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Flights from Madison to Chicago

Cheap flight deals from Madison to Chicago

We've found these cheap flights for you. You can book one-way or round-trip flight tickets.

  • Round-trip
  • One way

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

When is the cheapest time to fly from Madison to Chicago?

We monitor flight fares to help you find the best deals effortlessly

Cheapest flights
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  • 13 20
  • 20 27

  • May

    27 4
  • 4 11
  • 11 18
  • 18 25

  • Jun

    25 1
  • 1 8
  • 8 15
  • 15 22
  • 22 29

  • Jul

    29 6
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

How to find a cheap flight from Madison to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Madison to Chicago. Book your flights at the right time and save more.
1
Being flexible with your dates to get the cheapest Madison to Chicago ticket.
Tap "Date" on flight search bar to scan through the calender for Madison to Chicago airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Sun, May 4 at AED 429 for one-way flights.
2
Compare cheap Madison to Chicago flight deals from over hundreds of airlines.
Our extensive search allows you to compare prices from over 500 airlines to choose the cheapest flight tickets from Madison to Chicago. The cheapest airline operating is American Airlines.
3
Set up a Price Alert
By setting up a Price Alert for your Madison to Chicago route, you can easily track the price of your airline tickets from without manually checking every day.
4
Don't miss cheap Madison to Chicago flight deals and promo codes.
You can always get the latest deals through Trip.com Deals and Promo Codes for cheap flights. If registering a free membership, you can receive more deals for your flights.
5
Book early or wait unitl the last minute.
It's always better to book early. Flight tickets tend to be the cheapest when they are first released, normally about a year before the departure date. So, check online as soon as the flights you want become available. If you miss the cheapest time, you can still find lower-priced tickets as the flight date approaches.
6
Search for flights on the go.
To get the best flight booking experience on the go, download Trip.com and search for cheap flight tickets from Madison to Chicago to get exclusive deals for you.

Flight Info | Madison to Chicago

Cheapest one-way flight price AED 429
Cheapest return ticket price AED 819
Off-season for travel April
Peak season for travel June
Flight distance 197.9 km
Average flight time 1 hour 7 minutes
Popular airline United Airlines

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