Boston (BOS) → Chicago (ORD)
About Boston to Chicago Flights
Discover the best flights from Boston to Chicago, covering 1,391 km in approximately 2h 14m. Boston (BOS) to Chicago (ORD) is one of the busy short-haul routes within United States. With 6 major airlines operating this route including direct flights, travelers have plenty of options to choose from. Whether you're traveling for business or leisure, our comprehensive guide helps you find the best deals, understand seasonal price variations, and choose the right airline for your journey from Boston to Chicago.
12-Month Price History
Flight prices from Boston to Chicago vary significantly throughout the year. February typically offers the best deals with average prices around $254, while July sees the highest prices, averaging $432. Savvy travelers can save up to 41% by choosing their travel dates wisely.
Best Time to Fly
Cheapest Month
February
Save up to 40% on average
Most Expensive
July
Peak season pricing
Book in Advance
81 days
For best prices
Booking Tips
For the best prices on Boston to Chicago flights, we recommend booking 59 days in advance. Domestic flights typically see price increases as the departure date approaches, so early booking is advisable. Tuesday and Wednesday departures often offer the lowest fares, while Friday and Sunday flights tend to be more expensive due to business and leisure travel demand. Consider flying early morning or late evening for additional savings, as these off-peak times usually have lower demand.
Airlines Serving This Route
| Airline | Economy | Business | First |
|---|---|---|---|
JetBlue Airways B6 | $310 | $790 | - |
SkyWest Airlines OO | $390 | $1540 | $2590 |
American Airlines AA | $400 | $1600 | $2040 |
Kalitta Air K4 | $410 | $1530 | $2310 |
Delta Air Lines DL | $440 | $1720 | $2330 |
United Airlines UA | $450 | $1380 | $2060 |
JetBlue Airways
B6
Economy
$310
Business
$790
First
-
SkyWest Airlines
OO
Economy
$390
Business
$1540
First
$2590
American Airlines
AA
Economy
$400
Business
$1600
First
$2040
Kalitta Air
K4
Economy
$410
Business
$1530
First
$2310
Delta Air Lines
DL
Economy
$440
Business
$1720
First
$2330
United Airlines
UA
Economy
$450
Business
$1380
First
$2060
Prices shown are estimates based on historical data. Actual prices may vary based on dates, availability, and current promotions.
Alternative Flight Options
Hartford → Chicago
Bradley International (BDL) to O'Hare International (ORD)
Distance: 1,257 km
Average price: $289
Portland → Chicago
Portland International Jetport (PWM) to O'Hare International (ORD)
Distance: 1,445 km
Average price: $317
Boston → Milwaukee
Logan International (BOS) to Milwaukee Mitchell International (MKE)
Distance: 1,380 km
Average price: $307
Boston → Chicago
Logan International (BOS) to Chicago Midway International (MDW)
Distance: 1,381 km
Average price: $307
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Frequently Asked Questions
How long is the flight from Boston to Chicago?
The flight time from Boston (BOS) to Chicago (ORD) is approximately 2 hours and 14 minutes. This duration is for direct flights and may vary depending on aircraft type, weather conditions, and air traffic.
What is the distance between Boston and Chicago?
The aerial distance between Boston and Chicago is 1,391 kilometers (864 miles). This is the straight-line distance, which is used to calculate flight times.
Which airlines fly from Boston to Chicago?
Several airlines operate flights between Boston and Chicago, including American Airlines, Delta Air Lines, United Airlines and 3 more airlines. Direct flights are available on this route.
What is the cheapest month to fly from Boston to Chicago?
Based on historical data, February typically offers the lowest airfares for flights from Boston to Chicago. However, prices can vary based on holidays, events, and airline promotions. We recommend checking our price calendar for the most up-to-date information.
How far in advance should I book my flight to Chicago?
For the best prices on Boston to Chicago flights, we recommend booking 69 days in advance. Domestic flights can sometimes offer good last-minute deals, but advance booking is usually cheaper.
Do I need a visa to travel from Boston to Chicago?
Visa requirements depend on your nationality and the purpose of your visit. Since this is a domestic flight, no visa is required for citizens.
What is the time difference between Boston and Chicago?
Boston operates on America/New_York time zone, while Chicago is in the America/Chicago time zone. For current time differences and to plan your schedule, visit our partner site timezig.com for accurate timezone conversions.