Which airlines offer extra legroom and free seat selection on Madison to Chicago flights?

Among airlines operating Madison to Chicago flights: • United Airlines: offers free seat selection • American Airlines: offers free seat selection Extra legroom and free seat selection availability depends on fare class and route.

What airlines fly from Madison to Chicago?

2 airlines operate flights between Madison and Chicago. The airlines offering nonstop flights on this route include: • United Airlines • American Airlines

Which airports can I use when flying from Madison to Chicago?

Flights from Madison to Chicago usually depart from Madison Truax Field (MSN) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

Which airlines include bags at no extra cost on Madison to Chicago flights?

Here are some options for this route, based on selected ticket types and cabin classes: • United Airlines: a cabin bag and a checked bag in First Class • American Airlines: a cabin bag and a checked bag in First Class Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

What cabin classes can I book on flights from Madison to Chicago?

Two cabin classes are available on flights from Madison to Chicago: • Economy Class • First Class

What is the standard checked-bag allowance on flights from Madison to Chicago?

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

Can I save money by using flexible dates for flights from Madison to Chicago?

Yes. Flexible dates can save you up to 47% on flights from Madison to Chicago. Friday is the cheapest departure day at $239 round-trip on average, while Sunday is the most expensive at $449, a difference of $210. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

How are flight departures from Madison to Chicago spread across the day?

Morning is the busiest departure period on Madison to Chicago flights, with 54% of flights leaving in that window. Afternoon departures account for 26%, evening flights for 20%, and night flights for 0%.

What popular places can I visit in Chicago?

Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago on KAYAK.

What are the earliest and latest flights from Madison to Chicago?

These are the earliest and latest flight times available from Madison to Chicago: • Earliest: departs at 5:00 am and lands at 6:21 am • Latest: departs at 9:40 pm and lands at 11:01 pm. The flight takes about 1h 21m.

How long is a flight from Madison to Chicago?

A nonstop flight from Madison to Chicago takes 1h 21m, covering 123 miles.

Do I need a passport to fly from Madison to Chicago?

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

How are flight prices from Madison to Chicago looking right now?

One-way fares from Madison to Chicago are currently lower than usual. Average one-way flight prices are about $220, which is 15% below the typical average for this route.

What car rental options are available in Chicago?

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into. Near Chicago O'Hare Intl Airport (ORD) — daily rates averaging $64: • Routes Car & Truck Rentals • Europcar • Hertz • Ace • Dollar Near Chicago Midway Airport (MDW) — daily rates averaging $84: • Hertz • Dollar • Budget • Alamo • Rent-A-Wreck Near Chicago Greater Rockford Airport (RFD) — daily rates averaging $81: • Alamo • Enterprise Rent-A-Car • Budget • Avis • National

How much should I expect to pay for a Madison to Chicago flight?

Round-trip flights from Madison to Chicago range from $231 to $399, with an average of $289 over the past 12 months. Anything below $231 counts as a good deal.

Which airlines offer Wi-Fi on Madison to Chicago flights?

American Airlines is the only airline on the Madison to Chicago route offering in-flight Wi-Fi. Pricing depends on fare class.

How much is a round-trip flight from Madison to Chicago?

Round-trip flights from Madison to Chicago typically range from $231 to $399. The lowest price found in the past 5 days was $309, on American Airlines.

What is the cheapest Madison to Chicago flight route?

Madison (MSN) to Chicago O'Hare Intl Airport (ORD) is the cheapest Madison to Chicago route, averaging $289 round-trip. Other Madison to Chicago routes average $1,522, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Madison to Chicago?

Based on deals KAYAK users found in the last 12 months, Friday is the cheapest day of the week to fly from Madison to Chicago. It’s 18% cheaper than the average day, while Sunday is the most expensive, with prices 55% higher.

What’s the cheapest month to fly from Madison to Chicago?

•December is the cheapest month to fly from Madison to Chicago at $231 round-trip. •September ($1,522) and May ($449) are the most expensive months. •The price difference between flying in the cheapest and most expensive months is 558% on average. This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Which airline is the cheapest to fly from Madison to Chicago?

American Airlines ($309) and United Airlines ($309) are the cheapest airlines to fly round-trip from Madison to Chicago according to KAYAK data over the last 5 days.

Which airline offers the most nonstop flights between Madison and Chicago?

United Airlines and American Airlines offer the most frequent nonstop flights from Madison to Chicago, at 64 and 42 flights per week respectively. Based on KAYAK flight data over the last 3 months.

How many nonstop flights run daily between Madison and Chicago?

