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Cheap flights from Madison to Chicago from $130

1 adult
1 adult, Economy, 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.
American Airlines Logo
9:43 am - 11:00 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 17mnonstop
American Airlines Logo
10:09 pm - 11:19 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 10mnonstop
$309American Airlines
Fri, Dec 11 - Sun, Dec 13
American Airlines Logo
11:19 am - 12:39 pmMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 20mnonstop
American Airlines Logo
9:35 am - 10:45 amORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 10mnonstop
$309American Airlines
Fri, Dec 11 - Sun, Dec 13
United Airlines Logo
5:38 pm - 7:00 pmMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 22mnonstop
United Airlines Logo
1:45 pm - 2:50 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 05mnonstop
$309United Airlines
Thu, Dec 3 - Sun, Dec 6
United Airlines Logo
7:00 am - 8:23 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 23mnonstop
United Airlines Logo
8:45 am - 9:56 amORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 11mnonstop
$309United Airlines
Thu, Dec 17 - Sat, Jan 2
United Airlines Logo
5:43 pm - 7:05 pmMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 22mnonstop
United Airlines Logo
9:20 pm - 10:23 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 03mnonstop
$309United Airlines
Fri, Nov 27 - Fri, Dec 4
American Airlines Logo
9:25 am - 11:05 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 40mnonstop
American Airlines Logo
1:49 pm - 2:59 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 10mnonstop
$309American Airlines
Thu, Nov 19 - Sun, Nov 22
American Airlines Logo
5:30 am - 6:47 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 17mnonstop
American Airlines Logo
10:35 pm - 11:38 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 03mnonstop
$309American Airlines
Tue, Apr 20 - Mon, Apr 26
Multiple Airlines Logo
10:30 am - 1:08 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
14h 38m1 stop Orlando
Multiple Airlines Logo
5:59 pm - 5:30 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
47h 31m2 stops Atlanta Hartsfield-Jackson Orlando
$457Multiple Airlines
Tue, Dec 15 - Tue, Dec 22
Multiple Airlines Logo
2:40 pm - 5:13 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
14h 33m2 stops Phoenix Sky Harbor Intl Las Vegas Harry Reid Intl
Multiple Airlines Logo
5:15 am - 1:36 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
32h 21m2 stops Las Vegas Harry Reid Intl Phoenix Sky Harbor Intl
$492Multiple Airlines
Thu, Nov 19 - Sun, Nov 22
Multiple Airlines Logo
2:40 pm - 5:10 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
14h 30m2 stops Phoenix Sky Harbor Intl Las Vegas Harry Reid Intl
Multiple Airlines Logo
3:30 pm - 5:24 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
25h 54m1 stop Fort Myers SW Florida Intl
$550Multiple Airlines
Fri, Nov 27 - Fri, Dec 4

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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
Nov 14
MSN3:00 pmMadison Truax Field
1h 19m
ORD4:19 pmChicago O'Hare Intl
Nov 20
ORD8:45 amChicago O'Hare Intl
1h 16m
MSN10:01 amMadison Truax Field
$354
United Airlines
Jan 30
MSN10:45 amMadison Truax Field
1h 15m
ORD12:00 pmChicago O'Hare Intl
Feb 3
ORD3:35 pmChicago O'Hare Intl
1h 11m
MSN4:46 pmMadison Truax Field
$399
United Airlines
Nov 14
MSN10:42 amMadison Truax Field
1h 15m
ORD11:57 amChicago O'Hare Intl
Nov 18
ORD10:05 pmChicago O'Hare Intl
1h 02m
MSN11:07 pmMadison Truax Field
$429

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
Dec 11
MSN11:19 amMadison Truax Field
1h 20m
ORD12:39 pmChicago O'Hare Intl
Dec 13
ORD9:35 amChicago O'Hare Intl
1h 10m
MSN10:45 amMadison Truax Field
$309
American Airlines
Dec 15
MSN5:00 amMadison Truax Field
1h 21m
ORD6:21 amChicago O'Hare Intl
Dec 22
ORD6:04 pmChicago O'Hare Intl
1h 20m
MSN7:24 pmMadison Truax Field
$310
American Airlines
Nov 15
MSN9:15 amMadison Truax Field
1h 25m
ORD10:40 amChicago O'Hare Intl
Nov 22
ORD11:09 pmChicago O'Hare Intl
1h 16m
MSN12:25 amMadison Truax Field
$324

momondo Fare Finder

 
Use the filters below to find and compare flights from Madison to Chicago O'Hare Intl Airport that are best for you.

