Chicago to Boston Flights (ORD to BOS)
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Cheapest flight found
$95
Last updated Aug 23, 2026
Prices by Month
Price History
Tracking the Sep 16, 2026 departure — the cheapest date we found.
No price history yet. Check back after the next price check.
Price Behavior: ORD → BOS
Based on 7 months of fare data collected by Trip Manta.
Lowest Fare
$95
Highest Fare
$169
Median Fare
$109
Price Spread
$74
Prices vary significantly, so 24/7 tracking is especially valuable here.
Cheapest month to fly: September 2026 (from $95)
Most expensive month: August 2026 (from $169)
What This Means for You
Flights from Chicago to Boston range from $95 to $169, a $74 spread across the months we track. If your dates are flexible, September 2026 tends to have the lowest fares. Because prices on this route change significantly, setting up 24/7 tracking with instant alerts gives you the best chance of catching a short-lived drop before it corrects.
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From
Chicago (ORD)
To
Boston (BOS)
Airport Information
Chicago (ORD)
Chicago O'Hare International Airport (ORD) serves as a massive global gateway and a primary hub for both United and American Airlines. Located about 17 miles northwest of the Loop, it features four operational terminals and a vast array of amenities including high-end lounges, local culinary favorites like Tortas Frontera, and a diverse collection of public art. It is consistently ranked among the world's busiest airports, requiring travelers to arrive early to navigate security and the extensive concourses effectively.
Boston (BOS)
Boston Logan International Airport (BOS) is the largest airport in New England and is conveniently situated just across the harbor from downtown Boston. The airport consists of four terminals (A, B, C, and E) which are all connected by a free shuttle bus system and integrated moving walkways. It serves as a primary hub for JetBlue and a major focus city for Delta, offering modern facilities, a wide range of seafood-centric dining options like Legal Sea Foods, and exceptional views of the city skyline.
Frequently Asked Questions
How long is the flight from ORD to BOS?
The average non-stop flight duration is approximately 2 hours and 15 minutes to 2 hours and 40 minutes, depending on wind conditions and air traffic.
Which airlines fly non-stop from Chicago to Boston?
Major carriers including United Airlines, American Airlines, JetBlue, and Spirit Airlines offer frequent non-stop service between O'Hare and Logan.
What is the best time to book a flight to Boston?
For the best rates, it is generally recommended to book your tickets at least 3-6 weeks in advance, especially if you are traveling during the busy graduation season in May.
Is there a time difference between Chicago and Boston?
Yes, Boston is in the Eastern Time Zone (ET), which is one hour ahead of Chicago, which operates in the Central Time Zone (CT).
How do I get from Logan Airport to downtown Boston?
Travelers can use the MBTA Blue Line, the Silver Line (which is free from the airport to South Station), or take a water taxi for a unique scenic route across the harbor.
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