What’s the fastest layover option from Boston to Chicago?

Flights via Fort Lauderdale (FLL) have the shortest average one-way travel time for 1-stop routes: 10h 26m.

What’s the top layover airport for flights from Boston to Chicago?

Tampa (TPA) – chosen by Cheapflights users on 67% of 1-stop itineraries from Boston to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Boston to Chicago?

Tampa (TPA) is the most affordable 1-stop option, with an average round-trip price of $126.

How much does it cost to fly round-trip from Boston to Chicago?

Airfare is below average for this route at the moment. Boston to Chicago flights typically cost between $137 and $289 in November. The cheapest round-trip price found within the last 3 days was $123 on Southwest (Nov 4-Nov 5).

Which airport typically offers the quickest layover for flights from Boston to Chicago?

Flights via Fort Lauderdale (FLL) offer the fastest connection on this route, with an average layover time of 6h 16m.

How long is the flight from Boston to Chicago?

For as low as $133, Southwest can have you in Chicago from Boston in 2h 54m. Airlines will cover a distance of 864 mi. This flight may include one or multiple stops.

What are the cheapest airlines flying from Boston to Chicago round-trip?

Our cheapest airline available from Boston to Chicago is Spirit Airlines. Our recent data shows that you can find tickets from as low as $50 on this airline. Additional options worth looking into are JetBlue and United Airlines, starting at $83 and $97 round-trip. You may be able to fly from Boston to Chicago for 78% less than the average price by searching for these airlines.

What are the cheapest airlines to fly from Boston to Chicago one-way?

To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $69. Delta flights start at $69 while deals on JetBlue start at $69 one-way.

How far ahead should I book a flight from Boston to Chicago?

The best time to book flights from Boston to Chicago is 90 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Boston to Chicago?

Currently, August is the cheapest month in which you can book a flight from Boston to Chicago (average of $245). Flying from Boston to Chicago in March is currently the most expensive (average of $321). 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 is the cheapest day to fly from Boston to Chicago?

Travelers seeking maximum savings on their Boston to Chicago flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Boston to Chicago

The most flights from BOS to CHI are scheduled on a Monday (84 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (39 on average).

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What are the most popular routes from Boston to Chicago?

Most travelers choose Boston Logan Intl - Chicago O'Hare Intl, Boston Logan Intl - Chicago Midway or Boston Logan Intl - Chicago Greater Rockford when deciding on the best route from Boston to Chicago.

What are the cheapest flights from Boston to Chicago?

The cheapest flight price from Boston to Chicago is $65. On average you can expect to pay $755. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $117.

What are the most reliable airlines from Boston to Chicago?

Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Boston to Chicago on time: Icelandair (89%), TAP AIR PORTUGAL (87%), Avianca (84%).

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

The most popular airlines flying from Boston to Chicago are American Airlines, JetBlue and Delta. Something to consider prior to booking your flight.

What is the cheapest time of day to fly from BOS to CHI?

Unlike in the morning, when flights are generally more expensive, you can save up to 22% on flights from Boston to Chicago by exploring options for tickets in the evening.

What airport do you fly from for flights from Boston to Chicago?

Located just 2.6 mi from the city center, Boston Logan Intl is the airport most travelers will use when flying to Chicago from Boston. Booking flights from Logan Intl (BOS) to Chicago should be relatively easy as there are 67 daily outbound flights to Chicago from 7 different airlines.

Can I find deals for flights from Boston to Chicago that include hotel bookings?

Yes. In addition to deals on Boston to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Boston to Chicago?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Chicago.

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

Yes. Cheapflights offers flight deals from Boston to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$64+ Cheap Flights from Boston to Chicago

Round-trip from	$123 (Southwest)
One-way from	$64 (Southwest)
Popular in	March
Cheapest in	January
Average price	$199
Good round-trip deal	$203 or less
Good one-way deal	$106 or less

BOS

Use the FlyLogan App for real-time flight updates and pre-order food through BOS2GO to save time at the airport.

ORD

Use the 'L' train from ORD to downtown Chicago to avoid traffic and save time during peak hours.

MDW

Take the Orange Line from MDW to reach downtown Chicago in under 30 minutes, offering a convenient and cost-effective option.

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$50	Average$215	FlexibilityNo cancel fee	On-time65%
JetBlue	Cheapest$83	Average$197	FlexibilityNo cancel fee	On-time62%
United Airlines	Cheapest$97	Average$230	FlexibilityNo cancel fee	On-time69%
Frontier	Cheapest$100	Average$107	FlexibilityNo cancel fee	On-time62%
Delta	Cheapest$107	Average$298	FlexibilityNo cancel fee	On-timeN/A
Southwest	Cheapest$120	Average$235	FlexibilityNo cancel fee	On-time63%
American Airlines	Cheapest$137	Average$255	FlexibilityNo cancel fee	On-time71%

$64+ Cheap flights from Boston (BOS) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/4. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Boston to Chicago with Cheapflights

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Cheapflights Tip: The best prices from Boston Logan Intl to Chicago are usually found in January or September, booked 90 days in advance, depart on a Friday or Wednesday and return on a Thursday

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Cheapest flights from Boston to ChicagoExplore the most affordable flight options available from Boston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

Explore the most affordable flight options available from Boston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Boston to Chicago that are best for you.

The best insider tips for Boston to Chicago flights

Cheapflights partnered with top experts to bring you the best recommendations for your Boston to Chicago trip

Airports

BOS

ORD

MDW

Our travel experts

Best time to book a flight from Boston to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Boston with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Boston to Chicago

How far ahead should I book a flight from Boston to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Boston to Chicago. Price data was last updated on September 12, 2025.

What is the cheapest month to book a flight from Boston to Chicago?

What is the cheapest time of day to fly from BOS to CHI?

Find hourly flight availability from Boston to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2025.

What is the cheapest day to fly from Boston to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Boston to Chicago. Price data was last updated on September 14, 2025.

Weekly flight availability from Boston to Chicago

Explore weekly flight availability from Boston to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 17, 2025.

How much does it cost to fly round-trip from Boston to Chicago?

What’s the top layover airport for flights from Boston to Chicago?

Share of 1-stop round-trip flights from Boston to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

What’s the cheapest layover airport for flights from Boston to Chicago?

Average round-trip fare for 1-stop flights from Boston to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

What’s the fastest layover option from Boston to Chicago?

Shortest average travel time for 1-stop one-way flights from Boston to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Which airport typically offers the quickest layover for flights from Boston to Chicago?

Average layover duration for 1-stop one-way flights from Boston to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Reviews of airlines servicing Chicago

Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Boston to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Boston to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What airport do you fly from for flights from Boston to Chicago?

How long is the flight from Boston to Chicago?

What are the cheapest airlines flying from Boston to Chicago round-trip?

What are the cheapest airlines to fly from Boston to Chicago one-way?

What are the most popular routes from Boston to Chicago?

What are the most reliable airlines from Boston to Chicago?

What are the cheapest flights from Boston to Chicago?

Can I find deals for flights from Boston to Chicago that include hotel bookings?

How can I find direct flights from Boston to Chicago?

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

What is the cheapest month to book a flight from Boston to Chicago?

Traveling to a place near Chicago?

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Alternative routes for Boston to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Cheapest flights from Boston to Chicago
Explore the most affordable flight options available from Boston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.