Cheap Flights from Madison to Chicago from CAD 120️ 2024

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Find Madison to Chicago flights starting at CAD 120.

Book one-way or return flights from Madison to Chicago from as little as CAD 120. Choose from the popular airlines below and book your flight today!

One way
Round-trip

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

Searching for the best last minute flight from Madison to Chicago? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Madison to Chicago. Stay updated on price trends and snag the best deals for your upcoming trip.

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

Find Cheapest Airlines Flying from Madison to Chicago

View airlines operating flights from Madison to Chicago. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

American Airlines

From CAD 120

United Airlines

From CAD 154

Delta Air Lines

From CAD 395

ANA airlines

Find more flights and airlines

Alternative Routes for Madison to Chicago Flights

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Madison to Chicago.

Cheapest
MSN
18:43
1h 0m
Direct
ORD
19:43
Dane County Regional Airport - O'Hare International Airport
Wed, Jun 26American Airlines
CAD 120
MSN
11:00
7h 7m
1 transfer
MDW
18:07
Dane County Regional Airport - Midway International Airport
Mon, Jun 3Delta Air Lines
CAD 395
MSN
11:00
7h 7m
1 transfer
MDW
18:07
Dane County Regional Airport - Midway International Airport
Mon, Jun 3Delta Air Lines
CAD 395
Find More Flights

How do I find the cheapest flights?

When are flight tickets from Madison (MSN) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from Madison to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much are flights from Madison (MSN) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around CAD 489.
How long is the flight from Madison (MSN) to Chicago (CHI)?
It takes about 1 hour 5 minutes to fly from Madison (MSN) to Chicago (CHI).
What is the transportation method from the main airport to downtown in Chicago?
- The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
- The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
What are the most popular airlines that fly from Madison (MSN) to Chicago (CHI)?
Airlines with flights from Madison (MSN) to Chicago (CHI): American Airlines, Alaska Airlines, United Airlines, Japan Airlines, Lufthansa, Air New Zealand, British Airways, All Nippon Airways and Copa Airlines.
What's the most popular airline for direct flights from Madison (MSN) to Chicago (CHI)?
American Airlines operates 1 direct flights from Madison (MSN) to Chicago (CHI).
How many airports in Chicago (CHI)?
There are 5 airport(s) in Chicago (CHI): Chicago Du Page County Airport, Midway International Airport, O'Hare International Airport, Chicago Palwaukee Airport and Chicago Rockford International Airport.

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.

Book Early

Once prices are gone, they're gone. Lock in deals while you can!

Compare Flight Prices

Compare prices on travel agency and airline websites.

Look Out for Deals

Check airline and travel agency websites for latest flight deals

Check One-way Fares

Buying two cheap one-way flights can sometimes be a better deal than a round-trip.

Try Different Dates

Flying during the week, early in the morning, or late at night can help save money.

Use the Trip.com App

Save up to £10 per person when booking your flights on Trip.com

Flight Information for Madison to Chicago Flights

Cheapest direct flight price	CAD 120
Cheapest return ticket price	CAD 241
Cheapest month	January
Peak season for travel	October
Flight distance	197.9km
Average flight time	1 hour 5 minutes
Popular airline	United Airlines