United Airlines Boston to Chicago Flights

Return flight: Chicago – Boston

Cheapflightsplus.com will find cheap United Airlines flights from Boston to Chicago. Compare airline ticket prices and book air tickets starting from $147 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 april: one-way - $147, two-way – $252.
Direct flights
  • Check to choose departure date Check to choose departure date
Check prices for return flight
Find flights
Below is a detailed 2024 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 Arrival Flight Details Flight Time Price
11:27 am — 1:15 pm
11:27 am — 1:15 pm UA1732 United Airlines
Boston — Chicago
2h 48m
Find flight
from$147
4:36 pm — 6:32 pm
4:36 pm — 6:32 pm UA1783 United Airlines
Boston — Chicago
2h 56m
Find flight
from$147
6:00 am — 7:56 am
6:00 am — 7:56 am UA567 United Airlines
Boston — Chicago
2h 56m
Find flight
from$147
6:31 pm — 8:23 pm
6:31 pm — 8:23 pm UA1150 United Airlines
Boston — Chicago
2h 52m
Find flight
from$165
9:39 am — 11:35 am
9:39 am — 11:35 am UA408 United Airlines
Boston — Chicago
2h 56m
Find flight
from$147
10:31 am — 4:35 pm
10:31 am — 12:00 pm UA1343 United Airlines
Boston — Newark
2h 59m stop
2:59 pm — 4:35 pm UA1840 United Airlines
Newark — Chicago
7h 4m
including layover
Find flight
from$211
11:40 am — 6:39 pm
11:40 am — 1:12 pm UA3662 United Airlines
Boston — Newark
3h 47m stop
4:59 pm — 6:39 pm UA2113 United Airlines
Newark — Chicago
7h 59m
including layover
Find flight
from$211
1:30 pm — 8:39 pm
1:30 pm — 3:01 pm UA308 United Airlines
Boston — Newark
3h 55m stop
6:56 pm — 8:39 pm UA1232 United Airlines
Newark — Chicago
8h 9m
including layover
Find flight
from$211
2:16 pm — 8:25 pm
2:16 pm — 3:53 pm UA1470 United Airlines
Boston — Washington D.C.
3h 10m stop
7:03 pm — 8:25 pm UA5845 United Airlines
Washington D.C. — Chicago
7h 9m
including layover
Find flight
from$154
2:16 pm — 6:44 pm
2:16 pm — 3:53 pm UA1470 United Airlines
Boston — Washington D.C.
1h 37m stop
5:30 pm — 6:44 pm UA2497 United Airlines
Washington D.C. — Chicago
5h 28m
including layover
Find flight
from$249
3:31 pm — 10:06 pm
3:31 pm — 5:02 pm UA1627 United Airlines
Boston — Newark
3h 27m stop
8:29 pm — 10:06 pm UA1234 United Airlines
Newark — Chicago
7h 35m
including layover
Find flight
from$211
3:31 pm — 10:43 pm
3:31 pm — 5:02 pm UA1627 United Airlines
Boston — New York
3h 58m stop
9:00 pm — 10:43 pm UA1202 United Airlines
New York — Chicago
8h 12m
including layover
Find flight
from$399
4:54 pm — 10:06 pm
4:54 pm — 6:22 pm UA1461 United Airlines
Boston — Newark
2h 7m stop
8:29 pm — 10:06 pm UA1234 United Airlines
Newark — Chicago
6h 12m
including layover
Find flight
from$582
5:03 pm — 0:30 am
+1 day
5:03 pm — 7:40 pm UA1143 United Airlines
Boston — Denver
1h 23m stop
9:03 pm — 0:30 am UA377 United Airlines
Denver — Chicago
8h 27m
including layover
Find flight
from$526
5:33 pm — 0:40 am
+1 day
5:33 pm — 8:50 pm UA1066 United Airlines
Boston — Houston
1h 12m stop
10:02 pm — 0:40 am UA1252 United Airlines
Houston — Chicago
8h 7m
including layover
Find flight
from$547
6:00 am — 9:30 am
6:00 am — 7:35 am UA1785 United Airlines
Boston — Washington D.C.
50m stop
8:25 am — 9:30 am UA1744 United Airlines
Washington D.C. — Chicago
4h 30m
including layover
Find flight
from$154
7:41 pm — 11:22 pm
7:41 pm — 9:15 pm UA2136 United Airlines
Boston — Washington D.C.
1h 6m stop
10:21 pm — 11:22 pm UA2467 United Airlines
Washington D.C. — Chicago
4h 41m
including layover
Find flight
from$173
8:29 am — 2:45 pm
8:29 am — 9:59 am UA515 United Airlines
Boston — Newark
3h 12m stop
1:11 pm — 2:45 pm UA323 United Airlines
Newark — Chicago
7h 16m
including layover
Find flight
from$211
9:30 am — 4:03 pm
9:30 am — 11:07 am UA1157 United Airlines
Boston — Washington D.C.
3h 48m stop
2:55 pm — 4:03 pm UA2224 United Airlines
Washington D.C. — Chicago
7h 33m
including layover
Find flight
from$154
10:31 am — 6:30 am
+1 day
10:31 am — 12:00 pm UA1343 United Airlines
Boston — Newark
1h 25m stop
1:25 pm — 3:50 pm UA1213 United Airlines
Newark — Atlanta
13h 20m stop
5:10 am — 6:30 am F92310 Frontier Airlines
Atlanta — Chicago
20h 59m
including layover
Find flight
from$273
1:30 pm — 6:30 am
+1 day
1:30 pm — 3:01 pm UA308 United Airlines
Boston — Newark
1h 58m stop
4:59 pm — 7:22 pm UA1391 United Airlines
Newark — Atlanta
9h 48m stop
5:10 am — 6:30 am F92310 Frontier Airlines
Atlanta — Chicago
18h
including layover
Find flight
from$273
7:41 pm — 9:41 am
+2 days
7:41 pm — 9:15 pm UA2136 United Airlines
Boston — Baltimore
19h 2m stop
4:17 pm — 5:39 pm G4257 Allegiant Air
Baltimore — Fletcher
15h 21m stop
9:00 am — 9:41 am G4221 Allegiant Air
Fletcher — Chicago
39h
including layover
Find flight
from$207
8:29 am — 11:28 pm
8:29 am — 9:59 am UA515 United Airlines
Boston — Newark
54m stop
10:53 am — 1:18 pm UA685 United Airlines
Newark — Atlanta
9h 10m stop
10:28 pm — 11:28 pm F93762 Frontier Airlines
Atlanta — Chicago
15h 59m
including layover
Find flight
from$283
*Departure and arrival times are local. Last updated on 04/19/2024

Flight Information

There are 5 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 10:31 am to 9:39 am. Nonstop flight is 2h 48m. The time difference between Boston and Chicago is 1h.

  • The fastest flight 2h 48m
  • Average flight time 2h 56m
  • The earliest flight 10:31 am
  • The latest flight 9:39 am
  • Distance 852 ml

The cheapest months for traveling to Chicago are may (from 147 $).

The cheapest flight by United Airlines that our users were able to find is $147. This airfare is economy class on one-way UA1783 flight for May 31, 2023 leaving Logan in Boston at 4:36 pm, it includes all taxes and additional fees.

Find same flight?

Other Popular Airlines on the Route

Besides United Airlines there are other 1 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 7 direct flights every day from Boston. Airlines and fares are below:

See more direct flights

Connecting Flights

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

See more connecting flights

How to book an air ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected airfare.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

Back