There are 14 to 16 flights per day from Madison to Chicago, about 107 flights per week. Tuesday has the most departures, with 15% of weekly flights.

What time of day do most flights depart from Madison to Chicago?

Most nonstop flights from Madison to Chicago depart in the morning, accounting for 54% of nonstop departures. Around 8 flights are scheduled in that window over the next three months.

$155 CHEAP FLIGHTS from Madison to Chicago (MSN - CHI)

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Cheapest round-trip

$309

Typical prices: $231-$399

American Airlines

Sun 12/30Mon 1/8

MSN - ORD • Non-stop

Cheapest one-way

$155

Typical prices: $218-$338

American Airlines

Sat 12/22

MSN - ORD • Non-stop

Nonstop flights

Every day

You can fly direct with United Airlines and American Airlines. Average duration is 1h 21m

Direct flights

Top routes

MSN - ORD

Cheapest • 68% average savings

MSN - MDW

Most popular

Insights

When to travel

December

Cheapest • 20% price drop

January

Most popular

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We hope you love your trip to Chicago!

Flight Deals

Cheap Flights from Madison to Chicago (MSN-CHI)

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Madison to Chicago

Thu, Nov 19 - Sun, Nov 22

9:25 am - 11:05 amMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 40mnonstop

1:49 pm - 2:59 pmORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 10mnonstop

$309American Airlines

Wed, Dec 9 - Sat, Dec 12

5:51 am - 7:20 amMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 29mnonstop

6:36 pm - 7:52 pmORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 16mnonstop

$309American Airlines

Thu, Dec 3 - Sun, Dec 6

5:38 pm - 7:00 pmMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 22mnonstop

1:45 pm - 2:50 pmORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 05mnonstop

$309United Airlines

Wed, Nov 18 - Sat, Nov 21

7:00 pm - 8:22 pmMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 22mnonstop

5:54 pm - 7:07 pmORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 13mnonstop

$309United Airlines

Thu, Nov 19 - Sun, Nov 22

12:30 pm - 1:49 pmMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 19mnonstop

4:40 pm - 5:54 pmORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 14mnonstop

$309United Airlines

Fri, Dec 11 - Sun, Dec 13

9:43 am - 11:00 amMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 17mnonstop

10:09 pm - 11:19 pmORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 10mnonstop

$309American Airlines

Wed, Dec 30 - Fri, Jan 8

8:32 pm - 10:00 pmMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 28mnonstop

2:15 pm - 3:31 pmORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 16mnonstop

$309American Airlines

Sat, Feb 13 - Wed, Mar 3

11:00 am - 9:37 pmMSN Madison Truax Field-ORD Chicago O'Hare Intl

10h 37m1 stop Minneapolis St Paul

9:30 am - 7:05 pmORD Chicago O'Hare Intl-MSN Madison Truax Field

9h 35m1 stop Minneapolis St Paul

$365Delta

Sat, Feb 13 - Tue, Mar 2

11:00 am - 9:37 pmMSN Madison Truax Field-ORD Chicago O'Hare Intl

10h 37m1 stop Minneapolis St Paul

9:30 am - 7:05 pmORD Chicago O'Hare Intl-MSN Madison Truax Field

9h 35m1 stop Minneapolis St Paul

$365Delta

Wed, Feb 17 - Sat, Feb 27

7:55 pm - 8:43 amMSN Madison Truax Field-ORD Chicago O'Hare Intl

12h 48m1 stop Minneapolis St Paul

9:30 am - 10:55 pmORD Chicago O'Hare Intl-MSN Madison Truax Field

13h 25m1 stop Minneapolis St Paul

$365Delta

Recent last minute flight deals from Madison to Chicago

Tue, Nov 3 - Tue, Nov 10

6:00 am - 7:28 amMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 28mnonstop

6:55 am - 8:10 amORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 15mnonstop

$401American Airlines

Sun, Nov 1 - Sun, Nov 8

5:00 am - 6:20 amMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 20mnonstop

10:45 am - 11:59 amORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 14mnonstop

$419United Airlines

Mon, Nov 2 - Mon, Nov 9

5:43 pm - 7:05 pmMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 22mnonstop

7:59 pm - 9:05 pmORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 06mnonstop

$419United Airlines

Tue, Nov 3 - Tue, Nov 10

9:15 am - 10:40 amMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 25mnonstop

6:41 am - 11:39 amORD Chicago O'Hare Intl-MSN Madison Truax Field

4h 58m1 stop Charlotte Douglas

$470American Airlines

Tue, Nov 3 - Tue, Nov 10

7:08 pm - 8:29 pmMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 21mnonstop

