HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$62+ 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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

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 4, 2025.

This American Airlines deal was found by Cheapflights users on 12/3. 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.
Wed 12/315:40 pmBOS - ORD
Nonstop3h 12mAmerican Airlines
Wed 1/77:00 amORD - BOS
Nonstop2h 23mAmerican Airlines
Deal found 12/3$119
This United Airlines deal was found by Cheapflights users on 12/2. 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.
Wed 12/317:45 amBOS - ORD
Nonstop3h 04mUnited Airlines
Wed 1/77:30 amORD - BOS
Nonstop2h 22mUnited Airlines
Deal found 12/2$120
This Southwest deal was found by Cheapflights users on 12/4. 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.
Sat 12/134:45 pmBOS - MDW
Nonstop2h 45mSouthwest
Wed 12/171:30 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 12/4$127
This United Airlines deal was found by Cheapflights users on 12/4. 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.
Thu 12/116:00 amBOS - ORD
Nonstop3h 00mUnited Airlines
Sat 12/131:55 pmORD - BOS
Nonstop2h 20mUnited Airlines
Deal found 12/4$127
This American Airlines deal was found by Cheapflights users on 12/3. 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.
Sat 12/136:00 amBOS - ORD
Nonstop3h 17mAmerican Airlines
Mon 12/159:55 amORD - BOS
Nonstop2h 25mAmerican Airlines
Deal found 12/3$128
This American Airlines deal was found by Cheapflights users on 12/4. 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.
Sat 12/137:00 amBOS - ORD
Nonstop3h 32mAmerican Airlines
Wed 12/172:42 pmORD - BOS
Nonstop2h 29mAmerican Airlines
Deal found 12/4$129
This Expedia deal was found by Cheapflights users on 12/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/118:30 amBOS - ORD
Nonstop3h 05mJetBlue
Thu 12/187:41 pmORD - BOS
Nonstop2h 29mJetBlue
Deal found 12/4$132
This Southwest deal was found by Cheapflights users on 12/2. 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.
Tue 12/95:30 amBOS - MDW
Nonstop2h 45mSouthwest
Thu 12/189:35 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 12/2$137
This JetBlue deal was found by Cheapflights users on 12/4. 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.
Fri 12/125:29 pmBOS - ORD
Nonstop3h 14mJetBlue
Sun 12/217:41 pmORD - BOS
Nonstop2h 29mJetBlue
Deal found 12/4$137
This Priceline deal was found by Cheapflights users on 12/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/108:30 amBOS - ORD
Nonstop3h 05mJetBlue
Thu 12/118:38 pmORD - BOS
Nonstop2h 28mJetBlue
Deal found 12/4$142
This United Airlines deal was found by Cheapflights users on 12/2. 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.
Wed 12/317:45 amBOS - ORD
Nonstop3h 04mUnited Airlines
Sun 1/49:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/2$143
This United Airlines deal was found by Cheapflights users on 12/4. 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.
Fri 12/126:00 amBOS - ORD
Nonstop3h 00mUnited Airlines
Fri 12/126:17 pmORD - BOS
Nonstop2h 28mUnited Airlines
Deal found 12/4$144

Find 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 4, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$117
(Southwest)

One-way from

$62
(Southwest)

Popular in

April

Cheapest in

September

Average price

$241

Good round-trip deal

$196 or less

Good one-way deal

$121 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
Search Deals
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 ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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

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 December 4, 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

Fri 1/16

6:00 am-1:14 pm

1 stop8h 14m

Chicago O'Hare Intl

Mon 1/26

2:25 pm-5:54 pm

Nonstop2h 29m

$121

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 12/9

5:30 am-7:15 am

Nonstop2h 45m

Chicago Midway

Thu 12/11

6:15 pm-9:35 pm

Nonstop2h 20m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/9

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Sun 1/11

7:45 am-11:10 am

Nonstop2h 25m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 12/14

9:40 am-11:40 am

Nonstop3h 00m

Chicago O'Hare Intl

Mon 12/15

9:19 am-12:43 pm

Nonstop2h 24m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/7

7:30 am-9:41 am

Nonstop3h 11m

Chicago O'Hare Intl

Sat 1/10

6:15 am-2:08 pm

1 stop6h 53m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/9

7:55 pm-10:01 pm

Nonstop3h 06m

Chicago O'Hare Intl

Sun 1/11

7:05 am-10:40 am

Nonstop2h 35m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 1/20

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Sat 1/24

2:40 pm-8:30 pm

1 stop4h 50m

$128

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 2/24

7:00 am-9:10 am

Nonstop3h 10m

Chicago O'Hare Intl

Fri 2/27

6:04 am-2:14 pm

1 stop7h 10m

$129

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/16

6:00 am-1:14 pm

1 stop8h 14m

Chicago O'Hare Intl

Fri 1/23

2:25 pm-5:54 pm

Nonstop2h 29m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 5/7

6:00 am-7:50 am

Nonstop2h 50m

Chicago O'Hare Intl

Sun 5/10

6:00 am-9:24 am

Nonstop2h 24m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/3

Showing 1-10 of 58 results
1
2
3
...
6

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 Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
PricelinePrice Accuracy1 starTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 stars
Trip.comPrice Accuracy2 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
CheapfaremartPrice Accuracy-Trust 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 Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Boston-Chicago flight deals on Cheapflights vs. Mytrip >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 Mytrip the most. Mytrip 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.

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 November 28, 2025.

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, April is the cheapest month in which you can book a flight from Boston to Chicago (average of $89). Flying from Boston to Chicago in January is currently the most expensive (average of $121). 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 4, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 19% 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 November 29, 2025.

Travelers seeking maximum savings on their Boston to Chicago flight should consider departing on Thursday mornings 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 4, 2025.

The most flights from BOS to CHI are scheduled on a Thursday (67 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (20 on average).

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.

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?

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.

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

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.

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

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.

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

How often are flights from Boston to Chicago delayed?

About 13% of weekly flights between Boston and Chicago have experienced delays in the past year, with the average delay time being 168 minutes.

What is the most punctual flight time for Boston to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Saturday tends to have the lowest number of delays on this route, whereas Thursday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Boston to Chicago flights?

Over the last year, Spirit Airlines have had the lowest number of delays on this route, with just 3% of flights being delayed.

The best insider tips for Boston to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Boston to Chicago trip
Airports
BOS

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

Read more about BOSby Paul Rubio
ORD

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

Read more about ORDby Ramsey Qubein
MDW

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

Read more about MDWby Ramsey Qubein
Our travel experts
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

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 4, 2025.
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.
Southwest
8.0
Very good
4,250 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,250 reviews
Southwest
8.0
Very good
4,250 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,011 reviews
Southwest
8.0
Very good
4,250 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,066 reviews
Southwest
8.0
Very good
4,250 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,047 reviews
Southwest
8.0
Very good
4,250 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
JetBlue
7.2
Good
2,899 reviews
Southwest
8.0
Very good
4,250 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 49 daily outbound flights to Chicago from 6 different airlines.

  • How long is the flight from Boston to Chicago?

    For as low as $127, Delta can have you in Chicago from Boston in 2h 45m. Airlines will cover a distance of 857 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 JetBlue. Our recent data shows that you can find tickets from as low as $68 on this airline. Additional options worth looking into are Delta and Spirit Airlines, starting at $81 and $83 round-trip. You may be able to fly from Boston to Chicago for 70% 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 Spirit Airlines, which is currently one of the cheapest options available, starting at $46. Frontier flights start at $47 while deals on Southwest start at $58 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: ANA (84%), TAP AIR PORTUGAL (83%), JetBlue (81%).

  • What are the cheapest flights from Boston to Chicago?

    The cheapest flight price from Boston to Chicago is $63. On average you can expect to pay $681. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $88.

  • 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, April is the cheapest month in which you can book a flight from Boston to Chicago (average of $89). Flying from Boston to Chicago in January is currently the most expensive (average of $121). 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 Chicago?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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

Top 6 airlines flying from Boston to Chicago

Discover the top 6 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 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$76Average$190FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$83Average$308FlexibilityNo cancel feeOn-time65%
DeltaCheapest$115Average$287FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$117Average$236FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$125Average$271FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$129Average$256FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.