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Cheap flights from Madison (MSN) to Chicago (CHI) from $110

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 6/4. 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 4 — May 111
From?
To?
Sat 5/4
Sat 5/11
1 adult, Economy
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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 April 29, 2024.

Popular in

January

Cheapest in

October

Round-trip from

$222

One-way from

$142
High demand for flights, 41% potential price rise
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Best time to find cheap flights, 32% potential price drop
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From Madison Truax Field to Chicago (CHI)
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One-way flight from Madison Truax Field to Chicago (CHI)
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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 Thursday. 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 October. Prices to Chicago from Madison average $204. You can even find prices in October for less than $204, as users have found deals to Chicago from as low as $117. The month of January 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 68%.

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 20% on your trip compared to booking a flight at noon.

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 2,948,547 searches. Data last updated April 29, 2024.
Consider these cheap United Airlines flights we've found departing from Madison to Chicago. Make sure to check back often as deals are often changing.
Thu 5/306:20 amMSN - ORD
Nonstop1h 03mUnited Airlines
Sat 6/15:04 amORD - MSN
1 stop17h 18mUnited Airlines
Deal found 4/29$344
Tue 8/278:42 amMSN - ORD
1 stop13h 16mUnited Airlines
Tue 9/249:09 amORD - MSN
Nonstop1h 05mUnited Airlines
Deal found 4/28$347
Sun 8/254:00 pmMSN - ORD
Nonstop1h 05mUnited Airlines
Sat 8/319:08 pmORD - MSN
1 stop16h 26mUnited Airlines
Deal found 4/28$381
Tue 5/286:03 pmMSN - ORD
1 stop15h 32mUnited Airlines
Tue 6/48:10 pmORD - MSN
Nonstop1h 02mUnited Airlines
Deal found 4/28$387
Tue 8/278:42 amMSN - ORD
1 stop12h 19mUnited Airlines
Tue 9/245:15 amORD - MSN
1 stop15h 51mUnited Airlines
Deal found 4/28$416
Tue 5/75:35 pmMSN - ORD
Nonstop1h 04mUnited Airlines
Sat 5/1110:35 amORD - MSN
Nonstop0h 55mUnited Airlines
Deal found 4/27$489
Tue 5/73:55 pmMSN - ORD
Nonstop1h 03mUnited Airlines
Sat 5/117:10 amORD - MSN
1 stop13h 38mUnited Airlines
Deal found 4/27$502
Sat 5/46:30 amMSN - ORD
Nonstop1h 02mUnited Airlines
Sun 5/58:05 pmORD - MSN
Nonstop1h 02mUnited Airlines
Deal found 4/28$544

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 2,948,547 searches. Data last updated April 29, 2024.
Have a look at some of the cheapest available American 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.
Wed 8/78:00 amMSN - ORD
Nonstop1h 00mAmerican Airlines
Sat 8/179:01 pmORD - MSN
Nonstop0h 58mAmerican Airlines
Deal found 4/29$219
Sun 8/256:00 amMSN - ORD
Nonstop1h 00mAmerican Airlines
Sat 8/312:01 pmORD - MSN
Nonstop1h 05mAmerican Airlines
Deal found 4/28$249
Thu 5/308:01 amMSN - ORD
Nonstop0h 59mAmerican Airlines
Sat 6/110:16 amORD - MSN
Nonstop1h 01mAmerican Airlines
Deal found 4/29$253
Tue 5/288:01 amMSN - ORD
Nonstop0h 59mAmerican Airlines
Tue 6/48:42 pmORD - MSN
Nonstop1h 04mAmerican Airlines
Deal found 4/28$268
Thu 6/65:35 amMSN - ORD
Nonstop1h 00mAmerican Airlines
Mon 6/1011:04 amORD - MSN
Nonstop0h 58mAmerican Airlines
Deal found 4/28$298
Mon 7/154:22 pmMSN - ORD
Nonstop1h 13mAmerican Airlines
Thu 8/152:01 pmORD - MSN
Nonstop1h 05mAmerican Airlines
Deal found 4/28$328
Thu 6/61:25 pmMSN - ORD
1 stop8h 12mAmerican Airlines
Mon 6/108:30 pmORD - MSN
Nonstop1h 01mAmerican Airlines
Deal found 4/28$445
Tue 5/287:00 amMSN - ORD
1 stop5h 40mAmerican Airlines
Tue 6/45:15 amORD - MSN
1 stop4h 58mAmerican Airlines
Deal found 4/28$453
Thu 6/61:25 pmMSN - ORD
1 stop6h 05mAmerican Airlines
Mon 6/104:00 pmORD - MSN
1 stop7h 25mAmerican Airlines
Deal found 4/28$454

