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$59+ 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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
abr. 22 — abr. 291
mar. 4/22
mar. 4/29
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

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Boston Logan Intl to Chicago are usually found in September or January, booked 90 days in advance, depart on a Wednesday or Friday 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 abril 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$109
(Mytrip)

One-way from

$59
(American Airlines)

Popular in

May

Cheapest in

September

Average price

$269

Good round-trip deal

$196 or less

Good one-way deal

$114 or less
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)
Search Deals
One-way flight from Boston Logan Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a round-trip flight from Boston Logan Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Boston Logan Intl to Chicago (CHI).
Search Deals

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 abril 17, 2025.

This Mytrip deal was found by Cheapflights users on 4/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/73:49 pmBOS - ORD
1 stop8h 15mSpirit Airlines
mar. 5/135:05 amORD - BOS
1 stop8h 39mSpirit Airlines
Deal found 4/15$109
This JetBlue deal was found by Cheapflights users on 4/16. 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.
mar. 5/66:00 amBOS - ORD
Nonstop3h 00mJetBlue
mar. 5/67:31 pmORD - BOS
Nonstop2h 29mJetBlue
Deal found 4/16$117
This Southwest deal was found by Cheapflights users on 4/15. 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.
jue. 5/85:30 amBOS - MDW
1 stop4h 35mSouthwest
mar. 5/131:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Deal found 4/15$127
This Southwest deal was found by Cheapflights users on 4/16. 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.
vie. 5/25:30 amBOS - ORD
1 stop7h 20mSouthwest
mar. 5/61:50 pmORD - BOS
1 stop6h 15mSouthwest
Deal found 4/16$136
This United Airlines deal was found by Cheapflights users on 4/17. 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.
mié. 6/256:00 amBOS - ORD
Nonstop2h 58mUnited Airlines
vie. 6/279:32 pmORD - BOS
Nonstop2h 27mUnited Airlines
Deal found 4/17$138
This American Airlines deal was found by Cheapflights users on 4/15. 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.
dom. 6/15:15 amBOS - ORD
Nonstop3h 00mAmerican Airlines
vie. 6/68:40 pmORD - BOS
Nonstop2h 40mAmerican Airlines
Deal found 4/15$148
This FlightHub deal was found by Cheapflights users on 4/16. 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.
mar. 5/133:49 pmBOS - ORD
1 stop8h 15mMultiple Airlines
vie. 5/164:15 pmORD - BOS
1 stop7h 29mMultiple Airlines
Deal found 4/16$151
This Delta deal was found by Cheapflights users on 4/16. 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.
vie. 5/27:30 amBOS - ORD
Nonstop3h 00mDelta
jue. 5/87:00 amORD - BOS
Nonstop2h 25mDelta
Deal found 4/16$167
This Frontier deal was found by Cheapflights users on 4/17. 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.
mié. 5/2810:45 amBOS - MDW
1 stop12h 51mFrontier
dom. 6/19:12 pmMDW - BOS
1 stop10h 23mFrontier
Deal found 4/17$188
This Frontier deal was found by Cheapflights users on 4/16. 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.
vie. 5/212:52 pmBOS - ORD
1 stop11h 19mFrontier
sáb. 5/104:15 pmORD - BOS
1 stop7h 29mFrontier
Deal found 4/16$188
This Mytrip deal was found by Cheapflights users on 4/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/611:43 amBOS - RFD
1 stop22h 41mMultiple Airlines
dom. 6/84:06 pmRFD - BOS
2 stops30h 23mMultiple Airlines
Deal found 4/17$247
This Mytrip deal was found by Cheapflights users on 4/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/309:00 amBOS - MDW
1 stop11h 14mMultiple Airlines
lun. 6/28:04 pmMDW - BOS
2 stops26h 25mMultiple Airlines
Deal found 4/17$269

Cheapflights Fare Finder

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 abril 17, 2025.
Use the filters below to find and compare flights from Boston to Chicago that are best for you.

