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

United Airlines and American Airlines fly nonstop between Chicago (ORD) and Madison (MSN), roughly 167 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 ORD to MSN 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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167
Nonstop flights a week
108 mi
Nonstop distance
Free
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Chicago to Madison flight schedule

Scheduled nonstop departures for ORD to MSN, 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 Chicago (ORD) to Madison (MSN)
Date Flight Airline Departs ORD Arrives MSN Duration Aircraft
AA 4048American Airlines07:0308:141h 11mE70
UA 2849United Airlines07:5908:591h73G
UA 4587United Airlines08:5010:041h 14mCR5
UA 5843United Airlines10:3511:491h 14mE7W
UA 4166United Airlines10:4512:031h 18mCR5
AA 6195American Airlines11:1712:261h 9mCR7
AA 6256American Airlines11:1712:261h 9mCR7
UA 2349United Airlines12:4013:421h 2m738
AA 4038American Airlines13:4514:551h 10mE70
UA 1525United Airlines13:5514:591h 4m739
UA 1617United Airlines13:5514:591h 4m320
UA 5509United Airlines13:5515:051h 10mE7W
UA 5679United Airlines15:5917:131h 14mCR5
UA 4194United Airlines16:0017:141h 14mCR5
AA 3953American Airlines17:0518:241h 19mE75
AA 4448American Airlines17:0618:191h 13mE75
UA 2427United Airlines17:5218:561h 4m319
UA 2261United Airlines17:5719:001h 3m319
UA 5768United Airlines19:4520:571h 12mE7W
UA 630United Airlines19:4520:531h 8m739
AA 4217American Airlines20:5222:101h 18mE75
UA 4478United Airlines21:3422:451h 11mCR5
AA 4045American Airlines23:0000:171h 17mE75
AA 4048American Airlines07:0308:141h 11mE70
UA 2849United Airlines08:4009:401h739
UA 4587United Airlines08:5010:041h 14mCR5
UA 5843United Airlines10:3511:491h 14mE7W
UA 4166United Airlines10:4512:031h 18mCR5
AA 6256American Airlines11:1712:261h 9mCR7
UA 2349United Airlines12:4013:421h 2m738
AA 4038American Airlines13:4514:551h 10mE70
UA 1525United Airlines13:5514:581h 3m739
UA 1617United Airlines13:5514:591h 4m320
UA 5509United Airlines13:5515:051h 10mE7W
UA 4194United Airlines15:5917:131h 14mCR5
UA 5679United Airlines15:5917:131h 14mCR5
AA 3953American Airlines17:0518:241h 19mE75
AA 4448American Airlines17:0618:191h 13mE75
UA 2427United Airlines17:5218:561h 4m319
UA 2261United Airlines17:5619:001h 4m319

Showing the first 40 of 160 scheduled ORD to MSN 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 ORD to MSN date on the interactive map

Confirmed upgrade & award space on ORD to MSN departures

2LNR tracks confirmed upgrade and award space on American Airlines, segment by segment and date by date. Open the calendar for Chicago to Madison 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 ORD to MSN 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 ORD to MSN on the interactive route map, with schedules, connections, and route statistics.

Airlines flying Chicago to Madison nonstop

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

See ORD to MSN on the interactive map →

Frequently asked questions about ORD to MSN

How far is Madison from Chicago?
ORD to MSN 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 ORD to MSN?
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 ORD to MSN?
About 167 nonstop flights a week run between Chicago and Madison 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 ORD to MSN depart?
Scheduled ORD to MSN nonstops in the next 7 days with service leave between 07:03 and 23:00, local time at Chicago. 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 ORD to MSN?
Open the ORD to MSN 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 ORD to MSN 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.

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