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Cheap flights from Madison to Chicago from $153

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.
United Airlines Logo
7:00 am - 8:23 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 23mnonstop
United Airlines Logo
12:54 pm - 2:09 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 15mnonstop
$274United Airlines
Thu, Dec 17 - Sat, Jan 2
United Airlines Logo
7:00 am - 8:23 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 23mnonstop
United Airlines Logo
12:54 pm - 2:09 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 15mnonstop
$309United Airlines
Thu, Dec 17 - Thu, Dec 24
United Airlines Logo
5:00 am - 6:23 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 23mnonstop
United Airlines Logo
1:55 pm - 3:04 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 09mnonstop
$309United Airlines
Fri, Dec 18 - Mon, Dec 28
United Airlines Logo
8:15 am - 9:31 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 16mnonstop
United Airlines Logo
5:54 pm - 7:07 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 13mnonstop
$309United Airlines
Thu, Nov 26 - Mon, Nov 30
American Airlines Logo
9:25 am - 11:05 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 40mnonstop
American Airlines Logo
7:20 am - 8:36 amORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 16mnonstop
$317American Airlines
Sat, Nov 28 - Sun, Nov 29
American Airlines Logo
6:43 pm - 7:59 pmMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 16mnonstop
American Airlines Logo
8:07 am - 9:16 amORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 09mnonstop
$319American Airlines
Sat, Mar 27 - Sat, Apr 3
American Airlines Logo
5:00 am - 6:21 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
1h 21mnonstop
American Airlines Logo
11:00 pm - 12:08 amORD  Chicago O'Hare Intl-MSN Madison Truax Field
1h 08mnonstop
$319American Airlines
Wed, Dec 2 - Wed, Dec 9
Multiple Airlines Logo
12:12 pm - 12:02 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
11h 50m1 stop Fort Myers SW Florida Intl
Multiple Airlines Logo
4:47 pm - 9:58 amORD  Chicago O'Hare Intl-MSN Madison Truax Field
17h 11m2 stops Fort Lauderdale Tampa
$387Multiple Airlines
Mon, Jan 11 - Tue, Jan 12
Multiple Airlines Logo
12:12 pm - 12:02 amMSN  Madison Truax Field-ORD Chicago O'Hare Intl
11h 50m1 stop Fort Myers SW Florida Intl
Multiple Airlines Logo
4:47 pm - 9:58 amORD  Chicago O'Hare Intl-MSN Madison Truax Field
17h 11m2 stops Fort Lauderdale Tampa
$414Multiple Airlines
Mon, Jan 11 - Tue, Jan 12
Multiple Airlines Logo
6:04 pm - 10:49 pmMSN  Madison Truax Field-ORD Chicago O'Hare Intl
28h 45m1 stop Fort Myers SW Florida Intl
Multiple Airlines Logo
8:30 am - 5:30 pmORD  Chicago O'Hare Intl-MSN Madison Truax Field
33h 00m2 stops Atlanta Hartsfield-Jackson Orlando
$418Multiple Airlines
Wed, Dec 2 - Wed, Dec 9

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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 17
MSN7:00 amMadison Truax Field
1h 23m
ORD8:23 amChicago O'Hare Intl
Jan 2
ORD12:54 pmChicago O'Hare Intl
1h 15m
MSN2:09 pmMadison Truax Field
$274
United Airlines
Nov 26
MSN8:15 amMadison Truax Field
1h 16m
ORD9:31 amChicago O'Hare Intl
Nov 30
ORD5:54 pmChicago O'Hare Intl
1h 13m
MSN7:07 pmMadison Truax Field
$309
United Airlines
Nov 19
MSN12:30 pmMadison Truax Field
1h 19m
ORD1:49 pmChicago O'Hare Intl
Nov 22
ORD4:40 pmChicago O'Hare Intl
1h 14m
MSN5:54 pmMadison Truax Field
$349

