$139 Find Cheap Flights from Madison to Chicago - Compare and Save

Among airlines operating Madison to Chicago flights:

• United Airlines: offers extra legroom; offers free seat selection
• American Airlines: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

2 airlines operate flights between Madison and Chicago. The airlines offering nonstop flights on this route include:

• United Airlines
• American Airlines

Flights from Madison to Chicago usually depart from Madison Truax Field (MSN) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

Here are some options for this route, based on selected ticket types and cabin classes:

• United Airlines: a cabin bag and a checked bag in Economy Class
• American Airlines: a cabin bag in Economy Class class

Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

Three cabin classes are available on flights from Madison to Chicago:

• Economy Class
• Premium Economy Class
• First Class

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

Yes. Being flexible with your travel dates can save you up to 49% on the Madison to Chicago route. Monday is the cheapest departure day at $231 round-trip on average, while Sunday is the most expensive at $449, a difference of $218. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Morning is the busiest departure period on Madison to Chicago flights, with 54% of flights leaving in that window. Afternoon departures account for 26%, evening flights for 20%, and night flights for 0%.

Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago on KAYAK.

These are the earliest and latest flight times available from Madison to Chicago:

• Earliest: departs at 5:00 am and lands at 6:19 am
• Latest: departs at 9:40 pm and lands at 10:59 pm.

The flight takes about 1h 19m.

A nonstop flight from Madison to Chicago takes 1h 19m, covering 123 miles.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $269 to $1,557. That means the highest observed fare was about 6x higher than the lowest one.

One-way fares from Madison to Chicago are currently lower than usual. Average one-way flight prices are about $202, which is 19% below the typical average for this route.

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

• Routes Car & Truck Rentals
• Europcar
• Hertz
• Dollar
• Ace

Near Chicago Midway Airport (MDW) — daily rates from around $32:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

• Alamo
• Enterprise Rent-A-Car
• Budget
• Avis
• National

Round-trip flights from Madison to Chicago range from $209 to $361, with an average of $249 over the past 12 months. Anything below $209 counts as a good deal.

American Airlines is the only airline on the Madison to Chicago route offering in-flight Wi-Fi. Pricing depends on fare class.