Cheap flights from Chicago to Madison

Chicago FSS
CHI
Dane County
MSN

Flight deals from Chicago to 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 9 September, from $150.

Top 10 cheap flights from Chicago to Madison

F9
MX
$ 150

Chicago — Madison

15:50—17:20
9 Sep 2026
25 h 30 m
1 stop
F9
MX
$ 165

Chicago — Madison

19:44—17:25
1 Sep 2026
21 h 41 m
1 stop
F9
F9
F9
$ 180

Chicago — Madison

13:59—19:10
5 Sep 2026
29 h 11 m
2 stops
F9
MX
$ 189

Chicago — Madison

21:10—19:15
4 Sep 2026
22 h 5 m
1 stop
F9
F9
F9
$ 190

Chicago — Madison

11:45—19:10
5 Sep 2026
31 h 25 m
2 stops
F9
F9
F9
$ 194

Chicago — Madison

13:59—19:10
2 Sep 2026
29 h 11 m
2 stops
F9
F9
F9
$ 194

Chicago — Madison

07:05—19:10
2 Sep 2026
36 h 5 m
2 stops
F9
F9
F9
$ 199

Chicago — Madison

11:50—19:10
2 Sep 2026
31 h 20 m
2 stops
F9
F9
F9
$ 199

Chicago — Madison

06:05—19:10
2 Sep 2026
37 h 5 m
2 stops
F9
F9
F9
$ 200

Chicago — Madison

13:59—19:10
2 Sep 2026
29 h 11 m
2 stops

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Chicago — Madison flight

Looking for cheap flights from Chicago to Madison? Compare fares from different airlines, check the flight schedule and travel time — and book your Chicago — Madison ticket online at the best price.

The route has direct flights — around 185 flights per week, flights are operated by United Airlines, American Airlines, a nonstop flight takes about 1 h 7 min, the distance between the cities is around 197 km.

Planning your trip? You may find our Madison travel guide, how to get from the airport into town and Madison weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from $150Min. price
SeptemberCheapest
JulyPeak season
YesDirect flights
197 kmDistance
1 h 7 minTravel time
2Airlines
185 / wkFlights

Flight schedule from Chicago to Madison

The table shows direct flights from Chicago to 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.

Today
Any time
Last update: 15 Aug 2026

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 $150 in September, and the most expensive are around $281 in July. 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

Average one-way fares from Chicago to Madison by month. Tickets are usually cheapest in January (around $227) and priciest in June (about $324) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$227lowMay$238lowSep$238low
Feb$248mediumJun$324highOct$259medium
Mar$292highJul$302highNov$302high
Apr$259mediumAug$270mediumDec$292high

Some values are estimated based on seasonality.

When to fly

Weather in Madison: it is warmest in July (up to 28 °C on average) and coolest in January (around -2 °C). The driest month is November.

Tickets are usually cheapest in September and most expensive in July. Compare prices and weather by month in the charts below to pick the best time to fly.

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 ahead: fares for Chicago — Madison are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • Chicago is served by more than one airport — compare fares and travel time to each before you book.
  • The cheapest month to fly to Madison is usually September — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the Chicago — Madison route are operated by 2 airlines; United Airlines runs the most flights (around 68% of all flights). Compare carriers, flight shares and schedules below.

  • United AirlinesUA
    42x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight ORD → MSN42x/week
      Duration
      1h 13m
      Days
      MTWTFSS
    67.6%Open →
  • American AirlinesAA
    20x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight ORD → MSN20x/week
      Duration
      1h 5m
      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?

A nonstop Chicago — Madison flight takes about 1 h 7 min — the distance between the cities is around 197 km.

How far is it from Chicago to Madison?

The distance from Chicago to Madison is about 197 km, which a nonstop flight covers in around 1 h 7 min.

Are there direct flights from Chicago to Madison?

Yes, there are nonstop flights Chicago — Madison — around 185 flights per week.

Which airlines fly from Chicago to Madison?

Airlines operating Chicago — Madison include United Airlines, American Airlines. See the full list with schedules in the "Airlines" section on this page.

Which airports do Chicago — Madison flights use?

Flights from Chicago depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport, and arrive at Dane County Regional Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Chicago to Madison?

The price of a Chicago — Madison ticket depends on your travel date, season and demand: it is usually cheapest to fly in September, and most expensive in July. Tickets typically cost between $150 and $281. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Chicago — Madison?

Flights Chicago — Madison are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is September. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Chicago to Madison?

To catch a low fare Chicago — Madison, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually September.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from Chicago

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New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverLondonNashvilleIndianapolisSan DiegoMontrealSt. LouisMilwaukeeCharlottePhiladelphiaColumbusKansas CityMiamiPhoenixLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochesterCleveland

Where else you can fly from Madison

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DetroitNew York CityMinneapolisPhiladelphiaDenverWashington, D.C.CharlotteDallasAtlantaBostonPhoenixOrlandoLos AngelesTampa

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