Cheap flights from Madison to Chicago

One-way fares from $115 · MSN → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → Madison
Cheapest fare
$115

American Airlines · Fri, Nov 13

Cheapest month
November

from $115

Direct flights
Yes

American Airlines and United Airlines

Flight time
1h 14m

200 km

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Cheapest month to fly from Madison to Chicago

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

  1. November 2026 Cheapest $115

Cheapest dates in November 2026

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

American Airlines
Depart20:41 Fri, Nov 13MSN → ORD 1h 14m · Direct
$115one way, per person
View deal
United Airlines
Depart08:15 Sun, Nov 15MSN → ORD 1h 16m · Direct
$297one way, per person
View deal
See every date in November 2026 →

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

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Things to do

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Getting around

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About flights from Madison to Chicago

Madison (MSN) and Chicago (CHI) are about 200 km apart. Direct flights take around 1h 14m, and recent direct fares were with American Airlines and United Airlines. Over the next few months, one-way fares start from $115, 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 Madison to Chicago?

The cheapest one-way fare we've seen recently is $115 with American Airlines, departing Friday, November 13, 2026.

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

November 2026 currently has the lowest fares, from $115 one way.

Are there direct flights from Madison to Chicago?

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

How long is the flight from Madison to Chicago?

A direct flight takes about 1h 14m. Madison and Chicago are around 200 km apart.

Which airlines fly from Madison to Chicago?

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

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