Delta Air Lines Inc. Boston to Chicago Flights

Return flight: Chicago – Boston

Cheapflightsplus.com will find cheap Delta Air Lines Inc. flights from Boston to Chicago. Compare airline ticket prices and book air tickets starting from $161 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of Delta Air Lines Inc., arrivals and departure details below.

Find Cheap Airfare Boston (MA) — Chicago (IL) by Delta Air Lines Inc.

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 may: one-way - $161, two-way – $276.
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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
10:20 am — 12:06 pm
10:20 am — 12:06 pm DL3521 Delta Air Lines Inc.
Boston — Chicago
2h 46m
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from$161
1:45 pm — 3:31 pm
1:45 pm — 3:31 pm DL811 Delta Air Lines Inc.
Boston — Chicago
2h 46m
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5:05 pm — 7:00 pm
5:05 pm — 7:00 pm DL2218 Delta Air Lines Inc.
Boston — Chicago
2h 55m
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6:15 am — 8:05 am
6:15 am — 8:05 am DL684 Delta Air Lines Inc.
Boston — Chicago
2h 50m
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7:50 pm — 9:38 pm
7:50 pm — 9:38 pm DL3524 Delta Air Lines Inc.
Boston — Chicago
2h 48m
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10:00 am — 2:46 pm
10:00 am — 11:30 am DL5797 Delta Air Lines Inc.
Boston — New York
1h 29m stop
12:59 pm — 2:46 pm DL1264 Delta Air Lines Inc.
New York — Chicago
5h 46m
including layover
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from$166
11:21 am — 6:19 pm
11:21 am — 1:35 pm DL1138 Delta Air Lines Inc.
Boston — Minneapolis
3h 10m stop
4:45 pm — 6:19 pm DL3623 Delta Air Lines Inc.
Minneapolis — Chicago
7h 58m
including layover
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11:35 am — 6:23 pm
11:35 am — 1:00 pm DL3649 Delta Air Lines Inc.
Boston — New York
3h 20m stop
4:20 pm — 6:23 pm DL3579 Delta Air Lines Inc.
New York — Chicago
7h 48m
including layover
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12:00 pm — 6:26 pm
12:00 pm — 1:24 pm DL5687 Delta Air Lines Inc.
Boston — New York
3h 6m stop
4:30 pm — 6:26 pm DL1262 Delta Air Lines Inc.
New York — Chicago
7h 26m
including layover
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12:30 pm — 7:40 pm
12:30 pm — 3:15 pm DL363 Delta Air Lines Inc.
Boston — Atlanta
3h 15m stop
6:30 pm — 7:40 pm DL2879 Delta Air Lines Inc.
Atlanta — Chicago
8h 10m
including layover
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1:05 pm — 4:19 pm
1:05 pm — 3:14 pm DL2222 Delta Air Lines Inc.
Boston — Detroit
41m stop
3:55 pm — 4:19 pm DL1568 Delta Air Lines Inc.
Detroit — Chicago
4h 14m
including layover
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2:00 pm — 6:26 pm
2:00 pm — 3:30 pm DL5834 Delta Air Lines Inc.
Boston — New York
1h stop
4:30 pm — 6:26 pm DL1262 Delta Air Lines Inc.
New York — Chicago
5h 26m
including layover
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2:00 pm — 7:40 pm
2:00 pm — 4:47 pm DL376 Delta Air Lines Inc.
Boston — Atlanta
1h 43m stop
6:30 pm — 7:40 pm DL2879 Delta Air Lines Inc.
Atlanta — Chicago
6h 40m
including layover
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3:18 pm — 10:55 pm
3:18 pm — 5:33 pm DL1127 Delta Air Lines Inc.
Boston — Minneapolis
3h 56m stop
9:29 pm — 10:55 pm DL998 Delta Air Lines Inc.
Minneapolis — Chicago
8h 37m
including layover
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3:50 pm — 10:59 pm
3:50 pm — 6:43 pm DL322 Delta Air Lines Inc.
Boston — Atlanta
3h 12m stop
9:55 pm — 10:59 pm DL1423 Delta Air Lines Inc.
Atlanta — Chicago
8h 9m
including layover
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4:00 pm — 10:14 pm
4:00 pm — 5:30 pm DL5743 Delta Air Lines Inc.
Boston — New York
3h stop
8:30 pm — 10:14 pm DL1244 Delta Air Lines Inc.
New York — Chicago
7h 14m
including layover
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4:00 pm — 8:22 pm
4:00 pm — 5:30 pm DL5743 Delta Air Lines Inc.
Boston — New York
59m stop
6:29 pm — 8:22 pm DL1004 Delta Air Lines Inc.
New York — Chicago
5h 22m
including layover
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from$276
5:30 am — 9:10 am
5:30 am — 7:40 am DL2737 Delta Air Lines Inc.
Boston — Detroit
1h stop
8:40 am — 9:10 am DL1208 Delta Air Lines Inc.
Detroit — Chicago
4h 40m
including layover
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6:00 am — 9:54 am
6:00 am — 7:29 am DL2617 Delta Air Lines Inc.
Boston — New York
36m stop
8:05 am — 9:54 am DL3585 Delta Air Lines Inc.
New York — Chicago
4h 54m
including layover
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7:15 am — 2:05 pm
7:15 am — 10:06 am DL518 Delta Air Lines Inc.
Boston — Atlanta
3h 9m stop
1:15 pm — 2:05 pm DL2473 Delta Air Lines Inc.
Atlanta — Chicago
7h 50m
including layover
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8:05 am — 2:34 pm
8:05 am — 10:23 am DL1103 Delta Air Lines Inc.
Boston — Minneapolis
2h 37m stop
1:00 pm — 2:34 pm DL1616 Delta Air Lines Inc.
Minneapolis — Chicago
7h 29m
including layover
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8:15 am — 2:05 pm
8:15 am — 11:06 am DL540 Delta Air Lines Inc.
Boston — Atlanta
1h 54m stop
1:00 pm — 2:05 pm DL1477 Delta Air Lines Inc.
Atlanta — Chicago
6h 50m
including layover
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from$167
9:00 am — 1:25 pm
9:00 am — 10:31 am DL5696 Delta Air Lines Inc.
Boston — New York
1h 3m stop
11:34 am — 1:25 pm DL1559 Delta Air Lines Inc.
New York — Chicago
5h 25m
including layover
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from$167
9:20 am — 2:05 pm
9:20 am — 12:07 pm DL297 Delta Air Lines Inc.
Boston — Atlanta
53m stop
1:00 pm — 2:05 pm DL1477 Delta Air Lines Inc.
Atlanta — Chicago
5h 45m
including layover
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from$167
*Departure and arrival times are local. Last updated on 04/23/2024

Flight Information

There are 5 flights by Delta Air Lines Inc. 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 9:30 pm. Nonstop flight is 2h 46m. The time difference between Boston and Chicago is 1h.

  • The fastest flight 2h 46m
  • Average flight time 2h 48m
  • The earliest flight 10:00 am
  • The latest flight 9:30 pm
  • Distance 852 ml

The cheapest months for traveling to Chicago are may (from 161 $).

The cheapest flight by Delta Air Lines Inc. that our users were able to find is $161. This airfare is economy class on one-way DL2218 flight for May 31, 2023 leaving Logan in Boston at 5:05 pm, it includes all taxes and additional fees.

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Other Popular Airlines on the Route

Besides Delta Air Lines Inc. 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:

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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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