United Airlines Chicago to Boston Flights

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Cheapflightsplus.com will find cheap United Airlines flights from Chicago to Boston. Compare airline ticket prices and book air tickets starting from $95 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of United Airlines, arrivals and departure details below.

Find Cheap Airfare Chicago (IL) — Boston (MA) by United 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 august: one-way - $95, two-way – $163.

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Cheap Flights from Chicago to Boston by United Airlines

Look at the list of plane tickets for the most popular direct and connecting flights by United Airlines, their prices start from $95. The fastest nonstop flight takes 2h 26m. The fastest connecting flight — 4h 22m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $95 Find flight	7:53 pm Chicago O'Hare International	11:20 pm Boston Logan	2h 27m	United Airlines	UA2444
from $107 Find flight	6:30 am Chicago O'Hare International	9:56 am Boston Logan	2h 26m	United Airlines	UA2104
from $107 Find flight	7:49 am Chicago O'Hare International	11:16 am Boston Logan	2h 27m	United Airlines	UA2067
from $137 Find flight	6:00 am Chicago O'Hare International	1:28 pm Boston Logan	6h 28m layover 3h 0m - Newark	United Airlines	UA1658 UA2265
from $137 Find flight	7:10 am Chicago O'Hare International	1:28 pm Boston Logan	5h 18m layover 1h 45m - Newark	United Airlines	UA563 UA2265
from $172 Find flight	8:52 am Chicago O'Hare International	2:14 pm Boston Logan	4h 22m layover 0h 40m - Washington D.C.	United Airlines	UA2029 UA2710
from $257 Find flight	9:31 pm Chicago O'Hare International	5:41 pm+1 день Boston Logan	19h 10m layover 15h 30m - Washington D.C.	United Airlines	UA276 UA1856
from $264 Find flight	9:24 pm Chicago O'Hare International	10:23 am+1 день Boston Logan	11h 59m layover 8h 17m - Newark	United Airlines	UA396 UA375
from $337 Find flight	4:20 pm Chicago O'Hare International	6:01 am+1 день Boston Logan	12h 41m layover 5h 47m - Denver	United Airlines	UA1801 UA2610
from $472 Find flight	5:02 am Chicago O'Hare International	11:53 pm Boston Logan	17h 51m layover 11h 5m - Denver	United Airlines	UA2666 UA1218
from $622 Find flight	9:40 pm Chicago O'Hare International	12:27 pm+1 день Boston Logan	13h 47m layover 7h 0m - Houston	United Airlines	UA1115 UA1977
from $603 Find flight	9:05 pm Chicago O'Hare International	7:20 pm+1 день Boston Logan	21h 15m layover 14h 53m - Detroit 1h 29m - Washington D.C.	United Airlines	UA3493 UA6190 UA688
from $642 Find flight	9:05 pm Chicago O'Hare International	2:14 pm+1 день Boston Logan	16h 9m layover 10h 33m - Detroit 0h 49m - Washington D.C.	United Airlines	UA3493 UA3441 UA2710
from $642 Find flight	7:35 pm Chicago O'Hare International	2:14 pm+1 день Boston Logan	17h 39m layover 12h 2m - Detroit 0h 49m - Washington D.C.	United Airlines	UA5785 UA3441 UA2710
from $642 Find flight	2:25 pm Chicago O'Hare International	1:28 pm+1 день Boston Logan	22h 3m layover 16h 17m - Detroit 1h 13m - Newark	United Airlines	UA2329 UA3403 UA2265
from $642 Find flight	6:05 pm Chicago O'Hare International	2:14 pm+1 день Boston Logan	19h 9m layover 13h 31m - Detroit 0h 49m - Washington D.C.	United Airlines	UA5833 UA3441 UA2710

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 08/13/2025

United 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
6:30 am — 9:56 am	6:30 am — 9:56 am UA2104 United Airlines Chicago — Boston	2h 26m	Find flight from$107
7:49 am — 11:16 am	7:49 am — 11:16 am UA2067 United Airlines Chicago — Boston	2h 27m	Find flight from$107
7:53 pm — 11:20 pm	7:53 pm — 11:20 pm UA2444 United Airlines Chicago — Boston	2h 27m	Find flight from$95
10:35 am — 11:44 pm	10:35 am — 1:29 pm UA2483 United Airlines Chicago — Houston 5h 18m stop 6:47 pm — 11:44 pm UA1076 United Airlines Houston — Boston	12h 9m including layover	Find flight from$801
2:33 pm — 11:53 pm	2:33 pm — 4:26 pm UA503 United Airlines Chicago — Denver 1h 24m stop 5:50 pm — 11:53 pm UA1218 United Airlines Denver — Boston	8h 20m including layover	Find flight from$716
4:20 pm — 6:01 am +1 day	3:45 pm — 5:39 pm UA1801 United Airlines Chicago — Denver 5h 47m stop 11:40 pm — 5:39 am UA2610 United Airlines Denver — Boston	12h 41m including layover	Find flight from$337
5:02 am — 11:53 pm	5:02 am — 6:45 am UA2666 United Airlines Chicago — Denver 11h 5m stop 5:50 pm — 11:53 pm UA1218 United Airlines Denver — Boston	17h 51m including layover	Find flight from$472
5:57 pm — 1:28 pm +1 day	5:57 pm — 9:30 pm UA534 United Airlines Chicago — Newark 14h 43m stop 12:13 pm — 1:28 pm UA2265 United Airlines Newark — Boston	18h 31m including layover	Find flight from$643
6:00 am — 1:28 pm	6:00 am — 9:13 am UA1658 United Airlines Chicago — Newark 3h stop 12:13 pm — 1:28 pm UA2265 United Airlines Newark — Boston	6h 28m including layover	Find flight from$137
8:08 pm — 12:02 pm +1 day	8:08 pm — 9:58 pm UA2040 United Airlines Chicago — Denver 8h 2m stop 6:00 am — 12:02 pm UA2454 United Airlines Denver — Boston	14h 54m including layover	Find flight from$691
8:52 am — 2:14 pm	8:52 am — 11:55 am UA2029 United Airlines Chicago — Washington D.C. 40m stop 12:35 pm — 2:14 pm UA2710 United Airlines Washington D.C. — Boston	4h 22m including layover	Find flight from$172
9:24 pm — 10:23 am +1 day	9:24 pm — 0:45 am UA396 United Airlines Chicago — Newark 8h 17m stop 9:55 am — 11:14 am UA375 United Airlines Newark — Boston	11h 59m including layover	Find flight from$264
9:31 pm — 5:41 pm +1 day	9:31 pm — 0:30 am UA276 United Airlines Chicago — Washington D.C. 15h 30m stop 4:00 pm — 5:41 pm UA1856 United Airlines Washington D.C. — Boston	19h 10m including layover	Find flight from$257
2:25 pm — 1:28 pm +1 day	2:25 pm — 4:53 pm UA2329 United Airlines Chicago — Detroit 16h 17m stop 9:10 am — 11:00 am UA3403 United Airlines Detroit — Newark 1h 13m stop 12:13 pm — 1:28 pm UA2265 United Airlines Newark — Boston	22h 3m including layover	Find flight from$642

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

*Departure and arrival times are local. Last updated on 08/13/2025

Flight Information

There are 3 flights by United 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 10:35 am to 9:40 pm. Nonstop flight is 2h 26m. The time difference between Chicago and Boston is 1h.

The fastest flight 2h 26m
Average flight time 2h 27m
The earliest flight 10:35 am
The latest flight 9:40 pm
Distance 852 ml

The cheapest months for traveling to Boston are may (from 95 $), july (from 106 $), june (from 107 $).

The most expensive and popular months are september (from 110 $), october (from 110 $), august (from 107 $).

The cheapest flight by United Airlines that our users were able to find is $95. This airfare is economy class on one-way UA2444 flight for June 15, 2025 leaving O'Hare International in Chicago at 7:53 pm, it includes all taxes and additional fees.

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United Airlines Airplanes on the Route

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

Other Popular Airlines on the Route

Besides United 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 3 direct flights every day from Chicago. Airlines and fares are below:

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Connecting Flights

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

NK - Spirit Airlines

from $135

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AS - Alaska Airlines

from $489

Find
F9 - Frontier Airlines

from $116

Find
AY - Finnair

from $2099

Find
HA - Hawaiian Airlines

from $288

Find
LF - flynordic

from $188

Find

See more connecting flights

How to book an air ticket yourself?

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