Cheap flights from Chicago to Madison

One-way fares from $124 · CHI → MSN · prices found by travellers in the last 48 hours

Compare all dates Madison → Chicago
Cheapest fare
$124

United Airlines · Wed, Nov 4

Cheapest month
November

from $124

Direct flights
Yes

United Airlines and American Airlines

Flight time
1h 02m

200 km

Get a price alert

We'll email you when Chicago → Madison drops to your price. It's free, and you can stop any time.

Today's cheapest fare is $124. We'll send one email to confirm. See our privacy policy.

Cheapest month to fly from Chicago to Madison

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 Cheapest $124
  2. December 2026 $196

Cheapest dates in November 2026

The lowest fares we've seen for each day, cheapest first.

United Airlines
Depart10:42 Wed, Nov 4ORD → MSN 1h 13m · Direct
$124one way, per person
View deal
American Airlines
Depart06:55 Sat, Nov 7ORD → MSN 1h 15m · Direct
$143one way, per person
View deal
See every date in November 2026 →

Plan the rest of your trip to Madison

Where to stay, what to do and getting around, from our travel partners.

Where to stay

Hotels in MadisonCompare places to stay on Booking.com Find hotels →

Things to do

Things to do in MadisonTours, attractions and day trips on Klook Explore →

Getting around

Airport transfer in MadisonPre-book a driver to meet you at arrivals, with Kiwitaxi Book a transfer → Car hire in MadisonCompare rental cars from major brands on EconomyBookings Compare cars →

About flights from Chicago to Madison

Chicago (CHI) and Madison (MSN) are about 200 km apart. Direct flights take around 1h 02m, and recent direct fares were with United Airlines and American Airlines. Over the next few months, one-way fares start from $124, and November 2026 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from Chicago to Madison?

The cheapest one-way fare we've seen recently is $124 with United Airlines, departing Wednesday, November 4, 2026. Over the coming months, the lowest fare in each month ranges from $124 to $196.

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

November 2026 currently has the lowest fares, from $124 one way.

Are there direct flights from Chicago to Madison?

Yes. Recent direct fares were with United Airlines and American Airlines.

How long is the flight from Chicago to Madison?

A direct flight takes about 1h 02m. Chicago and Madison are around 200 km apart.

Which airlines fly from Chicago to Madison?

Recent fares on this route were with United Airlines, Frontier Airlines and American Airlines.

More cheap flights from Chicago

Compare flights to Madison from other cities →