Flights from Chicago, IL to Boston, MA
Compare prices from 900+ airlines and find the best deals on flights from ORD to BOS.*Prices shown are estimated based on historical data.
Chicago, IL to Boston, MA
Round-trip flights from ORD to BOS typically cost $751-$938 USD. Prices vary by season, demand, and how far in advance you book. The lowest fares are usually found 6-8 weeks before departure for domestic routes.
Non-stop flights from ORD to BOS take approximately 13h 29m. Actual flight times vary based on weather, air traffic, and aircraft type. Consider arriving at the airport 2 hours before domestic departures.
Airlines operating ORD to BOS include Avianca, JetBlue Airways, Lufthansa, ANA. Each airline offers different fare classes, baggage policies, and loyalty programs. Compare options to find the best value for your travel needs.
The cheapest day to fly ORD to BOS is typically Tuesday. Mid-week flights are 10-20% cheaper than weekend departures. For best prices, book 6-8 weeks before your trip. Avoid booking less than 2 weeks out when fares spike.
Fares range from $751 to $1407 depending on dates, class, and airline.
Prices based on 500 searches. Updated hourly.
Find the Best Fares for ORD→BOS
Compare 900+ airlines — live prices, flexible dates, free cancellation options
About Flights from Chicago, IL to Boston, MA
Looking for cheap flights from Chicago, IL (ORD) to Boston, MA (BOS)? You've come to the right place. Fly2Any compares prices from over 900 airlines to help you find the best deals on this popular route.
Flight Information
Flights from ORD to BOS typically take around 13h 29m. The flight covers a distance of 6441 miles. Multiple airlines operate this route, including Avianca, JetBlue Airways, Lufthansa, ANA.
Best Time to Book
For the best prices on ORD to BOS flights, we recommend booking 2-3 months in advance. Prices tend to be lowest for mid-week departures (Tuesday and Wednesday). Use our Price Calendar feature to compare prices across different dates and find the cheapest options.
Price data last updated: April 2026
Airlines on This Route
Several major airlines serve the Chicago, IL to Boston, MA route, including:
- Avianca (AV)
- JetBlue Airways (B6)
- Lufthansa (LH)
- ANA (NH)
Frequently Asked Questions - ORD to BOS Flights
How long is the flight from Chicago, IL to Boston, MA?
Direct flights from Chicago, IL (ORD) to Boston, MA (BOS) take approximately 13h 29m. Connecting flights may add 2-4 hours depending on layover location. For the fastest journey, look for nonstop flights which are typically available on this popular route.
When is the best time to book ORD to BOS flights?
For the best prices on ORD to BOS flights, book 6-8 weeks in advance for domestic routes or 2-4 months ahead for international travel. Domestic flights are typically 20-40% cheaper in off-peak months. Peak season months (July, August) have higher prices, while January and February typically offer the best deals.
What are the cheapest days to fly from Chicago, IL to Boston, MA?
Tuesday and Wednesday departures are typically 15-25% cheaper than weekend flights on the ORD to BOS route. Saturday is usually the most expensive day to fly. For additional savings, consider red-eye flights or early morning departures, which often have lower fares and less crowded airports.
Which airlines fly from ORD to BOS?
Major carriers on this route include American Airlines, United, and other domestic and international airlines. O'Hare is a major hub for both American and United. Check for connecting flight deals through Chicago.
What should I know about flying from Chicago, IL airport?
O'Hare is a major hub for both American and United. Check for connecting flight deals through Chicago. Book flights that depart mid-morning or early afternoon for the smoothest experience - these times typically have shorter security lines and fewer delays.
What is the cheapest month to fly from Chicago, IL to Boston, MA?
The cheapest months to fly from ORD to BOS are typically January, February, September. Domestic flights are typically 20-40% cheaper in off-peak months. Avoid peak travel periods like July and August when prices can be 30-50% higher. Use Fly2Any's price alerts to get notified when fares drop.
What is the baggage allowance for ORD to BOS flights?
Baggage allowances vary by airline and fare class. Most full-service carriers include one checked bag (up to 50 lbs) on this route. Budget carriers may charge $25-$60 for checked bags. All airlines allow one personal item free. Compare total costs including baggage fees when booking to get the best deal.
Are there direct flights from Chicago, IL to Boston, MA?
Yes, several airlines offer nonstop flights from ORD to BOS. Direct flights take approximately 13h 29m. If you're flexible with your schedule, connecting flights through major hubs like ATL or DFW may offer lower prices.
More Flights from Chicago, IL & to Boston, MA
Compare prices on similar routes — all searched live across 900+ airlines.
