HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news

Cheap flights from Madison (MSN) to Chicago (CHI) from $140

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/7. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
MSN — CHI
May 15 — May 221
From?
To?
Wed 5/15
Wed 5/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Cheap flight deals from Madison to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 10, 2024.

Popular in

November

Cheapest in

July

Average price

$268

Round-trip from

$223
High demand for flights, 43% potential price rise
Search Deals
Best time to find cheap flights, 36% potential price drop
Search Deals
Average for round-trip flights in May 2024
Search Deals
From Madison Truax Field to Chicago (CHI)
Search Deals

What is the cheapest day to fly round-trip from Madison to Chicago?

Flights from Madison to Chicago are found to be more expensive on Saturday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.

What is the cheapest month to fly from Madison to Chicago?

The best pricing can be found in the month of July. Prices to Chicago from Madison average $273. You can even find prices in July for less than $273, as users have found deals to Chicago from as low as $138. The month of November appears to be one of the more expensive times to travel to Chicago from Madison. Flying in the targeted month can save you up to 76%.

When is the cheapest time to fly from Madison to Chicago (MSN - CHI)?

A simple way to save on the total cost of your ticket is to fly from Madison to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 16% on your trip compared to booking a flight at noon.

Cheap American Airlines flights from Madison to Chicago

Explore cheap flight options specifically provided by American Airlines for the route between Madison and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,717,708 searches. Data last updated May 10, 2024.
Consider these cheap American Airlines flights we've found departing from Madison to Chicago. Make sure to check back often as deals are often changing.
Tue 8/272:50 pmMSN - ORD
Nonstop1h 03mAmerican Airlines
Tue 9/246:45 pmORD - MSN
Nonstop1h 17mAmerican Airlines
Deal found 5/8$219
Mon 6/36:30 pmMSN - ORD
Nonstop0h 59mAmerican Airlines
Mon 6/1011:04 amORD - MSN
Nonstop0h 58mAmerican Airlines
Deal found 5/9$279
Sun 6/235:35 amMSN - ORD
Nonstop1h 00mAmerican Airlines
Mon 7/811:10 amORD - MSN
Nonstop1h 01mAmerican Airlines
Deal found 5/9$298
Mon 6/37:00 amMSN - ORD
1 stop7h 20mAmerican Airlines
Mon 6/104:49 pmORD - MSN
Nonstop0h 54mAmerican Airlines
Deal found 5/9$505
Mon 6/37:00 amMSN - ORD
1 stop7h 20mAmerican Airlines
Fri 6/75:30 amORD - MSN
1 stop7h 25mAmerican Airlines
Deal found 5/8$513

Cheap United Airlines flights from Madison to Chicago

Explore cheap flight options specifically provided by United Airlines for the route between Madison and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,717,708 searches. Data last updated May 10, 2024.
Have a look at some of the cheapest available United Airlines flights departing from Madison and landing in Chicago. If these deals don't fit your criteria, make sure to check back soon as new deals are always added.
Mon 6/106:20 amMSN - ORD
Nonstop1h 03mUnited Airlines
Fri 6/143:35 pmORD - MSN
Nonstop1h 03mUnited Airlines
Deal found 5/9$297
Mon 5/276:20 amMSN - ORD
Nonstop1h 03mUnited Airlines
Mon 6/38:10 pmORD - MSN
Nonstop1h 02mUnited Airlines
Deal found 5/9$344
Tue 8/278:42 amMSN - ORD
1 stop10h 13mUnited Airlines
Tue 9/243:45 pmORD - MSN
Nonstop1h 03mUnited Airlines
Deal found 5/8$357
Mon 10/285:54 pmMSN - ORD
1 stop15h 49mUnited Airlines
Sun 11/37:50 pmORD - MSN
Nonstop1h 04mUnited Airlines
Deal found 5/9$387
Mon 6/106:20 amMSN - ORD
Nonstop1h 03mUnited Airlines
Fri 6/145:04 amORD - MSN
1 stop17h 18mUnited Airlines
Deal found 5/9$434
Mon 6/36:20 amMSN - ORD
Nonstop1h 03mUnited Airlines
Fri 6/75:04 amORD - MSN
1 stop17h 18mUnited Airlines
Deal found 5/8$450
Mon 5/276:03 pmMSN - ORD
1 stop15h 32mUnited Airlines
Mon 6/33:35 pmORD - MSN
Nonstop1h 03mUnited Airlines
Deal found 5/9$467
Thu 6/68:35 amMSN - ORD
Nonstop1h 11mUnited Airlines
Thu 6/135:04 amORD - MSN
1 stop17h 18mUnited Airlines
Deal found 5/9$486
Sun 6/2310:50 amMSN - ORD
Nonstop1h 06mUnited Airlines
Mon 7/88:32 pmORD - MSN
1 stop20h 30mUnited Airlines
Deal found 5/9$501

