American Airlines Chicago to Boston Flights

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Cheapflightsplus.com will find cheap American Airlines flights from Chicago to Boston. Compare airline ticket prices and book air tickets starting from $67 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of American Airlines, arrivals and departure details below.

Find Cheap Airfare Chicago (IL) — Boston (MA) by American Airlines

To find cheap tickets choose a day of your departure with attractive price on the graph below and click «Find flights». For round trip flights please click «Check prices for return flight». The cheapest airfare is in february: one-way - $67, two-way – $115.

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Cheap Flights from Chicago to Boston by American Airlines

Look at the list of plane tickets for the most popular direct and connecting flights by American Airlines, their prices start from $67. The fastest nonstop flight takes 2h 13m. The fastest connecting flight — 3h 54m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $67 Find flight	8:10 am Chicago O'Hare International	11:23 am Boston Logan	2h 13m	American Airlines	AA314
from $101 Find flight	7:00 am Chicago O'Hare International	10:20 am Boston Logan	2h 20m	American Airlines	AA3703
from $124 Find flight	4:00 pm Chicago O'Hare International	7:13 pm Boston Logan	2h 13m	American Airlines	AA1219
from $124 Find flight	8:20 pm Chicago O'Hare International	11:44 pm Boston Logan	2h 24m	American Airlines	AA4380
from $247 Find flight	2:50 pm Chicago O'Hare International	6:07 pm Boston Logan	2h 17m	American Airlines	AA3690
from $131 Find flight	4:35 pm Chicago O'Hare International	0:20 am+1 день Boston Logan	6h 45m layover 3h 13m - New York	American Airlines	AA696 B61518
from $131 Find flight	11:41 am Chicago O'Hare International	0:20 am+1 день Boston Logan	11h 39m layover 8h 6m - New York	American Airlines	AA532 B61518
from $131 Find flight	11:41 am Chicago O'Hare International	6:36 pm Boston Logan	5h 55m layover 2h 17m - New York	American Airlines	AA532 B61418
from $149 Find flight	6:00 am Chicago O'Hare International	5:16 pm Boston Logan	10h 16m layover 6h 55m - New York	American Airlines	AA2084 B61032
from $149 Find flight	8:43 am Chicago O'Hare International	4:00 pm Boston Logan	6h 17m layover 3h 3m - New York	American Airlines	AA2587 B6832
from $149 Find flight	8:43 am Chicago O'Hare International	5:16 pm Boston Logan	7h 33m layover 4h 13m - New York	American Airlines	AA2587 B61032
from $149 Find flight	6:00 am Chicago O'Hare International	4:00 pm Boston Logan	9h 0m layover 5h 45m - New York	American Airlines	AA2084 B6832
from $161 Find flight	12:40 pm Chicago O'Hare International	5:39 pm Boston Logan	3h 59m layover 0h 38m - Philadelphia	American Airlines	AA1606 AA2255
from $161 Find flight	11:49 am Chicago O'Hare International	5:35 pm Boston Logan	4h 46m layover 1h 26m - Washington D.C.	American Airlines	AA1200 AA464
from $161 Find flight	5:28 pm Chicago O'Hare International	10:44 pm Boston Logan	4h 16m layover 1h 0m - Philadelphia	American Airlines	AA1941 AA2775
from $186 Find flight	7:30 am Chicago O'Hare International	5:16 pm Boston Logan	8h 46m layover 5h 24m - New York	American Airlines	AA2283 B61032

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 01/30/2025

American Airlines Flight Schedule Chicago to Boston

Below is a detailed 2025 flight schedule for today, tomorrow and all other days. It may vary depending on season and a day of the week of your desired trip. We recommend booking your itinerary at least 2 weeks prior your travel to get the best price and availability by the airline.

