Cheap Flights from Boston, MA to Chicago, IL from $68

Return flight: Chicago – Boston

On Cheapflightsplus.com you will find 22 direct and 500 connecting flights from Boston to Chicago. You can compare airfare deals from 8 airlines and multiple travel sites from $68, book and save on cheap plane tickets and last minute offers. Also check out BOS-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Flight Information

Below we will explain in detail what the flights cost on the destination from Boston to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Boston and Chicago is 1370 miles. Time difference between the cities is 1h. Airplanes depart 05:30 to 21:40 from 4 Boston airports and arrive 05:30 to 21:40 to 7 Chicago airports. Average flight time is 2h 51m.

  • The fastest flight 2h 47m
  • Average flight time 2h 51m
  • The earliest flight 05:30
  • The latest flight 21:40
  • Distance 852 ml

The cheapest months to travel to Chicago are august (from 59 $), october (from 68 $), may (from 70 $).

The most expensive months are january (from 284 $), december (from 118 $), september (from 90 $).

What is the lowest airfare Boston to Chicago?

The cheapest plane ticket found by our users is $68. This airfare is for economy class on one-way NK2887 flight by Spirit Airlines for October 7, 2025 which leaves Logan in Boston at 11:56 am and arrives at Chicago O'Hare International at 20:40.

Economy class
$68
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Business class
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First class
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Flight Schedule Boston (Massachusetts) to Chicago (Illinois)

06:10 — 08:05
2h 55m flight time
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from$101
Boston — Chicago
UA1414 United Airlines
07:44 — 09:39
2h 55m flight time
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from$101
Boston — Chicago
UA1909 United Airlines
07:44 — 09:39
2h 55m flight time
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from$102
Boston — Chicago
UA1857 United Airlines
07:45 — 09:41
2h 56m flight time
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from$102
Boston — Chicago
UA2251 United Airlines
07:45 — 09:41
2h 56m flight time
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from$104
Boston — Chicago
UA449 United Airlines
09:03 — 10:54
2h 51m flight time
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from$102
Boston — Chicago
UA546 United Airlines
09:43 — 11:33
2h 50m flight time
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from$102
Boston — Chicago
UA365 United Airlines
10:40 — 12:31
2h 51m flight time
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from$124
Boston — Chicago
UA1298 United Airlines
11:02 — 12:52
2h 50m flight time
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from$104
Boston — Chicago
UA1314 United Airlines
12:30 — 14:20
2h 50m flight time
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from$104
Boston — Chicago
UA1732 United Airlines
15:16 — 17:05
2h 49m flight time
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from$102
Boston — Chicago
UA1504 United Airlines
15:18 — 17:05
2h 47m flight time
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from$102
Boston — Chicago
UA1989 United Airlines
16:27 — 18:20
2h 53m flight time
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from$74
Boston — Chicago
UA2040 United Airlines
18:11 — 20:05
2h 54m flight time
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from$102
Boston — Chicago
UA1015 United Airlines
20:44 — 22:32
2h 48m flight time
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from$104
Boston — Chicago
UA2229 United Airlines
Full flight schedule will help you in detecting at what time planes fly from Boston to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
*Departure and arrival times - local. Updated on October 7, 2025.

Popular Airlines on the Route

The flight Boston — Chicago is served by 8 regular airlines and 4 low-cost airlines. Most of the flights on this route are operated by Alaska Airlines - 27 departures per week at the price of from $ 203 . And the most expensive tickets are offered by SWISS International Air Lines airline - from $ 6035.

Direct flights

There are 22 nonstop flights on the route. The fastest direct flight is UA1989 by United Airlines takes 2h 47m and the cheapest is NK2887 by Spirit Airlines for $74.

  • UA - United Airlines
    from $74
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Connecting Flights

There are 500 flights with layovers on the route. The fastest connecting flight is NK2106 by Spirit Airlines takes 4h 23m and the cheapest is NK2887 by Spirit Airlines for $68.

  • AS - Alaska Airlines
    from $203
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  • F9 - Frontier Airlines
    from $94
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  • SY - Sun Country Airlines
    from $139
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  • HA - Hawaiian Airlines
    from $216
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  • UA - United Airlines
    from $114
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  • LX - SWISS International Air Lines
    from $6035
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  • NK - Spirit Airlines
    from $68
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  • G4 - Allegiant Air
    from $89
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Airports

You can fly from Boston to Chicago from 4 airports (Boston City Heliport, Boston RT128 Rail, Boston South Rail, Logan).

Boston airports

  • Boston City Heliport-JBC
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  • Boston RT128 Rail-ZRU
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  • Boston South Rail-ZTO
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  • Logan-BOS
    from $68
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Chicago airports

  • O'Hare International-ORD
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  • Midway-MDW
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  • Dupage County-DPA
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  • Chicago FSS-CHI
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  • Merrill C Meigs (closed)-CGX
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  • Pal-Waukee-PWK
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  • Chicago NAS-NOH
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How to book a plane 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 flight ticket.
  • 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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