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Cheap flights from Madison to Chicago from $145

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
5:00 am - 6:14 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 14mnonstop
American Airlines Logo
10:00 pm - 11:12 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 12mnonstop
$288American Airlines
Thu, Oct 8 - Sun, Oct 11
American Airlines Logo
11:22 am - 12:39 pmMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 17mnonstop
American Airlines Logo
6:59 am - 8:11 amORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 12mnonstop
$289American Airlines
Fri, Oct 23 - Sun, Oct 25
United Airlines Logo
6:25 am - 7:44 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 19mnonstop
United Airlines Logo
12:40 pm - 1:51 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 11mnonstop
$289United Airlines
Sat, Nov 21 - Tue, Dec 1
United Airlines Logo
6:25 am - 7:44 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 19mnonstop
United Airlines Logo
5:59 am - 7:09 amORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 10mnonstop
$289United Airlines
Tue, Nov 24 - Sun, Dec 27
United Airlines Logo
2:49 pm - 4:00 pmMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 11mnonstop
United Airlines Logo
9:30 pm - 10:35 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 05mnonstop
$289United Airlines
Mon, Oct 12 - Sat, Oct 17
American Airlines Logo
2:19 pm - 3:42 pmMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 23mnonstop
American Airlines Logo
9:33 am - 11:00 amORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 27mnonstop
$289American Airlines
Thu, Dec 24 - Fri, Jan 8
American Airlines Logo
6:10 am - 7:24 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 14mnonstop
American Airlines Logo
9:40 am - 10:52 amORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 12mnonstop
$289American Airlines
Mon, Oct 12 - Mon, Oct 19
Multiple Airlines Logo
10:30 am - 7:51 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
21h 21m1 stop Orlando
Multiple Airlines Logo
8:04 am - 9:58 amORD  Chicago O'Hare Intl-MSN Madison Truax Field
25h 54m2 stops Fort Lauderdale Tampa
$298Multiple Airlines
Tue, Oct 13 - Tue, Oct 20
Multiple Airlines Logo
10:30 am - 1:01 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
14h 31m1 stop Orlando
Multiple Airlines Logo
6:15 am - 5:30 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
11h 15m1 stop Orlando
$369Multiple Airlines
Tue, Dec 8 - Thu, Dec 10
Multiple Airlines Logo
10:30 am - 1:01 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
14h 31m1 stop Orlando
Multiple Airlines Logo
10:37 pm - 9:58 amORD  Chicago O'Hare Intl-MSN Madison Truax Field
35h 21m2 stops Atlanta Hartsfield-Jackson Tampa
$385Multiple Airlines
Tue, Dec 8 - Thu, Dec 10

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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
Oct 8
MSN5:00 amMadison Truax Field
1h 14m
ORD6:14 amChicago O'Hare Intl
Oct 11
ORD10:00 pmChicago O'Hare Intl
1h 12m
MSN11:12 pmMadison Truax Field
$288
American Airlines
Dec 11
MSN6:02 amMadison Truax Field
1h 28m
ORD7:30 amChicago O'Hare Intl
Dec 14
ORD5:15 pmChicago O'Hare Intl
1h 06m
MSN6:21 pmMadison Truax Field
$289
American Airlines
Oct 13
MSN6:10 amMadison Truax Field
1h 14m
ORD7:24 amChicago O'Hare Intl
Oct 27
ORD6:59 amChicago O'Hare Intl
1h 12m
MSN8:11 amMadison Truax Field
$290

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 21
MSN6:25 amMadison Truax Field
1h 19m
ORD7:44 amChicago O'Hare Intl
Nov 29
ORD10:05 pmChicago O'Hare Intl
1h 02m
MSN11:07 pmMadison Truax Field
$299
United Airlines
Sep 29
MSN8:10 amMadison Truax Field
1h 13m
ORD9:23 amChicago O'Hare Intl
Oct 3
ORD2:00 pmChicago O'Hare Intl
1h 04m
MSN3:04 pmMadison Truax Field
$319
United Airlines
Sep 23
MSN1:00 pmMadison Truax Field
1h 19m
ORD2:19 pmChicago O'Hare Intl
Sep 29
ORD10:35 amChicago O'Hare Intl
1h 18m
MSN11:53 amMadison Truax Field
$334

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

Depart

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Price

Cheapest round-trip

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Thu 10/8

5:00 am-6:14 am

Nonstop1h 14m

Chicago O'Hare Intl

Sun 10/11

10:00 pm-11:12 pm

Nonstop1h 12m

$288

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Fri 10/23

11:22 am-12:39 pm

Nonstop1h 17m

Chicago O'Hare Intl

Sun 10/25

6:59 am-8:11 am

Nonstop1h 12m

$289

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Sat 11/21

6:25 am-7:44 am

Nonstop1h 19m

Chicago O'Hare Intl

Tue 12/1

12:40 pm-1:51 pm

Nonstop1h 11m

$289

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Tue 11/24

6:25 am-7:44 am

Nonstop1h 19m

Chicago O'Hare Intl

Sun 12/27

5:59 am-7:09 am

Nonstop1h 10m

$289
Quickest round-trip

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Mon 10/12

2:49 pm-4:00 pm

Nonstop1h 11m

Chicago O'Hare Intl

Sat 10/17

9:30 pm-10:35 pm

Nonstop1h 05m

$289

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Thu 12/24

2:19 pm-3:42 pm

Nonstop1h 23m

Chicago O'Hare Intl

Fri 1/8

9:33 am-11:00 am

Nonstop1h 27m

$289

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Mon 10/12

6:10 am-7:24 am

Nonstop1h 14m

Chicago O'Hare Intl

Mon 10/19

9:40 am-10:52 am

Nonstop1h 12m

$289

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Tue 10/13

10:30 am-7:51 am

1 stop21h 21m

Chicago O'Hare Intl

Tue 10/20

8:04 am-9:58 am

2 stops25h 54m

$298

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Tue 12/8

10:30 am-1:01 am

1 stop14h 31m

Chicago O'Hare Intl

Thu 12/10

6:15 am-5:30 pm

1 stop11h 15m

$369

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Tue 12/8

10:30 am-1:01 am

1 stop14h 31m

Chicago O'Hare Intl

Thu 12/10

10:37 pm-9:58 am

2 stops35h 21m

$385

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 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 $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 $625.

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 $436 when looking at flights departing in the morning. Try not to purchase tickets in the evening because they tend to be around $593. 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 September 2026, prices for Madison to Chicago O'Hare Intl Airport flights are approximately 50% 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

$145

Fastest flight time

1h 11m

Direct flights

Mon, Wed, Fri, Sat and Sun
The best one-way flight to Chicago O'Hare Intl Airport from Madison in the past 72 hours is $145. The best round-trip flight deal from Madison to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $288.
The fastest flight from Madison to Chicago O'Hare Intl Airport takes 1h 11m
Direct flights go from Madison to Chicago O'Hare Intl Airport on Monday, Wednesday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
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 11m.

  • 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
12,080 reviews
Search American Airlines flights
United AirlinesPriceFrom $179Free CancellationRating
7.4
10,226 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 22 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 $345. Our users have rated United Airlines at 7.4/10.

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

    Across 12,080 American Airlines reviews on momondo, the average score is 7.1/10. American Airlines flies from Madison to Chicago O'Hare Intl Airport about 40 times each week, with ticket deals ranging from $179 to $259. 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
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Evanston
Skokie

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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