Cheap flights from Chicago to Boston

One-way fares from $110 · CHI → BOS · prices found by travellers in the last 48 hours

Compare all dates Boston → Chicago
Cheapest fare
$110

Frontier Airlines · Sat, Nov 21

Cheapest month
November

from $110

Direct flights
Yes

jetBlue, American Airlines, Southwest Airlines + 1 more

Flight time
2h 15m

1,370 km

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Cheapest month to fly from Chicago to Boston

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

  1. November 2026 Cheapest $110
  2. December 2026 $110
  3. March 2027 $177
  4. July 2027 $179

Cheapest dates in November 2026

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

Frontier Airlines
Depart20:42 Sat, Nov 21MDW → BOS 5h 53m · 1 stop
$110one way, per person
View deal
Allegiant Air
Depart15:16 Fri, Nov 13MDW → BOS 3h 49m · 1 stop
$150one way, per person
View deal
Southwest Airlines
Depart19:15 Wed, Nov 4MDW → BOS 2h 15m · Direct
$157one way, per person
View deal
Southwest Airlines
Depart07:50 Sun, Nov 8MDW → BOS 2h 20m · Direct
$159one way, per person
View deal
American Airlines
Depart17:52 Thu, Nov 12ORD → BOS 2h 34m · Direct
$159one way, per person
View deal
American Airlines
Depart12:06 Tue, Nov 10ORD → BOS 2h 30m · Direct
$162one way, per person
View deal
jetBlue
Depart13:00 Sat, Nov 14ORD → BOS 2h 49m · Direct
$178one way, per person
View deal
United Airlines
Depart21:20 Mon, Nov 30ORD → BOS 2h 25m · Direct
$185one way, per person
View deal
See every date in November 2026 →

Plan the rest of your trip to Boston

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

Where to stay

Hotels in BostonCompare places to stay on Booking.com Find hotels →

Things to do

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

Getting around

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

About flights from Chicago to Boston

Chicago (CHI) and Boston (BOS) are about 1,370 km apart. Direct flights take around 2h 15m, and recent direct fares were with jetBlue, American Airlines, Southwest Airlines and United Airlines. Over the next few months, one-way fares start from $110, 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 Chicago to Boston?

The cheapest one-way fare we've seen recently is $110 with Frontier Airlines, departing Saturday, November 21, 2026. Over the coming months, the lowest fare in each month ranges from $110 to $179.

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

November 2026 currently has the lowest fares, from $110 one way.

Are there direct flights from Chicago to Boston?

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

How long is the flight from Chicago to Boston?

A direct flight takes about 2h 15m. Chicago and Boston are around 1,370 km apart.

Which airlines fly from Chicago to Boston?

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

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