10:30 pm - 11:43 pmORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 13mnonstop

$527American Airlines

Mon, Nov 2 - Tue, Nov 3

7:09 pm - 8:30 pmMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 21mnonstop

5:15 pm - 6:21 pmORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 06mnonstop

$548American Airlines

Sun, Nov 1 - Sun, Nov 8

6:00 pm - 8:46 amMSN Madison Truax Field-ORD Chicago O'Hare Intl

14h 46m1 stop Orlando

7:50 pm - 9:50 amORD Chicago O'Hare Intl-MSN Madison Truax Field

38h 00m2 stops Atlanta Hartsfield-Jackson Orlando

$771Multiple Airlines

Sun, Nov 1 - Sun, Nov 8

6:15 am - 1:09 pmMSN Madison Truax Field-ORD Chicago O'Hare Intl

6h 54m1 stop Newark

10:05 pm - 11:07 pmORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 02mnonstop

$1,397United Airlines

Sun, Nov 1 - Sun, Nov 8

9:27 am - 12:47 pmMSN Madison Truax Field-MDW Chicago Midway

3h 20m1 stop Detroit Metropolitan Wayne County

1:27 pm - 5:18 pmMDW Chicago Midway-MSN Madison Truax Field

3h 51m1 stop Detroit Metropolitan Wayne County

$1,722Delta

Mon, Nov 2 - Mon, Nov 9

7:59 am - 11:47 amMSN Madison Truax Field-MDW Chicago Midway

3h 48m1 stop Minneapolis St Paul

9:30 am - 12:39 pmMDW Chicago Midway-MSN Madison Truax Field

3h 09m1 stop Detroit Metropolitan Wayne County

$1,803Delta

Recent direct flight deals from Madison to Chicago

Thu, Dec 3 - Sun, Dec 6

5:38 pm - 7:00 pmMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 22mnonstop

1:45 pm - 2:50 pmORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 05mnonstop

$309United Airlines

Thu, Nov 19 - Sun, Nov 22

12:30 pm - 1:49 pmMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 19mnonstop

4:40 pm - 5:54 pmORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 14mnonstop

$309United Airlines

Fri, Dec 11 - Sat, Dec 12

5:51 am - 7:20 amMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 29mnonstop

11:00 pm - 12:08 amORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 08mnonstop

$309American Airlines

Thu, Nov 19 - Sun, Nov 22

9:25 am - 11:05 amMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 40mnonstop

1:49 pm - 2:59 pmORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 10mnonstop

$309American Airlines

Sun, Nov 15 - Sun, Nov 22

9:15 am - 10:40 amMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 25mnonstop

5:17 pm - 6:29 pmORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 12mnonstop

$309American Airlines

Tue, Feb 16 - Tue, Mar 2

9:45 am - 11:03 amMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 18mnonstop

7:08 am - 8:17 amORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 09mnonstop

$309American Airlines

Wed, Dec 30 - Fri, Jan 8

8:32 pm - 10:00 pmMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 28mnonstop

2:15 pm - 3:31 pmORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 16mnonstop

$309American Airlines

Tue, Nov 24 - Tue, Dec 1

8:41 pm - 9:55 pmMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 14mnonstop

11:00 pm - 12:16 amORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 16mnonstop

$309American Airlines

Wed, Dec 9 - Sat, Dec 12

5:51 am - 7:20 amMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 29mnonstop

6:36 pm - 7:52 pmORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 16mnonstop

$309American Airlines

Fri, Dec 11 - Sun, Dec 13

9:43 am - 11:00 amMSN Madison Truax Field-ORD Chicago O'Hare Intl

1h 17mnonstop

10:09 pm - 11:19 pmORD Chicago O'Hare Intl-MSN Madison Truax Field

1h 10mnonstop

$309American Airlines

Booking Insights

Price, demand and travel trends for Madison to Chicago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

