Boston to Chicago
One-way flight prices over the last 60 days
$64
Lowest Price
$477
Highest Price
$155
Average Price
5
Airlines
Available Flights
Showing 20 of 545 flightsAbout Boston to Chicago Flights
Find the best flight deals from Boston to Chicago. This page shows real-time price data from 5 airlines, helping you track price trends and find the cheapest time to fly. Over the last 60 days, prices have ranged from $64 to $477, with an average of $155.
Price Trends for Boston to Chicago
Our 60-day price history chart above shows how flight prices fluctuate over time. Use this data to identify the best booking windows and spot price drops. Prices on this route typically vary based on seasonality, day of week, and how far in advance you book.
Airlines Flying Boston to Chicago
Compare prices across F9, NK, UA, B6, SY. Each carrier offers different amenities, baggage policies, and cabin classes. Filter by specific airports above to narrow your search.
Tips for Booking
For the best prices on Boston to Chicago flights, consider booking midweek departures, comparing multiple airlines, and setting up price alerts to be notified when fares drop. Being flexible with your travel dates can also help you find significant savings.
Frequently Asked Questions
What is the cheapest flight from Boston to Chicago?
The lowest price we've tracked for flights from Boston to Chicago in the last 60 days is $64. Prices vary by airline, date, and cabin class.
How many airlines fly from Boston to Chicago?
We track 5 airlines operating flights from Boston to Chicago. Compare prices across different carriers to find the best deal.
What is the average flight price from Boston to Chicago?
Based on our 60-day price history, the average flight price from Boston to Chicago is $155. Prices range from $64 to $477.
When is the best time to book flights from Boston to Chicago?
Check our price history chart above to identify pricing trends. Generally, booking during off-peak periods and being flexible with dates can help you find lower prices.
What is the best day to fly from Boston to Chicago?
Midweek flights (Tuesday, Wednesday, Thursday) are typically cheaper than weekend flights. Use our price history data to compare prices across different departure dates.
How far in advance should I book flights from Boston to Chicago?
For domestic flights, booking 1-3 months in advance often yields the best prices. For international routes, 2-6 months ahead is recommended. Monitor our price tracker to spot deals.
Which airlines operate flights from Boston to Chicago?
Airlines flying this route include F9, NK, UA, B6, SY. Compare prices above to find the best carrier for your trip.
Are there direct flights from Boston to Chicago?
Direct flight availability varies by airline and season. Check the flight listings above to see current options, including both direct and connecting flights.
Get Price Drop Alerts for Boston to Chicago
Set up personalized alerts and we'll notify you when prices drop below your target. Never miss a deal on this route.