Cheap Madison to Chicago flights in May & June 2024

Find cheap flight options from Madison to Chicago specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,717,708 searches. Prices were last updated on May 10, 2024.
Listed are some of the best fares we've found on flights departing from Madison to Chicago in 2024. For more flight deals, be sure to check back very soon.
Mon 6/36:30 pmMSN - ORD
Nonstop0h 59mAmerican Airlines
Mon 6/1011:04 amORD - MSN
Nonstop0h 58mAmerican Airlines
Deal found 5/9$279
Mon 6/106:20 amMSN - ORD
Nonstop1h 03mUnited Airlines
Fri 6/143:35 pmORD - MSN
Nonstop1h 03mUnited Airlines
Deal found 5/9$297
Sun 6/235:35 amMSN - ORD
Nonstop1h 00mAmerican Airlines
Mon 7/811:10 amORD - MSN
Nonstop1h 01mAmerican Airlines
Deal found 5/9$298
Mon 5/276:20 amMSN - ORD
Nonstop1h 03mUnited Airlines
Mon 6/38:10 pmORD - MSN
Nonstop1h 02mUnited Airlines
Deal found 5/9$344
Mon 6/106:20 amMSN - ORD
Nonstop1h 03mUnited Airlines
Fri 6/145:04 amORD - MSN
1 stop17h 18mUnited Airlines
Deal found 5/9$434
Mon 6/36:20 amMSN - ORD
Nonstop1h 03mUnited Airlines
Fri 6/75:04 amORD - MSN
1 stop17h 18mUnited Airlines
Deal found 5/8$450
Mon 5/276:03 pmMSN - ORD
1 stop15h 32mUnited Airlines
Mon 6/33:35 pmORD - MSN
Nonstop1h 03mUnited Airlines
Deal found 5/9$467
Thu 6/68:35 amMSN - ORD
Nonstop1h 11mUnited Airlines
Thu 6/135:04 amORD - MSN
1 stop17h 18mUnited Airlines
Deal found 5/9$486
Sun 6/2310:50 amMSN - ORD
Nonstop1h 06mUnited Airlines
Mon 7/88:32 pmORD - MSN
1 stop20h 30mUnited Airlines
Deal found 5/9$501

Madison to Chicago 2024 flight deals

Discover exclusive flight deals for travel between Madison and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,717,708 searches. Data last updated May 10, 2024.
Listed are some of the best fares we've found on flights departing from Madison to Chicago in 2024. For more flight deals, be sure to check back very soon.
Tue 8/272:50 pmMSN - ORD
Nonstop1h 03mAmerican Airlines
Tue 9/246:45 pmORD - MSN
Nonstop1h 17mAmerican Airlines
Deal found 5/8$219
Mon 6/36:30 pmMSN - ORD
Nonstop0h 59mAmerican Airlines
Mon 6/1011:04 amORD - MSN
Nonstop0h 58mAmerican Airlines
Deal found 5/9$279
Mon 6/106:20 amMSN - ORD
Nonstop1h 03mUnited Airlines
Fri 6/143:35 pmORD - MSN
Nonstop1h 03mUnited Airlines
Deal found 5/9$297
Sun 6/235:35 amMSN - ORD
Nonstop1h 00mAmerican Airlines
Mon 7/811:10 amORD - MSN
Nonstop1h 01mAmerican Airlines
Deal found 5/9$298
Mon 5/276:20 amMSN - ORD
Nonstop1h 03mUnited Airlines
Mon 6/38:10 pmORD - MSN
Nonstop1h 02mUnited Airlines
Deal found 5/9$344
Tue 8/278:42 amMSN - ORD
1 stop10h 13mUnited Airlines
Tue 9/243:45 pmORD - MSN
Nonstop1h 03mUnited Airlines
Deal found 5/8$357
Mon 10/285:54 pmMSN - ORD
1 stop15h 49mUnited Airlines
Sun 11/37:50 pmORD - MSN
Nonstop1h 04mUnited Airlines
Deal found 5/9$387
Mon 6/106:20 amMSN - ORD
Nonstop1h 03mUnited Airlines
Fri 6/145:04 amORD - MSN
1 stop17h 18mUnited Airlines
Deal found 5/9$434
Mon 6/36:20 amMSN - ORD
Nonstop1h 03mUnited Airlines
Fri 6/75:04 amORD - MSN
1 stop17h 18mUnited Airlines
Deal found 5/8$450

Non-stop flights to Chicago from Madison

Discover non-stop flight options from Madison to Chicago. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,717,708 searches. Data last updated May 10, 2024.
For a quicker trip, book one of these direct flights from Madison to Chicago. Select from other flights from Madison to Chicago by using the search form above.
Thu 5/306:20 amMSN - ORD
Nonstop1h 03mUnited Airlines
Sun 6/29:00 amORD - MSN
Nonstop1h 05mUnited Airlines
Deal found 5/7$254
Mon 6/176:18 pmMSN - ORD
Nonstop1h 00mAmerican Airlines
Wed 6/1911:04 amORD - MSN
Nonstop0h 58mAmerican Airlines
Deal found 5/8$264
Mon 6/36:30 pmMSN - ORD
Nonstop0h 59mAmerican Airlines
Mon 6/1011:04 amORD - MSN
Nonstop0h 58mAmerican Airlines
Deal found 5/9$279
Mon 6/106:20 amMSN - ORD
Nonstop1h 03mUnited Airlines
Fri 6/143:35 pmORD - MSN
Nonstop1h 03mUnited Airlines
Deal found 5/9$297
Thu 5/306:30 amMSN - ORD
Nonstop0h 59mAmerican Airlines
Sun 6/28:42 pmORD - MSN
Nonstop1h 04mAmerican Airlines
Deal found 5/7$298
Wed 6/56:20 amMSN - ORD
Nonstop1h 03mUnited Airlines
Wed 6/123:35 pmORD - MSN
Nonstop1h 03mUnited Airlines
Deal found 5/8$299
Fri 6/146:18 pmMSN - ORD
Nonstop1h 00mAmerican Airlines
Mon 6/1711:04 amORD - MSN
Nonstop0h 58mAmerican Airlines
Deal found 5/7$317
Fri 5/246:20 amMSN - ORD
Nonstop1h 03mUnited Airlines
Sun 5/269:00 amORD - MSN
Nonstop1h 05mUnited Airlines
Deal found 5/7$319
Fri 6/75:35 amMSN - ORD
Nonstop1h 00mAmerican Airlines
Fri 6/1411:04 amORD - MSN
Nonstop0h 58mAmerican Airlines
Deal found 5/8$328

One-way flights to Chicago from Madison

Search for one-way flight options from Madison to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,717,708 searches. Data last updated May 10, 2024.
Some of the best available deals we've found on one-way flights from Madison to Chicago. Those needing a return flight from Madison to Chicago can use the search form above.
Fri 6/76:20 amMSN - ORD
Nonstop1h 03mUnited Airlines
Deal found 5/8$140
Wed 6/128:35 amMSN - ORD
Nonstop1h 11mUnited Airlines
Deal found 5/9$155
Wed 6/126:50 pmMSN - ORD
2 stops22h 50mMultiple Airlines
Deal found 5/9$165
Thu 6/610:50 amMSN - ORD
Nonstop1h 06mUnited Airlines
Deal found 5/9$170
Wed 6/125:50 pmMSN - ORD
1 stop14h 44mMultiple Airlines
Deal found 5/9$194
Wed 6/126:50 pmMSN - ORD
3 stops30h 05mMultiple Airlines
Deal found 5/9$204
Sun 6/166:20 amMSN - ORD
Nonstop1h 03mUnited Airlines
Deal found 5/9$225
Thu 6/67:13 amMSN - ORD
1 stop5h 02mAmerican Airlines
Deal found 5/9$257
Sat 6/19:15 amMSN - MDW
3 stops33h 41mMultiple Airlines
Deal found 5/7$332

Find flights from Madison to Chicago within your budget

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, Cheapflights users made 2,717,708 searches. Data last updated May 10, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$219 - $566

