Boston to Chicago Flights (BOS to ORD)
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Cheapest flight found
$104
Last updated Jul 18, 2026
Prices by Month
Price History
Tracking the Sep 9, 2026 departure — the cheapest date we found.
No price history yet. Check back after the next price check.
Price Behavior: BOS → ORD
Based on 7 months of fare data collected by Trip Manta.
Lowest Fare
$104
Highest Fare
$144
Median Fare
$106
Price Spread
$40
Prices fluctuate moderately, so 24/7 tracking can help you catch dips.
Cheapest month to fly: September 2026 (from $104)
Most expensive month: July 2026 (from $144)
What This Means for You
Flights from Boston to Chicago range from $104 to $144, a $40 spread across the months we track. If your dates are flexible, September 2026 tends to have the lowest fares. Prices move enough that tracking can save you money. Drops often last only a few hours before the algorithm adjusts back up.
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From
Boston (BOS)
To
Chicago (ORD)
Airport Information
Boston (BOS)
Boston Logan International Airport (BOS) serves as the primary aviation gateway for New England, located just across the harbor from the heart of downtown Boston. It is a major hub for carriers like Delta Air Lines and JetBlue, offering a wide array of high-end amenities including local culinary favorites like fresh New England seafood. The airport is exceptionally well-connected to the city via the Silver Line bus and the Blue Line subway, ensuring travelers can reach their gates efficiently from anywhere in the Greater Boston area.
Chicago (ORD)
Chicago O'Hare International Airport (ORD) is one of the busiest and most significant aviation hubs in the world, serving as a primary base for both United Airlines and American Airlines. Located approximately 17 miles northwest of the Chicago Loop, it features four operational terminals and a vast array of international shopping and dining options. From its iconic neon-lit underground walkway in Terminal 1 to its extensive transit connections, O'Hare provides a grand entrance into the Midwest with efficient transport links to the city center.
Frequently Asked Questions
How long is the flight from Boston to Chicago?
A direct flight from BOS to ORD usually takes about 2 hours and 45 minutes, though tailwinds can often shorten the trip to around 2 hours and 20 minutes when heading west.
Which airlines fly non-stop between BOS and ORD?
Major carriers including American Airlines, United Airlines, JetBlue, and Spirit Airlines frequently offer multiple non-stop flights daily on this specific route.
Is there a time difference between Boston and Chicago?
Yes, Boston is in the Eastern Time Zone, while Chicago is in the Central Time Zone, meaning Chicago is exactly one hour behind Boston.
What is the best way to get from O'Hare to downtown Chicago?
The CTA Blue Line 'L' train is the most cost-effective and reliable method, operating 24/7 and avoiding the heavy traffic often found on the Kennedy Expressway, reaching the Loop in about 45 minutes.
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