Route guide

Chicago to Boston (ORD-BOS): Nonstop Upgrade & Award Space

American Airlines, United Airlines, Delta Air Lines, JetBlue Airways, and Iberia Airlines fly nonstop between Chicago (ORD) and Boston (BOS), roughly 184 times a week. Because so many carriers compete on this route, premium seats turn over daily, and upgrade or award space can open and close within hours. 2LNR tracks confirmed availability on every ORD to BOS departure, so you know which flights have space before you book.

Data current as of July 21, 2026, refreshed on an ongoing basis as new schedules and seats are confirmed.

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184
Nonstop flights a week
864 mi
Nonstop distance
Free
To get started

Confirmed upgrade & award space on every ORD to BOS departure

2LNR tracks confirmed upgrade and award availability on American, Delta, and Alaska and across 30 airlines, segment by segment, date by date. Open the calendar for Chicago to Boston to see which departures have real space, or watch the route and get alerted when space opens.

See real availability

Confirmed upgrade and award seats on each ORD to BOS 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 BOS on the interactive route map, with schedules, connections, and route statistics.

Airlines flying Chicago to Boston nonstop

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

  • American Airlines
  • United Airlines
  • Delta Air Lines
  • JetBlue Airways
  • Iberia Airlines
See ORD to BOS on the interactive map →

Frequently asked questions about ORD to BOS

How far is Boston from Chicago?
ORD to BOS covers about 864 miles nonstop. Flight times vary by aircraft and season; each scheduled departure on this page lists its own times.
Which airlines fly nonstop from ORD to BOS?
American Airlines, United Airlines, Delta Air Lines, JetBlue Airways, and Iberia Airlines fly the route nonstop. 2LNR tracks confirmed upgrade and award space on each of them.
How many flights a week are there from ORD to BOS?
About 184 nonstop flights a week run between Chicago and Boston in the current schedule, operated by American Airlines, United Airlines, Delta Air Lines, JetBlue Airways, and Iberia Airlines. Frequency shifts by season; the calendar on this page reflects what's currently scheduled.
How do I check upgrade or award availability on ORD to BOS?
Open the ORD to BOS calendar on this page to see confirmed upgrade and award space by date. You can also set an alert on the Chicago to Boston route, and 2LNR will notify you when space opens. It's free to start.

Never miss ORD to BOS upgrade or award space

Track confirmed availability, set alerts, and book with confidence. Free to start, no credit card required.

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