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Latest Flight Deals from Madison to Chicago

Book one-way or return flights from Madison to Chicago from as little as NZD 148. Choose from the popular airlines below and book your flight today!

  • One way
  • Round-trip
      • MSN18:43
        1h
        Direct
        ORD19:43
        Wed, Jun 26|Madison - Chicago|American Airlines
        NZD 148NZD 248
        40% OFF
        40% OFF
        NZD 248NZD 148
      • MSN06:51
        59m
        Direct
        ORD07:50
        Sun, May 26|Madison - Chicago|American Airlines
        NZD 152NZD 248
        39% OFF
        39% OFF
        NZD 248NZD 152
      • MSN06:00
        59m
        Direct
        ORD06:59
        Tue, May 7|Madison - Chicago|American Airlines
        NZD 153NZD 248
        38% OFF
        38% OFF
        NZD 248NZD 153
      • MSN08:01
        59m
        Direct
        ORD09:00
        Mon, Jun 3|Madison - Chicago|American Airlines
        NZD 154
        NZD 154
      • MSN16:37
        58m
        Direct
        ORD17:35
        Sat, May 4|Madison - Chicago|American Airlines
        NZD 155
        NZD 155
      • MSN06:30
        59m
        Direct
        ORD07:29
        Tue, Jun 4|Madison - Chicago|American Airlines
        NZD 155
        NZD 155
      • MSN06:30
        59m
        Direct
        ORD07:29
        Sat, Jun 1|Madison - Chicago|American Airlines
        NZD 155
        NZD 155
      • MSN18:11
        5h 48m
        1 stop
        ORD23:59
        Sat, May 25|Madison - Chicago|American Airlines
        NZD 164
        NZD 164
      • MSN08:01
        59m
        Direct
        ORD09:00
        Wed, May 22|Madison - Chicago|American Airlines
        NZD 189
        NZD 189
      • MSN06:30
        59m
        Direct
        ORD07:29
        Tue, May 21|Madison - Chicago|American Airlines
        NZD 190
        NZD 190
      • MSN13:00
        3h 5m
        Direct
        CHI14:00
        Mon, May 6|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.

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.
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 NZD 148
United Airlines
From NZD 190
Delta Air Lines
From NZD 488
ANA airlines

Find more flights and airlines

Alternative Routes from Madison to Chicago

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

  • Cheapest
    American Airlines
    MSN
    18:43
    1h 0m
    Direct
    ORD
    19:43
    Dane County Regional Airport - O'Hare International Airport
    Wed, Jun 26American Airlines
    NZD 148
  • Delta Air Lines
    MSN
    11:00
    7h 7m
    1 transfer
    MDW
    18:07
    Dane County Regional Airport - Midway International Airport
    Mon, Jun 3Delta Air Lines
    NZD 488
  • Delta Air Lines
    MSN
    11:00
    7h 7m
    1 transfer
    MDW
    18:07
    Dane County Regional Airport - Midway International Airport
    Mon, Jun 3Delta Air Lines
    NZD 488
    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 departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Madison (MSN) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around NZD 604.

  • How long does it take to fly from Madison (MSN) to Chicago (CHI) and what is the distance?

    It takes around 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. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14km. It takes about 30 minutes by taxi.

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

Cheapest nonstop flight price

NZD 148

Cheapest round-trip ticket price

NZD 298

Off-season for travel

January

Peak season for travel

October

Flight distance

197.9km

Average flight time

1 hour 5 minutes

Popular airline

United Airlines

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