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Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from Chicago to Madison. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
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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Answers to questions about the route that travelers are most interested in.
We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
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Chicago — Madison
05/29/2026
Departure
Direct flight
UA4472
starting at $145
Chicago — Madison
05/30/2026
Departure
Direct flight
UA4472
starting at $320
starting at $96
The route Chicago — Madison is served by a single airline — United Airlines. This means that when planning your trip, you won’t need to spend time choosing between dozens of carriers: all flights are operated by one provider, which simplifies the booking process. Despite the limited choice, passengers can still plan ahead, select optimal departure dates, and buy tickets at the lowest price — from $96. Using our service, you can quickly compare available United Airlines flights and book a seat in advance at a favorable rate.
The cheapest flight ticket from Chicago to Madison according to data for the last 48 hours costs $96
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: May.
The fastest flights from Chicago to Madison start from 1 hour 13 minutes in the air.
The following airlines operate direct flights on the route Chicago — Madison: United Airlines
The cheapest one-way flight from Chicago to Madison departs on 05/29/2026, is operated by United Airlines and costs $96
There is no information about the cheapest roundtrip flight from Chicago to Madison
Fastest flight from Chicago to Madison takes 1h 13m
There are direct flights on this route 2 days a week: Fr and Sa
The distance between Chicago and Madison is 198km (123 miles). There are 33 direct flights from Chicago to Madison. Chicago and Madison are in the same time zone. Flights from Chicago begin at 7:39 AM. The latest flight from Chicago departs at 11:00 PM
We couldn't find any special offers for flights from Chicago to Madison