Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Madison to Chicago from $157

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 5/29. 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.

Find the cheapest flights from Madison to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
8:25 pm - 9:42 pm
MSN
-
ORD
1h 17mnonstop
United Airlines Logo
7:42 am - 8:55 am
ORD
-
MSN
1h 13mnonstop
$239United Airlines
Fri, Jun 19 - Sun, Jun 21
American Airlines Logo
2:45 pm - 4:00 pm
MSN
-
ORD
1h 15mnonstop
American Airlines Logo
11:00 pm - 12:10 am
ORD
-
MSN
1h 10mnonstop
$244American Airlines
Thu, Aug 6 - Sat, Aug 8
American Airlines Logo
2:03 pm - 3:24 pm
MSN
-
ORD
1h 21mnonstop
American Airlines Logo
6:47 pm - 11:59 pm
ORD
-
MSN
5h 12m
1 stop
$251American Airlines
Sat, May 23 - Sun, May 24
American Airlines Logo
8:24 pm - 9:40 pm
MSN
-
ORD
1h 16mnonstop
American Airlines Logo
6:40 am - 7:49 am
ORD
-
MSN
1h 09mnonstop
$254American Airlines
Mon, May 18 - Mon, May 25
American Airlines Logo
5:37 pm - 7:05 pm
MSN
-
ORD
1h 28mnonstop
American Airlines Logo
3:53 pm - 5:06 pm
ORD
-
MSN
1h 13mnonstop
$269American Airlines
Thu, May 14 - Sun, May 17
American Airlines Logo
5:37 pm - 7:05 pm
MSN
-
ORD
1h 28mnonstop
American Airlines Logo
10:35 pm - 11:41 pm
ORD
-
MSN
1h 06mnonstop
$284American Airlines
Thu, May 14 - Sun, May 17
United Airlines Logo
9:40 am - 10:56 am
MSN
-
ORD
1h 16mnonstop
United Airlines Logo
9:47 pm - 10:59 pm
ORD
-
MSN
1h 12mnonstop
$309United Airlines
Tue, Jun 30 - Sat, Jul 4
United Airlines Logo
5:45 pm - 7:00 pm
MSN
-
ORD
1h 15mnonstop
United Airlines Logo
10:25 am - 11:38 am
ORD
-
MSN
1h 13mnonstop
$310United Airlines
Sat, May 23 - Sun, May 24
American Airlines Logo
5:00 am - 6:15 am
MSN
-
ORD
1h 15mnonstop
American Airlines Logo
4:48 pm - 11:57 pm
ORD
-
MSN
7h 09m
1 stop
$319American Airlines
Sun, Aug 2 - Sat, Aug 15
American Airlines Logo
5:11 pm - 12:42 am
MSN
-
ORD
7h 31m
1 stop
American Airlines Logo
4:45 pm - 11:59 pm
ORD
-
MSN
7h 14m
1 stop
$330American Airlines
Sat, May 23 - Sun, May 24

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

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
Jun 19
MSN8:25 pmMadison Truax Field
1h 17m
ORD9:42 pmChicago O'Hare Intl
Jun 21
ORD7:42 amChicago O'Hare Intl
1h 13m
MSN8:55 amMadison Truax Field
$239
United Airlines
Jun 30
MSN9:40 amMadison Truax Field
1h 16m
ORD10:56 amChicago O'Hare Intl
Jul 4
ORD9:47 pmChicago O'Hare Intl
1h 12m
MSN10:59 pmMadison Truax Field
$309
United Airlines
May 23
MSN5:45 pmMadison Truax Field
1h 15m
ORD7:00 pmChicago O'Hare Intl
May 24
ORD10:25 amChicago O'Hare Intl
1h 13m
MSN11:38 amMadison Truax Field
$310

