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Cheap flights from Madison to Chicago from $134

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 3/28. 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

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Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
1:16 pm - 2:29 pm
MSN
-
ORD
1h 13mnonstop
American Airlines Logo
8:11 am - 9:17 am
ORD
-
MSN
1h 06mnonstop
$179American Airlines
mié., feb. 11 - dom., feb. 15
United Airlines Logo
2:50 pm - 4:02 pm
MSN
-
ORD
1h 12mnonstop
United Airlines Logo
5:56 pm - 6:58 pm
ORD
-
MSN
1h 02mnonstop
$189United Airlines
lun., mar. 16 - lun., abr. 6
American Airlines Logo
5:22 pm - 6:44 pm
MSN
-
ORD
1h 22mnonstop
American Airlines Logo
9:45 am - 10:55 am
ORD
-
MSN
1h 10mnonstop
$209American Airlines
mar., feb. 3 - sáb., feb. 7
American Airlines Logo
8:24 pm - 9:31 pm
MSN
-
ORD
1h 07mnonstop
American Airlines Logo
8:15 am - 9:22 am
ORD
-
MSN
1h 07mnonstop
$250American Airlines
jue., mar. 19 - sáb., mar. 28
United Airlines Logo
6:30 am - 7:42 am
MSN
-
ORD
1h 12mnonstop
United Airlines Logo
5:45 pm - 6:44 pm
ORD
-
MSN
0h 59mnonstop
$267United Airlines
dom., mar. 8 - vie., mar. 13
United Airlines Logo
3:48 pm - 5:05 pm
MSN
-
ORD
1h 17mnonstop
United Airlines Logo
6:10 pm - 7:07 pm
ORD
-
MSN
0h 57mnonstop
$269United Airlines
mié., feb. 4 - dom., feb. 8
United Airlines Logo
6:45 am - 7:50 am
MSN
-
ORD
1h 05mnonstop
United Airlines Logo
2:20 pm - 3:25 pm
ORD
-
MSN
1h 05mnonstop
$277United Airlines
vie., jun. 19 - lun., jun. 22
Multiple Airlines Logo
6:36 pm - 10:41 am
MSN
-
ORD
16h 05m
1 stop
Multiple Airlines Logo
8:43 pm - 9:08 am
ORD
-
MSN
36h 25m
2 stops
$357Multiple Airlines
mié., feb. 4 - jue., feb. 5
Multiple Airlines Logo
6:36 pm - 8:00 pm
MSN
-
ORD
25h 24m
1 stop
Multiple Airlines Logo
5:30 am - 5:56 pm
ORD
-
MSN
12h 26m
1 stop
$358Multiple Airlines
mié., abr. 8 - mié., abr. 15
United Airlines Logo
2:56 pm - 4:17 pm
MSN
-
ORD
1h 21mnonstop
United Airlines Logo
1:55 pm - 2:52 pm
ORD
-
MSN
0h 57mnonstop
$359United Airlines
mié., feb. 4 - dom., feb. 8

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
Feb 11
MSN1:16 pmMadison Truax Field
1h 13m
ORD2:29 pmChicago O'Hare Intl
Feb 15
ORD8:11 amChicago O'Hare Intl
1h 06m
MSN9:17 amMadison Truax Field
$179
American Airlines
Feb 3
MSN5:22 pmMadison Truax Field
1h 22m
ORD6:44 pmChicago O'Hare Intl
Feb 7
ORD9:45 amChicago O'Hare Intl
1h 10m
MSN10:55 amMadison Truax Field
$209
American Airlines
Jan 27
MSN11:29 amMadison Truax Field
1h 11m
ORD12:40 pmChicago O'Hare Intl
Jan 31
ORD9:45 amChicago O'Hare Intl
1h 10m
MSN10:55 amMadison Truax Field
$239

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
Mar 16
MSN2:50 pmMadison Truax Field
1h 12m
ORD4:02 pmChicago O'Hare Intl
Apr 6
ORD5:56 pmChicago O'Hare Intl
1h 02m
MSN6:58 pmMadison Truax Field
$189
United Airlines
Mar 8
MSN6:30 amMadison Truax Field
1h 12m
ORD7:42 amChicago O'Hare Intl
Mar 13
ORD5:45 pmChicago O'Hare Intl
0h 59m
MSN6:44 pmMadison Truax Field
$267
United Airlines
Feb 4
MSN3:48 pmMadison Truax Field
1h 17m
ORD5:05 pmChicago O'Hare Intl
Feb 8
ORD6:10 pmChicago O'Hare Intl
0h 57m
MSN7:07 pmMadison Truax Field
$269

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 enero 21, 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

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

mié. 2/11

1:16 pm-2:29 pm

Nonstop1h 13m

Chicago O'Hare Intl

dom. 2/15

8:11 am-9:17 am

Nonstop1h 06m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

lun. 3/16

2:50 pm-4:02 pm

Nonstop1h 12m

Chicago O'Hare Intl

lun. 4/6

5:56 pm-6:58 pm

Nonstop1h 02m

$189

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

mar. 2/3

5:22 pm-6:44 pm

Nonstop1h 22m

Chicago O'Hare Intl

sáb. 2/7

9:45 am-10:55 am

Nonstop1h 10m

$209

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

jue. 3/19

8:24 pm-9:31 pm

Nonstop1h 07m

Chicago O'Hare Intl

sáb. 3/28

8:15 am-9:22 am

Nonstop1h 07m

$250

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

dom. 3/8

6:30 am-7:42 am

Nonstop1h 12m

Chicago O'Hare Intl

vie. 3/13

5:45 pm-6:44 pm

Nonstop0h 59m

$267

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

mié. 2/4

3:48 pm-5:05 pm

Nonstop1h 17m

Chicago O'Hare Intl

dom. 2/8

6:10 pm-7:07 pm

Nonstop0h 57m

$269

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

vie. 6/19

6:45 am-7:50 am

Nonstop1h 05m

Chicago O'Hare Intl

lun. 6/22

2:20 pm-3:25 pm

Nonstop1h 05m

$277

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

mié. 2/4

6:36 pm-10:41 am

1 stop16h 05m

Chicago O'Hare Intl

jue. 2/5

8:43 pm-9:08 am

2 stops36h 25m

$357

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

mié. 4/8

6:36 pm-8:00 pm

1 stop25h 24m

Chicago O'Hare Intl

mié. 4/15

5:30 am-5:56 pm

1 stop12h 26m

$358

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

mié. 2/4

2:56 pm-4:17 pm

Nonstop1h 21m

Chicago O'Hare Intl

dom. 2/8

1:55 pm-2:52 pm

Nonstop0h 57m

$359

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 $405. 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 $629.

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 $432 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 January 2026, prices for Madison to Chicago O'Hare Intl Airport flights are approximately 140% 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

$262

Fastest flight time

1h 05m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Madison in the past 72 hours is $262. The best round-trip flight deal from Madison to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $317.
The fastest flight from Madison to Chicago O'Hare Intl Airport takes 1h 05m
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 05m.

  • 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
7.2
11,174 reviews
Search American Airlines flights
United AirlinesPriceFrom $179Free CancellationRating
7.4
9,191 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 33 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 $279. Our users have rated United Airlines at 7.4/10.

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

    Across 11,174 American Airlines reviews on momondo, the average score is 7.2/10. American Airlines flies from Madison to Chicago O'Hare Intl Airport about 29 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
Naperville
Rosemont
New Buffalo
Kenosha
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
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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