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Cheap flights from Madison to Chicago from $129

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 5/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
8:24 pm - 9:40 pm
MSN
-
ORD
1h 16mnonstop
American Airlines Logo
8:40 am - 9:48 am
ORD
-
MSN
1h 08mnonstop
$218American Airlines
Thu, Apr 9 - Sun, Apr 12
American Airlines Logo
5:00 am - 6:08 am
MSN
-
ORD
1h 08mnonstop
American Airlines Logo
8:40 am - 9:48 am
ORD
-
MSN
1h 08mnonstop
$219American Airlines
Mon, Apr 6 - Mon, Apr 13
American Airlines Logo
5:00 am - 6:08 am
MSN
-
ORD
1h 08mnonstop
American Airlines Logo
7:39 am - 8:45 am
ORD
-
MSN
1h 06mnonstop
$234American Airlines
Thu, Apr 2 - Fri, Apr 17
United Airlines Logo
2:44 pm - 3:56 pm
MSN
-
ORD
1h 12mnonstop
United Airlines Logo
7:45 am - 8:56 am
ORD
-
MSN
1h 11mnonstop
$239United Airlines
Wed, Apr 15 - Wed, Apr 22
American Airlines Logo
8:24 pm - 9:40 pm
MSN
-
ORD
1h 16mnonstop
American Airlines Logo
10:35 pm - 11:38 pm
ORD
-
MSN
1h 03mnonstop
$241American Airlines
Fri, Apr 17 - Fri, Apr 24
American Airlines Logo
11:34 am - 12:42 pm
MSN
-
ORD
1h 08mnonstop
American Airlines Logo
7:50 pm - 8:52 pm
ORD
-
MSN
1h 02mnonstop
$249American Airlines
Tue, Mar 31 - Sat, Apr 4
United Airlines Logo
8:30 am - 9:37 am
MSN
-
ORD
1h 07mnonstop
United Airlines Logo
9:00 am - 10:11 am
ORD
-
MSN
1h 11mnonstop
$254United Airlines
Wed, Apr 8 - Wed, Apr 15
American Airlines Logo
5:07 am - 6:10 am
MSN
-
ORD
1h 03mnonstop
American Airlines Logo
10:00 pm - 11:04 pm
ORD
-
MSN
1h 04mnonstop
$259American Airlines
Sun, Sep 13 - Tue, Sep 22
American Airlines Logo
5:37 pm - 7:05 pm
MSN
-
ORD
1h 28mnonstop
American Airlines Logo
7:39 am - 8:45 am
ORD
-
MSN
1h 06mnonstop
$263American Airlines
Fri, Apr 24 - Sun, Apr 26
American Airlines Logo
5:00 am - 6:08 am
MSN
-
ORD
1h 08mnonstop
American Airlines Logo
8:02 am - 9:08 am
ORD
-
MSN
1h 06mnonstop
$269American Airlines
Thu, Apr 2 - Mon, Apr 6

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
Apr 15
MSN2:44 pmMadison Truax Field
1h 12m
ORD3:56 pmChicago O'Hare Intl
Apr 22
ORD7:45 amChicago O'Hare Intl
1h 11m
MSN8:56 amMadison Truax Field
$239
United Airlines
Apr 8
MSN8:30 amMadison Truax Field
1h 07m
ORD9:37 amChicago O'Hare Intl
Apr 15
ORD9:00 amChicago O'Hare Intl
1h 11m
MSN10:11 amMadison Truax Field
$254
United Airlines
Apr 1
MSN5:00 amMadison Truax Field
1h 10m
ORD6:10 amChicago O'Hare Intl
Apr 5
ORD7:45 amChicago O'Hare Intl
1h 11m
MSN8:56 amMadison Truax Field
$274

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
Apr 9
MSN8:24 pmMadison Truax Field
1h 16m
ORD9:40 pmChicago O'Hare Intl
Apr 12
ORD8:40 amChicago O'Hare Intl
1h 08m
MSN9:48 amMadison Truax Field
$218
American Airlines
Apr 6
MSN5:00 amMadison Truax Field
1h 08m
ORD6:08 amChicago O'Hare Intl
Apr 13
ORD8:40 amChicago O'Hare Intl
1h 08m
MSN9:48 amMadison Truax Field
$219
American Airlines
Apr 2
MSN5:00 amMadison Truax Field
1h 08m
ORD6:08 amChicago O'Hare Intl
Apr 17
ORD7:39 amChicago O'Hare Intl
1h 06m
MSN8:45 amMadison Truax Field
$234

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 March 20, 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

Thu 4/9

8:24 pm-9:40 pm

Nonstop1h 16m

Chicago O'Hare Intl

Sun 4/12

8:40 am-9:48 am

Nonstop1h 08m

$218

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Mon 4/6

5:00 am-6:08 am

Nonstop1h 08m

Chicago O'Hare Intl

Mon 4/13

8:40 am-9:48 am

Nonstop1h 08m

$219

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 4/2

5:00 am-6:08 am

Nonstop1h 08m

Chicago O'Hare Intl

Fri 4/17

7:39 am-8:45 am

Nonstop1h 06m

$234

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 4/15

2:44 pm-3:56 pm

Nonstop1h 12m

Chicago O'Hare Intl

Wed 4/22

7:45 am-8:56 am

Nonstop1h 11m

$239

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 4/17

8:24 pm-9:40 pm

Nonstop1h 16m

Chicago O'Hare Intl

Fri 4/24

10:35 pm-11:38 pm

Nonstop1h 03m

$241

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Tue 3/31

11:34 am-12:42 pm

Nonstop1h 08m

Chicago O'Hare Intl

Sat 4/4

7:50 pm-8:52 pm

Nonstop1h 02m

$249

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 4/8

8:30 am-9:37 am

Nonstop1h 07m

Chicago O'Hare Intl

Wed 4/15

9:00 am-10:11 am

Nonstop1h 11m

$254
Quickest round-trip

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sun 9/13

5:07 am-6:10 am

Nonstop1h 03m

Chicago O'Hare Intl

Tue 9/22

10:00 pm-11:04 pm

Nonstop1h 04m

$259

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 4/24

5:37 pm-7:05 pm

Nonstop1h 28m

Chicago O'Hare Intl

Sun 4/26

7:39 am-8:45 am

Nonstop1h 06m

$263

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 4/2

5:00 am-6:08 am

Nonstop1h 08m

Chicago O'Hare Intl

Mon 4/6

8:02 am-9:08 am

Nonstop1h 06m

$269

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 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 $394. 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 $621.

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 afternoon because they tend to be around $508. 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 March 2026, prices for Madison to Chicago O'Hare Intl Airport flights are approximately 98% 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

$242

Fastest flight time

1h 02m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Madison in the past 72 hours is $242. The best round-trip flight deal from Madison to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $346.
The fastest flight from Madison to Chicago O'Hare Intl Airport takes 1h 02m
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 02m.

  • 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
11,480 reviews
Search American Airlines flights
United AirlinesPriceFrom $179Free CancellationRating
7.4
9,451 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 44 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 11,480 American Airlines reviews on momondo, the average score is 7.1/10. American Airlines flies from Madison to Chicago O'Hare Intl Airport about 27 times each week, with ticket deals ranging from $179 to $273. 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
Kenosha
Oak Brook
Joliet
Racine
Janesville
Hammond
Aurora
Tinley Park
Elgin
South Holland

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.

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