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
Aug 6
MSN2:45 pmMadison Truax Field
1h 15m
ORD4:00 pmChicago O'Hare Intl
Aug 8
ORD11:00 pmChicago O'Hare Intl
1h 10m
MSN12:10 amMadison Truax Field
$244
American Airlines
May 23
MSN2:03 pmMadison Truax Field
1h 21m
ORD3:24 pmChicago O'Hare Intl
May 24
ORD6:47 pmChicago O'Hare Intl
5h 12m
1 stop
MSN11:59 pmMadison Truax Field
$251
American Airlines
May 18
MSN8:24 pmMadison Truax Field
1h 16m
ORD9:40 pmChicago O'Hare Intl
May 25
ORD6:40 amChicago O'Hare Intl
1h 09m
MSN7:49 amMadison Truax Field
$254

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 May 4, 2026.
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

Cheapest round-trip

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 6/19

8:25 pm-9:42 pm

Nonstop1h 17m

Chicago O'Hare Intl

Sun 6/21

7:42 am-8:55 am

Nonstop1h 13m

$239
Quickest round-trip

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 8/6

2:45 pm-4:00 pm

Nonstop1h 15m

Chicago O'Hare Intl

Sat 8/8

11:00 pm-12:10 am

Nonstop1h 10m

$244

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 5/23

2:03 pm-3:24 pm

Nonstop1h 21m

Chicago O'Hare Intl

Sun 5/24

6:47 pm-11:59 pm

1 stop5h 12m

$251

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Mon 5/18

8:24 pm-9:40 pm

Nonstop1h 16m

Chicago O'Hare Intl

Mon 5/25

6:40 am-7:49 am

Nonstop1h 09m

$254

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 5/14

5:37 pm-7:05 pm

Nonstop1h 28m

Chicago O'Hare Intl

Sun 5/17

3:53 pm-5:06 pm

Nonstop1h 13m

$269

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 5/14

5:37 pm-7:05 pm

Nonstop1h 28m

Chicago O'Hare Intl

Sun 5/17

10:35 pm-11:41 pm

Nonstop1h 06m

$284

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Tue 6/30

9:40 am-10:56 am

Nonstop1h 16m

Chicago O'Hare Intl

Sat 7/4

9:47 pm-10:59 pm

Nonstop1h 12m

$309

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 5/23

5:45 pm-7:00 pm

Nonstop1h 15m

Chicago O'Hare Intl

Sun 5/24

10:25 am-11:38 am

Nonstop1h 13m

$310

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sun 8/2

5:00 am-6:15 am

Nonstop1h 15m

Chicago O'Hare Intl

Sat 8/15

4:48 pm-11:57 pm

1 stop7h 09m

$319

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 5/23

5:11 pm-12:42 am

1 stop7h 31m

Chicago O'Hare Intl

Sun 5/24

4:45 pm-11:59 pm

1 stop7h 14m

$330

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 typical price of a round-trip flight between Madison and Chicago O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Madison averaging around $224.

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 Saturday when prices can be found for as low as $398. 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 $603.

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 $428 when looking at flights departing in the morning. Try not to purchase tickets in the evening 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

How have Madison to Chicago O'Hare Intl Airport flight prices changed over time?

As of May 2026, prices for Madison to Chicago O'Hare Intl Airport flights are approximately 20% 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

$240

Fastest flight time

1h 03m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Madison in the past 72 hours is $240. The best round-trip flight deal from Madison to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $379.
The fastest flight from Madison to Chicago O'Hare Intl Airport takes 1h 03m
Direct flights go from Madison to Chicago O'Hare Intl Airport every day.
Search flight deals

Frequently asked questions about flying from Madison to Chicago O'Hare Intl Airport

  • 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 03m.

  • 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
American AirlinesPriceFrom $179Free CancellationRating
7.1
11,672 reviews
Search American Airlines flights
United AirlinesPriceFrom $179Free CancellationRating
7.4
9,680 reviews
Search United 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 55 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 $407. Our users have rated United Airlines at 7.4/10.

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

    Across 11,673 American Airlines reviews on momondo, the average score is 7.1/10. American Airlines flies from Madison to Chicago O'Hare Intl Airport about 43 times each week, with ticket deals ranging from $179 to $231. 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
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Oak Brook
Kenosha
Joliet
Aurora
Janesville
Racine
Hammond
Tinley Park
Elgin
Evanston

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
Wed 6/3
Wed 6/10
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago