United Airlines Boston to Chicago Flights

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Cheapflightsplus.com will find cheap United Airlines flights from Boston to Chicago. Compare airline ticket prices and book air tickets starting from $107 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 Boston (MA) — Chicago (IL) 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 - $107, two-way – $183.

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Cheap Flights from Boston to Chicago 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 $107. The fastest nonstop flight takes 2h 50m. The fastest connecting flight — 4h 45m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $107 Find flight	9:43 am Boston Logan	11:33 am Chicago O'Hare International	2h 50m	United Airlines	UA365
from $107 Find flight	12:30 pm Boston Logan	2:20 pm Chicago O'Hare International	2h 50m	United Airlines	UA1732
from $107 Find flight	7:45 am Boston Logan	9:41 am Chicago O'Hare International	2h 56m	United Airlines	UA2251
from $141 Find flight	1:00 pm Boston Logan	7:48 pm Chicago O'Hare International	7h 48m layover 3h 57m - Washington D.C.	United Airlines	UA2692 UA2304
from $142 Find flight	7:12 pm Boston Logan	11:15 pm Chicago O'Hare International	5h 3m layover 1h 15m - Washington D.C.	United Airlines	UA2136 UA1738
from $142 Find flight	2:40 pm Boston Logan	7:48 pm Chicago O'Hare International	6h 8m layover 2h 17m - Washington D.C.	United Airlines	UA721 UA2304
from $142 Find flight	2:40 pm Boston Logan	6:25 pm Chicago O'Hare International	4h 45m layover 0h 47m - Washington D.C.	United Airlines	UA721 UA2497
from $149 Find flight	9:30 am Boston Logan	2:29 pm Chicago O'Hare International	5h 59m layover 2h 2m - Washington D.C.	United Airlines	UA2098 UA2331
from $214 Find flight	7:05 pm Boston Logan	11:25 pm Chicago O'Hare International	5h 20m layover 0h 59m - Newark	United Airlines	UA3571 UA1308
from $247 Find flight	5:30 am Boston Logan	5:10 pm Chicago O'Hare International	12h 40m layover 8h 45m - Washington D.C.	United Airlines	UA1734 UA265
from $251 Find flight	4:23 pm Boston Logan	11:25 pm Chicago O'Hare International	8h 2m layover 3h 45m - Newark	United Airlines	UA399 UA1308
from $251 Find flight	4:23 pm Boston Logan	9:56 pm Chicago O'Hare International	6h 33m layover 2h 16m - Newark	United Airlines	UA399 UA546
from $260 Find flight	8:05 am Boston Logan	6:29 pm Chicago O'Hare International	11h 24m layover 7h 19m - Newark	United Airlines	UA309 UA661
from $260 Find flight	7:10 am Boston Logan	5:00 pm Chicago O'Hare International	10h 50m layover 6h 50m - Newark	United Airlines	UA570 UA2394
from $260 Find flight	6:00 am Boston Logan	2:55 pm Chicago O'Hare International	9h 55m layover 5h 57m - Newark	United Airlines	UA1833 UA2053
from $686 Find flight	12:10 pm Boston Logan	5:00 pm Chicago O'Hare International	5h 50m layover 1h 56m - Newark	United Airlines	UA3706 UA2394

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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 Boston to Chicago

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
12:10 pm — 5:00 pm	12:10 pm — 1:29 pm UA3706 United Airlines Boston — Newark 1h 56m stop 3:25 pm — 5:00 pm UA2394 United Airlines Newark — Chicago	5h 50m including layover	Find flight from$686
12:30 pm — 2:20 pm	12:30 pm — 2:20 pm UA1732 United Airlines Boston — Chicago	2h 50m	Find flight from$107
1:00 pm — 7:48 pm	1:00 pm — 2:43 pm UA2692 United Airlines Boston — Washington D.C. 3h 57m stop 6:40 pm — 7:48 pm UA2304 United Airlines Washington D.C. — Chicago	7h 48m including layover	Find flight from$141
1:00 pm — 5:10 pm	1:00 pm — 2:43 pm UA2692 United Airlines Boston — Washington D.C. 1h 12m stop 3:55 pm — 5:10 pm UA265 United Airlines Washington D.C. — Chicago	5h 10m including layover	Find flight from$141
1:00 pm — 6:25 pm	1:00 pm — 2:43 pm UA2692 United Airlines Boston — Washington D.C. 2h 27m stop 5:10 pm — 6:25 pm UA2497 United Airlines Washington D.C. — Chicago	6h 25m including layover	Find flight from$214
1:00 pm — 11:15 pm	1:00 pm — 2:43 pm UA2692 United Airlines Boston — Washington D.C. 7h 27m stop 10:10 pm — 11:15 pm UA1738 United Airlines Washington D.C. — Chicago	11h 15m including layover	Find flight from$247
2:40 pm — 7:48 pm	2:40 pm — 4:23 pm UA721 United Airlines Boston — Washington D.C. 2h 17m stop 6:40 pm — 7:48 pm UA2304 United Airlines Washington D.C. — Chicago	6h 8m including layover	Find flight from$142
2:40 pm — 6:25 pm	2:05 pm — 3:49 pm UA721 United Airlines Boston — Washington D.C. 47m stop 5:20 pm — 6:34 pm UA2497 United Airlines Washington D.C. — Chicago	4h 45m including layover	Find flight from$142
4:23 pm — 11:25 pm	4:20 pm — 5:57 pm UA399 United Airlines Boston — Newark 3h 45m stop 9:44 pm — 11:25 pm UA1308 United Airlines Newark — Chicago	8h 2m including layover	Find flight from$251
4:23 pm — 9:56 pm	4:20 pm — 5:57 pm UA399 United Airlines Boston — Newark 2h 16m stop 8:15 pm — 9:56 pm UA546 United Airlines Newark — Chicago	6h 33m including layover	Find flight from$251
5:30 am — 9:36 am	5:30 am — 7:10 am UA1734 United Airlines Boston — Washington D.C. 1h 10m stop 8:20 am — 9:36 am UA2401 United Airlines Washington D.C. — Chicago	5h 6m including layover	Find flight from$142
5:30 am — 5:10 pm	5:30 am — 7:10 am UA1734 United Airlines Boston — Washington D.C. 8h 45m stop 3:55 pm — 5:10 pm UA265 United Airlines Washington D.C. — Chicago	12h 40m including layover	Find flight from$247
5:30 am — 2:29 pm	5:30 am — 7:04 am UA1734 United Airlines Boston — Washington D.C. 6h 5m stop 1:20 pm — 2:33 pm UA2331 United Airlines Washington D.C. — Chicago	9h 59m including layover	Find flight from$272
6:00 am — 2:55 pm	6:00 am — 7:23 am UA1833 United Airlines Boston — Newark 5h 57m stop 1:20 pm — 2:55 pm UA2053 United Airlines Newark — Chicago	9h 55m including layover	Find flight from$260
7:05 pm — 11:25 pm	7:05 pm — 8:45 pm UA3571 United Airlines Boston — Newark 59m stop 9:44 pm — 11:25 pm UA1308 United Airlines Newark — Chicago	5h 20m including layover	Find flight from$214
7:10 am — 5:00 pm	7:10 am — 8:35 am UA570 United Airlines Boston — Newark 6h 50m stop 3:25 pm — 5:00 pm UA2394 United Airlines Newark — Chicago	10h 50m including layover	Find flight from$260
7:12 pm — 11:15 pm	7:00 pm — 8:46 pm UA2136 United Airlines Boston — Washington D.C. 1h 15m stop 10:18 pm — 11:30 pm UA1738 United Airlines Washington D.C. — Chicago	5h 3m including layover	Find flight from$142
7:45 am — 9:41 am	7:45 am — 9:41 am UA2251 United Airlines Boston — Chicago	2h 56m	Find flight from$107
8:05 am — 6:29 pm	8:05 am — 9:30 am UA309 United Airlines Boston — Newark 7h 19m stop 4:49 pm — 6:29 pm UA661 United Airlines Newark — Chicago	11h 24m including layover	Find flight from$260
9:30 am — 2:29 pm	9:30 am — 11:13 am UA2098 United Airlines Boston — Washington D.C. 2h 2m stop 1:15 pm — 2:29 pm UA2331 United Airlines Washington D.C. — Chicago	5h 59m including layover	Find flight from$149
9:43 am — 11:33 am	9:43 am — 11:33 am UA365 United Airlines Boston — Chicago	2h 50m	Find flight from$107

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

Departures start from 12:10 pm to 9:43 am. Nonstop flight is 2h 50m. The time difference between Boston and Chicago is 1h.

The fastest flight 2h 50m
Average flight time 2h 50m
The earliest flight 12:10 pm
The latest flight 9:43 am
Distance 852 ml

The cheapest months for traveling to Chicago are august (from 107 $), october (from 110 $), september (from 113 $).

The most expensive and popular months are november (from 143 $), june (from 138 $), may (from 138 $).

The cheapest flight by United Airlines that our users were able to find is $107. This airfare is economy class on one-way UA365 flight for August 27, 2025 leaving Logan in Boston at 9:43 am, 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 Boston to Chicago:

Other Popular Airlines on the Route

Besides United Airlines there are other 3 airline carriers between Boston and Chicago. Please review schedules and prices from the most popular airlines to find the best airfare deals from Boston to Chicago.

Nonstop flights

There are 3 direct flights every day from Boston. Airlines and fares are below:

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Connecting Flights

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

AS - Alaska Airlines

from $727

Find
HA - Hawaiian Airlines

from $228

Find
NK - Spirit Airlines

from $98

Find

See more connecting flights

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