Departure	Flight Details	Flight Time	Price
12:30 pm — 3:50 pm	12:30 pm — 3:50 pm AA4384 American Airlines Chicago — Boston	2h 20m	Find flight from$283
2:50 pm — 6:07 pm	2:50 pm — 6:07 pm AA3690 American Airlines Chicago — Boston	2h 17m	Find flight from$247
4:00 pm — 7:13 pm	4:00 pm — 7:13 pm AA1219 American Airlines Chicago — Boston	2h 13m	Find flight from$124
7:00 am — 10:20 am	7:00 am — 10:20 am AA3703 American Airlines Chicago — Boston	2h 20m	Find flight from$101
8:10 am — 11:23 am	8:10 am — 11:23 am AA314 American Airlines Chicago — Boston	2h 13m	Find flight from$67
8:20 pm — 11:44 pm	8:20 pm — 11:44 pm AA4380 American Airlines Chicago — Boston	2h 24m	Find flight from$124
10:29 am — 4:07 pm	10:29 am — 1:29 pm AA2080 American Airlines Chicago — Charlotte 31m stop 2:00 pm — 4:07 pm AA1457 American Airlines Charlotte — Boston	4h 38m including layover	Find flight from$161
10:29 am — 7:08 pm	10:29 am — 1:29 pm AA2080 American Airlines Chicago — Charlotte 3h 31m stop 5:00 pm — 7:08 pm AA1978 American Airlines Charlotte — Boston	7h 39m including layover	Find flight from$164
11:41 am — 0:20 am +1 day	11:41 am — 2:53 pm AA532 American Airlines Chicago — New York 8h 6m stop 10:59 pm — 0:20 am B61518 JetBlue New York — Boston	11h 39m including layover	Find flight from$131
11:41 am — 6:36 pm	11:41 am — 2:53 pm AA532 American Airlines Chicago — New York 2h 17m stop 5:10 pm — 6:36 pm B61418 JetBlue New York — Boston	5h 55m including layover	Find flight from$131
12:40 pm — 5:39 pm	12:40 pm — 3:34 pm AA1606 American Airlines Chicago — Philadelphia 38m stop 4:12 pm — 5:39 pm AA2255 American Airlines Philadelphia — Boston	3h 59m including layover	Find flight from$161
12:40 pm — 8:35 pm	12:40 pm — 3:34 pm AA1606 American Airlines Chicago — Philadelphia 3h 36m stop 7:10 pm — 8:35 pm AA1874 American Airlines Philadelphia — Boston	6h 55m including layover	Find flight from$164
1:34 pm — 6:42 pm	1:34 pm — 4:19 pm AA1637 American Airlines Chicago — Washington D.C. 41m stop 5:00 pm — 6:42 pm AA1399 American Airlines Washington D.C. — Boston	4h 8m including layover	Find flight from$161
1:54 pm — 8:55 pm	1:54 pm — 4:51 pm AA326 American Airlines Chicago — Charlotte 1h 54m stop 6:45 pm — 8:55 pm AA3178 American Airlines Charlotte — Boston	6h 1m including layover	Find flight from$164
2:55 pm — 8:35 pm	2:55 pm — 5:47 pm AA2840 American Airlines Chicago — Philadelphia 1h 23m stop 7:10 pm — 8:35 pm AA1874 American Airlines Philadelphia — Boston	4h 40m including layover	Find flight from$164
2:55 pm — 10:44 pm	2:55 pm — 5:47 pm AA2840 American Airlines Chicago — Philadelphia 3h 33m stop 9:20 pm — 10:44 pm AA2775 American Airlines Philadelphia — Boston	6h 49m including layover	Find flight from$164
3:00 pm — 9:20 pm	3:00 pm — 5:02 pm AA3892 American Airlines Chicago — Indianapolis 2h 6m stop 7:08 pm — 9:20 pm AA4732 American Airlines Indianapolis — Boston	5h 20m including layover	Find flight from$214
3:34 pm — 10:29 pm	3:34 pm — 6:25 pm AA533 American Airlines Chicago — Raleigh 2h stop 8:25 pm — 10:29 pm DL1021 Delta Air Lines Inc. Raleigh — Boston	5h 55m including layover	Find flight from$238
4:35 pm — 0:20 am +1 day	4:35 pm — 7:46 pm AA696 American Airlines Chicago — New York 3h 13m stop 10:59 pm — 0:20 am B61518 JetBlue New York — Boston	6h 45m including layover	Find flight from$131
5:00 am — 11:29 am	5:00 am — 7:56 am AA2842 American Airlines Chicago — Charlotte 1h 19m stop 9:15 am — 11:29 am AA3252 American Airlines Charlotte — Boston	5h 29m including layover	Find flight from$164
5:28 pm — 10:44 pm	5:28 pm — 8:20 pm AA1941 American Airlines Chicago — Philadelphia 1h stop 9:20 pm — 10:44 pm AA2775 American Airlines Philadelphia — Boston	4h 16m including layover	Find flight from$161
6:00 am — 5:16 pm	6:00 am — 9:00 am AA2084 American Airlines Chicago — New York 6h 55m stop 3:55 pm — 5:16 pm B61032 JetBlue New York — Boston	10h 16m including layover	Find flight from$149
6:00 am — 4:00 pm	6:00 am — 9:00 am AA2084 American Airlines Chicago — New York 5h 45m stop 2:45 pm — 4:00 pm B6832 JetBlue New York — Boston	9h including layover	Find flight from$149
7:00 am — 1:51 pm	7:00 am — 9:56 am AA1784 American Airlines Chicago — Charlotte 1h 29m stop 11:25 am — 1:51 pm AA3026 American Airlines Charlotte — Boston	5h 51m including layover	Find flight from$164
9:55 am — 3:05 pm	9:55 am — 12:51 pm AA2098 American Airlines Chicago — Philadelphia 49m stop 1:40 pm — 3:05 pm AA1453 American Airlines Philadelphia — Boston	4h 10m including layover	Find flight from$161
9:55 am — 5:02 pm	9:55 am — 12:04 pm AA4637 American Airlines Chicago — Indianapolis 2h 46m stop 2:50 pm — 5:02 pm AA4569 American Airlines Indianapolis — Boston	6h 7m including layover	Find flight from$164