Cheap Madison to Chicago flights in April & May 2024

Find cheap flight options from Madison to Chicago specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,948,547 searches. Prices were last updated on April 29, 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.
Thu 5/308:01 amMSN - ORD
Nonstop0h 59mAmerican Airlines
Sat 6/110:16 amORD - MSN
Nonstop1h 01mAmerican Airlines
Deal found 4/29$253
Tue 5/288:01 amMSN - ORD
Nonstop0h 59mAmerican Airlines
Tue 6/48:42 pmORD - MSN
Nonstop1h 04mAmerican Airlines
Deal found 4/28$268
Thu 5/306:20 amMSN - ORD
Nonstop1h 03mUnited Airlines
Sat 6/15:04 amORD - MSN
1 stop17h 18mUnited Airlines
Deal found 4/29$344
Tue 5/286:03 pmMSN - ORD
1 stop15h 32mUnited Airlines
Tue 6/48:10 pmORD - MSN
Nonstop1h 02mUnited Airlines
Deal found 4/28$387
Tue 5/287:00 amMSN - ORD
1 stop5h 40mAmerican Airlines
Tue 6/45:15 amORD - MSN
1 stop4h 58mAmerican Airlines
Deal found 4/28$453
Tue 5/75:35 pmMSN - ORD
Nonstop1h 04mUnited Airlines
Sat 5/1110:35 amORD - MSN
Nonstop0h 55mUnited Airlines
Deal found 4/27$489
Tue 5/73:55 pmMSN - ORD
Nonstop1h 03mUnited Airlines
Sat 5/117:10 amORD - MSN
1 stop13h 38mUnited Airlines
Deal found 4/27$502
Tue 5/76:30 amMSN - ORD
Nonstop0h 59mAmerican Airlines
Sat 5/1110:16 amORD - MSN
Nonstop1h 01mAmerican Airlines
Deal found 4/28$509
Tue 5/711:45 amMSN - ORD
Nonstop1h 01mAmerican Airlines
Sat 5/115:15 amORD - MSN
1 stop4h 58mAmerican Airlines
Deal found 4/28$517

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 2,948,547 searches. Data last updated April 29, 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.
Wed 8/78:00 amMSN - ORD
Nonstop1h 00mAmerican Airlines
Sat 8/179:01 pmORD - MSN
Nonstop0h 58mAmerican Airlines
Deal found 4/29$219
Sun 8/256:00 amMSN - ORD
Nonstop1h 00mAmerican Airlines
Sat 8/312:01 pmORD - MSN
Nonstop1h 05mAmerican Airlines
Deal found 4/28$249
Thu 5/308:01 amMSN - ORD
Nonstop0h 59mAmerican Airlines
Sat 6/110:16 amORD - MSN
Nonstop1h 01mAmerican Airlines
Deal found 4/29$253
Tue 5/288:01 amMSN - ORD
Nonstop0h 59mAmerican Airlines
Tue 6/48:42 pmORD - MSN
Nonstop1h 04mAmerican Airlines
Deal found 4/28$268
Thu 6/65:35 amMSN - ORD
Nonstop1h 00mAmerican Airlines
Mon 6/1011:04 amORD - MSN
Nonstop0h 58mAmerican Airlines
Deal found 4/28$298
Mon 7/154:22 pmMSN - ORD
Nonstop1h 13mAmerican Airlines
Thu 8/152:01 pmORD - MSN
Nonstop1h 05mAmerican Airlines
Deal found 4/28$328
Thu 5/306:20 amMSN - ORD
Nonstop1h 03mUnited Airlines
Sat 6/15:04 amORD - MSN
1 stop17h 18mUnited Airlines
Deal found 4/29$344
Tue 8/278:42 amMSN - ORD
1 stop13h 16mUnited Airlines
Tue 9/249:09 amORD - MSN
Nonstop1h 05mUnited Airlines
Deal found 4/28$347
Sun 8/254:00 pmMSN - ORD
Nonstop1h 05mUnited Airlines
Sat 8/319:08 pmORD - MSN
1 stop16h 26mUnited Airlines
Deal found 4/28$381

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 2,948,547 searches. Data last updated April 29, 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.
Wed 8/78:00 amMSN - ORD
Nonstop1h 00mAmerican Airlines
Sat 8/179:01 pmORD - MSN
Nonstop0h 58mAmerican Airlines
Deal found 4/29$219
Sun 8/256:00 amMSN - ORD
Nonstop1h 00mAmerican Airlines
Sat 8/312:01 pmORD - MSN
Nonstop1h 05mAmerican Airlines
Deal found 4/28$249
Thu 5/308:01 amMSN - ORD
Nonstop0h 59mAmerican Airlines
Sat 6/110:16 amORD - MSN
Nonstop1h 01mAmerican Airlines
Deal found 4/29$253
Tue 5/288:01 amMSN - ORD
Nonstop0h 59mAmerican Airlines
Tue 6/48:42 pmORD - MSN
Nonstop1h 04mAmerican Airlines
Deal found 4/28$268
Thu 6/65:35 amMSN - ORD
Nonstop1h 00mAmerican Airlines
Mon 6/1011:04 amORD - MSN
Nonstop0h 58mAmerican Airlines
Deal found 4/28$298
Mon 7/154:22 pmMSN - ORD
Nonstop1h 13mAmerican Airlines
Thu 8/152:01 pmORD - MSN
Nonstop1h 05mAmerican Airlines
Deal found 4/28$328

Madison to Chicago flights leaving soon

Find last-minute flight options from Madison to Chicago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,948,547 searches. Data last updated April 29, 2024.
Book one of these great deals on flights from Madison to Chicago. To prevent any unwanted surprises, users should verify their flight info before booking.
Tue 5/75:35 pmMSN - ORD
Nonstop1h 04mUnited Airlines
Sat 5/1110:35 amORD - MSN
Nonstop0h 55mUnited Airlines
Deal found 4/27$489
Tue 5/73:55 pmMSN - ORD
Nonstop1h 03mUnited Airlines
Sat 5/117:10 amORD - MSN
1 stop13h 38mUnited Airlines
Deal found 4/27$502
Tue 5/76:30 amMSN - ORD
Nonstop0h 59mAmerican Airlines
Sat 5/1110:16 amORD - MSN
Nonstop1h 01mAmerican Airlines
Deal found 4/28$509
Tue 5/711:45 amMSN - ORD
Nonstop1h 01mAmerican Airlines
Sat 5/115:15 amORD - MSN
1 stop4h 58mAmerican Airlines
Deal found 4/28$517
Tue 5/710:45 amMSN - ORD
1 stop6h 41mAmerican Airlines
Sat 5/115:15 amORD - MSN
1 stop4h 58mAmerican Airlines
Deal found 4/27$519
Tue 5/77:00 amMSN - ORD
1 stop7h 20mAmerican Airlines
Sat 5/115:15 amORD - MSN
1 stop4h 58mAmerican Airlines
Deal found 4/28$525
Sat 5/46:30 amMSN - ORD
Nonstop1h 02mUnited Airlines
Sun 5/58:05 pmORD - MSN
Nonstop1h 02mUnited Airlines
Deal found 4/28$544
Sat 5/46:45 amMSN - ORD
1 stop5h 39mAmerican Airlines
Sun 5/58:31 pmORD - MSN
Nonstop0h 59mAmerican Airlines
Deal found 4/28$552
Sat 5/44:36 pmMSN - ORD
1 stop14h 49mAmerican Airlines
Sun 5/510:39 amORD - MSN
1 stop7h 55mAmerican Airlines
Deal found 4/28$656

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 2,948,547 searches. Data last updated April 29, 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.
Tue 6/48:01 amMSN - ORD
Nonstop0h 59mAmerican Airlines
Deal found 4/28$110
Sat 5/189:40 amMSN - ORD
1 stop8h 54mMultiple Airlines
Deal found 4/28$122
Sun 8/256:42 pmMSN - ORD
Nonstop0h 58mAmerican Airlines
Deal found 4/29$140
Sat 5/189:40 amMSN - ORD
3 stops18h 55mMultiple Airlines
Deal found 4/28$142
Tue 5/286:20 amMSN - ORD
Nonstop1h 03mUnited Airlines
Deal found 4/28$195
Thu 5/166:30 amMSN - ORD
Nonstop0h 59mAmerican Airlines
Deal found 4/28$205
Tue 6/47:00 amMSN - ORD
1 stop5h 40mAmerican Airlines
Deal found 4/28$227
Fri 5/1712:11 pmMSN - ORD
Nonstop1h 03mUnited Airlines
Deal found 4/29$235
Sun 5/55:35 pmMSN - ORD
Nonstop1h 04mUnited Airlines
Deal found 4/28$255

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 2,948,547 searches. Data last updated April 29, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$219 - $387

