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Flights from Chicago to Madison
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Find Chicago to Madison flights starting at CAD 125.

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

  • One way
  • Round-trip
      • Cheapest nonstop
        ORD10:06
        1h 1m
        Nonstop
        MSN11:07
        Wed, Dec 18|Chicago - Madison|American Airlines
        CAD 125CAD 420
        70% OFF
        70% OFF
        CAD 420CAD 125

        Choose American Airlines flights from Chicago to Madison. The one-way direct flight with American Airlines departs from O'Hare International Airport on Wed, Dec 18, arriving at Dane County Regional Airport. One-way Prices start from CAD 125 including taxes and charges.

      • ORD10:05
        1h 7m
        Nonstop
        MSN11:12
        Tue, Dec 31|Chicago - Madison|American Airlines
        CAD 126CAD 420
        70% OFF
        70% OFF
        CAD 420CAD 126

        Choose American Airlines flights from Chicago to Madison. The one-way direct flight with American Airlines departs from O'Hare International Airport on Tue, Dec 31, arriving at Dane County Regional Airport. One-way Prices start from CAD 126 including taxes and charges.

      • ORD10:11
        1h 2m
        Nonstop
        MSN11:13
        Fri, Jan 17|Chicago - Madison|American Airlines
        CAD 128CAD 420
        70% OFF
        70% OFF
        CAD 420CAD 128

        Choose American Airlines flights from Chicago to Madison. The one-way direct flight with American Airlines departs from O'Hare International Airport on Fri, Jan 17, arriving at Dane County Regional Airport. One-way Prices start from CAD 128 including taxes and charges.

      • ORD10:11
        1h 2m
        Nonstop
        MSN11:13
        Tue, Jan 14|Chicago - Madison|American Airlines
        CAD 130
        CAD 130

        Choose American Airlines flights from Chicago to Madison. The one-way direct flight with American Airlines departs from O'Hare International Airport on Tue, Jan 14, arriving at Dane County Regional Airport. One-way Prices start from CAD 130 including taxes and charges.

      • ORD20:40
        1h 20m
        Nonstop
        MSN22:00
        Sun, Jan 5|Chicago - Madison|American Airlines
        CAD 134
        CAD 134

        Choose American Airlines flights from Chicago to Madison. The one-way direct flight with American Airlines departs from O'Hare International Airport on Sun, Jan 5, arriving at Dane County Regional Airport. One-way Prices start from CAD 134 including taxes and charges.

      • ORD16:55
        54m
        Nonstop
        MSN17:49
        Sat, Jan 11|Chicago - Madison|American Airlines
        CAD 136
        CAD 136

        Choose American Airlines flights from Chicago to Madison. The one-way direct flight with American Airlines departs from O'Hare International Airport on Sat, Jan 11, arriving at Dane County Regional Airport. One-way Prices start from CAD 136 including taxes and charges.

      • ORD12:40
        1h 6m
        Nonstop
        MSN13:46
        Wed, Jan 15|Chicago - Madison|American Airlines
        CAD 136
        CAD 136

        Choose American Airlines flights from Chicago to Madison. The one-way direct flight with American Airlines departs from O'Hare International Airport on Wed, Jan 15, arriving at Dane County Regional Airport. One-way Prices start from CAD 136 including taxes and charges.

      • ORD10:11
        1h 2m
        Nonstop
        MSN11:13
        Wed, Jan 29|Chicago - Madison|American Airlines
        CAD 153
        CAD 153

        Choose American Airlines flights from Chicago to Madison. The one-way direct flight with American Airlines departs from O'Hare International Airport on Wed, Jan 29, arriving at Dane County Regional Airport. One-way Prices start from CAD 153 including taxes and charges.

      • ORD10:09
        1h 7m
        Nonstop
        MSN11:16
        Tue, Dec 24|Chicago - Madison|American Airlines
        CAD 160
        CAD 160

        Choose American Airlines flights from Chicago to Madison. The one-way direct flight with American Airlines departs from O'Hare International Airport on Tue, Dec 24, arriving at Dane County Regional Airport. One-way Prices start from CAD 160 including taxes and charges.

      • ORD13:55
        54m
        Nonstop
        MSN14:49
        Wed, Dec 18|Chicago - Madison|United Airlines
        CAD 161
        CAD 161

        Choose United Airlines flights from Chicago to Madison. The one-way direct flight with United Airlines departs from O'Hare International Airport on Wed, Dec 18, arriving at Dane County Regional Airport. One-way Prices start from CAD 161 including taxes and charges.

      • CHI01:00 pm
        3h 5m
        Nonstop
        MSN02:00 pm
        Tue, Dec 24|Chicago - Madison|American Airlines
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        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 Chicago to Madison?

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 Chicago to Madison

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

American Airlines
From CAD 125
United Airlines
From CAD 161
Delta Air Lines
From CAD 310

Find more flights and airlines

Alternative Routes for Chicago to Madison Flights

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

  • Cheapest
    American Airlines
    ORD
    10:06
    1h 1m
    Nonstop
    MSN
    11:07
    O'Hare International Airport - Dane County Regional Airport
    Wed, Dec 18American Airlines
    CAD 125
  • Delta Air Lines
    MDW
    16:50
    5h 19m
    1 transfer
    MSN
    22:09
    Midway International Airport - Dane County Regional Airport
    Wed, Dec 25Delta Air Lines
    CAD 310
  • Delta Air Lines
    MDW
    16:50
    5h 19m
    1 transfer
    MSN
    22:09
    Midway International Airport - Dane County Regional Airport
    Wed, Dec 25Delta Air Lines
    CAD 310
    Find More Flights

FAQ

  • When are flight tickets from Chicago (CHI) to Madison (MSN) the cheapest?

    Airlines adjust prices for flights from Chicago to Madison 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 Chicago (CHI) to Madison (MSN) cost?

    According to Trip.com's data, the lowest price is around CAD 376.

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

    It takes about 1 hour 3 minutes to fly from Chicago (CHI) to Madison (MSN).

  • What is the transportation method from the main airport to downtown in Madison?

    • The distance from Dane County Regional Airport to downtown is about 9km, by taxi about 20 minutes.

  • What are the most popular airlines that fly from Chicago (CHI) to Madison (MSN)?

    Airlines with flights from Chicago (CHI) to Madison (MSN): American Airlines, United Airlines, Qatar Airways, Emirates, Iberia, Alaska Airlines, avianca, Lufthansa, Copa Airlines and Air New Zealand.

  • What's the most popular airline for direct flights from Chicago (CHI) to Madison (MSN)?

    United Airlines operates 1 direct flights from Chicago (CHI) to Madison (MSN).

  • How many airports in Madison (MSN)?

    There are 1 airport(s) in Madison (MSN): Dane County Regional Airport.

How to find a cheap flight from Chicago to Madison

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 Chicago to Madison. 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 Chicago to Madison Flights

Cheapest direct flight priceCAD 125
Cheapest return ticket priceCAD 252
Off-season travel monthJanuary
Peak season for travelSeptember
Flight distance197.9km
Average flight time1 hour 3 minutes
Popular airlineAmerican Airlines

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