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Cheap flights from Madison to Chicago from $164

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 10/9. 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
8:08 pm - 9:29 pm
MSN
-
ORD
1h 21mnonstop
American Airlines Logo
3:02 pm - 4:09 pm
ORD
-
MSN
1h 07mnonstop
$239American Airlines
Fri, Dec 11 - Sun, Dec 13
American Airlines Logo
6:43 pm - 8:13 pm
MSN
-
ORD
1h 30mnonstop
American Airlines Logo
8:00 am - 9:11 am
ORD
-
MSN
1h 11mnonstop
$244American Airlines
Mon, Jul 13 - Mon, Jul 20
American Airlines Logo
6:42 pm - 8:09 pm
MSN
-
ORD
1h 27mnonstop
American Airlines Logo
5:00 pm - 6:12 pm
ORD
-
MSN
1h 12mnonstop
$254American Airlines
Wed, Jul 1 - Tue, Jul 7
American Airlines Logo
9:18 am - 10:30 am
MSN
-
ORD
1h 12mnonstop
American Airlines Logo
11:22 am - 12:32 pm
ORD
-
MSN
1h 10mnonstop
$255American Airlines
Sun, Jul 26 - Sun, Aug 2
American Airlines Logo
6:42 pm - 8:09 pm
MSN
-
ORD
1h 27mnonstop
American Airlines Logo
11:03 pm - 12:13 am
ORD
-
MSN
1h 10mnonstop
$269American Airlines
Wed, Jul 1 - Fri, Jul 3
American Airlines Logo
6:34 am - 8:00 am
MSN
-
ORD
1h 26mnonstop
American Airlines Logo
6:40 am - 7:45 am
ORD
-
MSN
1h 05mnonstop
$284American Airlines
Thu, Jun 25 - Sat, Jun 27
United Airlines Logo
6:45 am - 7:50 am
MSN
-
ORD
1h 05mnonstop
United Airlines Logo
7:50 pm - 8:54 pm
ORD
-
MSN
1h 04mnonstop
$309United Airlines
Fri, Nov 13 - Sat, Nov 21
United Airlines Logo
8:10 am - 9:19 am
MSN
-
ORD
1h 09mnonstop
United Airlines Logo
10:00 pm - 11:12 pm
ORD
-
MSN
1h 12mnonstop
$339United Airlines
Fri, Jun 26 - Tue, Jun 30
American Airlines Logo
6:43 pm - 8:13 pm
MSN
-
ORD
1h 30mnonstop
American Airlines Logo
5:45 pm - 11:42 pm
ORD
-
MSN
5h 57m
1 stop
$371American Airlines
Sun, Jul 26 - Sun, Aug 2
Multiple Airlines Logo
4:40 pm - 12:02 pm
MSN
-
ORD
19h 22m
2 stops
Multiple Airlines Logo
9:26 am - 5:20 pm
ORD
-
MSN
7h 54m
1 stop
$395Multiple Airlines
Tue, Sep 22 - Thu, Sep 24

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American Airlines flights from Madison to Chicago

Our best American Airlines deals on Madison to Chicago flight tickets
American Airlines
Dec 11
MSN8:08 pmMadison Truax Field
1h 21m
ORD9:29 pmChicago O'Hare Intl
Dec 13
ORD3:02 pmChicago O'Hare Intl
1h 07m
MSN4:09 pmMadison Truax Field
$239
American Airlines
Jul 13
MSN6:43 pmMadison Truax Field
1h 30m
ORD8:13 pmChicago O'Hare Intl
Jul 20
ORD8:00 amChicago O'Hare Intl
1h 11m
MSN9:11 amMadison Truax Field
$244
American Airlines
Jul 1
MSN6:42 pmMadison Truax Field
1h 27m
ORD8:09 pmChicago O'Hare Intl
Jul 7
ORD5:00 pmChicago O'Hare Intl
1h 12m
MSN6:12 pmMadison Truax Field
$254

