Flight schedule from Boston (BOS) to Chicago (CHI)
Select a travel date in the flight schedule for the route from Boston (BOS) to Chicago (CHI) and compare affordable flight deals.
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Matching outbound flights56 of 56
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- August 2 – 8, 2026
- August 9 – 15, 2026
- August 16 – 22, 2026
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Tips and tricks to help you find cheap flights from Boston to Chicago
Favorite airline: Sun Country Airlines
Sun Country Airlines is the most popular airline for flights from Boston to Chicago.
Sun Country Airlines
30 %
American Airlines
19 %
United Airlines
16 %
Important flight information
Frequently Asked Questions (FAQ)
A nonstop flight from Boston to Chicago typically takes around 2 hours 47 minutes. This makes the nonstop service the fastest and most convenient way to travel between Boston and Chicago. It is worth checking flight times when searching, as they can vary by airline and travel date.
Yes, there are nonstop flights from Boston to Chicago, 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 Boston to Chicago are operated by, among others, United Airlines, American Airlines and Delta. These flights take you to Chicago 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 Boston to Chicago 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 Boston to Chicago, 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 Boston to Chicago, 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 Boston to Chicago usually departs at 5:24 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 Chicago.
The last nonstop flight from Boston to Chicago usually departs at 10:25 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.