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times are local. Last updated on 01/30/2025

Flight Information

There are 6 flights by American Airlines from Chicago to Boston every week with departures from Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee. All flights arrive at Logan, Boston City Heliport, Boston RT128 Rail, Boston South Rail.

Departures start from 10:29 am to 9:55 am. Nonstop flight is 2h 13m. The time difference between Chicago and Boston is 1h.

The fastest flight 2h 13m
Average flight time 2h 19m
The earliest flight 10:29 am
The latest flight 9:55 am
Distance 852 ml

The cheapest months for traveling to Boston are november (from 67 $).

The cheapest flight by American Airlines that our users were able to find is $67. This airfare is economy class on one-way AA314 flight for November 12, 2024 leaving O'Hare International in Chicago at 8:10 am, it includes all taxes and additional fees.

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American Airlines Airplanes on the Route

List of the most popular American Airlines airplanes flying from Chicago to Boston:

Boeing 737-800

from $67

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Embraer 175 (short wing)

from $101

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Airbus A319

from $149

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Airbus A321

from $161

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Airbus A320

from $161

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Boeing 737 MAX 8

from $164

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Canadair Regional Jet 700

from $164

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Embraer 170

from $164

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Other Popular Airlines on the Route

Besides American Airlines there are other 6 airline carriers between Chicago and Boston. Please review schedules and prices from the most popular airlines to find the best airfare deals from Chicago to Boston.

Nonstop flights

There are 11 direct flights every day from Chicago. Airlines and fares are below:

UA - United Airlines

from $125

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See more direct flights

Connecting Flights

List of flights with layovers (1 and more stops):

AS - Alaska Airlines

from $221

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F9 - Frontier Airlines

from $92

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UA - United Airlines

from $134

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NK - Spirit Airlines

from $87

Find
TK - Turkish Airlines

from $1143

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LX - SWISS International Air Lines

from $6055

Find

See more connecting flights

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