Cheap flights from Boston, MA
to Chicago, IL

Flights starting at $90. Choose between Delta Air Lines, American Airlines, or Frontier Airlines to find the best price.

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Tips to know when travelling to Chicago

Cheapest one-way trip

Cheapest round-trip

Average round-trip

Nonstop flights in June

Most popular airline

Round trips

One-way trips

Boston BOSChicago ORD
$96
Boston BOSChicago ORD
$97
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Travelers usually depart from Logan International, Boston South Station, Boston, MA - Back Bay Station, or Boston, MA - North Station when they travel from Boston to Chicago. Book your trip to arrive at O Hare International, Chicago Midway International, Chicago, IL - Union Station, Chicago Rockford International, or Chicago, IL - California Ave. The distance between Boston and Chicago is 1392 km. The most popular airlines for this route are Delta Air Lines, American Airlines, Frontier Airlines, United Airlines, and JetBlue Airways. Boston and Chicago have 401 direct flights per week.

Weekly direct flights

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

Weekly direct flights for Sun 28.05 - Sat 03.06

AirlineSun 28.05Mon 29.05Tue 30.05Wed 31.05Thu 01.06Fri 02.06Sat 03.06
61351---5
43351---1
3253------2
1111------1

Weekly direct flights for Sun 04.06 - Sat 10.06

AirlineSun 04.06Mon 05.06Tue 06.06Wed 07.06Thu 08.06Fri 09.06Sat 10.06
1575225
American Airlines
11341------
---211---------
---111---------

Weekly direct flights for Sun 11.06 - Sat 17.06

AirlineSun 11.06Mon 12.06Tue 13.06Wed 14.06Thu 15.06Fri 16.06Sat 17.06
2575526
2444322
---354412
---1113---1

Weekly direct flights for Sun 18.06 - Sat 24.06

AirlineSun 18.06Mon 19.06Tue 20.06Wed 21.06Thu 22.06Fri 23.06Sat 24.06
2374124
225521---
124431---
---1111---1

Check-in for a flight from Boston to Chicago

NameCarrier codeIATA CodePassport needed during bookingOnline check-in available
Delta Air LinesDALDLYesOpens 24 days before flight
Closes 1 hours before flight
American AirlinesAALAAYesNo
Frontier AirlinesFFTF9NoOpens 24 days before flight
Closes 1 hours before flight
United AirlinesUALUAYesNo
JetBlue AirwaysJBUB6NoOpens 24 days before flight
Closes 2 hours before flight

United States COVID-19 travel restrictions

Your trip summary

Departure

Travel restrictions
  • Travel is allowed
  • Proof of pre-departure COVID-19 test is not required
  • Quarantine is not required

Return

Travel restrictions
  • Travel is allowed
  • No proof of a negative COVID-19 test required for entry
  • Quarantine is not required

Frequently asked questions

How long does it take to travel from Boston to Chicago?
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Is it possible to combine flights, buses, and trains in one itinerary when traveling between Boston and Chicago?
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