Cheap Flights from Boston, MA to Chicago, IL from $137

Return flight: Chicago – Boston
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On Cheapflightsplus.com you will find 1 direct flights from Boston to Chicago. You can compare airfare deals from 1 airlines and multiple travel sites from $137, 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.

Find One-Way and Round-Trip Boston to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $137 (one-way), $235 (round-trip).
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Best Flights from Boston to Chicago Today

Take a look at the list of non stop flights and flights with layovers from Boston to Chicago with the lowest price of $137. Take a look at the list of non stop flights from Boston to Chicago from $137. The fastest direct flight takes 2h 56m. There’re no connecting flights.
Price Departure Arrival Flight Duration Airline Flight
from $137
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19:59
Boston
Logan
 21:55
Chicago
O'Hare International
 2h 56m United Airlines
UA1783
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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on February 22, 2025
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 Arrival Flight Details Flight Duration Price
19:59 — 21:55
19:59 — 21:55 UA1783 United Airlines
Boston — Chicago
2h 56m
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from$137
*Departure and arrival times - local. Updated on February 22, 2025

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 19:59 to 19:59 from 4 Boston airports and arrive 19:59 to 19:59 to 7 Chicago airports. Average flight time is 2h 56m.

  • The fastest flight 2h 56m
  • Average flight time 2h 56m
  • The earliest flight 19:59
  • The latest flight 19:59
  • Distance 852 ml

The cheapest months to travel to Chicago are february (from 137 $), november (from 166 $).

What is the lowest airfare Boston to Chicago?

The cheapest plane ticket found by our users is $137. This airfare is for economy class on one-way UA1783 flight by United Airlines for February 26, 2025 which leaves Logan in Boston at 19:59 am and arrives at Chicago O'Hare International at 21:55.

Economy class
$137
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Business class
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Popular Airlines on the Route

The flight Boston — Chicago is served by 1 regular airline . Most of the flights on this route are operated by United Airlines - 1 departures per week at the price of from $ 137 . And the most expensive tickets are offered by United Airlines airline - from $ 137.

Direct flights

There are 1 nonstop flights on the route. The fastest direct flight is UA1783 by United Airlines takes 2h 56m and the cheapest is UA1783 by United Airlines for $137.

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Connecting Flights

There’re no flights with layovers. Try direct flights or departure from nearby cities.

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 $137
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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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Airplanes

There are flights to Chicago from Boston by 1 airlines that use 1 aircraft brands. They range from huge modern airplanes to small-sized.

  • Boeing 737-900
    from $137
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Top Domestic Destinations from Boston

You may also consider searching for discounted plane tickets to some other popular places from Boston within United States.

Top International Destinations from Boston

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

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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