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Route

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Price

Cheapest round-trip

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Fri 12/11

9:43 am-11:00 am

Nonstop1h 17m

Chicago O'Hare Intl

Sun 12/13

10:09 pm-11:19 pm

Nonstop1h 10m

$309

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Fri 12/11

11:19 am-12:39 pm

Nonstop1h 20m

Chicago O'Hare Intl

Sun 12/13

9:35 am-10:45 am

Nonstop1h 10m

$309

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Thu 12/3

5:38 pm-7:00 pm

Nonstop1h 22m

Chicago O'Hare Intl

Sun 12/6

1:45 pm-2:50 pm

Nonstop1h 05m

$309

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Thu 12/17

7:00 am-8:23 am

Nonstop1h 23m

Chicago O'Hare Intl

Sat 1/2

8:45 am-9:56 am

Nonstop1h 11m

$309

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Fri 11/27

5:43 pm-7:05 pm

Nonstop1h 22m

Chicago O'Hare Intl

Fri 12/4

9:20 pm-10:23 pm

Nonstop1h 03m

$309

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Thu 11/19

9:25 am-11:05 am

Nonstop1h 40m

Chicago O'Hare Intl

Sun 11/22

1:49 pm-2:59 pm

Nonstop1h 10m

$309
Quickest round-trip

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Tue 4/20

5:30 am-6:47 am

Nonstop1h 17m

Chicago O'Hare Intl

Mon 4/26

10:35 pm-11:38 pm

Nonstop1h 03m

$309

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Tue 12/15

10:30 am-1:08 am

1 stop14h 38m

Chicago O'Hare Intl

Tue 12/22

5:59 pm-5:30 pm

2 stops47h 31m

$457

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Thu 11/19

2:40 pm-5:13 am

2 stops14h 33m

Chicago O'Hare Intl

Sun 11/22

5:15 am-1:36 pm

2 stops32h 21m

$492

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Fri 11/27

2:40 pm-5:10 am

2 stops14h 30m

Chicago O'Hare Intl

Fri 12/4

3:30 pm-5:24 pm

1 stop25h 54m

$550

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 month to fly to Chicago O'Hare Intl Airport?

The month of January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Madison averaging around $269.

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 $427. 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 $632.

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 $451 when looking at flights departing in the morning. Try not to purchase tickets in the evening because they tend to be around $589. 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 to Chicago O'Hare Intl Airport flights?

There are 4 cabin classes available to choose from on Madison to Chicago O'Hare Intl Airport 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 November 2026, prices for Madison to Chicago O'Hare Intl Airport flights are approximately 91% 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

$130

Fastest flight time

1h 13m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Madison in the past 72 hours is $130. The best round-trip flight deal from Madison to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $309.
The fastest flight from Madison to Chicago O'Hare Intl Airport takes 1h 13m
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 13m.

  • 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
7.3
10,460 reviews
Search United Airlines flights
American AirlinesPriceFrom $219Free CancellationRating
7.0
12,230 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 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 $389. Our users have rated United Airlines at 7.3/10.

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

    Across 12,230 American Airlines reviews on momondo, the average score is 7.0/10. American Airlines flies from Madison to Chicago O'Hare Intl Airport about 42 times each week, with ticket deals ranging from $219 to $373. 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
Merrillville
Rockford
South Haven
Oak Brook
Rosemont
Gurnee
Orland Park
Joliet
Naperville
New Buffalo
Kenosha
Hammond
Aurora
Racine
Elgin
Janesville
Skokie
Waukegan

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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