United Airlines flights from Madison to Chicago

Our best United Airlines deals on Madison to Chicago flight tickets
United Airlines
Jun 24
MSN10:40 amMadison Truax Field
1h 17m
ORD11:57 amChicago O'Hare Intl
Jul 5
ORD10:00 pmChicago O'Hare Intl
1h 12m
MSN11:12 pmMadison Truax Field
$269
United Airlines
Nov 13
MSN6:45 amMadison Truax Field
1h 05m
ORD7:50 amChicago O'Hare Intl
Nov 21
ORD7:50 pmChicago O'Hare Intl
1h 04m
MSN8:54 pmMadison Truax Field
$309
United Airlines
Jun 26
MSN8:10 amMadison Truax Field
1h 09m
ORD9:19 amChicago O'Hare Intl
Jun 30
ORD10:00 pmChicago O'Hare Intl
1h 12m
MSN11:12 pmMadison Truax Field
$339

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 June 15, 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

Fri 12/11

8:08 pm-9:29 pm

Nonstop1h 21m

Chicago O'Hare Intl

Sun 12/13

3:02 pm-4:09 pm

Nonstop1h 07m

$239

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Mon 7/13

6:43 pm-8:13 pm

Nonstop1h 30m

Chicago O'Hare Intl

Mon 7/20

8:00 am-9:11 am

Nonstop1h 11m

$244

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 7/1

6:42 pm-8:09 pm

Nonstop1h 27m

Chicago O'Hare Intl

Tue 7/7

5:00 pm-6:12 pm

Nonstop1h 12m

$254

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sun 7/26

9:18 am-10:30 am

Nonstop1h 12m

Chicago O'Hare Intl

Sun 8/2

11:22 am-12:32 pm

Nonstop1h 10m

$255

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 7/1

6:42 pm-8:09 pm

Nonstop1h 27m

Chicago O'Hare Intl

Fri 7/3

11:03 pm-12:13 am

Nonstop1h 10m

$269

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 6/25

6:34 am-8:00 am

Nonstop1h 26m

Chicago O'Hare Intl

Sat 6/27

6:40 am-7:45 am

Nonstop1h 05m

$284
Quickest round-trip

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 11/13

6:45 am-7:50 am

Nonstop1h 05m

Chicago O'Hare Intl

Sat 11/21

7:50 pm-8:54 pm

Nonstop1h 04m

$309

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 6/26

8:10 am-9:19 am

Nonstop1h 09m

Chicago O'Hare Intl

Tue 6/30

10:00 pm-11:12 pm

Nonstop1h 12m

$339

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sun 7/26

6:43 pm-8:13 pm

Nonstop1h 30m

Chicago O'Hare Intl

Sun 8/2

5:45 pm-11:42 pm

1 stop5h 57m

$371

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Tue 9/22

4:40 pm-12:02 pm

2 stops19h 22m

Chicago O'Hare Intl

Thu 9/24

9:26 am-5:20 pm

1 stop7h 54m

$395

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 December is, on average, the cheapest month to fly to Chicago from Madison, with most prices found around $179. If you’re not able to fly to Chicago in December, then November is your next best option. Flight prices from Madison to Chicago during November average around $179.

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 $402. 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 $614.

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 $430. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $538.

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

$277

Fastest flight time

1h 10m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Madison in the past 72 hours is $277. The best round-trip flight deal from Madison to Chicago found on momondo in the last 72 hours is $383.
The fastest flight from Madison to Chicago takes 1h 10m
Direct flights go from Madison to Chicago every day.
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 10m.

  • 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
11,660 reviews
Search American Airlines flights
United AirlinesPriceFrom $179Free CancellationRating
7.4
9,830 reviews
Search United Airlines flights

  • United Airlines Flights From Madison to Chicago

    Across 33 United Airlines flights from Madison to Chicago this week, the average price was $324, with the best United Airlines deals starting from $179 round-trip. 9,830 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, 11,660 ratings). American Airlines flies from Madison to Chicago around 35 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
Benton Harbor
Portage
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
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