Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Madison to Chicago from $124

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 10/5. 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 (MSN-ORD)

Cheap round-trip flights

United Airlines Logo
5:43 pm - 6:50 pmMSN-ORD
1h 07mnonstop
United Airlines Logo
8:45 am - 9:45 amORD-MSN
1h 00mnonstop
$179United Airlines
Find Deal
Wed, Sep 10 - Sat, Sep 13
American Airlines Logo
5:00 am - 6:00 amMSN-ORD
1h 00mnonstop
American Airlines Logo
7:59 am - 9:05 amORD-MSN
1h 06mnonstop
$180American Airlines
Find Deal
Sat, Sep 27 - Sat, Oct 4
American Airlines Logo
6:44 pm - 7:49 pmMSN-ORD
1h 05mnonstop
American Airlines Logo
3:03 pm - 4:04 pmORD-MSN
1h 01mnonstop
$184American Airlines
Find Deal
Sat, Aug 30 - Thu, Sep 4
American Airlines Logo
6:44 pm - 7:49 pmMSN-ORD
1h 05mnonstop
American Airlines Logo
8:17 am - 9:18 amORD-MSN
1h 01mnonstop
$189American Airlines
Find Deal
Fri, Aug 29 - Sat, Aug 30
United Airlines Logo
3:58 pm - 5:05 pmMSN-ORD
1h 07mnonstop
United Airlines Logo
12:50 pm - 1:50 pmORD-MSN
1h 00mnonstop
$191United Airlines
Find Deal
Fri, Sep 19 - Sun, Oct 5
United Airlines Logo
12:26 pm - 1:38 pmMSN-ORD
1h 12mnonstop
United Airlines Logo
12:50 pm - 1:50 pmORD-MSN
1h 00mnonstop
$194United Airlines
Find Deal
Wed, Oct 1 - Sun, Oct 5
American Airlines Logo
6:24 pm - 7:40 pmMSN-ORD
1h 16mnonstop
American Airlines Logo
8:59 am - 10:15 amORD-MSN
1h 16mnonstop
$224American Airlines
Find Deal
Fri, Oct 3 - Mon, Oct 6
Delta Logo
10:58 am - 9:19 pmMSN-ORD
10h 21m1 stop
Delta Logo
11:05 am - 10:29 pmORD-MSN
11h 24m1 stop
$265Delta
Find Deal
Sat, Oct 18 - Sat, Oct 25
Frontier Logo
7:59 pm - 9:37 amMSN-ORD
13h 38m1 stop
Frontier Logo
10:42 am - 7:14 pmORD-MSN
8h 32m1 stop
$350Frontier
Find Deal
Sun, Sep 21 - Thu, Oct 2
Frontier Logo
7:59 pm - 9:37 amMSN-ORD
13h 38m1 stop
Frontier Logo
10:42 am - 7:14 pmORD-MSN
8h 32m1 stop
$527Frontier
Find Deal
Thu, Oct 2 - Sun, Oct 5

American Airlines flights from Madison to Chicago O'Hare Intl Airport

Our best American Airlines deals on Madison to Chicago O'Hare Intl Airport flight tickets
American Airlines
Sep 27
MSN5:00 amMadison Truax Field
1h 00m
ORD6:00 amChicago O'Hare Intl
Oct 4
ORD7:59 amChicago O'Hare Intl
1h 06m
MSN9:05 amMadison Truax Field
$180
Find similar
American Airlines
Aug 30
MSN6:44 pmMadison Truax Field
1h 05m
ORD7:49 pmChicago O'Hare Intl
Sep 4
ORD3:03 pmChicago O'Hare Intl
1h 01m
MSN4:04 pmMadison Truax Field
$184
Find similar
American Airlines
Aug 29
MSN6:44 pmMadison Truax Field
1h 05m
ORD7:49 pmChicago O'Hare Intl
Aug 30
ORD8:17 amChicago O'Hare Intl
1h 01m
MSN9:18 amMadison Truax Field
$189
Find similar

United Airlines flights from Madison to Chicago O'Hare Intl Airport

Our best United Airlines deals on Madison to Chicago O'Hare Intl Airport flight tickets
United Airlines
Sep 10
MSN5:43 pmMadison Truax Field
1h 07m
ORD6:50 pmChicago O'Hare Intl
Sep 13
ORD8:45 amChicago O'Hare Intl
1h 00m
MSN9:45 amMadison Truax Field
$179
Find similar
United Airlines
Sep 19
MSN3:58 pmMadison Truax Field
1h 07m
ORD5:05 pmChicago O'Hare Intl
Oct 5
ORD12:50 pmChicago O'Hare Intl
1h 00m
MSN1:50 pmMadison Truax Field
$191
Find similar
United Airlines
Oct 1
MSN12:26 pmMadison Truax Field
1h 12m
ORD1:38 pmChicago O'Hare Intl
Oct 5
ORD12:50 pmChicago O'Hare Intl
1h 00m
MSN1:50 pmMadison Truax Field
$194
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Madison to Chicago O'Hare Intl Airport 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 August 14, 2025.
Use the filters below to find and compare flights from Madison to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 9/10

