- Fastest flight
- non-stop flights
- 364x / week
- Flight distance
- 1,371 km
- Time difference
- Airports in Chicago
- O'Hare International Airport, IL
- Midway International Airport, IL
- Rockford, IL
- Most popular airlines
- United Airlines

- American Airlines

- Delta Air Lines

- Southwest Airlines

- JetBlue Airways

- Royal Jordanian

- United Airlines
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 flightsCHI–BOS · 63 of 63
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durationstopovers
- September 13 – 19, 2026
- September 20 – 26, 2026
- Sep 27 – Oct 3, 2026
- MDWBOSnonstop
- MDWBOSnonstop
- ORDBOSnonstop
- ORDBOSnonstop
- ORDBOSnonstop
- MDWBOSnonstop
- ORDBOSnonstop
- ORDBOSnonstop
- ORDBOSnonstop
- ORDBOSnonstop
- ORDBOSnonstop
- ORDBOSnonstop
- MDWBOSnonstop
- ORDBOS1 stopover
- MDWBOSnonstop
Tips and tricks to help you find cheap flights from Chicago to Boston
Important flight information
Frequently Asked Questions (FAQ)
How long is the flight from Chicago to Boston?
A nonstop flight from Chicago to Boston typically takes around 2 hours 28 minutes. If you choose a connecting flight, allow more travel time. Typical one-stop itineraries take around 25 hours 15 minutes. For the quickest trip, a nonstop flight is usually the most comfortable choice.
Are there nonstop flights from Chicago to Boston?
Yes, there are nonstop flights from Chicago to Boston, averaging around 52 to 53 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.
Which airlines fly from Chicago to Boston?
Direct flights from Chicago to Boston are operated by, among others, United Airlines, American Airlines and Delta. Connecting flights with one stop are also available, for example with Frontier Airlines (via Orlando) and Sun Country Airlines (via Minneapolis). If travel time matters to you, a direct flight is usually the most convenient option. Connecting flights often give you more choice of departure times and airlines.
On which days are there nonstop flights from Chicago to Boston?
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.
How many flights are there per day from Chicago to Boston?
From Chicago to Boston, there are on average around 52 to 53 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.
How many flights per week are there from Chicago to Boston?
From Chicago to Boston, there are around 366 to 367 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.
When does the first flight from Chicago to Boston depart?
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.
When does the last flight from Chicago to Boston depart?
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.