American Airlines flights from Madison to Chicago

Our best American Airlines deals on Madison to Chicago flight tickets
American Airlines
Nov 28
MSN9:25 amMadison Truax Field
1h 40m
ORD11:05 amChicago O'Hare Intl
Nov 29
ORD7:20 amChicago O'Hare Intl
1h 16m
MSN8:36 amMadison Truax Field
$317
American Airlines
Dec 11
MSN9:43 amMadison Truax Field
1h 17m
ORD11:00 amChicago O'Hare Intl
Dec 13
ORD10:09 pmChicago O'Hare Intl
1h 10m
MSN11:19 pmMadison Truax Field
$319
American Airlines
Nov 26
MSN5:01 amMadison Truax Field
1h 29m
ORD6:30 amChicago O'Hare Intl
Nov 30
ORD10:00 pmChicago O'Hare Intl
1h 16m
MSN11:16 pmMadison Truax Field
$320

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

Thu 12/17

7:00 am-8:23 am

Nonstop1h 23m

Chicago O'Hare Intl

Sat 1/2

12:54 pm-2:09 pm

Nonstop1h 15m

$274

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Thu 12/17

7:00 am-8:23 am

Nonstop1h 23m

Chicago O'Hare Intl

Thu 12/24

12:54 pm-2:09 pm

Nonstop1h 15m

$309

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Fri 12/18

5:00 am-6:23 am

Nonstop1h 23m

Chicago O'Hare Intl

Mon 12/28

1:55 pm-3:04 pm

Nonstop1h 09m

$309

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Thu 11/26

8:15 am-9:31 am

Nonstop1h 16m

Chicago O'Hare Intl

Mon 11/30

5:54 pm-7:07 pm

Nonstop1h 13m

$309

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Sat 11/28

9:25 am-11:05 am

Nonstop1h 40m

Chicago O'Hare Intl

Sun 11/29

7:20 am-8:36 am

Nonstop1h 16m

$317
Quickest round-trip

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Sat 3/27

6:43 pm-7:59 pm

Nonstop1h 16m

Chicago O'Hare Intl

Sat 4/3

8:07 am-9:16 am

Nonstop1h 09m

$319

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Wed 12/2

5:00 am-6:21 am

Nonstop1h 21m

Chicago O'Hare Intl

Wed 12/9

11:00 pm-12:08 am

Nonstop1h 08m

$319

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Mon 1/11

12:12 pm-12:02 am

1 stop11h 50m

Chicago O'Hare Intl

Tue 1/12

4:47 pm-9:58 am

2 stops17h 11m

$387

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Mon 1/11

12:12 pm-12:02 am

1 stop11h 50m

Chicago O'Hare Intl

Tue 1/12

4:47 pm-9:58 am

2 stops17h 11m

$414

MadisonChicago

MSN Madison Truax Field - ORD Chicago O'Hare Intl

MSNORD

Madison Truax Field

Wed 12/2

6:04 pm-10:49 pm

1 stop28h 45m

Chicago O'Hare Intl

Wed 12/9

8:30 am-5:30 pm

2 stops33h 00m

$418

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 $239. If you’re not able to fly to Chicago in December, 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 $430. 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 $637.

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 $454. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $587.

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.

How have Madison to Chicago flight prices changed over time?

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

$153

Fastest flight time

1h 05m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Madison in the past 72 hours is $153. The best round-trip flight deal from Madison to Chicago found on momondo in the last 72 hours is $274.
The fastest flight from Madison to Chicago takes 1h 05m
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 05m.

  • 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
United AirlinesPriceFrom $179Free CancellationRating
7.3
10,475 reviews
Search United Airlines flights
American AirlinesPriceFrom $219Free CancellationRating
7.0
12,225 reviews
Search American Airlines flights

  • United Airlines Flights From Madison to Chicago

    Across 51 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. 10,475 users have rated United Airlines on momondo, with an average score of 7.3/10.

  • American Airlines Flights From Madison to Chicago

    Another popular option for Madison to Chicago flights is American Airlines (7.0/10, 12,225 ratings). American Airlines flies from Madison to Chicago around 44 times per week, with deals starting from $219 round-trip and rising to an average price of around $373.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Lansing
Benton Harbor
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