Hare Intl
Nov 11
ORD12:21 pmChicago O'Hare Intl
1h 05m
MSN1:26 pmMadison Truax Field
$179
Find similar
American Airlines
Nov 6
MSN1:14 pmMadison Truax Field
1h 13m
ORD2:27 pmChicago O'Hare Intl
Nov 9
ORD8:15 amChicago O'Hare Intl
1h 03m
MSN9:18 amMadison Truax Field
$180
Find similar
American Airlines
Oct 29
MSN4:29 pmMadison Truax Field
1h 11m
ORD5:40 pmChicago O'Hare Intl
Nov 5
ORD12:17 pmChicago O'Hare Intl
1h 06m
MSN1:23 pmMadison Truax Field
$184
Find similar

United Airlines flights from Madison to Chicago

Our best United Airlines deals on Madison to Chicago flight tickets
United Airlines
Oct 28
MSN3:58 pmMadison Truax Field
1h 11m
ORD5:09 pmChicago O'Hare Intl
Nov 1
ORD10:35 amChicago O'Hare Intl
1h 08m
MSN11:43 amMadison Truax Field
$189
Find similar
United Airlines
Oct 25
MSN12:26 pmMadison Truax Field
1h 12m
ORD1:38 pmChicago O'Hare Intl
Oct 30
ORD7:35 pmChicago O'Hare Intl
1h 00m
MSN8:35 pmMadison Truax Field
$199
Find similar
United Airlines
Oct 29
MSN2:48 pmMadison Truax Field
1h 15m
ORD4:03 pmChicago O'Hare Intl
Nov 2
ORD12:57 pmChicago O'Hare Intl
1h 06m
MSN2:03 pmMadison Truax Field
$249
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Madison to Chicago 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 October 14, 2025.
Use the filters below to find and compare flights from Madison to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Tue 11/4

9:48 am-11:02 am

Nonstop1h 14m

Chicago O'Hare Intl

Tue 11/11

12:21 pm-1:26 pm

Nonstop1h 05m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 11/6

1:14 pm-2:27 pm

Nonstop1h 13m

Chicago O'Hare Intl

Sun 11/9

8:15 am-9:18 am

Nonstop1h 03m

$180

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Tue 10/28

3:58 pm-5:09 pm

Nonstop1h 11m

Chicago O'Hare Intl

Sat 11/1

10:35 am-11:43 am

Nonstop1h 08m

$189

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 10/25

12:26 pm-1:38 pm

Nonstop1h 12m

Chicago O'Hare Intl

Thu 10/30

7:35 pm-8:35 pm

Nonstop1h 00m

$199

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Mon 11/10

8:00 pm-3:39 pm

1 stop19h 39m

Chicago O'Hare Intl

Mon 11/17

6:00 am-7:15 pm

1 stop13h 15m

$261

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Mon 11/10

8:00 pm-3:39 pm

1 stop19h 39m

Chicago O'Hare Intl

Mon 11/17

6:30 pm-9:08 am

2 stops38h 38m

$268

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Mon 10/27

7:59 pm-12:12 am

1 stop28h 13m

Chicago O'Hare Intl

Fri 10/31

6:00 am-7:15 pm

1 stop13h 15m

$272

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Mon 10/27

7:59 pm-12:12 am

1 stop28h 13m

Chicago O'Hare Intl

Fri 10/31

1:55 pm-9:08 am

2 stops19h 13m

$276

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Wed 3/4

6:15 am-1:08 pm

1 stop6h 53m

Chicago Midway

Sat 3/7

9:20 am-10:08 pm

1 stop12h 48m

$416

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Wed 3/4

6:15 am-6:08 pm

1 stop11h 53m

Chicago Midway

Sat 3/7

9:30 am-10:08 pm

2 stops12h 38m

$421

Flights are sorted by cheapest round-trip flights first.

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

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 $434. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Madison to Chicago for around $628.

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 $466. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $523.

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?

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

$214

Fastest flight time

1h 05m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Madison in the past 72 hours is $214. The best round-trip flight deal from Madison to Chicago found on momondo in the last 72 hours is $296.
The fastest flight from Madison to Chicago takes 1h 05m
Direct flights go from Madison to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
Search flight deals

  • 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 11m.

  • 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 $179Free CancellationRating
7.2
11,042 reviews
Search American Airlines flights
United AirlinesPriceFrom $219Free CancellationRating
7.4
8,976 reviews
Search United Airlines flights

  • United Airlines Flights From Madison to Chicago

    Across 36 United Airlines flights from Madison to Chicago this week, the average price was $295, with the best United Airlines deals starting from $219 round-trip. 8,976 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, 11,042 ratings). American Airlines flies from Madison to Chicago around 47 times per week, with deals starting from $179 round-trip and rising to an average price of around $274.

Traveling to a place near Chicago?

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

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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 11/13
Thu 11/20
By creating a price alert you accept our terms of use and privacy policy.

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
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport