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Cheap flights from Madison to Chicago from $130

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 10/7. 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

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
7:05 pm - 8:30 pm
MSN
-
ORD
1h 25mnonstop
American Airlines Logo
1:49 pm - 2:55 pm
ORD
-
MSN
1h 06mnonstop
$249American Airlines
Thu, Dec 24 - Sat, Jan 9
American Airlines Logo
6:09 am - 7:30 am
MSN
-
ORD
1h 21mnonstop
American Airlines Logo
11:00 pm - 12:10 am
ORD
-
MSN
1h 10mnonstop
$249American Airlines
Sat, Aug 29 - Sun, Aug 30
United Airlines Logo
4:14 pm - 5:30 pm
MSN
-
ORD
1h 16mnonstop
United Airlines Logo
12:40 pm - 1:42 pm
ORD
-
MSN
1h 02mnonstop
$249United Airlines
Wed, Sep 16 - Mon, Sep 21
United Airlines Logo
1:00 pm - 2:19 pm
MSN
-
ORD
1h 19mnonstop
United Airlines Logo
10:35 am - 11:53 am
ORD
-
MSN
1h 18mnonstop
$249United Airlines
Wed, Sep 23 - Tue, Sep 29
American Airlines Logo
5:00 am - 6:25 am
MSN
-
ORD
1h 25mnonstop
American Airlines Logo
7:03 am - 8:14 am
ORD
-
MSN
1h 11mnonstop
$249American Airlines
Wed, Sep 23 - Tue, Sep 29
United Airlines Logo
6:30 am - 7:43 am
MSN
-
ORD
1h 13mnonstop
United Airlines Logo
7:52 pm - 9:00 pm
ORD
-
MSN
1h 08mnonstop
$249United Airlines
Sat, Sep 19 - Tue, Sep 29
American Airlines Logo
9:53 am - 11:10 am
MSN
-
ORD
1h 17mnonstop
American Airlines Logo
1:49 pm - 2:55 pm
ORD
-
MSN
1h 06mnonstop
$249American Airlines
Fri, Dec 11 - Sun, Dec 13
Multiple Airlines Logo
8:00 pm - 11:21 am
MSN
-
ORD
15h 21m
1 stop
Multiple Airlines Logo
7:11 am - 9:53 am
ORD
-
MSN
26h 42m
2 stops
$275Multiple Airlines
Sun, Sep 13 - Fri, Sep 18
Multiple Airlines Logo
6:50 pm - 12:50 pm
MSN
-
ORD
42h 00m
2 stops
Multiple Airlines Logo
2:41 pm - 7:10 pm
ORD
-
MSN
28h 29m
1 stop
$326Multiple Airlines
Mon, Aug 24 - Sat, Aug 29
Frontier Logo
8:00 pm - 12:23 am
MSN
-
ORD
28h 23m
1 stop
Frontier Logo
6:30 am - 7:15 pm
ORD
-
MSN
12h 45m
1 stop
$337Frontier
Sun, Sep 13 - Sun, Sep 20

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United Airlines flights from Madison to Chicago

Our best United Airlines deals on Madison to Chicago flight tickets
United Airlines
Dec 24
MSN7:43 amMadison Truax Field
1h 20m
ORD9:03 amChicago O'Hare Intl
Jan 9
ORD1:55 pmChicago O'Hare Intl
1h 05m
MSN3:00 pmMadison Truax Field
$249
United Airlines
Aug 14
MSN6:30 amMadison Truax Field
1h 13m
ORD7:43 amChicago O'Hare Intl
Aug 15
ORD1:49 pmChicago O'Hare Intl
1h 02m
MSN2:51 pmMadison Truax Field
$279
United Airlines
Aug 14
MSN5:48 pmMadison Truax Field
1h 17m
ORD7:05 pmChicago O'Hare Intl
Aug 17
ORD1:55 pmChicago O'Hare Intl
1h 04m
MSN2:59 pmMadison Truax Field
$294

American Airlines flights from Madison to Chicago

Our best American Airlines deals on Madison to Chicago flight tickets
American Airlines
Aug 22
MSN5:00 amMadison Truax Field
1h 12m
ORD6:12 amChicago O'Hare Intl
Aug 23
ORD11:00 pmChicago O'Hare Intl
1h 10m
MSN12:10 amMadison Truax Field
$250
American Airlines
Aug 28
MSN9:48 amMadison Truax Field
1h 13m
ORD11:01 amChicago O'Hare Intl
Sep 4
ORD11:00 pmChicago O'Hare Intl
1h 10m
MSN12:10 amMadison Truax Field
$251
American Airlines
Aug 20
MSN5:00 amMadison Truax Field
1h 12m
ORD6:12 amChicago O'Hare Intl
Aug 23
ORD8:15 amChicago O'Hare Intl
1h 07m
MSN9:22 amMadison Truax Field
$266

momondo Fare Finder

 
Customize your flight search to find flights from Madison to Chicago 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 August 3, 2026.
Use the filters below to find and compare flights from Madison to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 12/24

7:05 pm-8:30 pm

Nonstop1h 25m

Chicago O'Hare Intl

Sat 1/9

1:49 pm-2:55 pm

Nonstop1h 06m

$249

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 8/29

6:09 am-7:30 am

Nonstop1h 21m

Chicago O'Hare Intl

Sun 8/30

11:00 pm-12:10 am

Nonstop1h 10m

$249
Quickest round-trip

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 9/16

4:14 pm-5:30 pm

Nonstop1h 16m

Chicago O'Hare Intl

Mon 9/21

12:40 pm-1:42 pm

Nonstop1h 02m

$249

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 9/23

1:00 pm-2:19 pm

Nonstop1h 19m

Chicago O'Hare Intl

Tue 9/29

10:35 am-11:53 am

Nonstop1h 18m

$249

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 9/23

5:00 am-6:25 am

Nonstop1h 25m

Chicago O'Hare Intl

Tue 9/29

7:03 am-8:14 am

Nonstop1h 11m

$249

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 9/19

6:30 am-7:43 am

Nonstop1h 13m

Chicago O'Hare Intl

Tue 9/29

7:52 pm-9:00 pm

Nonstop1h 08m

$249

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 12/11

9:53 am-11:10 am

Nonstop1h 17m

Chicago O'Hare Intl

Sun 12/13

1:49 pm-2:55 pm

Nonstop1h 06m

$249

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sun 9/13

8:00 pm-11:21 am

1 stop15h 21m

Chicago O'Hare Intl

Fri 9/18

7:11 am-9:53 am

2 stops26h 42m

$275

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Mon 8/24

6:50 pm-12:50 pm

2 stops42h 00m

Chicago O'Hare Intl

Sat 8/29

2:41 pm-7:10 pm

1 stop28h 29m

$326

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sun 9/13

8:00 pm-12:23 am

1 stop28h 23m

Chicago O'Hare Intl

Sun 9/20

6:30 am-7:15 pm

1 stop12h 45m

$337

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

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?

The month of October is, on average, the cheapest month to fly to Chicago from Madison, with most prices found around $199. If you’re not able to fly to Chicago in October, then September is your next best option. Flight prices from Madison to Chicago during September average around $239.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $401. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Madison to Chicago for around $612.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Madison to Chicago during this time can be as low as $432. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $572.

What is the cheapest Madison Truax Field to Chicago flight route?

Fly from Madison Truax Field to Chicago O'Hare Intl for the best Madison Truax Field - Chicago flight prices

What cabin class options are available on Madison to Chicago flights?

There are 4 cabin classes available to choose from on Madison to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

When to book flights from Madison to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Madison to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Madison to Chicago (MSN to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Madison to Chicago

Best Price Found

$281

Fastest flight time

1h 15m

Direct flights

Mon, Tue, Wed, Fri, Sat and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Madison in the past 72 hours is $281. The best round-trip flight deal from Madison to Chicago found on momondo in the last 72 hours is $363.
The fastest flight from Madison to Chicago takes 1h 15m
Direct flights go from Madison to Chicago on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. The only airline offering direct flights is United Airlines.
There are 3 airports in Chicago. From Madison there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Madison to Chicago

  • How far is Madison Truax Field to Chicago by plane?

    Madison Truax Field and Chicago are 122.4 mi apart from one another. In terms of flight time, this usually takes a little over 1h 15m.

  • When did momondo last update prices for flights from Madison Truax Field Airport to Chicago?

    Prices for flights from Madison Truax Field Airport to Chicago were last updated today.

  • How many operators does momondo search for flights from Madison Truax Field Airport to Chicago?

  • How old do you have to be to fly from Madison Truax Field Airport to Chicago?

    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.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Madison to Chicago?

  • What is the most popular airline from Madison to Chicago?

Best airlines flying from Madison to Chicago

Compare and see reviews for airlines that fly from Madison to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $179Free CancellationRating
7.1
11,842 reviews
Search American Airlines flights
United AirlinesPriceFrom $179Free CancellationRating
7.4
10,058 reviews
Search United Airlines flights

  • United Airlines Flights From Madison to Chicago

    Across 41 United Airlines flights from Madison to Chicago this week, the average price was $389, with the best United Airlines deals starting from $179 round-trip. 10,058 users have rated United Airlines on momondo, with an average score of 7.4/10.

  • American Airlines Flights From Madison to Chicago

    Another popular option for Madison to Chicago flights is American Airlines (7.1/10, 11,842 ratings). American Airlines flies from Madison to Chicago around 16 times per week, with deals starting from $179 round-trip and rising to an average price of around $231.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Madison to Chicago?

Finding the right flight to Chicago from Madison is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Madison to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Madison to Chicago flights to just show those with flexible booking policies.

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?

Of course. momondo tracks the price of Madison to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport