Boston to Chicago (BOS-ORD): nonstop upgrade & award space

American Airlines, United Airlines, Delta Air Lines, and JetBlue Airways fly nonstop between Boston (BOS) and Chicago (ORD), roughly 222 times a week. With this many departures on a short sector, premium cabins are small and turn over daily, so upgrade or award space opens and closes within hours. 2LNR tracks confirmed upgrade and award space on American Airlines and Delta Air Lines, on every BOS 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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222
Nonstop flights a week
864 mi
Nonstop distance
Free
To get started

Boston to Chicago flight schedule

Scheduled nonstop departures for BOS 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 Boston (BOS) to Chicago (ORD)
Date Flight Airline Departs BOS Arrives ORD Duration Aircraft
UA 1414United Airlines06:0007:592h 59m7M9
AA 3324American Airlines06:1408:203h 6m738
UA 2631United Airlines07:0509:032h 58m7M9
AA 1509American Airlines07:1009:163h 6m738
DL 2570Delta Air Lines07:3009:242h 54m738
UA 717United Airlines07:4609:452h 59m738
B6 311JetBlue Airways08:1510:112h 56m223
UA 1834United Airlines08:1510:122h 57m739
AA 1239American Airlines08:2710:303h 3m738
UA 1349United Airlines09:0010:592h 59m32Q
AA 547American Airlines10:2812:293h 1m738
AA 2607American Airlines10:3012:32—738
UA 503United Airlines10:3812:292h 51m7M8
AA 3048American Airlines11:5813:593h 1m738
DL 2816Delta Air Lines12:1514:042h 49m223
UA 472United Airlines12:2714:202h 53m739
UA 1732United Airlines12:3014:232h 53m739
UA 463United Airlines12:3714:292h 52m739
AA 4386American Airlines13:0115:103h 9mE75
AA 4533American Airlines13:0115:153h 14mE75
AA 3711American Airlines14:0016:053h 5mE75
UA 1475United Airlines15:1317:052h 52m739
AA 1563American Airlines15:1917:293h 10m738
AA 1479American Airlines15:5318:043h 11m738
DL 2646Delta Air Lines16:0518:012h 56m223
UA 2040United Airlines17:0119:002h 59m7M9
B6 811JetBlue Airways17:2019:253h 5m223
AA 2837American Airlines17:4520:043h 19m738
UA 1015United Airlines18:4220:402h 58m7M9
AA 3160American Airlines19:1721:353h 18m738
UA 2229United Airlines20:2122:202h 59m738
DL 2804Delta Air Lines20:5022:322h 42m223
AA 3324American Airlines06:0008:103h 10m321
UA 1414United Airlines06:0007:592h 59m7M9
AA 1509American Airlines07:0009:063h 6m321
B6 111JetBlue Airways07:0008:482h 48m223
UA 2631United Airlines07:0509:032h 58m7M9
DL 2570Delta Air Lines07:3009:242h 54m738
UA 717United Airlines07:4609:452h 59m738
UA 1834United Airlines08:1510:122h 57m739

Showing the first 40 of 216 scheduled BOS 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 BOS to ORD date on the interactive map

Confirmed upgrade & award space on BOS to ORD departures

2LNR tracks confirmed upgrade and award space on American Airlines and Delta Air Lines, segment by segment and date by date. Open the calendar for Boston 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 BOS 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 BOS to ORD on the interactive route map, with schedules, connections, and route statistics.

Airlines flying Boston to Chicago nonstop

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

See BOS to ORD on the interactive map →

Frequently asked questions about BOS to ORD

How far is Chicago from Boston?
BOS to ORD covers about 864 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 BOS to ORD?
American Airlines, United Airlines, Delta Air Lines, and JetBlue Airways fly the route nonstop. 2LNR tracks confirmed upgrade and award space on American Airlines and Delta Air Lines, and award seats on JetBlue Airways.
How many flights a week are there from BOS to ORD?
About 222 nonstop flights a week run between Boston and Chicago in the current schedule, operated by American Airlines, United Airlines, Delta Air Lines, and JetBlue Airways. Frequency shifts by season, and the schedule table on this page shows what is scheduled next.
What time do flights from BOS to ORD depart?
Scheduled BOS to ORD nonstops in the next 7 days with service leave between 06:00 and 20:50, local time at Boston. 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 BOS to ORD?
Open the BOS to ORD route on the interactive map or the matrix to see confirmed upgrade and award space by date on American Airlines and Delta Air Lines, 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 BOS 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.

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