Boston to Chicago flights

Routavio compares airline fares from several flight booking sites. The lowest one-way fare it found for Boston to Chicago is €78 (checked on 24 Oct 2026).

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Lowest observed

€78

Average observed

€122

Cheapest month

November 2026

Last checked

24 Oct 2026

Observed fares. Prices may change.

Your next trip, last seen at €78

Lowest observed

19 Nov 2026

One way

Cheapest observed day · Last checked: 24 Oct 2026

When to fly

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The lowest fare we observed for each month. Open a month to see its days, then pick your outbound and return. A day with no price is one we will search for you.

One-way fare

One-way fare · No data: click and we will search

Lowest observed: €78, departing 19 Nov 2026 (Last checked: 24 Oct 2026)One-way fare · Priced departure days checked in the last 14 days: 6Check live prices for this route
Airlines seen: American Airlines, JetBlue, United Airlines, Southwest Airlines, Delta Air Lines, Frontier Airlines
Reported fastest flight: 2h 50m
Non-stop: Yes

Short answer

Routavio has seen American Airlines fares from Boston to Chicago, non-stop. The lowest fare Routavio's own searches returned is €78, seen on 24 Oct 2026. The average across the fares we caught is €122. November 2026 is the cheapest month in our observations, at €78. These are prices Routavio's searches returned on the dates shown, not quotes; run a live search for today's fare.

About this route

Explore the fares we observed from Boston to Chicago. Prices move often, so pick your dates to see the latest options.

Route distance: 1,366 km
Reported fastest flight: 2h 50m
Alternative airports: PSM, CGX, DPA, MDW, PWK, RFD

Route-level information; individual journeys vary.
Published schedules report non-stop service with American Airlines, JetBlue, United Airlines, Southwest Airlines, Spirit Airlines. Check current timetables.

A clearer picture of your fare

Observed, not guaranteed

Every price is a fare we actually saw, and it may change at any time.

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The price is final on the provider's site, where your booking is completed.

How our prices work

Non-stop airlines seen on this route

Non-stop airlines seen on this route
Airline	Non-stop days / priced days	Fastest non-stop
American Airlines	5 / 6
Delta Air Lines	5 / 6

Departure days with a non-stop fare checked in the last 14 days. A carrier listed here had a non-stop fare on at least 3 days; schedules may differ.

Airport to city: straight-line distance

Portsmouth International Airport at Pease (PSM) → Boston, city gazetteer reference point (42.3584, -71.0598): ≈ 82 km.
Chicago Midway International Airport (MDW) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 14 km.
Chicago O'Hare International Airport (ORD) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 25 km.
Chicago Rockford International Airport (RFD) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 126 km.

Approximate distances calculated from coordinates, not road distances or travel times. These airports serve the city; they are not confirmed endpoints of an offer.

Lowest one-way fare we saw per airline

Cheapest airline from Boston to Chicago: American Airlines, from €95 (checked 24 Oct 2026).

Lowest one-way fare we saw per airline
Airline	Lowest fare	Priced days
American Airlines	€95Nov 19, 2026	5
Delta Air Lines	€95Nov 19, 2026	5
JetBlue	€95Jan 26, 2027	4
United Airlines	€95Nov 19, 2026	5

One-way fares checked in the last 14 days. An airline listed here had a fare on at least 3 departure days. Each figure is the lowest we saw, not a guaranteed fare. Connecting itineraries are included; the date is the departure day of that fare.

Frequently asked

How much is a flight from Boston to Chicago?

The lowest fare Routavio has observed is €78, found on 24 Oct 2026. Prices move, so read it as a floor rather than a quote.

When is the cheapest month to fly from Boston to Chicago?

In our observations November 2026 is the cheapest month so far, at €78.

Are there direct flights from Boston to Chicago?

Yes. Published schedules report non-stop flights on this route with American Airlines, JetBlue, United Airlines, Southwest Airlines, Spirit Airlines.

Which airlines fly from Boston to Chicago?

Routavio has seen these carriers on the route: American Airlines, JetBlue, United Airlines, Southwest Airlines, Delta Air Lines, Frontier Airlines.

How many of the observed Boston to Chicago fares were non-stop?

6 of the 14 fares we observed were non-stop; the rest included at least one stop. That describes our observations, not every flight that operates.

Which airlines had non-stop offers on at least 3 departure dates from Boston to Chicago?

For Boston to Chicago, examples of observed one-way non-stop offers checked within the last 14 days: American Airlines (5), Delta Air Lines (5). Each number counts distinct departure dates, not weekly flights; check current availability in search.

Which airline has the lowest fare from Boston to Chicago?

Cheapest airline from Boston to Chicago: American Airlines, from €95 (checked 24 Oct 2026).

How observed prices work, what "No data" means and what a fare includes: Read the flight price guide