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 six months.
BOSORD
Boston to Chicagoaward flights
Compare 5 loyalty programs for Boston to Chicago award flights, 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, American Airlines, and Delta. Award pricing spans five programs, and the cheapest economy award is 88 points via Lufthansa Miles & More, 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 compares every way to book BOS–ORD on points.
- 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
- From 29,000 pts
- Best first class price
- From 25,000 pts
Award pricing comparison
Best one-way award prices per airline over the next 12 months.
| Airline | Economy | Business | First |
|---|---|---|---|
 United AirlinesUA | 88Lowest | Not available | Not available |
 American AirlinesAA | 7,500pts | 29,000Lowest | 25,000Lowest |
 DeltaDL | 8,600pts | Not available | 25,800pts |
 Air CanadaAC | 15,000pts | Not available | Not available |
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 | 7,500 |
| 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 AirlinesAAAir CanadaACDeltaDLUnited 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. Compare 5 loyalty programs to find the best value for your points. 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. Nonstop award space in the data comes from United Airlines, American Airlines, and Delta. The Airbus A319 and Boeing 737-800 both appear 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. Its $289 in taxes and fees is the catch, well above the route's typical economy taxes; more points and less cash can come out ahead. Run the miles-or-cash math each time: a cheap fare usually beats spending points.
Best Points & Miles Programs
Lufthansa Miles & More takes economy at 88 points on a United Airlines nonstop. Qantas Frequent Flyer is cheapest in business class at 29,000 points. Alaska Atmos Rewards wins first class at 25,000 points. Also in the mix: Delta SkyMiles and Virgin Australia Velocity. First class is a partner award on American Airlines too. No program wins more than one cabin here, so pick the seat first, then the currency.
Airlines & Routing Options
On points, Boston–Chicago has nonstop seats from United Airlines (Star Alliance), American Airlines (oneworld), and Delta (SkyTeam), which puts partner programs from all three alliances in play for a nonstop. The business-class floor is a oneworld partner award: Qantas Frequent Flyer prices American Airlines seats. Only four airlines show award space here, but five programs sell their seats, so the program matters more than the carrier.
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. With five programs pricing the route, it pays to check several. The pricing table above shows each cabin's low at last check.