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Cheap flights from Madison to Chicago from $159

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 - 6:21 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 21mnonstop
American Airlines Logo
9:59 pm - 11:12 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 13mnonstop
$289American Airlines
Fri, Dec 11 - Sun, Dec 13
American Airlines Logo
3:28 pm - 4:44 pmMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 16mnonstop
American Airlines Logo
6:59 am - 8:11 amORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 12mnonstop
$289American Airlines
Sat, Oct 17 - Sun, Oct 18
United Airlines Logo
6:35 pm - 7:55 pmMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 20mnonstop
United Airlines Logo
5:03 pm - 6:17 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 14mnonstop
$289United Airlines
Sun, Oct 18 - Sun, Oct 25
United Airlines Logo
8:15 am - 9:31 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 16mnonstop
United Airlines Logo
12:48 pm - 2:00 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 12mnonstop
$289United Airlines
Fri, Nov 20 - Fri, Nov 27
United Airlines Logo
5:00 am - 6:23 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 23mnonstop
United Airlines Logo
7:53 pm - 9:03 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 10mnonstop
$289United Airlines
Sun, Dec 20 - Sun, Jan 17
American Airlines Logo
7:09 pm - 8:30 pmMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 21mnonstop
American Airlines Logo
5:15 pm - 6:21 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 06mnonstop
$289American Airlines
Fri, Nov 13 - Sun, Nov 15
American Airlines Logo
9:15 am - 10:40 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 25mnonstop
American Airlines Logo
10:30 pm - 11:43 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 13mnonstop
$289American Airlines
Sat, Nov 7 - Sat, Nov 14
Multiple Airlines Logo
2:25 pm - 9:35 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
19h 10m2 stops Phoenix Sky Harbor Intl Dallas/Fort Worth
Multiple Airlines Logo
6:30 am - 1:26 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
30h 56m2 stops Denver Intl Phoenix Sky Harbor Intl
$456Multiple Airlines
Mon, Oct 26 - Wed, Oct 28
Multiple Airlines Logo
10:38 am - 9:21 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
22h 43m2 stops Tampa Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:36 am - 9:50 amORD  Chicago O'Hare Intl-MSN Madison Truax Field
25h 14m1 stop Orlando
$472Multiple Airlines
Sat, Oct 24 - Mon, Oct 26
Multiple Airlines Logo
6:00 pm - 7:02 pmMSN  Madison Truax Field-ORD Chicago O'Hare Intl
25h 02m1 stop Orlando
Multiple Airlines Logo
7:44 pm - 9:50 amORD  Chicago O'Hare Intl-MSN Madison Truax Field
38h 06m2 stops Atlanta Hartsfield-Jackson Orlando
$477Multiple Airlines
Sun, Oct 18 - Sun, Oct 25

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American Airlines flights from Madison to Chicago

Our best American Airlines deals on Madison to Chicago flight tickets
American Airlines
Oct 19
MSN5:00 amMadison Truax Field
1h 14m
ORD6:14 amChicago O'Hare Intl
Oct 26
ORD11:00 pmChicago O'Hare Intl
1h 12m
MSN12:12 amMadison Truax Field
$290
American Airlines
Oct 4
MSN8:05 pmMadison Truax Field
1h 25m
ORD9:30 pmChicago O'Hare Intl
Oct 16
ORD6:59 amChicago O'Hare Intl
1h 12m
MSN8:11 amMadison Truax Field
$304
American Airlines
Oct 6
MSN3:28 pmMadison Truax Field
1h 16m
ORD4:44 pmChicago O'Hare Intl
Oct 10
ORD6:59 amChicago O'Hare Intl
1h 12m
MSN8:11 amMadison Truax Field
$319

United Airlines flights from Madison to Chicago

Our best United Airlines deals on Madison to Chicago flight tickets
United Airlines
Oct 15
MSN6:35 pmMadison Truax Field
1h 20m
ORD7:55 pmChicago O'Hare Intl
Oct 18
ORD12:40 pmChicago O'Hare Intl
0h 57m
MSN1:37 pmMadison Truax Field
$289
United Airlines
Oct 2
MSN6:35 pmMadison Truax Field
1h 20m
ORD7:55 pmChicago O'Hare Intl
Oct 15
ORD12:40 pmChicago O'Hare Intl
0h 57m
MSN1:37 pmMadison Truax Field
$319
United Airlines
Sep 28
MSN2:49 pmMadison Truax Field
1h 11m
ORD4:00 pmChicago O'Hare Intl
Oct 5
ORD9:30 pmChicago O'Hare Intl
1h 05m
MSN10:35 pmMadison Truax Field
$334

momondo Fare Finder

 
Use the filters below to find and compare flights from Madison to Chicago 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

Fri 12/11

5:00 am-6:21 am

Nonstop1h 21m

Chicago O'Hare Intl

Sun 12/13

9:59 pm-11:12 pm

Nonstop1h 13m

$289

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Sat 10/17

3:28 pm-4:44 pm

Nonstop1h 16m

Chicago O'Hare Intl

Sun 10/18

6:59 am-8:11 am

Nonstop1h 12m

$289

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Sun 10/18

6:35 pm-7:55 pm

Nonstop1h 20m

Chicago O'Hare Intl

Sun 10/25

5:03 pm-6:17 pm

Nonstop1h 14m

$289

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Fri 11/20

8:15 am-9:31 am

Nonstop1h 16m

Chicago O'Hare Intl

Fri 11/27

12:48 pm-2:00 pm

Nonstop1h 12m

$289

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Sun 12/20

5:00 am-6:23 am

Nonstop1h 23m

Chicago O'Hare Intl

Sun 1/17

7:53 pm-9:03 pm

Nonstop1h 10m

$289
Quickest round-trip

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Fri 11/13

7:09 pm-8:30 pm

Nonstop1h 21m

Chicago O'Hare Intl

Sun 11/15

5:15 pm-6:21 pm

Nonstop1h 06m

$289

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Sat 11/7

9:15 am-10:40 am

Nonstop1h 25m

Chicago O'Hare Intl

Sat 11/14

10:30 pm-11:43 pm

Nonstop1h 13m

$289

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Mon 10/26

2:25 pm-9:35 am

2 stops19h 10m

Chicago O'Hare Intl

Wed 10/28

6:30 am-1:26 pm

2 stops30h 56m

$456

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Sat 10/24

10:38 am-9:21 am

2 stops22h 43m

Chicago O'Hare Intl

Mon 10/26

8:36 am-9:50 am

1 stop25h 14m

$472

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Sun 10/18

6:00 pm-7:02 pm

1 stop25h 02m

Chicago O'Hare Intl

Sun 10/25

7:44 pm-9:50 am

2 stops38h 06m

$477

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 March is your next best option. Flight prices from Madison to Chicago during March 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 $408. 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 $628.

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 $438. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $585.

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

$159

Fastest flight time

1h 13m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Madison in the past 72 hours is $159. The best round-trip flight deal from Madison to Chicago found on momondo in the last 72 hours is $289.
The fastest flight from Madison to Chicago takes 1h 13m
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 13m.

  • 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
7.0
12,074 reviews
Search American Airlines flights
United AirlinesPriceFrom $179Free CancellationRating
7.4
10,233 reviews
Search United Airlines flights

  • United Airlines Flights From Madison to Chicago

    Across 8 United Airlines flights from Madison to Chicago this week, the average price was $339, with the best United Airlines deals starting from $179 round-trip. 10,233 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 (7.0/10, 12,074 ratings). American Airlines flies from Madison to Chicago around 40 times per week, with deals starting from $179 round-trip and rising to an average price of around $259.

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

Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport