Cheap flights from Boston to Chicago

One-way fares from $134 · BOS → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → Boston
Cheapest fare
$134

Frontier Airlines · Fri, Nov 20

Cheapest month
November

from $134

Direct flights
Yes

Southwest Airlines, jetBlue and American Airlines

Flight time
2h 45m

1,370 km

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Cheapest month to fly from Boston to Chicago

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 Cheapest $134
  2. December 2026 $140
  3. January 2027 $149
  4. March 2027 $178
  5. July 2027 $179

Cheapest dates in November 2026

The lowest fares we've seen for each day, cheapest first.

Frontier Airlines
Depart11:06 Fri, Nov 20BOS → MDW 6h 30m · 1 stop
$134one way, per person
View deal
jetBlue
Depart09:59 Wed, Nov 4BOS → ORD 3h 01m · Direct
$144one way, per person
View deal
Frontier Airlines
Depart12:39 Mon, Nov 9BOS → ORD 5h 51m · 1 stop
$155one way, per person
View deal
See every date in November 2026 →

Plan the rest of your trip to Chicago

Where to stay, what to do and getting around, from our travel partners.

Where to stay

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Things to do

Things to do in ChicagoTours, attractions and day trips on Klook Explore →

Getting around

Airport transfer in ChicagoPre-book a driver to meet you at arrivals, with Kiwitaxi Book a transfer → Car hire in ChicagoCompare rental cars from major brands on EconomyBookings Compare cars →

About flights from Boston to Chicago

Boston (BOS) and Chicago (CHI) are about 1,370 km apart. Direct flights take around 2h 45m, and recent direct fares were with Southwest Airlines, jetBlue and American Airlines. Over the next few months, one-way fares start from $134, and November 2026 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from Boston to Chicago?

The cheapest one-way fare we've seen recently is $134 with Frontier Airlines, departing Friday, November 20, 2026. Over the coming months, the lowest fare in each month ranges from $134 to $179.

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

November 2026 currently has the lowest fares, from $134 one way.

Are there direct flights from Boston to Chicago?

Yes. Recent direct fares were with Southwest Airlines, jetBlue and American Airlines.

How long is the flight from Boston to Chicago?

A direct flight takes about 2h 45m. Boston and Chicago are around 1,370 km apart.

Which airlines fly from Boston to Chicago?

Recent fares on this route were with Frontier Airlines, Southwest Airlines, jetBlue and American Airlines.

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