Fly from

Boston

Fly to

Chicago

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mié. 5/7

3:49 pm-11:04 pm

1 stop8h 15m

Chicago O'Hare Intl

mar. 5/13

5:05 am-2:44 pm

1 stop8h 39m

$109

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

mar. 5/6

2:05 pm-3:40 pm

Nonstop2h 35m

Chicago Midway

mar. 5/6

6:25 pm-9:45 pm

Nonstop2h 20m

$117

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mar. 5/6

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

mar. 5/6

7:31 pm-11:00 pm

Nonstop2h 29m

$117

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

vie. 5/2

5:30 am-11:50 am

1 stop7h 20m

Chicago O'Hare Intl

mar. 5/6

1:50 pm-9:05 pm

1 stop6h 15m

$136

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mié. 6/25

6:00 am-7:58 am

Nonstop2h 58m

Chicago O'Hare Intl

vie. 6/27

9:32 pm-12:59 am

Nonstop2h 27m

$138

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

dom. 6/1

6:35 am-8:31 am

Nonstop2h 56m

Chicago O'Hare Intl

mié. 6/4

4:40 pm-8:01 pm

Nonstop2h 21m

$148

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mar. 5/13

3:49 pm-11:04 pm

1 stop8h 15m

Chicago O'Hare Intl

vie. 5/16

4:15 pm-12:44 am

1 stop7h 29m

$151

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

vie. 5/2

7:30 am-9:30 am

Nonstop3h 00m

Chicago O'Hare Intl

jue. 5/8

7:00 am-10:25 am

Nonstop2h 25m

$167

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

mié. 5/28

10:45 am-10:36 pm

1 stop12h 51m

Chicago Midway

dom. 6/1

9:12 pm-8:35 am

1 stop10h 23m

$188

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

vie. 5/2

12:52 pm-11:11 pm

1 stop11h 19m

Chicago O'Hare Intl

sáb. 5/10

4:15 pm-12:44 am

1 stop7h 29m

$188

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Showing 1-10 of 30 results
1
2
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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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy1 starTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
FareScanPrice Accuracy-Trust Score*3 stars

*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 eDreams the most. eDreams 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

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

United's Economy Plus offers extra legroom, perfect for comfort on short flights.


United's MileagePlus program allows pooling miles, useful for frequent flyers.

Read more about United Airlinesby Harriet Baskas
Spirit Airlines

Spirit's Big Front Seats offer 11 extra inches of legroom, ideal for short flights.


Spirit's self-service bag drop saves time; print your boarding pass in advance to avoid fees.

Read more about Spirit Airlinesby Daniel Scheffler
Southwest

Southwest offers two free checked bags, including oversized items like skis or golf clubs.


Southwest's Early Bird check-in provides priority boarding, ideal for business travelers.

Read more about Southwestby Marisa Garcia
Airports
BOS

Use the FlyLogan App to pre-order food and save time at BOS. Most eateries participate, making it a convenient option.

Read more about BOSby Paul Rubio
ORD

For a quick city transfer, use the 'L' train from ORD to downtown Chicago. It's often faster than driving.

Read more about ORDby Ramsey Qubein
MDW

Take the Orange Line train from MDW to reach downtown Chicago in less than 30 minutes. It's a cost-effective option.

Read more about MDWby Ramsey Qubein
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

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
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
Marisa Garcia

Marisa Garcia

Expert on Southwest

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
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

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.

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 April 11, 2025.

The best time to book flights from Boston to Chicago is 49 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 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 abril 17, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 29% 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 March 30, 2025.

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

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 abril 17, 2025.

The most flights from BOS to CHI are scheduled on a Monday (60 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (20 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 abril 17, 2025.
See what other customers who have flown with Alaska Airlines, Southwest and Delta 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.
Alaska Airlines
8.0
Very good
9,882 reviews

Boarding

8.2

Overall

8.0

Food

7.1

Crew

8.5

Comfort

7.9

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,882 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Boarding

8.2

Overall

8.0

Food

7.1

Crew

8.5

Comfort

7.9

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,280 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Boarding

8.2

Overall

8.0

Food

7.1

Crew

8.5

Comfort

7.9

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,917 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Boarding

8.2

Overall

8.0

Food

7.1

Crew

8.5

Comfort

7.9

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,667 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Boarding

8.2

Overall

8.0

Food

7.1

Crew

8.5

Comfort

7.9

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
JetBlue
7.3
Good
2,926 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Boarding

8.2

Overall

8.0

Food

7.1

Crew

8.5

Comfort

7.9

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 46 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 Spirit Airlines. Our recent data shows that you can find tickets from as low as $109 on this airline. Additional options worth looking into are Southwest and JetBlue, starting at $117 and $117 round-trip. You may be able to fly from Boston to Chicago for 54% 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 American Airlines, which is currently one of the cheapest options available, starting at $59. United Airlines flights start at $64 while deals on Southwest start at $68 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 (91%), ANA (89%), United Airlines (87%).

  • What are the cheapest flights from Boston to Chicago?

    The cheapest flight price from Boston to Chicago is $55. On average you can expect to pay $596. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $117.

  • 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 $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.

See more FAQs

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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
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Hyannis to O'Hare Intl flights
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Boston to Bloomington flights
Boston to Paducah flights
Hartford to Springfield flights
Albany to Evansville flights
Boston to Dubuque flights
Boston to Decatur flights
Albany to Springfield flights
Albany to Moline flights
Nantucket to O'Hare Intl flights
Provincetown to O'Hare Intl flights
West Tisbury to St. Louis flights
New Bedford to O'Hare Intl flights
Boston to Burlington 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 abril 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$104FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$84Average$225FlexibilityNo cancel feeOn-time62%
DeltaCheapest$93Average$327FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$97Average$268FlexibilityNo cancel feeOn-time69%
FrontierCheapest$99Average$151FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$140Average$263FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$141Average$317FlexibilityNo cancel feeOn-time63%

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