Cheap Flights from Boston to Chicago from S$ 63

Frequently Asked Questions

• Which airlines offer the cheapest flights from Boston (BOS) to Chicago (CHI)?

  Based on Trip.com data, American Airlines offers one-way fares as low as S$ 63 on Cheapest nonstop routes (e.g. BOS to ORD on Wed, Apr 8), while Jetblue Airways offers Cheapest nonstop round-trips from S$ 108 departing on Wed, Apr 8 and returning on Mon, Apr 13.

• Which airlines offer direct flights from Boston to Chicago?

  At the moment, you can catch a direct flight from Boston to Chicago with the following airlines, including: American Airlines Delta Air Lines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.

• How long is a flight from Boston (BOS) to Chicago (CHI)?

  It takes about 3 hours 7 minutes to fly from Boston (BOS) to Chicago (CHI).

• When is the best time to book flights from Boston to Chicago?

  By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Boston to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.

• How many flights are there per week from Boston to Chicago?

  Based on Trip.com data in the past 4 weeks, there is 95 flight per week flying from Boston to Chicago. You can check the weekly schedule for popular airlines on this route below: American Airlines: -/M/T/W/T/F/- -- AA1174 (17:56)

• How can I find the best deals on flights from Boston to Chicago?

  To find best deals on flights from Boston to Chicago, you can use various tools on Trip.com:
  · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Wed, Apr 8, with one-way flights priced at just S$ 63.
  · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is American Airlines.
  · Set up price alerts to easily monitor ticket prices without having to check every day.
  · Check Trip.com flight deals and promo codes frequently.
  · Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around July.
  · Get exclusive promo codes for Trip.com app users.

• When is the best time to book a flight from Boston to Chicago to get the best price?

  The cheapest months to fly from Boston to Chicago is October, when demand for travel is lower.

• Which upcoming date is the cheapest for flights from Boston to Chicago?

  After crunching the numbers on our March flight calendar, it's currently cheapest to fly from Boston to Chicago on March 10, 2026 with Jetblue Airways, with prices starting at S$ 112.

• Which airports can I fly through when travelling to Chicago from Boston?

  You can land at any one of the following hubs in Chicago, with Logan International Airport to O'Hare International Airport (BOS-ORD) is by far the most common option on this route: O'Hare International Airport (ORD) Midway International Airport (MDW) Chicago Rockford International Airport (RFD).

• What is the time difference between Boston and Chicago?

  The time difference between Chicago and Boston is 1h.

• How can I change or cancel my flight ticket from Boston to Chicago?

  Tickets can only be changed or cancelled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.