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Flights Chicago — Madison

Chicago
CHI
Madison
MSN

Cheap flights Chicago — Madison

Below you can see the best deals on flights Chicago — Madison for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 4 August, from AED 781.

Top 10 cheap flights Chicago — Madison

Direct flights Chicago — Madison

Direct flight options for Chicago — Madison with no stopovers on upcoming dates. A direct flight is faster and more convenient — especially when travelling with luggage or children.

The fastest direct flight is operated by United Airlines — travel time is 58 min.

Top 10 direct flights Chicago — Madison

About the Chicago — Madison flight

On this page, you can book flights from Chicago to Madison. Despite the short distance of 197 km, there are approximately 62 flights per week on this route. Information on the most convenient ways to reach the departure terminal can be found in the Chicago transportation section.

Flights on this route are operated by United Airlines and American Airlines. Ticket prices are dynamic, so use the low-fare calendar to find the best deals. Upon arrival, check out the Madison transportation options to quickly reach the city center.

Flight schedule Chicago — Madison

The table shows direct flights Chicago → Madison on the selected date. The flight takes approximately 1 h 7 min. Regular flights are operated by United Airlines and American Airlines. Departures from O'Hare International Airport, Chicago Midway International Airport and Midway International Airport airports, arrivals at Dane County Regional Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

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Flight ticket prices by day: Chicago — Madison

Below is a calendar of the lowest flight ticket prices for Chicago — Madison by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from AED 781 in ,, and the most expensive are around AED 1,237 in r. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Chicago → Madison, average one-way price

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
JanAED 880lowMayAED 922lowSepAED 922low
FebAED 964mediumJunAED 1,257highOctAED 1,006medium
MarAED 1,132highJulAED 1,174highNovAED 1,174high
AprAED 1,006mediumAugAED 1,048mediumDecAED 1,132high

Some values are estimated based on seasonality.

When to fly

The climate in Madison is characterized by warm summers and freezing winters. The hottest month is July, with an average temperature of around 27.9°C, while the coldest is January, when temperatures drop to -9.5°C. Precipitation peaks in May and June, with up to 13 rainy days per month.

When planning your budget, it is worth noting that the most affordable tickets are offered in August, starting AED 781. The most expensive month to fly from Chicago is June, when the minimum cost starts AED 1,237. During other periods, prices remain relatively stable, starting AED 818.

August is considered the optimal time for a trip in terms of both savings and weather: comfortable temperatures persist during this period while flight costs are at their lowest. It is best to avoid June if you are looking to minimize your travel expenses.

Temperature · Madison

Dry and wet days · Madison

Wind speed and direction · Madison

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How to get the best deal on a Chicago — Madison ticket

  • Book in advance: On short regional routes, prices tend to rise 7–10 days before departure, so purchasing a ticket at least 3 weeks ahead can help you find options AED 788.
  • Choose weekdays: Flights on Tuesdays and Wednesdays are usually cheaper than departures on Fridays or Sundays, when demand from business travelers and weekend tourists is at its peak.
  • Check baggage policies: UA and AA often offer Basic Economy fares that restrict carry-on bags, so review the rules carefully before paying.
  • Use search tools: The price trend chart on this page allows you to compare flight costs for nearby dates and select the most advantageous option in seconds.

Airlines

Regular air service on this route is provided by two major airlines: United Airlines and American Airlines. Collectively, there are approximately 62 direct flights per week, allowing you to choose a convenient departure time throughout the day. Detailed information about flight schedules and available fares for each airline can be found in the interactive list below.

  • United Airlines
    United AirlinesUA
    42x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight ORD → MSN42x/week
      Duration
      1h 11m
      Days
      MTWTFSS
    67.6%Open →
  • American Airlines
    American AirlinesAA
    20x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight ORD → MSN20x/week
      Duration
      1h 7m
      Days
      MTWTFSS
    32.4%Open →

Cities and airports on the Chicago — Madison route

Flights Chicago — Madison depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport and arrive at Dane County Regional Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Arrival

Madison

MSN
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

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Frequently asked questions about the Chicago — Madison flight

How long is the flight from Chicago to Madison?

The distance between the cities is only 197 km. A direct flight on a regional jet typically lasts from 50 minutes to 1 hour.

Which airlines fly this route?

The main carriers serving this route are United Airlines and American Airlines.

Are there direct flights?

Yes, direct flights predominate on this route. Given the frequency of about 62 flights per week, finding a non-stop option is easy.

How much is the cheapest ticket?

Flight prices change constantly depending on the season and demand. You can check the current minimum for specific dates in the low-fare calendar on this page.

Which airport does the flight arrive at?

Flights from Chicago arrive at Dane County Regional Airport (MSN), located directly in Madison.

Where else you can fly from Chicago

New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverNashvilleLondonIndianapolisMilwaukeeCharlottePhiladelphiaColumbusKansas CityMiamiPhoenixLas VegasCincinnatiGrand RapidsDes MoinesSan FranciscoDaytonGreen BayTampaPittsburghClevelandFort LauderdaleCedar RapidsMexico CityAppletonPortlandOklahoma CityAustin
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