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Cheapest flights for Boston – Chicago (BOS – CHI)

Aviasales.ge will find you the cheapest airfare for Boston – Chicago by comparing the ticket prices to Chicago using 45 agencies, five booking systems, and 728 airlines. Where exactly you buy your tickets for Boston – Chicago is up to you.

Boston – Chicago is most popular in April. During this period the average ticket price is 587.

Direct flight for from Boston to Chicago

The easiest way to to get to your destination is a direct flight. Direct flights for from Boston to Chicago are offered by:

  • United Airlines (daily UA2040)
  • American Airlines (6 days per week, flight AA3593)
  • Delta Air Lines (5 days per week, flight DL2570)
  • Southwest Airlines (4 days per week, flight WN1159)
  • JetBlue Airways (3 days per week, flight B6611)

Chicago is served by 6 airports: DuPage Airport, Chicago Rockford International Airport, Chicago Executive Airport, O'Hare International Airport, Chicago Midway International Airport and Merrill C Meigs. Direct flights for Boston – Chicago are operated by:
  • Southwest Airlines from Logan International Airport to Chicago Midway International Airport
  • United Airlines, Delta Air Lines, American Airlines, JetBlue Airways from Logan International Airport to O'Hare International Airport
Flight with layover for the route from Boston to Chicago

An alternative option for Boston – Chicago (round-trip) would be a flight with a layover. Prices start at 535 .

A flight with a layover on the route Boston – Chicago will allow you to make your trip more interesting. The layover could be in:

  • Philadelphia (flight AA1414 American Airlines)
  • Baltimore (flight WN1839 Southwest Airlines)
  • Charlotte (flight AA922 American Airlines)

This is a great chance to get to know these cities. Layovers are usually at least six hours.

Please keep in mind that depending on the number of days remaining until your departure, ticket prices for Boston – Chicago could change by more than 140%.

Aviasales.ge suggests buying tickets for Boston – Chicago in advance in order to choose the conditions for your flight that best suit your preferences and budget.

General information on flight Boston – Chicago (BOS – CHI)
1,365 km
Distance
1 ⁠hr
Current time difference
151
Number of flights per week
₾174
Lowest price
Average ticket price
05:00
Earliest flight out
20:25
Latest flight out

Ticket prices for Boston – Chicago by month *

Month One-way Round-trip
April 2025 01.04.2025
18.04 - 22.04.2025

* Prices found by users over the last 48 hours (they do not represent an offer).

Cheapest flight for from Boston to Chicago found by our users over the last 48 hours: ticket with American Airlines with a departure on 18.04.2025 and a price of 587 GEL.
Fastest flight for from Boston to Chicago: ticket with Southwest Airlines with the nearest departure on 29.05.2025 and a flight duration of 2hrs. 40min..
Airlines flying from Boston to Chicago
Airports serving Boston – Chicago

Boston airports serving flights to Chicago:

  • Logan International Airport (BOS)

Chicago airports accepting flights from Boston:

  • Chicago Midway International Airport (MDW)
  • O'Hare International Airport (ORD)