Cheap flights from Boston (BOS) to Chicago (CHI) from $36

Tue 6/46:25 amBOS - ORD

Nonstop2h 55mDelta

Sat 6/87:00 amORD - BOS

Nonstop2h 31mDelta

Deal found 4/29$162

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Sun 5/268:05 amBOS - ORD

Nonstop2h 58mDelta

Wed 5/296:27 amORD - BOS

Nonstop2h 27mDelta

Deal found 4/28$178

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Wed 5/296:25 amBOS - ORD

Nonstop2h 55mDelta

Tue 6/46:00 amORD - BOS

1 stop8h 16mDelta

Deal found 4/29$190

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Tue 5/286:25 amBOS - ORD

Nonstop2h 55mDelta

Wed 5/298:10 pmORD - BOS

Nonstop2h 36mDelta

Deal found 4/29$193

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Thu 5/232:10 pmBOS - ORD

Nonstop2h 54mDelta

Tue 5/286:27 amORD - BOS

Nonstop2h 27mDelta

Deal found 4/28$214

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Mon 5/276:25 amBOS - ORD

Nonstop2h 55mDelta

Thu 6/66:13 amORD - BOS

Nonstop2h 26mDelta

Deal found 4/29$230

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Sat 5/184:25 pmBOS - ORD

Nonstop2h 52mDelta

Tue 5/216:27 amORD - BOS

Nonstop2h 27mDelta

Deal found 4/28$254

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Thu 5/96:25 amBOS - ORD

Nonstop2h 55mDelta

Thu 5/167:10 amORD - BOS

1 stop7h 12mDelta

Deal found 4/27$263

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Sat 5/184:25 pmBOS - ORD

Nonstop2h 52mDelta

Mon 5/208:10 pmORD - BOS

Nonstop2h 36mDelta

Deal found 4/29$274

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• If you’re traveling from Boston to Chicago, one of the more common airlines traveling that route is Delta. Boston to Chicago flights are typically 174% more expensive than other airlines traveling the same route. Flights from Delta typically cost $93.90 RT. The cheapest Delta flight found for this route was $39. Boston Logan Intl Airport is the most common Boston airport to take off from when flying to Chicago. Chicago O'Hare Intl Airport is the most popular arrival airport in Chicago. When flying from Boston to Chicago, Delta flights are 11% more popular than any other airline flying that same route.

Tue 7/27:30 pmBOS - ORD

Nonstop2h 56mAmerican Airlines

Mon 7/85:00 amORD - BOS

1 stop4h 14mAmerican Airlines

Deal found 4/28$187

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Thu 5/3012:22 pmBOS - ORD

Nonstop2h 58mAmerican Airlines

Sun 6/26:30 amORD - BOS

1 stop4h 44mAmerican Airlines

Deal found 4/29$196

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Wed 6/56:00 amBOS - ORD

Nonstop3h 06mAmerican Airlines

Fri 6/77:13 pmORD - BOS

Nonstop2h 29mAmerican Airlines

Deal found 4/28$208

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Tue 5/77:10 amBOS - ORD

Nonstop3h 04mAmerican Airlines

Fri 5/103:27 pmORD - BOS

Nonstop2h 17mAmerican Airlines

Deal found 4/27$209

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Mon 5/275:25 amBOS - ORD

Nonstop2h 56mAmerican Airlines

Sat 6/14:53 pmORD - BOS

1 stop5h 37mAmerican Airlines

Deal found 4/28$217

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Sun 5/125:25 amBOS - ORD

Nonstop2h 52mAmerican Airlines

Fri 5/174:53 pmORD - BOS

1 stop5h 37mAmerican Airlines

Deal found 4/27$218

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Thu 5/95:25 amBOS - ORD

Nonstop2h 56mAmerican Airlines

Mon 5/136:30 amORD - BOS

1 stop4h 44mAmerican Airlines

Deal found 4/28$232

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Mon 5/65:55 pmBOS - ORD

1 stop5h 38mAmerican Airlines

Sat 5/117:05 amORD - BOS

Nonstop2h 26mAmerican Airlines

Deal found 4/28$233

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Wed 5/88:50 amBOS - ORD

Nonstop2h 57mAmerican Airlines

Tue 5/284:02 pmORD - BOS

1 stop4h 41mAmerican Airlines

Deal found 4/28$235

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• One of the most popular airlines traveling from Boston to Chicago is American Airlines. Flights from American Airlines traveling this route typically cost $367.57 RT. This price is typically 51% more expensive than other airlines that offer Boston to Chicago flights. When booking this route, the cheapest RT price found was $94. When traveling from Boston to Chicago on American Airlines, the most popular airport to depart from is Boston Logan Intl Airport and the most popular airport to arrive at is Chicago O'Hare Intl Airport. When flying from Boston to Chicago, American Airlines flights are 11% more popular than any other airline flying that same route.

Currently, February is the cheapest month in which you can book a flight from Boston to Chicago (average of $245). Flying from Boston to Chicago in June is currently the most expensive (average of $356). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

• What Boston airport do you fly from when flying to Chicago?

  The majority of travelers in the Boston area will take a flight out of Boston Logan Intl when flying to Chicago. Logan Intl (BOS) has 51 outbound flights to Chicago per day, on average, offered by 8 airlines. The Boston airport is a quick 2.6 mi trip from the center of the city, but be sure to give yourself enough time to get to the airport before your departure.

• What is a great deal on a flight from Boston to Chicago?

  On Priceline, users have found cheap flights from Boston to Chicago for as low as $200. The average price found was around $137, however the best flight deal found in the last week was $120 (a Frontier flight from Boston to Chicago).

• Are there direct flights from Boston to Chicago?

  Yes. Over 20 direct flights from Boston to Chicago were found in the last week, with better deals found between $100 and $129.

• How much does a last minute flight from Boston to Chicago cost?

  $200 is the best price for last minute Boston to Chicago flights. Priceline has found over 20 Boston - Chicago flights departing in the next week.

• When are nonstop flights from Boston to Chicago available?

  The following days have nonstop flights scheduled for this route: Monday, Tuesday, Wednesday, Thursday, Friday, Saturday.

• How many flights from Boston to Chicago are there per day?

  57 flights are scheduled to fly from Boston to Chicago per day. However this is just an average and airline schedules may vary based on a variety of factors.
  Early Morning (Midnight to 6am) - 12% of flight departures
  Morning (6am - Noon) - 33% of flight departures
  Afternoon (Noon - 6pm) - 44% of flight departures
  Evening (6pm - Midnight) - 11% of flight departures

• How long is the flight from Boston to Chicago?

  Departing from Boston to Chicago will take you 2h 50m when flying with Frontier, Spirit Airlines, or United Airlines. If you plan on flying with Frontier, which offers the fastest flight from Boston to Chicago, then you may find flights for as low as $120. There are 869 mi between Boston and Chicago, though your travel time may vary depending on whether you have a nonstop or multi-stop flight. Flight options will be for both nonstop flights and flights with stops.

• What are the cheapest airlines offering flights to Chicago from Boston round-trip?

  With prices as low as $120, Frontier offers cheap flights from Boston to Chicago and back. Search Priceline for Spirit Airlines and United Airlines flight deals - these airlines fly from Boston to Chicago for as low as $136 and $139, respectively. You might be able to find flights to Chicago from Boston for 53% lower than the average price by looking for these airlines.

• Which airlines flying from Boston to Chicago one-way offer the cheapest flights?

  $36 per ticket on Spirit Airlines is the cheapest price our users have found recently for a one-way flight from Boston to Chicago. Frontier and JetBlue have also been known to have cheap one-way flights for this route, with prices starting at $60 and $64, respectively.

• What are the most popular routes from Boston to Chicago?

  While some choose either Boston Logan Intl - Chicago Midway or Boston Logan Intl - Chicago Greater Rockford, Boston Logan Intl - Chicago O'Hare Intl is the most popular route from Boston to Chicago.

• What airlines fly from Boston to Chicago?

  Undisclosed Carrier, American Airlines and Alaska Airlines are all popular choices that operate Boston - Chicago flights.

• What airlines that fly from Boston to Chicago are the most reliable?

  Scandinavian Airlines, LATAM Airlines, and ANA arrive at Chicago on schedule the most often. They avoid delays on between 96% to 97% flights from Boston to Chicago.

• What is best Boston to Chicago flight price on Priceline?

  Finding a cheap flight from Boston to Chicago means finding a price under $677. The best price found recently was $89. The most popular route, Boston Logan Intl - Chicago O'Hare Intl, averages around $74.

• What is BOS to ORD?

  They are IATA (International Air Transport Association) codes! Airlines use these IATA codes to signify the airport in flight routes. A BOS to ORD flight simply means the flight departs from Boston Logan Intl Airport to Chicago O'Hare Intl Airport. We have got more helpful popular IATA codes here for you, in case you need them — Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

• Can I discover flight deals from Boston to Chicago that include extra baggage allowance?

  Baggage allowance for Boston to Chicago flights depends on the airline and fare type. Once you've entered your flight details, you can see the baggage policies for each deal in the search results. Some deals might include extra baggage allowance.

• Can I search for flight deals from Boston to Chicago with specific airlines?

  Absolutely! On Priceline, you can find and filter for flight deals based on your preferred airline. Simply search with your preferred dates, origin, and destination, and use the filters to see flights from the airlines you prefer.

• Can I score deals for flights from Boston to Chicago that bundle with hotel bookings?

  Absolutely. Besides flight deals from Boston to Chicago, Priceline also offers vacation packages that bundle flights and hotel stays.

• How do I find direct flights from Boston to Chicago?

  To find direct flights from Boston to Chicago, enter your preferred dates, origin, and destination, and then apply the non-stop filter on the search result page to see all the direct flights available for that route.

• Can I find deals for business class flights from Boston to Chicago?

  Definitely! Priceline offers flight deals from Boston to Chicago sorted by cabin class. You can browse deals or filter by cabin class on the search result page after making a flight search.

• Can I find flight deals from Boston to Chicago that allow pets onboard?

  While Priceline mainly focuses on finding users the best flight deals, many airlines do allow pets. After picking a Boston to Chicago flight deal, you can find more info about the airline's pet policy on their official website or by getting in touch with the airline directly. Keep in mind, additional fees and restrictions might apply.

• Can I locate any last-minute flight deals from Boston to Chicago?

  Absolutely! Priceline offers last-minute deals on flights from Boston to Chicago. Do keep in mind, these bargains pop up often but they might not always be available. For the latest information on deals, we recommend frequent visits or subscribing to our price alerts.

• How frequently are the flight deals from Boston to Chicago updated?

  The Boston to Chicago flight deals you see on this page were last updated on 4/29.