Cheapest€115.19
- United Airlines UA606518:112h 18m20:29Boston BOSChicago MDW
Door to door 5h 28mCO2 346.6 kgChanges 0Fixed, no changes
Boston to Chicago flight
Flights from Boston to Chicago start at €138.20 and take 5h 21m at their fastest.
The Flights from Boston to Chicago 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 September 29, 2026
Two journeys we can sell today, with the service number each operator files them under.
Fastest€142.33
- American Airlines AA483712:332h 11m14:44Boston BOSChicago MDW
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 |
Chicago sits on the water, which usually settles which side of town you want to wake up on. Rooms are not ours to sell.
Looking for somewhere to stay in Chicago?
Hotels and apartments near downtown, most of them with free cancellation, on a map that shows what is walkable.
Search Chicago on Booking.comOr compare on Expedia
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 Boston to Chicago
The same search run across the whole booking window, so the shape of the curve is visible rather than described.
- €117.5590 days
- €89.8260 days
- €108.1145 days
- €116.3730 days
- €140.5621 days
- €180.6814 days
- €223.757 days
- €243.223 days
- €299.271 days
- Cheapest lead time
- Fares bottom out around 60 days ahead, at €89.82.
- How much it moves
- The gap between the cheapest and most expensive lead time is 233 percent. The most expensive point is €299.27, 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.
Boston
Air
- BOS
- BED
Chicago
Air
- ORD
- MDW
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 Boston 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 Boston to Chicago
The questions people actually ask about this trip, 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 Boston to Chicago take?
The Flight from Boston to Chicago 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 Boston to Chicago cost?
The Flight from Boston to Chicago starts at €138.20 for one passenger, checked on September 29, 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 Boston to Chicago?
7 operators run the Flight from Boston to Chicago: 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 Boston to Chicago use?
The Flight from Boston to Chicago leaves from Boston BOS and arrives at Chicago MDW. 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 Boston to Chicago?
Fares for the Flight from Boston to Chicago bottom out around 60 days ahead, at €89.82. The gap between the cheapest and most expensive lead time across the window is 233 percent, measured on September 29, 2026. Booking inside the final week has consistently cost more.
How much CO2 does the Flight from Boston to Chicago produce?
The Flight from Boston to Chicago produces about 346.6 kg of CO2 per passenger over 1409 km, which works out at roughly 246 grams per passenger kilometer. That figure is for the whole journey and for one traveler, 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 modeled 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 Boston to Chicago on September 10, 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.
Related journeys
Chicago to Boston flightCompare every mode from Boston to ChicagoAbu Dhabi to Chicago flightAguascalientes to Chicago flightAkron to Chicago flightAlbany to Chicago flightAlbuquerque to Chicago flightAllentown to Chicago flightAmman to Chicago flightAmsterdam to Chicago flightAnchorage to Chicago flightAppleton to Chicago flightAsheville to Chicago flightAtlanta to Chicago flight