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$79+ 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
Dec 28 — Jan 41
Sat 12/28
Sat 1/4
1 adult, Economy
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Find cheap flights from Boston to Chicago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
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The best prices from Boston Logan Intl to Chicago are usually found in September or January, booked 23 days in advance, depart on a Tuesday or Saturday and return on a Wednesday

Cheap flight deals from Boston to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 23, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$137
(Frontier)

One-way from

$79
(Southwest)

Popular in

April

Cheapest in

September

Average price

$266
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
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From Boston Logan Intl to Chicago (CHI)
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One-way flight from Boston Logan Intl to Chicago (CHI)
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High demand for flights, 14% potential price rise
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Best time to find cheap flights, 2% potential price drop
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Average for round-trip flights in December 2024
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Find flight deals from Boston to Chicago

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 December 23, 2024.

This Frontier deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/3011:10 amBOS - MDW
1 stop10h 54mFrontier
Mon 1/62:20 pmMDW - BOS
1 stop9h 21mFrontier
Deal found 12/22$178
This FlightHub deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/286:27 amBOS - ORD
1 stop13h 52mMultiple Airlines
Mon 1/64:28 pmORD - BOS
1 stop7h 13mMultiple Airlines
Deal found 12/22$205
This American Airlines deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/305:55 pmBOS - ORD
1 stop6h 03mAmerican Airlines
Tue 1/76:45 pmORD - BOS
Nonstop2h 27mAmerican Airlines
Deal found 12/22$222
This FlightHub deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/245:00 amBOS - ORD
1 stop12h 06mSpirit Airlines
Mon 1/68:14 pmORD - BOS
1 stop12h 44mSpirit Airlines
Deal found 12/22$233
This Frontier deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/315:45 amBOS - ORD
1 stop11h 43mFrontier
Mon 1/64:28 pmORD - BOS
1 stop7h 13mFrontier
Deal found 12/22$238
This JetBlue deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/316:00 amBOS - ORD
Nonstop3h 07mJetBlue
Sun 1/58:42 amORD - BOS
Nonstop2h 29mJetBlue
Deal found 12/22$247
This Delta deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/305:25 amBOS - ORD
1 stop4h 56mDelta
Mon 1/66:25 pmORD - BOS
Nonstop2h 43mDelta
Deal found 12/22$263
This United Airlines deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/316:02 amBOS - ORD
Nonstop3h 03mUnited Airlines
Mon 1/610:51 amORD - BOS
1 stop6h 37mUnited Airlines
Deal found 12/22$274
This Southwest deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/268:00 pmBOS - MDW
Nonstop2h 45mSouthwest
Sun 1/56:25 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 12/22$314
This Southwest deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/305:25 amBOS - ORD
1 stop9h 35mSouthwest
Fri 1/311:25 amORD - BOS
2 stops6h 40mSouthwest
Deal found 12/22$341
This Delta deal was found by Cheapflights users on 12/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/256:55 amBOS - MDW
1 stop8h 39mDelta
Fri 12/275:04 pmMDW - BOS
1 stop5h 55mDelta
Deal found 12/23$366
This eDestinos deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/226:45 amBOS - MDW
3 stops39h 24mMultiple Airlines
Thu 12/267:17 amMDW - BOS
1 stop24h 08mMultiple Airlines
Deal found 12/21$1,704

Find flights from Boston to Chicago within your budget

Customize your flight search to find flights from Boston to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 23, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 1/17

12:56 pm-12:54 am

1 stop12h 58m

Chicago Midway

Fri 1/24

3:37 pm-12:27 am

1 stop7h 50m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/24

11:46 am-8:45 pm

1 stop9h 59m

Chicago O'Hare Intl

Tue 1/28

2:59 pm-12:39 am

1 stop8h 40m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 2/20

4:50 pm-11:58 pm

1 stop8h 08m

Chicago O'Hare Intl

Tue 2/25

3:14 pm-12:44 am

1 stop8h 30m

$140

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/29

6:25 am-4:10 pm

1 stop10h 45m

Chicago O'Hare Intl

Sat 2/1

12:25 pm-10:00 pm

1 stop8h 35m

$143

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/18

3:52 pm-5:59 pm

Nonstop3h 07m

Chicago O'Hare Intl

Tue 1/21

7:00 am-10:15 am

Nonstop2h 15m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 1/16

7:00 am-8:55 am

Nonstop2h 55m

Chicago Midway

Tue 1/21

10:05 am-1:20 pm

Nonstop2h 15m

$158

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/18

6:00 am-8:08 am

Nonstop3h 08m

Chicago O'Hare Intl

Sun 1/19

6:30 am-10:03 am

Nonstop2h 33m

$159

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 2/25

9:20 am-11:22 am

Nonstop3h 02m

Chicago O'Hare Intl

Sun 3/2

7:30 am-10:49 am

Nonstop2h 19m

$177

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 1/18

3:50 pm-11:29 pm

1 stop8h 39m

Chicago Midway

Sun 1/19

8:45 am-5:59 pm

1 stop8h 14m

$199

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 4/16

7:00 am-9:01 am

Nonstop3h 01m

Chicago O'Hare Intl

Thu 4/24

6:30 am-9:56 am

Nonstop2h 26m

$223

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 28 results
1
2
3

Compare providers for flights from Boston to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Boston to Chicago in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 star
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy2 starsTrust Score*2 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
FareScanPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Boston-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Boston-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Boston-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Boston-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

The best insider tips for Boston to Chicago flights

Find out what our experts recommend to make the most of your Boston to Chicago trip
Airlines
American Airlines

American Airlines offers Main Cabin Extra seats with more legroom for added comfort.


Flagship Business class includes priority boarding and lounge access for a seamless experience.

Read more about American Airlinesby Marisa Garcia
United Airlines

United Economy Plus offers extra legroom seats for a more comfortable journey.


United's Polaris Business Class features lie-flat seats and upscale amenities.

Read more about United Airlinesby Harriet Baskas
Delta

Delta offers free Wi-Fi for SkyMiles members, enhancing productivity during flights.


Delta Comfort Plus provides extra legroom and earlier boarding for added convenience.

Read more about Deltaby Harriet Baskas
JetBlue

JetBlue offers free onboard Wi-Fi and seatback screens for entertainment.


Even More Space seats provide up to 38 inches of legroom for added comfort.

Read more about JetBlueby Blane Bachelor
Spirit Airlines

Spirit's Big Front Seats offer 11 inches more legroom for a comfortable ride.


Spirit's self-service bag drop saves time at the airport.

Read more about Spirit Airlinesby Daniel Scheffler
Airports
BOS

Use the FlyLogan App to pre-order food and save time at BOS. Most restaurants participate, ensuring your meal is ready for pick-up.

Read more about BOSby Paul Rubio
ORD

Use the free shuttle train at ORD to navigate between terminals. It's essential for connecting flights, especially from Terminal 5.

Read more about ORDby Ramsey Qubein
MDW

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

Read more about MDWby Ramsey Qubein
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on American Airlines

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Harriet Baskas

Harriet Baskas

Expert on United Airlines and Delta

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Blane Bachelor

Blane Bachelor

Expert on JetBlue

Blane Bachelor

Blane Bachelor

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

Daniel Scheffler

Daniel Scheffler

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Paul Rubio

Paul Rubio

Expert on BOS

Paul Rubio

Paul Rubio

Travel journalist and photographer Paul Rubio is a Miami native (and current resident), who has lived in nine countries and traveled to 137. He is an expert in luxury travel, eco-travel, loyalty programs, hotels, airports and airlines. He is a contributing editor at AFAR, Condé Nast Traveler, LUXURY Magazine, and Palm Beach Illustrated.

Read more

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.

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.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Boston to Chicago

Get recent, data-driven insights about flights from Boston to Chicago including ideal travel times, pricing trends, and more.

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 December 20, 2024.

The best time to book flights from Boston to Chicago is 23 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 $317). 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 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 December 23, 2024.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 15% on flights from Boston to Chicago by exploring options for tickets in the evening.

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 December 16, 2024.

Travelers seeking maximum savings on their Boston to Chicago flight should consider departing on Saturday 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

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 December 23, 2024.

The most flights from BOS to CHI are scheduled on a Monday (53 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (12 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

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.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

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).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated December 23, 2024.
See what other customers who have flown with United Airlines, Southwest and Spirit Airlines from Boston to Chicago have to say. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,780 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,780 reviews
Southwest
8.1
Very good
4,780 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,549 reviews
Southwest
8.1
Very good
4,780 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,588 reviews
Southwest
8.1
Very good
4,780 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,263 reviews
Southwest
8.1
Very good
4,780 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,020 reviews
Southwest
8.1
Very good
4,780 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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?

    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 38 daily outbound flights to Chicago from 7 different airlines.

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

    Our cheapest airline available from Boston to Chicago is Frontier. Our recent data shows that you can find tickets from as low as $137 on this airline. Additional options worth looking into are Spirit Airlines and JetBlue, starting at $143 and $157 round-trip. You may be able to fly from Boston to Chicago for 44% 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 $79. Delta flights start at $79 while deals on Frontier start at $80 one-way.

  • 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 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: Avianca (98%), Japan Airlines (95%), Spirit Airlines (94%).

  • What are the cheapest flights from Boston to Chicago?

    The cheapest flight price from Boston to Chicago is $78. On average you can expect to pay $918. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $109.

  • 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.

  • 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 $317). 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.

See more FAQs

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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.
Boston to O'Hare Intl flights
Hartford to O'Hare Intl flights
Boston to Midway flights
Albany to O'Hare Intl flights
Boston to St. Louis flights
Hartford to Midway flights
Albany to Midway flights
Boston to Moline flights
Hartford to St. Louis flights
Albany to St. Louis flights
Worcester to O'Hare Intl flights
Hyannis to O'Hare Intl flights
West Tisbury to O'Hare Intl flights
Boston to Peoria flights
Hartford to Peoria flights
Hartford to Rockford flights
Hartford to Moline flights
Hartford to Bloomington flights
Boston to Rockford flights
Boston to Paducah flights
Albany to Peoria flights
Albany to Moline flights
Provincetown to O'Hare Intl flights
Albany to Champaign flights
Boston to Bloomington flights
Boston to Decatur flights
Boston to Dubuque flights
Boston to Burlington flights
Boston to Springfield flights
Hartford to Evansville flights
Albany to Springfield flights
Nantucket to O'Hare Intl flights
Boston to Evansville flights
Boston to Champaign flights
Hartford to Springfield flights
New Bedford to O'Hare Intl flights
West Tisbury to St. Louis flights
Albany to Evansville flights

Top 7 airlines flying from Boston to Chicago

Discover the top 7 airlines that operate flights from Boston to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 23, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$105FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$81Average$232FlexibilityNo cancel feeOn-time62%
DeltaCheapest$93Average$345FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$98Average$144FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$137Average$266FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$147Average$318FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$148Average$294FlexibilityNo cancel feeOn-time63%
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