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Cheap flights from Chicago to Boston

One-way from $101, found by travellers in the last 7 days. Aviasales checks the live price.

Departure
Return
Prices for nearby dates
Sun, Oct 11$167Mon, Oct 12$216Tue, Oct 13Any priceWed, Oct 14$101Thu, Oct 15$124Fri, Oct 16Any priceSat, Oct 17Any priceSun, Oct 18Any price

Cheapest one-way tickets

Recent finds on different dates, for 1 adult. Baggage and fare rules are shown on Aviasales, where the price is checked live.

Cheapest
$101
jetBlue, flight B6 1012Found 5 days ago, 1 adult
Check price on Aviasales
8:04pmChicagoWed, Oct 14
Travel time 2h 55m, nonstopORDBOS
11:59pmBostonWed, Oct 14
$108
Southwest Airlines, flight WN 1266Found 6 days ago, 1 adult
Check price on Aviasales
6:10pmChicagoTue, Oct 27
Travel time 2h 20m, nonstopMDWBOS
9:30pmBostonTue, Oct 27
$118
Frontier Airlines, flight F9 1458Found 7 days ago, 1 adult
Check price on Aviasales
8:42pmChicagoFri, Nov 20
Travel time 5h 53m, 1 stopMDWBOS
3:35amBostonSat, Nov 21
$123
jetBlue, flight B6 1012Found 5 days ago, 1 adult
Check price on Aviasales
8:04pmChicagoThu, Oct 22
Travel time 2h 55m, nonstopORDBOS
11:59pmBostonThu, Oct 22
$124
United Airlines, flight UA 2759Found 4 days ago, 1 adult
Check price on Aviasales
5:00amChicagoThu, Oct 15
Travel time 3h 26m, 1 stopORDBOS
9:26amBostonThu, Oct 15

Round trips

The cheapest return tickets found recently, price for the whole trip.

Plan the rest of the trip

  • Mobile data in United StatesTravel eSIM from $4, installed before you fly.
    Compare plans
  • Getting from the airportTransfers and car hire in Boston, booked ahead at a fixed price.
    See options
  • Things to do in BostonPopular tours from $36 per person.
    See ideas
  • Flight delayed?Delayed or cancelled? See which passenger rights cover this route.
    Check

Price calendar

The lowest one-way fare found for each day over the next 60 days. A dash means no recent fare; you can still pick that day.

October 2026

MoTuWeThFrSaSu1234–5–6–7$1448$1869$17810$13711$16712$21613–14$10115$12416–17–18–19–20–21–22$12323–24–25–26–27$10828–29–30–31–

November 2026

MoTuWeThFrSaSu1–2–3–4–5–6–7–8–9–10–11–12–13–14–15–16–17–18–19–20$11821$14122$13423–24–25–26$15327–28–29–30–

December 2026

MoTuWeThFrSaSu1–2–345678910111213141516171819202122232425262728293031
$123 or lessGreen: the cheapest fifth of fares on this route. Lowest in these 60 days: Oct 14, $101.

Lowest fares by month

In the fares found this week, October has the lowest: from $101 one-way, against $168 in April 2027. Pick a month to see its cheapest date.

$0$100$200$101OctNovDecJanFebMarAprMayJunJulAugSep
Show as a table
MonthCheapest one-wayDateStops
October$101Wed, Oct 14Nonstop
November$118Fri, Nov 201 stop
December—
January 2027—
February 2027—
March 2027—
April 2027$168Mon, Apr 19Nonstop
May 2027—
June 2027—
July 2027—
August 2027—
September 2027—

Questions travellers ask

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

In the fares found this week, October has the lowest: from $101 one-way, against $168 in April 2027.

Are there direct flights from Chicago to Boston?

Yes. Recent fares include nonstop flights with jetBlue, Southwest Airlines and American Airlines.

How long is the flight from Chicago to Boston?

A nonstop flight takes about 2h 20m. The distance is 863 mi.

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