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Flights from Madison to Chicago
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Find Madison to Chicago flights starting at CAD 129.

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

  • One way
  • Round-trip
      • Cheapest nonstop
        MSN10:38
        1h 12m
        Nonstop
        ORD11:50
        Wed, Jan 22|Madison - Chicago|American Airlines
        CAD 129CAD 193
        33% OFF
        33% OFF
        CAD 193CAD 129

        Choose American Airlines flights from Madison to Chicago. The one-way direct flight with American Airlines departs from Dane County Regional Airport on Wed, Jan 22, arriving at O'Hare International Airport. One-way Prices start from CAD 129 including taxes and charges.

      • MSN05:30
        1h 11m
        Nonstop
        ORD06:41
        Fri, Jan 24|Madison - Chicago|American Airlines
        CAD 129CAD 193
        33% OFF
        33% OFF
        CAD 193CAD 129

        Choose American Airlines flights from Madison to Chicago. The one-way direct flight with American Airlines departs from Dane County Regional Airport on Fri, Jan 24, arriving at O'Hare International Airport. One-way Prices start from CAD 129 including taxes and charges.

      • MSN18:27
        1h 8m
        Nonstop
        ORD19:35
        Tue, Jan 21|Madison - Chicago|American Airlines
        CAD 130CAD 193
        33% OFF
        33% OFF
        CAD 193CAD 130

        Choose American Airlines flights from Madison to Chicago. The one-way direct flight with American Airlines departs from Dane County Regional Airport on Tue, Jan 21, arriving at O'Hare International Airport. One-way Prices start from CAD 130 including taxes and charges.

      • MSN12:33
        1h 13m
        Nonstop
        ORD13:46
        Wed, Dec 18|Madison - Chicago|American Airlines
        CAD 142
        CAD 142

        Choose American Airlines flights from Madison to Chicago. The one-way direct flight with American Airlines departs from Dane County Regional Airport on Wed, Dec 18, arriving at O'Hare International Airport. One-way Prices start from CAD 142 including taxes and charges.

      • MSN14:54
        1h 11m
        Nonstop
        ORD16:05
        Tue, Dec 31|Madison - Chicago|American Airlines
        CAD 149
        CAD 149

        Choose American Airlines flights from Madison to Chicago. The one-way direct flight with American Airlines departs from Dane County Regional Airport on Tue, Dec 31, arriving at O'Hare International Airport. One-way Prices start from CAD 149 including taxes and charges.

      • MSN15:53
        1h 12m
        Nonstop
        ORD17:05
        Sat, Feb 8|Madison - Chicago|United Airlines
        CAD 157
        CAD 157

        Choose United Airlines flights from Madison to Chicago. The one-way direct flight with United Airlines departs from Dane County Regional Airport on Sat, Feb 8, arriving at O'Hare International Airport. One-way Prices start from CAD 157 including taxes and charges.

      • MSN05:00
        1h 13m
        Nonstop
        ORD06:13
        Tue, Dec 31|Madison - Chicago|United Airlines
        CAD 158
        CAD 158

        Choose United Airlines flights from Madison to Chicago. The one-way direct flight with United Airlines departs from Dane County Regional Airport on Tue, Dec 31, arriving at O'Hare International Airport. One-way Prices start from CAD 158 including taxes and charges.

      • MSN08:10
        1h 13m
        Nonstop
        ORD09:23
        Wed, Jan 1|Madison - Chicago|United Airlines
        CAD 158
        CAD 158

        Choose United Airlines flights from Madison to Chicago. The one-way direct flight with United Airlines departs from Dane County Regional Airport on Wed, Jan 1, arriving at O'Hare International Airport. One-way Prices start from CAD 158 including taxes and charges.

      • MSN10:38
        1h 12m
        Nonstop
        ORD11:50
        Wed, Jan 8|Madison - Chicago|American Airlines
        CAD 163
        CAD 163

        Choose American Airlines flights from Madison to Chicago. The one-way direct flight with American Airlines departs from Dane County Regional Airport on Wed, Jan 8, arriving at O'Hare International Airport. One-way Prices start from CAD 163 including taxes and charges.

      • MSN06:20
        1h 13m
        Nonstop
        ORD07:33
        Mon, Dec 30|Madison - Chicago|United Airlines
        CAD 164
        CAD 164

        Choose United Airlines flights from Madison to Chicago. The one-way direct flight with United Airlines departs from Dane County Regional Airport on Mon, Dec 30, arriving at O'Hare International Airport. One-way Prices start from CAD 164 including taxes and charges.

      • MSN01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Sun, Dec 22|Madison - Chicago|American Airlines
        Find More Flights
        Find More Flights

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

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

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

American Airlines
From CAD 129
United Airlines
From CAD 157
Delta Air Lines
From CAD 340

Find more flights and airlines

Alternative Routes for Madison to Chicago Flights

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Madison to Chicago.

  • Cheapest
    American Airlines
    MSN
    05:30
    1h 11m
    Nonstop
    ORD
    06:41
    Dane County Regional Airport - O'Hare International Airport
    Fri, Jan 24American Airlines
    CAD 129
  • Delta Air Lines
    MSN
    17:04
    15h 46m
    1 transfer
    MDW
    08:50
    Dane County Regional Airport - Midway International Airport
    Tue, Dec 31Delta Air Lines
    CAD 340
  • Delta Air Lines
    MSN
    17:04
    15h 46m
    1 transfer
    MDW
    08:50
    Dane County Regional Airport - Midway International Airport
    Tue, Dec 31Delta Air Lines
    CAD 340
    Find More Flights

FAQ

  • 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 414.

  • How long is the flight from Madison (MSN) to Chicago (CHI)?

    It takes about 1 hour 7 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, Qatar Airways, avianca and United 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)?

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
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
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 priceCAD 129
Cheapest return ticket priceCAD 250
Off-season travel monthJanuary
Peak season for travelSeptember
Flight distance197.9km
Average flight time1 hour 7 minutes
Popular airlineUnited Airlines

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