United Airlines Boston to Chicago Flights

Cheapflightsplus.com will find cheap United Airlines flights from Boston to Chicago. Compare airline ticket prices and book air tickets starting from $35 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 - $35, two-way – $60.
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Below is a detailed 2023 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
10:20 am — 12:04 pm
10:20 am — 12:04 pm UA1251 United Airlines
Boston — Chicago
2h 44m
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from$35
12:00 pm — 1:50 pm
12:00 pm — 1:50 pm UA1564 United Airlines
Boston — Chicago
2h 50m
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from$241
1:01 pm — 2:51 pm
1:01 pm — 2:51 pm UA1564 United Airlines
Boston — Chicago
2h 50m
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from$298
3:00 pm — 4:50 pm
3:00 pm — 4:50 pm UA2283 United Airlines
Boston — Chicago
2h 50m
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from$35
4:30 pm — 6:17 pm
4:30 pm — 6:17 pm UA503 United Airlines
Boston — Chicago
2h 47m
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from$35
5:00 am — 6:53 am
5:00 am — 6:53 am UA774 United Airlines
Boston — Chicago
2h 53m
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from$35
6:27 pm — 8:10 pm
6:27 pm — 8:10 pm UA1141 United Airlines
Boston — Chicago
2h 43m
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from$35
7:02 am — 9:02 am
7:02 am — 9:02 am UA449 United Airlines
Boston — Chicago
3h
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from$35
8:31 am — 10:13 am
8:31 am — 10:13 am UA775 United Airlines
Boston — Chicago
2h 42m
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from$35
9:45 am — 11:43 am
9:45 am — 11:43 am UA273 United Airlines
Boston — Chicago
2h 58m
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from$188
10:07 am — 3:57 pm
10:07 am — 11:44 am UA525 United Airlines
Boston — Washington D.C.
3h 1m stop
2:45 pm — 3:57 pm UA5409 United Airlines
Washington D.C. — Chicago
6h 50m
including layover
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from$41
11:00 am — 5:46 pm
11:00 am — 12:25 pm UA2394 United Airlines
Boston — Newark
3h 34m stop
3:59 pm — 5:46 pm UA1608 United Airlines
Newark — Chicago
7h 46m
including layover
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from$41
12:00 pm — 4:46 pm
12:00 pm — 1:38 pm UA249 United Airlines
Boston — Newark
1h 21m stop
2:59 pm — 4:46 pm UA2193 United Airlines
Newark — Chicago
5h 46m
including layover
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from$41
1:55 pm — 10:50 pm
1:55 pm — 5:03 pm UA619 United Airlines
Boston — Houston
3h 2m stop
8:05 pm — 10:50 pm UA2131 United Airlines
Houston — Chicago
9h 55m
including layover
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from$493
2:00 pm — 6:46 pm
2:00 pm — 3:38 pm UA2248 United Airlines
Boston — Newark
1h 21m stop
4:59 pm — 6:46 pm UA1180 United Airlines
Newark — Chicago
5h 46m
including layover
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from$41
3:10 pm — 6:55 pm
3:10 pm — 4:50 pm UA216 United Airlines
Boston — Washington D.C.
53m stop
5:43 pm — 6:55 pm UA210 United Airlines
Washington D.C. — Chicago
4h 45m
including layover
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from$41
4:00 pm — 8:10 pm
4:00 pm — 5:20 pm UA3651 United Airlines
Boston — Newark
1h 15m stop
6:35 pm — 8:10 pm UA1601 United Airlines
Newark — Chicago
5h 10m
including layover
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from$41
5:45 am — 7:15 am
+1 day
5:45 am — 7:08 am UA601 United Airlines
Boston — Newark
22h 22m stop
5:30 am — 7:15 am AA2485 American Airlines
Newark — Chicago
26h 30m
including layover
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from$333
6:00 am — 11:56 am
6:00 am — 7:34 am UA389 United Airlines
Boston — Washington D.C.
3h 11m stop
10:45 am — 11:56 am UA330 United Airlines
Washington D.C. — Chicago
6h 56m
including layover
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from$41
7:00 am — 11:58 am
7:00 am — 8:20 am UA2180 United Airlines
Boston — Newark
1h 53m stop
10:13 am — 11:58 am UA2075 United Airlines
Newark — Chicago
5h 58m
including layover
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from$41
8:00 am — 12:21 pm
8:00 am — 9:42 am UA1157 United Airlines
Boston — Washington D.C.
1h 33m stop
11:15 am — 12:21 pm UA285 United Airlines
Washington D.C. — Chicago
5h 21m
including layover
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from$41
9:40 am — 1:42 pm
9:40 am — 11:15 am UA1157 United Airlines
Boston — Washington D.C.
1h 20m stop
12:35 pm — 1:42 pm UA221 United Airlines
Washington D.C. — Chicago
5h 2m
including layover
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from$41
*Departure and arrival times are local. Last updated on 03/29/2023

Flight Information

There are 26 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 10:00 am to 9:45 am. Nonstop flight is 2h 41m. The time difference between Boston and Chicago is 1h.

  • The fastest flight 2h 41m
  • Average flight time 2h 50m
  • The earliest flight 10:00 am
  • The latest flight 9:45 am
  • Distance 852 ml

The cheapest flight by United Airlines that our users were able to find is $35. This airfare is economy class on one-way UA2283 flight for October 29, 2020 leaving Logan in Boston at 3:00 pm, it includes all taxes and additional fees.

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Other Popular Airlines on the Route

Besides United Airlines there are other 12 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 119 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):

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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.

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