United Airlines Boston to Chicago Flights

One way Round trip

Adults

Children under 12

Infants under 2 without place

Economy

Business

First

done

Return flight: Chicago – Boston

Page navigation

Best Airfare Price Calendar Flights Schedule

Cheapflightsplus.com will find cheap United Airlines flights from Boston to Chicago. Compare airline ticket prices and book air tickets starting from $78 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 june: one-way - $78, two-way – $134.

Direct flights

Check to choose departure date Check to choose departure date

Check prices for return flight

Find flights

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 $78. The fastest nonstop flight takes 2h 47m. The fastest connecting flight — 4h 45m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $78 Find flight	6:10 am Boston Logan	8:05 am Chicago O'Hare International	2h 55m	United Airlines	UA1414
from $78 Find flight	8:44 pm Boston Logan	10:32 pm Chicago O'Hare International	2h 48m	United Airlines	UA2229
from $78 Find flight	7:44 am Boston Logan	9:39 am Chicago O'Hare International	2h 55m	United Airlines	UA1909
from $78 Find flight	6:11 pm Boston Logan	8:05 pm Chicago O'Hare International	2h 54m	United Airlines	UA1015
from $78 Find flight	9:43 am Boston Logan	11:33 am Chicago O'Hare International	2h 50m	United Airlines	UA378
from $78 Find flight	12:45 pm Boston Logan	2:35 pm Chicago O'Hare International	2h 50m	United Airlines	UA1732
from $78 Find flight	9:43 am Boston Logan	11:33 am Chicago O'Hare International	2h 50m	United Airlines	UA365
from $78 Find flight	3:18 pm Boston Logan	5:05 pm Chicago O'Hare International	2h 47m	United Airlines	UA1989
from $78 Find flight	9:03 am Boston Logan	10:54 am Chicago O'Hare International	2h 51m	United Airlines	UA546
from $78 Find flight	7:45 am Boston Logan	9:41 am Chicago O'Hare International	2h 56m	United Airlines	UA2251
from $78 Find flight	7:44 am Boston Logan	9:39 am Chicago O'Hare International	2h 55m	United Airlines	UA1857
from $96 Find flight	10:40 am Boston Logan	12:31 pm Chicago O'Hare International	2h 51m	United Airlines	UA1298
from $123 Find flight	3:18 pm Boston Logan	5:05 pm Chicago O'Hare International	2h 47m	United Airlines	UA1032
from $88 Find flight	6:59 pm Boston Logan	11:37 pm Chicago O'Hare International	5h 38m layover 1h 30m - Newark	United Airlines	UA1308 UA1308
from $104 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 $126 Find flight	9:00 am Boston Logan	1:12 pm Chicago O'Hare International	5h 12m layover 1h 16m - Newark	United Airlines	UA2016 UA1875

Show All Flights

*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 06/06/2025

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
10:40 am — 12:31 pm	10:40 am — 12:31 pm UA1298 United Airlines Boston — Chicago	2h 51m	Find flight from$96
10:40 am — 12:31 pm	10:40 am — 12:31 pm UA2430 United Airlines Boston — Chicago	2h 51m	Find flight from$102
11:02 am — 12:52 pm	11:02 am — 12:52 pm UA1314 United Airlines Boston — Chicago	2h 50m	Find flight from$81
11:02 am — 12:53 pm	11:02 am — 12:53 pm UA345 United Airlines Boston — Chicago	2h 51m	Find flight from$101
12:45 pm — 2:35 pm	12:45 pm — 2:35 pm UA1732 United Airlines Boston — Chicago	2h 50m	Find flight from$78
3:15 pm — 5:05 pm	3:15 pm — 5:05 pm UA1301 United Airlines Boston — Chicago	2h 50m	Find flight from$81
3:16 pm — 5:05 pm	3:16 pm — 5:05 pm UA1504 United Airlines Boston — Chicago	2h 49m	Find flight from$101
3:18 pm — 5:05 pm	3:18 pm — 5:05 pm UA1989 United Airlines Boston — Chicago	2h 47m	Find flight from$78
3:18 pm — 5:05 pm	3:18 pm — 5:05 pm UA1032 United Airlines Boston — Chicago	2h 47m	Find flight from$123
4:27 pm — 6:20 pm	4:27 pm — 6:20 pm UA2040 United Airlines Boston — Chicago	2h 53m	Find flight from$101
6:10 am — 8:05 am	6:10 am — 8:05 am UA1414 United Airlines Boston — Chicago	2h 55m	Find flight from$78
6:11 pm — 8:05 pm	6:11 pm — 8:05 pm UA1015 United Airlines Boston — Chicago	2h 54m	Find flight from$78
7:44 am — 9:39 am	7:44 am — 9:39 am UA1909 United Airlines Boston — Chicago	2h 55m	Find flight from$78
7:44 am — 9:39 am	7:44 am — 9:39 am UA1857 United Airlines Boston — Chicago	2h 55m	Find flight from$78
7:45 am — 9:41 am	7:45 am — 9:41 am UA2251 United Airlines Boston — Chicago	2h 56m	Find flight from$78
7:45 am — 9:41 am	7:45 am — 9:41 am UA449 United Airlines Boston — Chicago	2h 56m	Find flight from$81
7:45 am — 9:41 am	7:45 am — 9:41 am UA2401 United Airlines Boston — Chicago	2h 56m	Find flight from$83
8:44 pm — 10:32 pm	8:44 pm — 10:32 pm UA2229 United Airlines Boston — Chicago	2h 48m	Find flight from$78
9:03 am — 10:54 am	9:03 am — 10:54 am UA546 United Airlines Boston — Chicago	2h 51m	Find flight from$78
9:03 am — 10:54 am	9:03 am — 10:54 am UA600 United Airlines Boston — Chicago	2h 51m	Find flight from$102
9:43 am — 11:33 am	9:43 am — 11:33 am UA378 United Airlines Boston — Chicago	2h 50m	Find flight from$78
9:43 am — 11:33 am	9:43 am — 11:33 am UA365 United Airlines Boston — Chicago	2h 50m	Find flight from$78
12:40 pm — 4:35 pm	12:40 pm — 2:01 pm UA475 United Airlines Boston — Newark 54m stop 2:55 pm — 4:35 pm UA2009 United Airlines Newark — Chicago	4h 55m including layover	Find flight from$109
1:35 pm — 8:10 pm	1:35 pm — 2:56 pm UA2454 United Airlines Boston — Newark 3h 33m stop 6:29 pm — 8:10 pm UA2310 United Airlines Newark — Chicago	7h 35m including layover	Find flight from$114
1:35 pm — 6:29 pm	1:35 pm — 2:56 pm UA2454 United Airlines Boston — Newark 1h 53m stop 4:49 pm — 6:29 pm UA661 United Airlines Newark — Chicago	5h 54m including layover	Find flight from$165
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$105
2:46 pm — 6:40 pm	2:46 pm — 4:30 pm UA539 United Airlines Boston — Washington D.C. 43m stop 5:18 pm — 6:45 pm UA2497 United Airlines Washington D.C. — Chicago	4h 54m including layover	Find flight from$99
4:32 pm — 9:28 pm	4:32 pm — 5:59 pm UA521 United Airlines Boston — Newark 1h 47m stop 7:46 pm — 9:28 pm UA546 United Airlines Newark — Chicago	5h 56m including layover	Find flight from$105
5:30 am — 9:43 am	5:30 am — 7:04 am UA1734 United Airlines Boston — Washington D.C. 1h 26m stop 8:30 am — 9:43 am UA1909 United Airlines Washington D.C. — Chicago	5h 13m including layover	Find flight from$104
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$105
8:00 am — 11:49 am	7:00 am — 8:21 am UA570 United Airlines Boston — Newark 45m stop 10:26 am — 12:05 pm UA1525 United Airlines Newark — Chicago	4h 49m including layover	Find flight from$105

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

*Departure and arrival times are local. Last updated on 06/06/2025

Flight Information

There are 22 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 10:30 am to 9:43 am. Nonstop flight is 2h 47m. The time difference between Boston and Chicago is 1h.

The fastest flight 2h 47m
Average flight time 2h 51m
The earliest flight 10:30 am
The latest flight 9:43 am
Distance 852 ml

The cheapest months for traveling to Chicago are november (from 77 $), june (from 77 $), may (from 105 $).

The most expensive and popular months are january (from 294 $), december (from 122 $), september (from 111 $).

The cheapest flight by United Airlines that our users were able to find is $78. This airfare is economy class on one-way UA1414 flight for June 6, 2025 leaving Logan in Boston at 6:10 am, it includes all taxes and additional fees.

Find same flight?

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 6 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 22 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):

AS - Alaska Airlines

from $157

Find
F9 - Frontier Airlines

from $73

Find
SY - Sun Country Airlines

from $108

Find
HA - Hawaiian Airlines

from $177

Find
NK - Spirit Airlines

from $45

Find
G4 - Allegiant Air

from $69

Find

See more connecting flights

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.