One Way Flights Vs Round Trip Flights From Boston To Chicago
We have found that there is often no price difference between buying a round trip flight versus a one way flight. Increased flexibility is the main benefit when it comes to buying a one way flight from Boston to Chicago. However, booking a round trip flight can be a simpler process. You can compare round trip and one way flights by using our flight comparison.
The average price for one way flights from Boston to Chicago is $190.
The average price for round trip flights from Boston to Chicago is $196.
Tips On Booking Cheap Flights
Looking for the best time to buy airline tickets to get a cheap flight to everywhere? Weve got you covered anytime, anywhere. Heres how to find the best deal for flight booking no matter where you want to go in the world.
Which day of the week is the best day to buy cheap airline tickets?
For both U.S. domestic and international travel, Sundays can be cheaper for airline ticket purchases. Fridays tend to be the most expensive day to book a flight. Booking on the right day of the week could save you up to 6% on your airfare, according to historical data*.
When is the best time to buy airline tickets?
Based on 2020 And 2021 global flight data for Economy tickets, prices usually start to increase 56 days before departure for domestic flights. When traveling internationally, prices usually start to increase 21 days before departure*. Keep in mind that this isnt a hard-and-fast rule keeping an eye on prices is a good idea when trying to find the best airfare deals. Compare fares across different airlines, and set up a price alert for your preferred route.
Which are the cheapest days to fly?
Analysis of domestic and international airfare prices shows that flying out on Fridays can be cheaper. Many travelers start their trips on Sundays, so your chances of a lower price are better when departing early in the week instead. Starting your trip on a Friday could be almost 11% cheaper than air travel on Sundays, so book flights online wisely*!
Which is the cheapest month to fly?
Low Cost Flights From Boston To Chicago
Find the best deals on flights from Boston to Chicago with Jetcost! Compare airfare prices and find your flight at the best price. Compare airfare prices from Boston to Chicago with Jetcost and find the best deal available: once you enter your travel dates, Jetcost will compare flight prices for you among thousands of offers from the best airlines and online travel agencies.
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Delta Air Lines Flight Schedule From Chicago To Boston
All weekly departures with Delta Air Lines. The week calendar shows every flight departure from Chicago to Boston . Click on a blue date to see a list of flights.
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The Southwest Travel Experience

Chicago Midway International Airport is a quick 30-minute ‘L’ ride from downtown Chicago. Get goingadventure awaits.
At Southwest, we know it takes more than great deals on Chicago airfares and convenient scheduling options to make your trip memorable. So from booking to boarding, we offer services and features designed to make your travel from Boston Logan to Chicago the best it can be. Learn more about the Southwest® travel experience before you book your flight from Logan International Airport to Chicago Midway International Airport.
Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. When you search for your next flight to Chicago , know that you wont be surprised at checkout. Low fares and no hidden fees. That’s Transfarency®. And as always, two bags fly free®1. Want the latest news, information, and promotional offers from Southwest? from us. Book your flight today and know that you’ll earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
3Failure to cancel a reservation at least 10 minutes prior to departure may result in forfeited Travel Funds.
4Flight credits unexpired on or created on or after July 28, 2022, do not expire and will show an expiration date until our systems are updated. See full details here.
5Available only on WiFi-enabled aircraft. Limited-time offer. Where available.
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Airlines: Delta American Airlines And United Flights From Boston To Chicago
Buy your official DELTA, American Airlines and United flight tickets to Chicago from Boston from $75 with Omio. Find flight times and tickets for over 1000 travel companies to compare and book the most convenient route.
Delta Airlines is one of the USAs leading airlines. Check which ticket fare is the best option for your flight to Chicago from Boston from: Main Cabin, Comfort+ and First Class.
Save time and money by searching for and booking your DELTA flight between Boston and Chicago online with Omio! If youre looking for the cheapest, fastest or earliest DELTA flight from Boston to Chicago, Omio can help you out every step of the way. Check current DELTA flight schedules for the ideal departure and arrival times, compare the best connections for the 848 miles journey between Boston and Chicago as well as ticket information for the flight , and then book a cheap plane ticket all in one convenient place. If you are using the Omio app to search for flights between Boston and Chicago, you can check straight away if the DELTA ticket is a mobile ticket, which makes it easy for you to go paperless when traveling without needing to purchase tickets in person at the airport. Buy your official DELTA Boston to Chicago plane tickets online on Omio quickly and easily and enjoy the travel experience!