5:43 pm-6:50 pm

Nonstop1h 07m

Chicago O'Hare Intl

Sat 9/13

8:45 am-9:45 am

Nonstop1h 00m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 9/27

5:00 am-6:00 am

Nonstop1h 00m

Chicago O'Hare Intl

Sat 10/4

7:59 am-9:05 am

Nonstop1h 06m

$180

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 8/30

6:44 pm-7:49 pm

Nonstop1h 05m

Chicago O'Hare Intl

Thu 9/4

3:03 pm-4:04 pm

Nonstop1h 01m

$184

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 8/29

6:44 pm-7:49 pm

Nonstop1h 05m

Chicago O'Hare Intl

Sat 8/30

8:17 am-9:18 am

Nonstop1h 01m

$189

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 9/19

3:58 pm-5:05 pm

Nonstop1h 07m

Chicago O'Hare Intl

Sun 10/5

12:50 pm-1:50 pm

Nonstop1h 00m

$191

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 10/1

12:26 pm-1:38 pm

Nonstop1h 12m

Chicago O'Hare Intl

Sun 10/5

12:50 pm-1:50 pm

Nonstop1h 00m

$194

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 10/3

6:24 pm-7:40 pm

Nonstop1h 16m

Chicago O'Hare Intl

Mon 10/6

8:59 am-10:15 am

Nonstop1h 16m

$224

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 10/18

10:58 am-9:19 pm

1 stop10h 21m

Chicago O'Hare Intl

Sat 10/25

11:05 am-10:29 pm

1 stop11h 24m

$265

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sun 9/21

7:59 pm-9:37 am

1 stop13h 38m

Chicago O'Hare Intl

Thu 10/2

10:42 am-7:14 pm

1 stop8h 32m

$350

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 10/2

7:59 pm-9:37 am

1 stop13h 38m

Chicago O'Hare Intl

Sun 10/5

10:42 am-7:14 pm

1 stop8h 32m

$527

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 O'Hare Intl Airport

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 month to fly to Chicago O'Hare Intl Airport?

The month of December is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Madison averaging around $246.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $453. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Madison because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $641.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Madison in the morning is the least expensive time of day to depart. momondo users have found prices as low as $485 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $530. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Madison Truax Field to Chicago O'Hare Intl flight route?

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

What cabin class options are available on Madison Truax Field to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Madison Truax Field to Chicago O'Hare Intl 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 O'Hare Intl Airport flight prices changed over time?

As of August 2025, prices for Madison to Chicago O'Hare Intl Airport flights are approximately 340% more expensive when compared to flights at the same time last year.

When to book flights from Madison to Chicago O'Hare Intl Airport

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

Cheap Madison to Chicago O'Hare Intl Airport (MSN to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Madison to Chicago O'Hare Intl Airport

Best Price Found

$124

Fastest flight time

1h 00m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Madison in the past 72 hours is $124. The best round-trip flight deal from Madison to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $179.
The fastest flight from Madison to Chicago O'Hare Intl Airport takes 1h 00m
Direct flights go from Madison to Chicago O'Hare Intl Airport every day.
Search flight deals

  • How far is Madison Truax Field to Chicago O'Hare Intl by plane?

    A flight from Madison Truax Field to Chicago O'Hare Intl will travel around 107.2 mi. By plane, this route typically takes 1h 00m.

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

    Prices for flights from Madison Truax Field Airport to Chicago O'Hare Intl Airport are updated daily.

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

  • How old do you have to be to fly from Madison Truax Field Airport to Chicago O'Hare Intl 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 Madison Truax Field Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Madison to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Madison to Chicago O'Hare Intl Airport?

Best airlines flying from Madison to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Madison to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $179Free CancellationRating
7.4
8,916 reviews
Search United Airlines flights
American AirlinesPriceFrom $219Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

  • United Airlines Flights From Madison to Chicago O'Hare Intl Airport

    United Airlines is one of the most popular airlines flying from Madison to Chicago O'Hare Intl Airport, operating 25 flights/week on average for this route. A good United Airlines flight deal for Madison to Chicago O'Hare Intl Airport starts from $179 round-trip, up to an average price of $291. Our users have rated United Airlines at 7.4/10.

  • American Airlines Flights From Madison to Chicago O'Hare Intl Airport

    Across 10,000 American Airlines reviews on momondo, the average score is 7.2/10. American Airlines flies from Madison to Chicago O'Hare Intl Airport about 35 times each week, with ticket deals ranging from $219 to $283. Price data is based on momondo searches in the last 72 hours.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Rockford
South Haven
Schaumburg
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Tinley Park
Orland Park
Elgin
Aurora
Janesville
Benton Harbor

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Madison.

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

Yes. All flights to Chicago from Madison on momondo can be compared and filtered by various policies on offer, including flexible booking.

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?

Yes. momondo can track prices for Madison to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Chicago O'Hare Intl Airport 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
Tue 8/19
Tue 8/26
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago