Flights Chicago → Boston

One way · Economy · 1 adult · price per person · next 14 days from September 10, 2026

Last observed price on Aviasales for 5 of 15 dates; the lowest is $122. Prices are not guaranteed and are confirmed at booking time.

Last observed price by date

Date	Last observed price	Flight	Departure	Arrival	Stops
Thu, Sep 10	—	—	—	—	—
Fri, Sep 11	—	—	—	—	—
Sat, Sep 12	—	—	—	—	—
Sun, Sep 13	—	—	—	—	—
Mon, Sep 14	$167	American Airlines AA2294	1:54 PM O'Hare (ORD)	5:35 PM Logan (BOS)	Direct
Tue, Sep 15	—	—	—	—	—
Wed, Sep 16	$153	Frontier Airlines F93044 (1st of 2 flights)	3:50 PM O'Hare (ORD)	10:22 AM (+1) Logan (BOS)	1 stop · Orlando International
Thu, Sep 17	$122lowest	JetBlue B61012	8:24 PM O'Hare (ORD)	12:09 AM (+1) Logan (BOS)	Direct
Fri, Sep 18	—	—	—	—	—
Sat, Sep 19	$140	Frontier Airlines F93044 (1st of 2 flights)	3:50 PM O'Hare (ORD)	10:58 AM (+1) Logan (BOS)	1 stop · Orlando International
Sun, Sep 20	—	—	—	—	—
Mon, Sep 21	$142	Southwest Airlines WN3094	5:45 AM Midway (MDW)	9:00 AM Logan (BOS)	Direct
Tue, Sep 22	—	—	—	—	—
Wed, Sep 23	—	—	—	—	—
Thu, Sep 24	—	—	—	—	—

Price not guaranteed: it is confirmed on Aviasales at booking time. How it works

Chicago, United States (CHI, city code)

Chicago O'Hare (ORD), Chicago Midway (MDW).

Boston, United States (BOS, city code)

Boston Logan (BOS).

FromToDeparture date