Chicago, IL to Boston, MA flights

Flights starting at $45. Choose between United Airlines, Spirit Airlines, or JetBlue Airways to find the best price.

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Cheapest one-way trip

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Cheapest round-trip

Average round-trip

Nonstop flights in September

One-way trips

Round trips

Chicago ORDBoston BOS
$113
Chicago ORDBoston BOS
$128
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Travelers usually depart from O Hare International, Chicago Midway International, Chicago, IL - Union Station, Chicago Downtown Greyhound Station, or Chicago Rockford International when they travel from Chicago to Boston. Book your trip to arrive at Logan International, Boston South Station, Boston, MA - Back Bay Station, or Boston, MA - North Station. The distance between Chicago and Boston is 1392 km. The most popular airlines for this route are United Airlines, Spirit Airlines, JetBlue Airways, Frontier Airlines, and American Airlines. Chicago and Boston have 401 direct flights per week.

Weekly direct flights

Discover the top airlines offering direct flights from Chicago to Boston in the next month. You’ll find the number of daily direct flights per airline in the table.

Weekly direct flights for Sun 24.09 - Sat 30.09

AirlineSun 24.09Mon 25.09Tue 26.09Wed 27.09Thu 28.09Fri 29.09Sat 30.09
---534---13
2757113
---111---11

Weekly direct flights for Sun 01.10 - Sat 07.10

AirlineSun 01.10Mon 02.10Tue 03.10Wed 04.10Thu 05.10Fri 06.10Sat 07.10
3754---17
3373------2
---11---------1

Weekly direct flights for Sun 08.10 - Sat 14.10

AirlineSun 08.10Mon 09.10Tue 10.10Wed 11.10Thu 12.10Fri 13.10Sat 14.10
4---15137
2------4------3
1---1------11

Weekly direct flights for Sun 15.10 - Sat 21.10

AirlineSun 15.10Mon 16.10Tue 17.10Wed 18.10Thu 19.10Fri 20.10Sat 21.10
1666627
1346---24
---111---11

Check-in for a flight from Chicago to Boston

NameCarrier codeIATA CodePassport needed during bookingOnline check-in available
United AirlinesUALUAYesNo
Spirit AirlinesNKSNKNoOpens 24 days before flight
Closes 1 hours before flight
JetBlue AirwaysJBUB6NoOpens 24 days before flight
Closes 2 hours before flight
Frontier AirlinesFFTF9NoOpens 24 days before flight
Closes 1 hours before flight
American AirlinesAALAANoNo
Learn more about COVID-19 restrictions in United States in our dedicated Stories article.

Frequently asked questions

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