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

United Airlines and American Airlines fly nonstop between Madison (MSN) and Chicago (ORD), roughly 153 times a week. The timetable below shows the nonstop scheduled at 1h 9m to 1h 25m 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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153
Flights a week, 4-week average
1h 9m to 1h 25m
Scheduled flight time
108 mi
Nonstop distance
Free
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Madison to Chicago flight schedule

Scheduled nonstop departures for MSN to ORD starting October 28, 2026, last checked against our schedule feed on October 25, 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 4775American Airlines05:0006:141h 14mEmbraer E175
UA 5902United Airlines05:0006:201h 20mEmbraer E175
AA 4669American Airlines06:1007:241h 14mEmbraer E175
UA 2137United Airlines06:2507:441h 19mBoeing 737-700
UA 2037United Airlines08:1009:261h 16mBoeing 737-900
AA 4460American Airlines10:1311:301h 17mEmbraer E175
UA 5730United Airlines10:4211:571h 15mCR5
AA 4717American Airlines11:2212:391h 17mEmbraer E175
UA 4455United Airlines12:3213:541h 22mCR5
UA 4178United Airlines13:0014:191h 19mCR5
AA 6478American Airlines13:1114:201h 9mBombardier CRJ-700
UA 1776United Airlines14:5016:061h 16mBoeing 737-700
UA 5781United Airlines15:0016:191h 19mCR5
AA 4038American Airlines15:2816:441h 16mEmbraer E170
UA 5413United Airlines15:4917:051h 16mEmbraer E175
UA 5563United Airlines17:4319:051h 22mEmbraer E175
UA 4603United Airlines17:4919:051h 16mCR5
AA 4441American Airlines19:0520:301h 25mEmbraer E175
UA 5941United Airlines19:1520:291h 14mCR5
AA 4775American Airlines05:0006:141h 14mEmbraer E175
UA 5902United Airlines05:0006:201h 20mEmbraer E175
AA 4669American Airlines06:1007:241h 14mEmbraer E175
UA 2137United Airlines06:2507:441h 19mBoeing 737-700
UA 2037United Airlines08:1509:311h 16mBoeing 737-900
AA 4460American Airlines10:1311:301h 17mEmbraer E175
UA 5730United Airlines10:4211:571h 15mCR5
AA 4717American Airlines11:2212:391h 17mEmbraer E175
UA 4455United Airlines12:3213:541h 22mCR5
UA 4178United Airlines12:4114:001h 19mCR5
AA 6478American Airlines13:1114:201h 9mBombardier CRJ-700
UA 1776United Airlines14:5016:061h 16mBoeing 737-700
UA 5781United Airlines15:0016:191h 19mCR5
AA 4038American Airlines15:2816:441h 16mEmbraer E170
UA 5413United Airlines15:4917:051h 16mEmbraer E175
UA 5563United Airlines17:4319:051h 22mEmbraer E175
UA 4603United Airlines17:4919:051h 16mCR5
AA 4441American Airlines19:0520:301h 25mEmbraer E175
UA 5941United Airlines19:1520:291h 14mCR5
AA 4775American Airlines05:0006:141h 14mEmbraer E175
UA 5902United Airlines05:0006:201h 20mEmbraer E175

Showing the first 40 of 148 scheduled MSN to ORD departures across 7 days with service, starting October 28, 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 MSN to ORD date on the interactive map

Aircraft on the Madison to Chicago nonstop

In the schedule table on this page, United Airlines flies the Bombardier CRJ, the Embraer E175, the Boeing 737-700, and the Boeing 737-900, and American Airlines flies the Embraer E175, the Bombardier CRJ-700, 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 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.

American Airlines award space was open on 9 of the 14 Madison to Chicago departure dates from October 26 to November 8 that 2LNR checked in the 7 days to October 26, 2026.

See real availability

Confirmed upgrade or award seats by date on the MSN to ORD 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 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. Where 2LNR tracks the carrier, its departures show confirmed upgrade or award space by date.

See MSN to ORD on the interactive map →

Frequently asked questions about MSN to ORD

How long is the flight from Madison (MSN) to Chicago (ORD)?
Scheduled flight times from Madison (MSN) to Chicago (ORD) run from 1h 9m to 1h 25m 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 MSN to ORD?
United Airlines and American Airlines fly MSN to ORD nonstop. 2LNR tracks confirmed upgrade and award space on American Airlines.
How many flights a week are there from MSN to ORD?
About 153 nonstop flights a week run between Madison (MSN) and Chicago (ORD) 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 19:15, local time at Madison. The schedule table on this page lists every departure by date, with its arrival time and aircraft.
Which flights operate MSN to ORD nonstop?
The schedule table on this page lists 19 flight numbers for MSN to ORD nonstops, including UA 2037, UA 2137, UA 5730, and UA 5902 on United Airlines, and AA 4460, AA 4669, AA 4717, and AA 4775 on American Airlines. The table lists each departure by date with its times 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'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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