There are most likely no direct flights on the Chicago — Madison route
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We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from Chicago to Madison
A non-stop flight is the most convenient and comfortable way to fly from Chicago to Madison, despite the fact that sometimes flights with transfers can cost significantly less.
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There are most likely no direct flights on the Chicago — Madison route
All airports
Chicago — Madison
11/07/2026
Departure
Direct flight
AA4462
starting at $143
Chicago — Madison
11/07/2026
Departure
Direct flight
AA4717
starting at $143
Chicago — Madison
12/21/2026
Departure
Direct flight
UA1758
starting at $274
The route Chicago — Madison is served by several airlines: American Airlines, United Airlines, and Frontier Airlines. This gives passengers more freedom in choosing flights. You can consider not only the price but also schedules, baggage policies, and onboard service. Our service compares all offers so you can find tickets from $143 and choose the most convenient option. Thanks to airline competition, you may also find promotional fares or special offers, helping you save even more. Plan your trip in advance and choose the best flights without overpaying.
The cheapest flight ticket from Chicago to Madison according to data for the last 48 hours costs $143
Often the best time to buy tickets from Chicago to Madison is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Chicago to Madison can be found flying in these months: October.
The fastest flights from Chicago to Madison start from 1 hour 15 minutes in the air.
The following airlines operate direct flights on the route Chicago — Madison: American Airlines, United Airlines
The cheapest one-way flight from Chicago to Madison departs on 11/06/2026, is operated by American Airlines and costs $143
There is no information about the cheapest roundtrip flight from Chicago to Madison
Fastest flight from Chicago to Madison takes 1h 15m
There are direct flights on this route 2 days a week: Mo and Sa
The distance between Chicago and Madison is 196km (122 miles). There are 112 direct flights from Chicago to Madison. Chicago and Madison are in the same time zone. Flights from Chicago begin at 6:34 AM. The latest flight from Chicago departs at 11:00 PM
We couldn't find any special offers for flights from Chicago to Madison