Route

Depart

Return

Price

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Tue 8/27

Nonstop1h 03m

Chicago O'Hare Intl

Tue 9/24

Nonstop1h 17m

$219

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Mon 6/3

Nonstop0h 59m

Chicago O'Hare Intl

Mon 6/10

Nonstop0h 58m

$279

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Mon 6/10

Nonstop1h 03m

Chicago O'Hare Intl

Fri 6/14

Nonstop1h 03m

$297

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Sun 6/23

Nonstop1h 00m

Chicago O'Hare Intl

Mon 7/8

Nonstop1h 01m

$298

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Mon 5/27

Nonstop1h 03m

Chicago O'Hare Intl

Mon 6/3

Nonstop1h 02m

$344

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Tue 8/27

1 stop10h 13m

Chicago O'Hare Intl

Tue 9/24

Nonstop1h 03m

$357

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Mon 10/28

1 stop15h 49m

Chicago O'Hare Intl

Sun 11/3

Nonstop1h 04m

$387

Madison Truax FieldChicago Midway

MSN - MDW

MSNMDW

Madison Truax Field

Sat 5/25

1 stop15h 14m

Chicago Midway

Sun 5/26

1 stop14h 57m

$564

Madison Truax FieldChicago Midway

MSN - MDW

MSNMDW

Madison Truax Field

Sat 5/25

1 stop15h 14m

Chicago Midway

Tue 5/28

1 stop7h 36m

$566

Flights are sorted by cheapest first

Deals found on 5/8

When is the cheapest time to fly from Madison to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Madison to Chicago. Price data was last updated on May 5, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Madison to Chicago flight should consider departing on Tuesday mornings when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Average price of flights to Chicago by month

Plan your trip from Madison to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight from Madison to Chicago is currently $205 while a round-trip flight costs $368. Price data was last updated on May 5, 2024.

Currently, February is the cheapest month in which you can book a flight from Madison to Chicago (average of $244). Flying from Madison to Chicago in June is currently the most expensive (average of $348). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

January

$248

February

$244

March

$280

April

$258

May

$278

June

$348

July

$330

August

$274

September

$258

October

$248

November

$270

December

$248

Temperature and rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

23 - 73.4 °F

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated May 10, 2024.
To help decide which airline to fly from Madison to Chicago, see what other customers have to say about American Airlines, United Airlines and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
10,778 reviews
Check prices

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.6

Entertainment

8.0

Food

7.4

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Delta
8.0
Very good
10,778 reviews
Delta
8.0
Very good
10,778 reviews
Check prices

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.6

Entertainment

8.0

Food

7.4

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

WestJet
7.6
Good
2,942 reviews
Delta
8.0
Very good
10,778 reviews
Check prices

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.6

Entertainment

8.0

Food

7.4

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

United Airlines
7.4
Good
11,027 reviews
Delta
8.0
Very good
10,778 reviews
Check prices

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.6

Entertainment

8.0

Food

7.4

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

American Airlines
7.3
Good
14,665 reviews
Delta
8.0
Very good
10,778 reviews
Check prices

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.6

Entertainment

8.0

Food

7.4

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Related info for your journey

Find useful and relevant information for your journey from Madison to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Madison to Chicago?

    For a flight from Madison to Chicago, you will be flying from Truax Field. Madison Truax Field (MSN) is just 5.4 mi from the center of the city. Truax Field is the only Madison airport and it handles 28 outbound flights to Chicago per day. 2 airlines have flights to Chicago from Madison Truax Field on a regular basis.

  • Can I find flights from Madison to Chicago for under $300 on Cheapflights?

    Yes, there are multiple flights from Madison to Chicago for under $300. The cheapest flight booked recently is on American Airlines for just $219, but on average you can expect to pay $433.

  • Are there nonstop flights from Madison to Chicago for under $300 on Cheapflights?

    Cheapflights has at least 20 direct flights from Madison to Chicago under $300. A good price for a nonstop flight from Madison to Chicago is less than $380.

  • What days are nonstop flights available from Madison to Chicago?

    Days when nonstop flights are available for this flight are: Sunday, Tuesday, Saturday.

  • How many flights depart from Madison to Chicago on average per day?

    On average, you can expect to see 5 flights from Madison to Chicago a day.
    Early Morning (Midnight to 6am) - 40% of flight departures
    Morning (6am - Noon) - 60% of flight departures

  • How long is the flight from Madison to Chicago?

    There are many flights that can get you from Madison to Chicago in 1h 03m. Fly via American Airlines, United Airlines, or Delta to get the fastest option. Airlines will cover a distance of 109 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Madison to Chicago round-trip?

    According to our current data, American Airlines ($219), United Airlines ($297), and Delta ($564) offers the cheapest pricing from Madison to Chicago. American Airlines is priced at 19% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Madison to Chicago one-way?

