Flight schedule from Chicago (CHI) to Boston (BOS)
Select a travel date in the flight schedule for the route from Chicago (CHI) to Boston (BOS) and compare affordable flight deals.
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Matching outbound flights67 of 67
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durationstopovers
- August 16 – 22, 2026
- August 23 – 29, 2026
- Aug 30 – Sep 5, 2026
- ORDBOS1 stopover
- MDWBOSnonstop
- MDWBOSnonstop
- ORDBOS1 stopover
- ORDBOSnonstop
- ORDBOSnonstop
- MDWBOSnonstop
- ORDBOSnonstop
- ORDBOSnonstop
- ORDBOSnonstop
- ORDBOSnonstop
- MDWBOSnonstop
- ORDBOSnonstop
- ORDBOSnonstop
- MDWBOSnonstop
Tips and tricks to help you find cheap flights from Chicago to Boston
Favorite airline: Spirit Airlines
Flight tickets on the route Chicago – Boston are most frequently booked with Spirit Airlines.
Spirit Airlines
33 %
United Airlines
20 %
Delta
15 %
Important flight information
Frequently Asked Questions (FAQ)
A nonstop flight from Chicago to Boston typically takes around 2 hours 28 minutes. This makes the nonstop service the fastest and most convenient way to travel between Chicago and Boston. It is worth checking flight times when searching, as they can vary by airline and travel date.
Yes, there are nonstop flights from Chicago to Boston, averaging around 53 to 54 flights per day, operated by, among others, United Airlines, American Airlines and Delta. If you want to fly without a layover, it is worth filtering specifically for nonstop flights when searching.
Direct flights from Chicago to Boston are operated by, among others, United Airlines, American Airlines and Delta. These flights take you to Boston nonstop, making them especially practical for short trips or weekend getaways. It is still worth comparing departure times and airline policies, as baggage rules and fees can vary.
Nonstop flights from Chicago to Boston operate daily. The schedule may vary by season, so it is worth comparing several travel dates. If your preferred day does not have a nonstop flight, nearby departure days or short connecting flights may be a good alternative.
From Chicago to Boston, there are on average around 53 to 54 flights per day. This usually means you have a good choice of departure times. If you are flexible, you can easily compare times, prices, and airlines.
From Chicago to Boston, there are around 373 to 374 flights per week. This means you usually have connections available on several days and at various times. Beyond the price, it is worth comparing flight duration, airline, and any potential additional fees.
The earliest nonstop flight from Chicago to Boston usually departs at 5:15 AM. The exact departure time may vary by day of the week and airline. Early flights are especially useful if you want to make the most of your arrival day in Boston.
The last nonstop flight from Chicago to Boston usually departs at 9:42 PM. Late flights can be convenient if you want to travel after work or in the evening. Do check whether it is a nonstop flight, as a connecting itinerary could push the arrival time significantly later.