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Cheap flights from Boston to Chicago

One-way from $96, found by travellers in the last 7 days. Aviasales checks the live price.

Departure
Return
Prices for nearby dates
Sun, Oct 18Any priceMon, Oct 19Any priceTue, Oct 20Any priceWed, Oct 21$96Thu, Oct 22$108Fri, Oct 23Any priceSat, Oct 24Any priceSun, Oct 25Any 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
$96
jetBlue, flight B6 811Found 4 days ago, 1 adult
Check price on Aviasales
5:12pmBostonWed, Oct 21
Travel time 3h 2m, nonstopBOSORD
7:14pmChicagoWed, Oct 21
$108
Southwest Airlines, flight WN 909Found 5 days ago, 1 adult
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10:00pmBostonThu, Oct 22
Travel time 2h 40m, nonstopBOSMDW
11:40pmChicagoThu, Oct 22
$108
jetBlue, flight B6 811Found 6 days ago, 1 adult
Check price on Aviasales
5:15pmBostonTue, Oct 27
Travel time 3h 14m, nonstopBOSORD
7:29pmChicagoTue, Oct 27
$124
Frontier Airlines, flight F9 3511Found 5 days ago, 1 adult
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12:39pmBostonFri, Oct 30
Travel time 5h 50m, 1 stopBOSORD
5:29pmChicagoFri, Oct 30
$142
Frontier Airlines, flight F9 3511Found 7 days ago, 1 adult
Check price on Aviasales
12:39pmBostonFri, Nov 13
Travel time 5h 50m, 1 stopBOSORD
5:29pmChicagoFri, Nov 13

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 Chicago, booked ahead at a fixed price.
    See options
  • Things to do in ChicagoPopular tours from $27.95 per person.
    See ideas
  • Flight delayed?Delayed or cancelled? See which passenger rights cover this route.
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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$1695–6–7$1898$1869–10$19511–12$18313–14–15–16–17–18–19–20–21$9622$10823–24–25–26–27$10828–29–30$12431–

November 2026

MoTuWeThFrSaSu1–2$1493–4–5–6–7–8–9–10–11–12–13$14214–15–16–17–18–19–20–21–22–23–24–25–26–27$15328–29–30–

December 2026

MoTuWeThFrSaSu1–2–345678910111213141516171819202122232425262728293031
$108 or lessGreen: the cheapest fifth of fares on this route. Lowest in these 60 days: Oct 21, $96.

Lowest fares by month

In the fares found this week, October has the lowest: from $96 one-way, against $167 in March 2027. Pick a month to see its cheapest date.

$0$100$200$96OctNovDecJanFebMarAprMayJunJulAugSep
Show as a table
MonthCheapest one-wayDateStops
October$96Wed, Oct 21Nonstop
November$142Fri, Nov 131 stop
December—
January 2027—
February 2027—
March 2027$167Tue, Mar 16Nonstop
April 2027—
May 2027—
June 2027—
July 2027—
August 2027—
September 2027—

Questions travellers ask

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

In the fares found this week, October has the lowest: from $96 one-way, against $167 in March 2027.

Are there direct flights from Boston to Chicago?

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

How long is the flight from Boston to Chicago?

A nonstop flight takes about 2h 40m. The distance is 863 mi.

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