Route information
- 860 miles
- ~2h 15m flight
- -1h time difference
- Data Nov 2026 – Oct 2027
About 860 miles, roughly 2h15 nonstop. Chicago is 1 hour behind Boston. The data runs November 2026–October 2027, with calendar prices for five months.
BOSORD
Boston to Chicagoaward flights
Compare award prices for Boston to Chicago, with economy seats from 88 points.
From
BOS
BOS
To
ORD
ORD
Depart
860 miles~2h 15m
Route snapshot
Boston to Chicago is a short-haul domestic hop; nonstop award space turns up on United Airlines. Lufthansa Miles & More was the lone program pricing it at last check, with economy from 88 points, on a United Airlines nonstop. On a flight this short, compare the cash fare first and spend points only when the award price drops low. This page lays out BOS–ORD award pricing in full.
- Route
- BOS to ORD
- Direct service
- 148 direct award flights
- Airlines with award availability
- 4
- Best economy price
- From 88 pts
- Best premium economy price
- N/A
- Best business price
- N/A
- Best first class price
- N/A
Award pricing comparison
Best one-way award prices per airline over the next 12 months.
| Airline | Economy |
|---|---|
 United AirlinesUA | 88Lowest |
Lowest in each cabin—No award seats foundPoints, one-way. Live award pricing from FlightFlyer data, computed 10/25/2026. Prices vary by date and availability.
Award pricing by month
When award seats between Boston and Chicago price cheapest over the next year.
Cheapest monthJanuary 2027 · 88 pts
CheapestNext 12 months| Month | Cheapest award (points) |
|---|---|
| Nov 2026 | No award data |
| Dec 2026 | No award data |
| Jan 2027 | 88 |
| Feb 2027 | 90 |
| Mar 2027 | 90 |
| Apr 2027 | 30,873 |
| May 2027 | No award data |
| Jun 2027 | No award data |
| Jul 2027 | 90 |
| Aug 2027 | No award data |
| Sep 2027 | No award data |
| Oct 2027 | No award data |
Jan, Feb, Mar currently price cheapest on this route, with awards from 88 pts one-way based on recent award data.
Airlines with award seats on this route
4 airlines with award seats between Boston and Chicago, nonstop or connecting.
American AirlinesAA
Air CanadaAC
DeltaDLUnited AirlinesUARoute notes
What to know before booking Boston to Chicago with points.
About this route
Boston to Chicago is served by American Airlines, Air Canada, Delta and 1 more, offering multiple options for award travelers. Award prices start from 88 points in economy. Use our search tool to check real-time award availability on this route.
Boston–Chicago Flights
Flying Boston to Chicago covers about 860 miles, linking Boston Logan International Airport (BOS) with O'Hare International Airport (ORD); a nonstop takes roughly 2h15, with winds moving it either way. United Airlines carries all of the nonstop award space in the data. The Boeing 737-800 shows up on those nonstop award segments. Nonstops make up about 55% of the award options in the data, which makes a direct award a realistic target.
Best Ways to Book With Points & Miles
Boston–Chicago is a domestic route, so the first question is whether to spend points at all. The economy floor is a partner booking on a United Airlines nonstop, with no connection to trade off against the points. Taxes and fees on that seat run about $289, in line with the route's typical economy taxes. Run the miles-or-cash math each time: a cheap fare usually beats spending points. Transfers out of bank programs can't be reversed, so confirm the exact flight is bookable first.
Best Points & Miles Programs
Lufthansa Miles & More is the only program pricing Boston–Chicago: economy at 88 points on a United Airlines nonstop.
Airlines & Routing Options
United Airlines is the only airline with nonstop award space on Boston–Chicago in the data. Only four airlines show award inventory on the route, and Lufthansa Miles & More prices every award in the data.
Alternative Airports & Routes
Neither Boston nor Chicago shows a same-metro alternate airport in the data, so the live price table above is the one to watch. For another option from Boston, Atlanta prices from 11,000 points at last check. For a longer redemption from Boston, Aruba and Amsterdam are tracked too.
Booking tips
- 1Search flexible dates first, since saver award seats can appear on scattered days.
- 2Compare partner programs before transferring points, since the same seat can price very differently.
- 3Check both direct and connecting options when direct award seats are limited.
- 4Book early for peak travel periods, when saver space disappears fastest.
- 5Recheck availability often, since airlines may release more award seats closer to departure.
Similar routes
Alternative corridors travelers consider alongside Boston to Chicago.
BOSCUNBoston to Cancun
From 3,200 ptsBusiness 20,000 pts
BOSBWIBoston to Baltimore
From 4,000 ptsBusiness 29,000 pts
BOSDCABoston to Washington
From 4,000 ptsBusiness 19,300 pts
BOSYYZBoston to Toronto
From 4,500 ptsBusiness 15,000 pts
BOSZRHBoston to Zurich
From 4,520 ptsBusiness 45,000 pts
JFKORDNew York to Chicago
From 5,200 ptsBusiness 24,600 pts
FAQ
Frequently Asked Questions
Common questions travelers ask about the Boston to Chicago route.
At last check, economy starts at 88 points one-way through Lufthansa Miles & More on United Airlines, nonstop. Only Lufthansa Miles & More prices this route, so the real decision is points versus cash. The pricing table above shows each cabin's low at last check.