Prices

Airlines

How much is a round-trip flight from Madison to Chicago? This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Madison to Chicago departing in december.
What is the cheapest Madison to Chicago flight route? KAYAK tracks online flight deals over the last 12 months and analyzes pricing trends to identify the best available fares.: Madison (MSN) to Chicago O'Hare Intl Airport (ORD) is the cheapest Madison to Chicago route, averaging $289 round-trip. Other Madison to Chicago routes average $1,522, based on KAYAK data over the past 12 months.
What's the cheapest day of the week to fly from Madison to Chicago?: Based on deals KAYAK users found in the last 12 months, Friday is the cheapest day of the week to fly from Madison to Chicago. It’s 18% cheaper than the average day, while Sunday is the most expensive, with prices 55% higher.
What’s the cheapest month to fly from Madison to Chicago? KAYAK internal proprietary data takes all prices for each month over the last 12 months for round-trip flights from Madison to Chicago, removes the top 0.1% to account for outliers and then takes the median of all values for each month.: •December is the cheapest month to fly from Madison to Chicago at $231 round-trip.
•September ($1,522) and May ($449) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 558% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Find deals

Expert advice

Our travel experts

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Low season	October
High season	January
Cheapest flight	$155

Beat the crowds with an average 43% drop in travelers.

The most popular month to fly with an average 52% increase in travelers.

One-way flight from Madison to Chicago O'Hare Intl Airport

When to book flights from Madison to Chicago

Are your dates flexible? Find out the best times to travel from Madison to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.

Estimated round-trip price

KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

What are the earliest and latest flights from Madison to Chicago?
These are the earliest and latest flight times available from Madison to Chicago:

• Earliest: departs at 5:00 am and lands at 6:21 am
• Latest: departs at 9:40 pm and lands at 11:01 pm.

The flight takes about 1h 21m.
What cabin classes can I book on flights from Madison to Chicago?
Two cabin classes are available on flights from Madison to Chicago:

• Economy Class
• First Class
How long is a flight from Madison to Chicago?
A nonstop flight from Madison to Chicago takes 1h 21m, covering 123 miles.
Do I need a passport to fly from Madison to Chicago?
No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.
How much should I expect to pay for a Madison to Chicago flight?
Round-trip flights from Madison to Chicago range from $231 to $399, with an average of $289 over the past 12 months. Anything below $231 counts as a good deal.
What is the standard checked-bag allowance on flights from Madison to Chicago?
There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.
How are flight departures from Madison to Chicago spread across the day?
Morning is the busiest departure period on Madison to Chicago flights, with 54% of flights leaving in that window. Afternoon departures account for 26%, evening flights for 20%, and night flights for 0%.
Which airlines offer Wi-Fi on Madison to Chicago flights?
American Airlines is the only airline on the Madison to Chicago route offering in-flight Wi-Fi. Pricing depends on fare class.
How are flight prices from Madison to Chicago looking right now?
One-way fares from Madison to Chicago are currently lower than usual. Average one-way flight prices are about $220, which is 15% below the typical average for this route.
What car rental options are available in Chicago?
Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) — daily rates averaging $64:

• Routes Car & Truck Rentals
• Europcar
• Hertz
• Ace
• Dollar

Near Chicago Midway Airport (MDW) — daily rates averaging $84:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) — daily rates averaging $81:

• Alamo
• Enterprise Rent-A-Car
• Budget
• Avis
• National
Which airports can I use when flying from Madison to Chicago?
Flights from Madison to Chicago usually depart from Madison Truax Field (MSN) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).
Can I save money by using flexible dates for flights from Madison to Chicago?
Yes. Flexible dates can save you up to 47% on flights from Madison to Chicago. Friday is the cheapest departure day at $239 round-trip on average, while Sunday is the most expensive at $449, a difference of $210.

KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.
What airlines fly from Madison to Chicago?
2 airlines operate flights between Madison and Chicago. The airlines offering nonstop flights on this route include:

• United Airlines
• American Airlines
What popular places can I visit in Chicago?
Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago on KAYAK.
Which airlines offer extra legroom and free seat selection on Madison to Chicago flights?
Among airlines operating Madison to Chicago flights:

• United Airlines: offers free seat selection
• American Airlines: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.
Which airlines include bags at no extra cost on Madison to Chicago flights?
Here are some options for this route, based on selected ticket types and cabin classes:

• United Airlines: a cabin bag and a checked bag in First Class
• American Airlines: a cabin bag and a checked bag in First Class

Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

If your dates are flexible, aim for a Friday departure and avoid flying on Sunday. On this route, Friday flights average $239, about $210 less than Sunday fares (47% savings) based on the last 12 months.
If you can choose when to travel, plan your Madison to Chicago trip for December. Fares historically average $231 round-trip in that month - typically $1,291 less than the most expensive month, which is September (based on the last 12 months).
If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

• DoubleTree by Hilton Chicago Midway Airport
• Holiday Inn Chicago - Midway Airport S by IHG
• Skylark Motel Chicago Midway Airport

Direct departures

Madison Truax Field to Chicago

Monday