Cheapest€115.19
- United Airlines UA708318:112h 16m20:27Chicago ORDBoston BED
Door to door 5h 26mCO2 346.6 kgChanges 0Fixed, no changes
Chicago to Boston flight
Flights from Chicago to Boston start at €138.20 and take 5h 21m at their fastest.
The Flights from Chicago to Boston starts at €138.20 and takes 5h 21m door to door, run by 7 operators over 1,409 km, with around 56 departures a day. Fares bottom out about 60 days before departure.
- 5h 21mDoor to door
- 2h 11mMoving
- €138.20From
- 346.6 kgCO2
The cheapest and the fastest on 29 September 2026
Two journeys we can sell today, with the service number each operator files them under.
Fastest€165.34
- American Airlines AA466708:042h 11m10:15Chicago ORDBoston BED
Door to door 5h 21mCO2 346.6 kgChanges 0Fixed, no changes
Airlines
Speed, flexibility and what is on board. Nothing here is a rating, because we have not earned one.
| Operator | From |
|---|---|
 American Airlines | €118.14 |
 JetBlue Airways | €118.73 |
 Delta Air Lines | €116.37 |
| United Airlines | €115.19 |
 Southwest Airlines | €120.50 |
 Republic Airways | €116.96 |
 Iberia Airlines | €115.19 |
The flight gets you into Boston. It does not get you a bed, and neither do we.
Where to sleep in Boston
Filter by neighbourhood and by price per night, and the map tells you what is a walk and what is a taxi.
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Partner links. We do not sell accommodation. We earn a commission when a booking completes, and it never changes what you pay.
When to book Chicago to Boston
The same search run across the whole booking window, so the shape of the curve is visible rather than described.
- €146.4690 days
- €87.4660 days
- €95.1345 days
- €108.1130 days
- €133.4821 days
- €167.1114 days
- €206.057 days
- €211.363 days
- €300.451 days
- Cheapest lead time
- Fares bottom out around 60 days ahead, at €87.46.
- How much it moves
- The gap between the cheapest and dearest lead time is 244 percent. The dearest point is €300.45, 1 days out.
- What that means
- Today sits inside the cheap window, which closes about 60 days before departure. Waiting from here has usually cost money on this corridor rather than saved it.
Which departure day costs least
Median cheapest fare for each weekday, taken across the next three weeks of real prices.
- €160.03Sun
- €138.20Mon
- €139.97Tue
- €145.28Wed
- €180.68Thu
- €167.11Fri
- €176.55Sat
Where you leave from and where you arrive
The stations, airports and ports each mode on this corridor actually uses.
Chicago
Air
- ORD
- MDW
Boston
Air
- BOS
- BED
What the journey actually looks like
Direct or connecting, how far the route really runs, and what happens when a connection is missed.
- How far it really runs
- The route covers 1,409 km against 1,368 km in a straight line, a detour of 3 percent. Track and road geometry account for the difference.
- First and last departure
- The first service of the day leaves Chicago at 06:14 and the last at 20:53, across 56 departures. The return direction keeps its own timetable, so the times back are not these times reversed.
Questions about Chicago to Boston
The questions people actually ask about this journey, answered from the same prices and times the page above is built on rather than written once and left to go stale.
How long does the Flight from Chicago to Boston take?
The Flight from Chicago to Boston takes 5h 21m door to door, of which 2h 11m is spent moving. The route runs 1,409 km. The difference between the two times is reaching the terminal and leaving it at the far end, which every time on this page includes.
How much does the Flight from Chicago to Boston cost?
The Flight from Chicago to Boston starts at €138.20 for one passenger, checked on 29 September 2026. A typical fare is €140.86. Both are the total including taxes, supplier fees and our service fee, so the price here is the price at checkout.
Who runs the Flight from Chicago to Boston?
7 operators run the Flight from Chicago to Boston: American Airlines, JetBlue Airways, Delta Air Lines, United Airlines, Southwest Airlines. Between them they file around 56 departures a day. The operator table on this page compares them on fare, journey time, cruising speed, fare conditions and what is provided on board.
Which terminal does the Flight from Chicago to Boston use?
The Flight from Chicago to Boston leaves from Chicago ORD and arrives at Boston BED. Allow about 3h 10m for reaching the departure terminal and leaving the arrival one. That time is already inside every door to door figure quoted on this page.
When should I book the Flight from Chicago to Boston?
Fares for the Flight from Chicago to Boston bottom out around 60 days ahead, at €87.46. The gap between the cheapest and dearest lead time across the window is 244 percent, measured on 29 September 2026. Booking inside the final week has consistently cost more.
How much CO2 does the Flight from Chicago to Boston produce?
The Flight from Chicago to Boston produces about 346.6 kg of CO2 per passenger over 1409 km, which works out at roughly 246 grams per passenger kilometre. That figure is for the whole journey and for one traveller, not for the vehicle.
Where these numbers come from
Observed service A carrier record shows this named operator serving this named pair, and we carry that through unchanged.
Schedules, seat counts and fares are generated by our own model until the supplier contracts are signed. Places, coordinates, operators, which operator serves which pair, and every distance are real. We would rather say that on every page than let a modelled number pass for a filed one.
Defined in full at Door to door, Fares, The booking window, Carbon
- On this page
- Every figure above was computed for Chicago to Boston on 11 September 2026: 1409 km of route against 1368 km in a straight line, 56 services a day, 7 operators, a cheapest fare of €138.20, and 5h 21m door to door on the fastest mode. The return direction is computed separately and its numbers are not these numbers.
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