    One-way options have recently been found by users for as low as $140 on United Airlines. Other airlines that offer cheap prices include American Airlines from $257 and WestJet from $947 one-way.

  • What are the most reliable airlines from Madison to Chicago?

    No one likes to see their flight delayed. When booking a flight from Madison to Chicago consider choosing Piedmont Airlines (100%), Japan Airlines (96%) or Republic Airways (94%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Madison to Chicago?

    Looking for the cheapest flight from Madison to Chicago? While on average our users pay $1,914, our data indicates the cheapest price to be $163. The most popular route (Madison Truax Field - Chicago O'Hare Intl), is priced around $264.

  • What does MSN to ORD mean?

    Great question - MSN to ORD just means Madison Truax Field Airport to Chicago O'Hare Intl Airport. Now you’ll know what these unique codes when you look for flights! Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.

  • Can I find deals for flights from Madison to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Madison to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Madison to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Madison to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Madison to Chicago that include hotel bookings?

    Yes. In addition to deals on Madison to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Chicago.

  • Can I find deals for business class flights from Madison to Chicago?

    Yes. Cheapflights offers flight deals from Madison to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Madison to Chicago that allow pets onboard?

    Many airlines flying from Madison to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Madison to Chicago?

    Yes, you can often find last-minute deals on Madison to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Madison to Chicago flight deals updated?

    The Madison to Chicago flight deals you see on this page were last updated on 5/9.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Madison to Chicago
See prices for flight routes from nearby airports that may be better suited for you.

Appleton to O'Hare Intl flights
Green Bay to O'Hare Intl flights
Milwaukee to St. Louis flights
Milwaukee to O'Hare Intl flights
Appleton to St. Louis flights
Madison to O'Hare Intl flights
Madison to St. Louis flights
Green Bay to St. Louis flights
Appleton to Midway flights
Green Bay to Midway flights
La Crosse to O'Hare Intl flights
Wausau to O'Hare Intl flights
Madison to Midway flights
Milwaukee to Midway flights
Wausau to Midway flights
Wausau to St. Louis flights
La Crosse to St. Louis flights
La Crosse to Midway flights
La Crosse to Peoria flights
Madison to Marion flights
Eau Claire to O'Hare Intl flights
Appleton to Peoria flights
Rhinelander to St. Louis flights

Top 2 airlines flying from Madison to Chicago

Discover the top 2 airlines that operate flights from Madison to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,717,708 searches. Data last updated May 10, 2024.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$111Average$206FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapest$138Average$248FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Philadelphia to Nashville flights
Washington, D.C. to Las Vegas flights
Detroit to Atlanta flights
San Francisco to Las Vegas flights
San Francisco to Boston flights
Pittsburgh to New York flights
New Orleans to Los Angeles flights
Denver to Miami flights
Orlando to Baltimore flights
Detroit to Dallas flights
Madison to Charlottesville flights

Search flights from Madison to Chicago by cabin class

Find flights from Madison to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

Hourly flight availability from Madison to Chicago

Find hourly flight availability from Madison to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 10, 2024.
4%of flight departuresEarly morningMidnight to 6 am
64%of flight departuresMorning6 am to noon
32%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Madison to Chicago

Explore weekly flight availability from Madison to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 10, 2024.
Sunday31daily flights
Monday33daily flights
Tuesday26daily flights
Wednesday27daily flights
Thursday31daily flights
Friday33daily flights
Saturday17daily flights

Book a flight to one of these trending destinations

User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Flights to Ordu/Giresun
Flights to Hakodate
Flights to Gazipasa
Flights to Kirkwall Arpt
Flights to Skiathos
Flights to Bourgas
Flights to Kalamata
Flights to Menorca/Mahon
Flights to Mytilene
Flights to Mason City
Flights to Pau Pyrénées
Flights to Neiva La Marguita
Flights to Cortez Montezuma County
Flights to Biarritz Parme
Flights to Parikia Paros
Flights to Ohrid
Flights to Edremit/Korfez
Flights to Naxos
Flights to Dalaman
Flights to Lublin
Flights to Miyakojima Hirara
Flights to Champaign University-Willard
Flights to Kagoshima
Flights to Constanţa Mihail Kogalniceanu

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Madison to Chicago?

Cheapflights helps you search for flights from Madison to Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Madison to Chicago?

Cheapflights helps you find that perfect flight to Chicago from Madison by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Madison to Chicago with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Madison to Chicago, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Madison to Chicago become cheaper?

Yes! Start tracking prices for Madison to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines