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

United Airlines and American Airlines fly nonstop between Chicago (ORD) and Madison (MSN), roughly 142 times a week. The timetable below shows the nonstop scheduled at 57 minutes to 1h 19m for the 108 miles. 2LNR checks confirmed upgrade and award space on American Airlines flights on this route, so you can see which departures have space before you book.

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

Updated .

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142
Flights a week, 4-week average
57 minutes to 1h 19m
Scheduled flight time
108 mi
Nonstop distance
Free
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Chicago to Madison flight schedule

Scheduled nonstop departures for ORD to MSN starting October 23, 2026, last checked against our schedule feed on October 18, 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 4460American Airlines06:5908:111h 12mEmbraer E175
UA 4382United Airlines08:4509:541h 9mCR5
AA 4717American Airlines09:4010:521h 12mEmbraer E175
UA 4737United Airlines10:3511:531h 18mCR5
UA 2349United Airlines12:4013:3757 minutesBoeing 737-900
AA 4038American Airlines13:4914:551h 6mEmbraer E170
UA 1595United Airlines14:0015:041h 4mBoeing 737-700
UA 5530United Airlines15:5517:081h 13mCR5
AA 4441American Airlines17:1618:351h 19mEmbraer E175
UA 5679United Airlines18:1019:271h 17mCR5
UA 630United Airlines19:5221:001h 8mBoeing 737-700
UA 1251United Airlines21:3022:351h 5mBoeing 737-800
AA 4601American Airlines22:0023:121h 12mEmbraer E175
AA 4776American Airlines23:0000:121h 12mEmbraer E175
AA 4460American Airlines06:5908:111h 12mEmbraer E175
UA 4382United Airlines08:4509:541h 9mCR5
AA 4717American Airlines09:4010:521h 12mEmbraer E175
UA 4737United Airlines10:3511:541h 19mBombardier CRJ-200
UA 2349United Airlines12:4013:3757 minutesBoeing 737-900
AA 4038American Airlines13:4914:551h 6mEmbraer E170
UA 1595United Airlines14:0015:041h 4mBoeing 737-700
UA 5530United Airlines16:0017:141h 14mBombardier CRJ-200
AA 4441American Airlines17:1618:351h 19mEmbraer E175
UA 630United Airlines19:5221:001h 8mBoeing 737-700
UA 1251United Airlines21:3022:351h 5mBoeing 737-800
AA 4601American Airlines22:0023:121h 12mEmbraer E175
AA 4776American Airlines23:0000:121h 12mEmbraer E175
AA 4460American Airlines06:5908:111h 12mEmbraer E175
UA 1097United Airlines08:4009:441h 4mBoeing 737-700
AA 4717American Airlines09:4010:521h 12mEmbraer E175
UA 4166United Airlines10:4512:031h 18mCR5
UA 4404United Airlines12:2913:411h 12mCR5
UA 623United Airlines12:4513:501h 5mBoeing 737-700
AA 4038American Airlines13:4914:551h 6mEmbraer E170
UA 3517United Airlines13:5515:071h 12mEmbraer E175
UA 5530United Airlines15:5017:021h 12mEmbraer E175
UA 5904United Airlines15:5017:021h 12mEmbraer E175
UA 4194United Airlines15:5917:131h 14mCR5
UA 5703United Airlines17:0318:171h 14mCR5
AA 4441American Airlines17:1618:351h 19mEmbraer E175

Showing the first 40 of 123 scheduled ORD to MSN departures across 7 days with service, starting October 23, 2026. 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 hasn't filed that value in the schedule data we hold. Aircraft are the equipment the airline filed, named where the code pins down one type and shown as the family or the bare code where it doesn't. Swaps can happen up to departure.

See every ORD to MSN date on the interactive map

Aircraft on the Chicago to Madison nonstop

In the schedule table on this page, United Airlines flies the Bombardier CRJ, the Boeing 737-700, the Embraer E175, the Boeing 737-900, the Boeing 737-800, and the Bombardier CRJ-200, and American Airlines flies the Embraer E175 and the Embraer E170. Each linked aircraft page shows where that airline schedules it. Airlines can swap aircraft up to departure.

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.

American Airlines award space was open on 11 of the 14 Chicago to Madison departure dates from October 19 to November 1 that 2LNR checked in the 7 days to October 19, 2026.

See real availability

Confirmed upgrade or award seats by date on the ORD to MSN departures 2LNR tracks, checked against live inventory so you know what's open before you book.

Set an alert

Premium inventory turns over fast. Watch this route on Pro and 2LNR notifies you when space appears on a date you're 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. Where 2LNR tracks the carrier, its departures show confirmed upgrade or award space by date.

See ORD to MSN on the interactive map →

Frequently asked questions about ORD to MSN

How long is the flight from Chicago (ORD) to Madison (MSN)?
Scheduled flight times from Chicago (ORD) to Madison (MSN) run from 57 minutes to 1h 19m across the departures in the schedule table on this page. The nonstop covers about 108 miles, and airlines adjust scheduled times by season, so confirm with the airline before you book.
Which airlines fly nonstop from ORD to MSN?
United Airlines and American Airlines fly ORD to MSN nonstop. 2LNR tracks confirmed upgrade and award space on American Airlines.
How many flights a week are there from ORD to MSN?
About 142 nonstop flights a week run between Chicago (ORD) and Madison (MSN) 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 06:59 and 23:00, local time at Chicago. The schedule table on this page lists every departure by date, with its arrival time and aircraft.
Which flights operate ORD to MSN nonstop?
The schedule table on this page lists 22 flight numbers for ORD to MSN nonstops, including UA 2349, UA 4382, UA 4737, and UA 5530 on United Airlines, and AA 4038, AA 4441, AA 4460, and AA 4717 on American Airlines. The table lists each departure by date with its times 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's open by date on this route, the next 14 days free on every product and the full horizon on Pro.

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