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Cheap flights from Boston to Chicago
from 108 US$

From 201 USD — compare hundreds of airlines

We search 100+ flight sitesDirect flights~2h 12mReturn route: Chicago → Boston

The cheapest month is usually 2026-10 · 108 US$

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Live fares from 100+ sites — free, with no hidden fees.

About this route

Compare flights from Boston to Chicago, a about 1,366 km route (around 2h 12m nonstop). We gather live prices from hundreds of airlines and agencies so you can find the cheapest and book on the official site, with no hidden fees. Direct flights are available. Airlines such as American Airlines, Alaska Airlines, jetBlue operate this route.

Nonstop time
2h 12m
Distance
1,366 km
Stops
Nonstop
Airlines
6+

When to buy and when to fly

Prices by date

Fares found by date — cheapest days in green.

See prices for my dates →
130 US$
01/10
127 US$
02/10
127 US$
03/10
127 US$
04/10
127 US$
05/10
127 US$
06/10
127 US$
07/10
127 US$
08/10
127 US$
09/10
127 US$
10/10
127 US$
11/10
127 US$
12/10

How to get the best price

1The sticker price is real — but it moves fastLow fares last hours or days. If the number works, search it today; waiting rarely improves it.
2Buy 4–8 weeks aheadThat window usually holds the best fares; holidays call for even more margin.
3Flexibility = moneyShifting departure 2–3 days can move the fare 100+ US$. Tuesdays and Wednesdays tend to be cheap.

Airlines on this route

American AirlinesAlaska AirlinesjetBlueSpirit AirlinesUnited AirlinesSouthwest Airlines

FAQ

What's the cheapest month to fly Boston to Chicago?

It's usually 2026-10, from 108 USD. Use the price calendar to compare other dates.

How long is the flight from Boston to Chicago?

A nonstop flight takes about 2h 12m and covers around 1,366 km. Connecting itineraries take longer.

Are there direct flights from Boston to Chicago?

Yes, this route has nonstop flights. Filter by "nonstop" to see them.

Which airlines fly from Boston to Chicago?

American Airlines, Alaska Airlines, jetBlue, Spirit Airlines operate this route, among others. Compare them all in the results.

When should I book Boston–Chicago flights?

As a rule of thumb, booking 3–8 weeks ahead and avoiding weekends and holidays tends to give the best prices. Use the calendar to spot the cheapest dates.

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Boston → Chicago · Live fares from 100+ sites — free, with no hidden fees.

Search flights →Return route: Chicago → Boston

Flights to this destination from other cities

Munich → ChicagoZurich → ChicagoStockholm → ChicagoCopenhagen → ChicagoHong Kong → ChicagoBurlington → ChicagoDecatur → ChicagoSaint Louis → ChicagoQuebec → ChicagoMontreal → Chicago

Other routes from Boston

NantucketAlbanyAugustaBar HarborHyannisLebanonMartha's VineyardProvincetownRocklandRutland
Return route: Chicago → Boston →Chicago · Travel guide →All flights from Boston →