Madison to Chicago (MSN-ORD): nonstop upgrade & award space

United Airlines and American Airlines fly nonstop between Madison (MSN) and Chicago (ORD), roughly 148 times a week. With United Airlines running most of the schedule, the shape of a week is predictable, which makes an open premium seat on a given date easy to spot and quick to lose. 2LNR tracks confirmed upgrade and award space on American Airlines, on every MSN to ORD departure, so you know which flights have space before you book.

Schedule last confirmed . Departure times come from 2LNR's schedule data; confirm with the airline before you book.

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148
Nonstop flights a week
108 mi
Nonstop distance
Free
To get started

Madison to Chicago flight schedule

Scheduled nonstop departures for MSN to ORD, last checked against our schedule feed on September 6, 2026. Airlines retime and cancel flights, so confirm with the airline before you book.

Schedule data dated .

Scheduled nonstop departures from Madison (MSN) to Chicago (ORD)
Date Flight Airline Departs MSN Arrives ORD Duration Aircraft
AA 3819American Airlines05:0006:251h 25mE75
UA 4415United Airlines05:0006:151h 15mCR5
UA 4477United Airlines05:0006:151h 15mCR5
UA 2137United Airlines06:3007:431h 13m319
AA 4216American Airlines07:1508:461h 31mE75
UA 394United Airlines08:0509:181h 13m739
UA 2151United Airlines08:1009:201h 10m738
AA 3923American Airlines09:4010:551h 15mE70
UA 4535United Airlines10:4311:591h 16mCR5
UA 2378United Airlines10:4611:591h 13m739
UA 5447United Airlines12:3013:421h 12mE7W
UA 4178United Airlines12:4114:001h 19mCR5
AA 6256American Airlines12:5614:201h 24mCR7
UA 1400United Airlines14:4415:571h 13m738
AA 4038American Airlines15:2516:411h 16mE70
UA 5262United Airlines15:4617:011h 15mE7W
UA 264United Airlines15:5517:111h 16m320
UA 4603United Airlines17:4919:051h 16mCR5
UA 5629United Airlines17:4919:051h 16mCR5
AA 3748American Airlines20:0521:301h 25mE75
AA 3819American Airlines05:0006:251h 25mE75
UA 4415United Airlines05:0006:151h 15mCR5
UA 4477United Airlines05:0006:151h 15mCR5
UA 2137United Airlines06:3007:431h 13m319
AA 4216American Airlines07:1508:461h 31mE75
UA 394United Airlines08:0509:181h 13m739
UA 2151United Airlines08:1009:201h 10m738
AA 3923American Airlines09:4010:551h 15mE70
UA 4535United Airlines10:4311:591h 16mCR5
UA 2378United Airlines10:4611:591h 13m739
UA 5447United Airlines12:3013:421h 12mE7W
UA 4178United Airlines12:4114:001h 19mCR5
AA 6256American Airlines12:5614:201h 24mCR7
UA 1400United Airlines14:4415:571h 13m738
AA 4038American Airlines15:2516:411h 16mE70
UA 5262United Airlines15:4617:011h 15mE7W
UA 264United Airlines15:5517:111h 16m320
UA 4603United Airlines17:4919:051h 16mCR5
UA 5629United Airlines17:4919:051h 16mCR5
AA 3748American Airlines20:0521:301h 25mE75

Showing the first 40 of 138 scheduled MSN to ORD departures across the next 7 days with service. Every remaining date is on the interactive map.

Departure and arrival times are local at their own airport, so an arrival can fall on a different local date than the departure; the duration column is the true elapsed flying time. A dash means the airline has not filed that value in the schedule data we hold. Aircraft are IATA equipment codes as filed, and can change up to departure.

See every MSN to ORD date on the interactive map

Confirmed upgrade & award space on MSN to ORD departures

2LNR tracks confirmed upgrade and award space on American Airlines, segment by segment and date by date. Open the calendar for Madison to Chicago to see which departures have space, the next 14 days free on every product and the full horizon on Pro.

See real availability

Confirmed upgrade and award seats on each MSN to ORD departure, checked against live inventory so you know what is open before you book.

Set an alert

Premium inventory turns over fast. Watch this route and 2LNR notifies you when space appears on a date you are tracking.

Plan on the map

See MSN to ORD on the interactive route map, with schedules, connections, and route statistics.

Airlines flying Madison to Chicago nonstop

Carriers operating MSN to ORD nonstop in the current schedule. 2LNR tracks confirmed upgrade and award space on each of them.

See MSN to ORD on the interactive map →

Frequently asked questions about MSN to ORD

How far is Chicago from Madison?
MSN to ORD covers about 108 miles nonstop. Flight times vary by aircraft and season; the schedule table on this page lists each scheduled departure with its own times.
Which airlines fly nonstop from MSN to ORD?
United Airlines and American Airlines fly the route nonstop. 2LNR tracks confirmed upgrade and award space on American Airlines.
How many flights a week are there from MSN to ORD?
About 148 nonstop flights a week run between Madison and Chicago in the current schedule, operated by United Airlines and American Airlines. Frequency shifts by season, and the schedule table on this page shows what is scheduled next.
What time do flights from MSN to ORD depart?
Scheduled MSN to ORD nonstops in the next 7 days with service leave between 05:00 and 20:05, local time at Madison. The schedule table on this page lists every departure by date, with its arrival time and aircraft.
How do I check upgrade or award availability on MSN to ORD?
Open the MSN to ORD route on the interactive map or the matrix to see confirmed upgrade and award space by date on American Airlines, the next 14 days free and the full horizon on Pro. On Pro you can also set an alert on the route and 2LNR notifies you when space opens.

Never miss MSN to ORD upgrade or award space

See what is open by date on this route, the next 14 days free on every product and the full horizon on Pro.

Get started free