- Average Price: $75
- Average Price: $107
American Airlines Flight Schedule From Chicago To Boston
All weekly departures with American Airlines. The week calendar shows every flight departure from Chicago to Boston . Click on a blue date to see a list of flights.
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The Fastest Flightsfrom Bostonto Chicago
Fastest Journey
Distance
1368 km
Of the 8 flights that leave Boston for Chicago every day 8 travel direct so its quite easy to avoid journeys where youll have to change along the way.
These direct flights cover the 1368 km distance in an average of 3 h 59 m but if you time it right, some flights will get you there in just 2 h 52 m .
The slowest flights will take 6 h 27 m and usually involve a change or two along the way, but you might be able to save a few pennies if youre on a budget.
The Airports Of Boston And Chicago
Boston is approximately 1380 km from Chicago. Departing from a different Boston airport or to a different Chicago airport can be even more convenient. Here are the currently available options for flights Boston – Chicago:
- Airports in Boston: Boston has only one airport available at the moment: Boston – Logan.
- Airports in Chicago: Chicago is served by 3 airports: Midway, O’Hare, Rockford. If you don’t know which airport to choose, simply select a date and with Jetcost you can view the deals for all available airports in Chicago, so you can evaluate which is the most convenient for your trip.
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Book Flight Tickets From Boston Logan International To Chicago With Extra Peace Of Mind
Back in 2020, most airlines introduced policies to make travel during COVID-19 as easy as possible. The worst of the pandemic is now over, but some of these policies remain in place for you to take advantage of as you fly between Boston Logan International-Chicago and other routes.
- Find flexible getaways. Some airlines introduced flexible booking policies in 2020 and many of these are still available. If you book a flexible plane ticket from Boston Logan International to Chicago, it means your money is still safe if your flights are changed or cancelled due to COVID-19.
- Stay in the know. From testing to entry requirements, make sure youve read up on what travel restrictions apply for Chicago before your flight. Well even keep you updated in real-time via email if youd prefer.
Where To Buy Cheap Flights From Boston To Chicago
The best way to find a great deal on airfare is to search multiple sites. When you run a search on FareCompare, we search multiple sites and fare sources all at once so you don’t have to – which is why we think FareCompare is the best place to find cheap tickets. Airlines can adjust prices for tickets from Boston to Chicago based on the day and time that you decide to book your flight. We have collected data from all airlines, and have found that Tuesdays, Wednesdays, and Saturdays are often the best days to book flights. If you’d like to learn more, read our article about the best time to buy airline tickets.
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How To Find Cheap Flights From Boston Logan International To Chicago
Looking for cheap flight tickets from Boston Logan International to Chicago? Skyscanner compares flight prices across more than 1,200 airlines and travel providers.
Regardless of whether you’re looking for a one-way ticket from Boston Logan International to Chicago or a return flight, here are some tips to secure the best flight price and make planning your journey as smooth as possible.
Boston To Chicago Flight Time Distance Route Map

Flight time from Boston, United States to Chicago, United States is 1 hours 41 minutes under avarage conditions. Our flight time calculator assumes an average flight speed for a commercial airliner of 500 mph, which is equivalent to 805 km/hr or 434 knots. Actual flight times may vary depending on aircraft type, cruise speed, routing, weather conditions, passenger load, and other factors.
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United Airlines Flight Schedule From Chicago To Boston
All weekly departures with United Airlines. The week calendar shows every flight departure from Chicago to Boston . Click on a blue date to see a list of flights.
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Flights From Boston To Chicago
Staying on budget when planning a trip can be a challenge, but Orbitz.com makes it a little easier. You will discover cheap flights from Boston to Chicago as well as discount ground transportation and accommodations. Chicago is home to more than 2.7 million people, making it the third-largest city in the United States.
Boston Information
When you leave Boston, you will depart from the Logan International Airport, which is located on the east side of Boston. It is host to several airlines, including Delta, Spirit, American, JetBlue, US Airways, and AirTran. All these airlines provide air service to Chicago, and their best rates can be found on Orbitz.com. The most convenient public transportation option for getting to the airport is the T Bus, which costs $2 from downtown. Numerous taxi companies are readily available, and their rates range from $25 to $35 from downtown.
Abundant parking spaces are available at the airport, including short-term, long-term, and economy parking. Economy has the cheapest rate of $18 per day, and regular parking will cost about $27 daily. Whether you want a quick snack or a full meal, you will discover a variety of restaurants and menu items inside the terminals. Johnny Rockets, Ozone, Boston Beer Works, and Asian Too are a few of your options, and you’ll find pizzas, burgers, and more.
Chicago Information
Start Planning Your Trip to Chicago
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What Are The Cheapest Airlines Flying From Boston To Chicago Round
Our cheapest airline available from Boston to Chicago is American Airlines. Our recent data shows that you can find tickets from as low as $141 on this airline. Additional options worth looking into are JetBlue and United Airlines, starting at $147 and $148 round-trip. You may be able to fly from Boston to Chicago for 35% less than the average price by searching for these airlines.
Overview: Boston To Chicago Flight
Distance | |
Airlines | Spirit Airlines, JetBlue Airways, Delta Air Lines, American Airlines, Southwest Airlines or United |
Flights from Boston to Chicago cover the 848 miles long journey taking on average 3 h with our travel partners like Spirit Airlines, JetBlue Airways, Delta Air Lines, American Airlines, Southwest Airlines or United. There are direct flight services available. While the average ticket price for this trip costs around $96 , you can find the cheapest plane ticket for as low as $75 .
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Flying Time From Boston Ma To Chicago Il
The total flight duration from Boston, MA to Chicago, IL is 2 hours, 12 minutes.
This is the average in-air flight time based onactual flights taken over the past year, including routes like BOS to MDW.It covers the entire time on a typical commercial flight includingtake-off and landing.
If you’re planning a trip, you should also factorin extra time for the plane to pull back from the gate and taxi tothe runway, as well as reaching the destination gate after landing.If you include this extra time on the tarmac, the average totalelapsed time from gate to gate flying from Boston, MA to Chicago, IL is 2 hours, 33 minutes.
Finally, pilots might want to estimate the flight timeusing an average flight speed for a commercial airliner of 500 mph,which is equivalent to 805 km/h or 434 knots. If you don’t add anyextra time to increase or decrease speed for take-off and landing,then at constant speed your flight time would be 1 hour, 42 minutes.
If you’re booking a flight, make sure you check thescheduled departure and arrival times. You should also factor inairport wait times and possible equipment or weather delays.If you’re trying to figure out what time you’ll arriveat the destination, you may want to see if there’s atime difference between Boston, MA and Chicago, IL.
The calculation of flight time is based on thestraight line distance from Boston, MA to Chicago, IL , which is about 851 miles or 1369 kilometers.
Your flight direction from Boston, MA to Chicago, IL is West .
Book Flights From Boston Logan International To Chicago With Peace Of Mind
- Find flexible flights. Your airline might be offering flexible flight tickets from Boston Logan International to Chicago , which means you won’t lose out if your trip has to be changed or canceled.
- Add travel cost protection. Avoid travel pitfalls and choose travel cost protection – it’s available at the checkout as you book your Boston Logan International-Chicago flight with us.
- Reduce your carbon footprint by selecting a greener flight option. To check whether there are any lower emissions plane tickets available when flying from Boston Logan International to Chicago , simply check the only show flights with lower CO emissions box later on in your search.
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Massdot Sumner Tunnel Weekend Closures
The Sumner Tunnel, one of two tunnels from Logan to Boston, will be closed weekends from 11pm Fridays to 5am Mondays while MassDOT completes restoration work, excluding holidays. Allow extra time to get to and from the airport. For more information on the project and detours, please visit MassDOT. For information on ways to get to Boston Logan, .
Boston To Chicago Flight Schedule

Scan through flights from Logan International Airport to O’Hare International Airport for the upcoming week. Sort the list by any column, and click on a dollar sign to see the latest prices available for each flight.
Flights.com only offers pricing for airlines that display a check fare on the days of the week each flight is available. A dot indicates a flight is scheduled, but online booking is not currently available.
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Jetblue Airways Flight Schedule From Chicago To Boston
All weekly departures with JetBlue Airways. The week calendar shows every flight departure from Chicago to Boston . Click on a blue date to see a list of flights.
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