Route

Depart

Return

Price

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Wed 8/7

Nonstop1h 00m

Chicago O'Hare Intl

Sat 8/17

Nonstop0h 58m

$219

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Sun 8/25

Nonstop1h 00m

Chicago O'Hare Intl

Sat 8/31

Nonstop1h 05m

$249

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Thu 5/30

Nonstop0h 59m

Chicago O'Hare Intl

Sat 6/1

Nonstop1h 01m

$253

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Tue 5/28

Nonstop0h 59m

Chicago O'Hare Intl

Tue 6/4

Nonstop1h 04m

$268

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Thu 6/6

Nonstop1h 00m

Chicago O'Hare Intl

Mon 6/10

Nonstop0h 58m

$298

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Thu 5/30

Nonstop1h 03m

Chicago O'Hare Intl

Sat 6/1

1 stop17h 18m

$344

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Tue 8/27

1 stop13h 16m

Chicago O'Hare Intl

Tue 9/24

Nonstop1h 05m

$347

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Sun 8/25

Nonstop1h 05m

Chicago O'Hare Intl

Sat 8/31

1 stop16h 26m

$381

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Tue 5/28

1 stop15h 32m

Chicago O'Hare Intl

Tue 6/4

Nonstop1h 02m

$387

Flights are sorted by cheapest first

Deals found on 4/29

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 April 21, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Madison to Chicago flight should consider departing on Tuesday at noon 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 $181 while a round-trip flight costs $305. Price data was last updated on April 21, 2024.

Currently, February is the cheapest month in which you can book a flight from Madison to Chicago (average of $245). Flying from Madison to Chicago in June is currently the most expensive (average of $356). 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

$245

March

$280

April

$273

May

$282

June

$356

July

$336

August

$276

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 April 29, 2024.
To help decide which airline to fly from Madison to Chicago, see what other customers have to say about United Airlines, American Airlines and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
11,202 reviews
Check prices

Boarding

7.7

Overall

7.4

Food

6.7

Crew

8.1

Comfort

7.2

Entertainment

7.1

Reviews

1 / 10

Plane makes you pay for in flight entertainment. Unacceptable in this day and age. Plane was old and outdated. Luggage was lost

United Airlines
7.4
Good
11,202 reviews
United Airlines
7.4
Good
11,202 reviews
Check prices

Boarding

7.7

Overall

7.4

Food

6.7

Crew

8.1

Comfort

7.2

Entertainment

7.1

Reviews

1 / 10

Plane makes you pay for in flight entertainment. Unacceptable in this day and age. Plane was old and outdated. Luggage was lost

American Airlines
7.3
Good
14,834 reviews
United Airlines
7.4
Good
11,202 reviews
Check prices

Boarding

7.7

Overall

7.4

Food

6.7

Crew

8.1

Comfort

7.2

Entertainment

7.1

Reviews

1 / 10

Plane makes you pay for in flight entertainment. Unacceptable in this day and age. Plane was old and outdated. Luggage was lost

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 $371.

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

    Cheapflights has at least 6 direct flights from Madison to Chicago under $300. A good price for a nonstop flight from Madison to Chicago is less than $269.

  • Are there last-minute flights available from Madison to Chicago for under $500?

    There are currently 12+ open flights from Madison to Chicago within the next 7 days for less than $500.

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

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

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

    On average, you can expect to see 32 flights from Madison to Chicago a day.
    Early Morning (Midnight to 6am) - 6% of flight departures
    Morning (6am - Noon) - 50% of flight departures
    Afternoon (Noon - 6pm) - 44% 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. Fly via American Airlines or United Airlines to get the fastest option. Airlines will cover a distance of 109 mi. All flights are typically nonstop.

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

    According to our current data, American Airlines ($219), and United Airlines ($344) offers the cheapest pricing from Madison to Chicago.

  • 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%), Republic Airways (95%) or Japan Airlines (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 $760, our data indicates the cheapest price to be $153. The most popular route (Madison Truax Field - Chicago O'Hare Intl), is priced around $219.

  • 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 4/29.

See more FAQs

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

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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 2,948,547 searches. Data last updated April 29, 2024.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$111Average$207FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapest$138Average$248FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
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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 April 29, 2024.
19%of flight departuresEarly morningMidnight to 6 am
54%of flight departuresMorning6 am to noon
27%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 April 29, 2024.
Sunday31daily flights
Monday33daily flights
Tuesday26daily flights
Wednesday27daily flights
Thursday31daily flights
Friday33daily flights
Saturday17daily flights

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Fly with Cheapflights

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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.

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