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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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
nov. 25 — dic. 21
lun. 11/25
lun. 12/2
1 adult, Economy
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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 Wednesday 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 noviembre 20, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

April

Cheapest in

September

Round-trip from

$124
(CheapOair)

One-way from

$79
(Southwest)
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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High demand for flights, 19% potential price rise
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Best time to find cheap flights, 24% potential price drop
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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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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 noviembre 20, 2024.

This CheapOair deal was found by Cheapflights users on 11/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/116:00 amBOS - MDW
1 stop6h 42mFrontier
vie. 12/137:00 amMDW - BOS
1 stop16h 30mFrontier
Deal found 11/19$124
This CheapOair deal was found by Cheapflights users on 11/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/116:00 amBOS - ORD
1 stop27h 24mFrontier
dom. 12/159:35 amORD - BOS
1 stop13h 55mFrontier
Deal found 11/18$124
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/105:00 amBOS - ORD
1 stop12h 06mMultiple Airlines
vie. 12/1310:59 amORD - BOS
1 stop12h 31mMultiple Airlines
Deal found 11/19$129
This Expedia deal was found by Cheapflights users on 11/19. 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.
sáb. 12/75:00 amBOS - ORD
1 stop12h 06mSpirit Airlines
mar. 12/109:58 amORD - BOS
1 stop13h 40mSpirit Airlines
Deal found 11/19$134
This JetBlue deal was found by Cheapflights users on 11/20. 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.
vie. 12/66:00 amBOS - ORD
Nonstop3h 06mJetBlue
mié. 12/118:51 amORD - BOS
Nonstop2h 22mJetBlue
Deal found 11/20$157
This Southwest deal was found by Cheapflights users on 11/20. 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.
mié. 12/47:00 amBOS - MDW
Nonstop2h 45mSouthwest
vie. 12/66:25 pmMDW - BOS
Nonstop2h 10mSouthwest
Deal found 11/20$158
This American Airlines deal was found by Cheapflights users on 11/20. 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.
vie. 12/136:47 amBOS - ORD
Nonstop3h 05mAmerican Airlines
jue. 1/27:19 amORD - BOS
Nonstop2h 31mAmerican Airlines
Deal found 11/20$182
This United Airlines deal was found by Cheapflights users on 11/20. 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. 12/187:38 pmBOS - ORD
1 stop4h 42mUnited Airlines
mié. 12/259:30 pmORD - BOS
Nonstop2h 24mUnited Airlines
Deal found 11/20$183
This Delta deal was found by Cheapflights users on 11/19. 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.
dom. 12/297:40 pmBOS - ORD
Nonstop3h 01mDelta
vie. 1/37:35 amORD - BOS
Nonstop2h 28mDelta
Deal found 11/19$223
This Mytrip deal was found by Cheapflights users on 11/19. 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. 12/65:05 amBOS - RFD
1 stop13h 05mMultiple Airlines
dom. 12/84:11 pmRFD - BOS
1 stop17h 30mMultiple Airlines
Deal found 11/19$246
This Delta deal was found by Cheapflights users on 11/19. 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.
dom. 12/85:20 amBOS - MDW
1 stop4h 38mDelta
vie. 12/135:50 pmMDW - BOS
1 stop4h 57mDelta
Deal found 11/19$316
This Mytrip deal was found by Cheapflights users on 11/18. 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.
dom. 11/2410:22 amBOS - RFD
2 stops22h 29mAllegiant Air
sáb. 11/306:39 pmRFD - BOS
1 stop15h 56mAllegiant Air
Deal found 11/18$987

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 2,629,791 searches. Data last updated noviembre 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

mié. 12/11

6:00 am-11:42 am

1 stop6h 42m

Chicago Midway

vie. 12/13

7:00 am-12:30 am

1 stop16h 30m

$124

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mié. 12/11

6:00 am-8:24 am

1 stop27h 24m

Chicago O'Hare Intl

dom. 12/15

9:35 am-12:30 am

1 stop13h 55m

$124

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mar. 12/10

5:00 am-4:06 pm

1 stop12h 06m

Chicago O'Hare Intl

mar. 12/17

5:38 pm-12:35 am

1 stop5h 57m

$129

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

sáb. 12/7

5:00 am-4:06 pm

1 stop12h 06m

Chicago O'Hare Intl

mar. 12/10

9:58 am-12:38 am

1 stop13h 40m

$134

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

vie. 12/6

6:00 am-8:06 am

Nonstop3h 06m

Chicago O'Hare Intl

mié. 12/11

8:51 am-12:13 pm

Nonstop2h 22m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

mié. 12/4

7:00 am-8:45 am

Nonstop2h 45m

Chicago Midway

vie. 12/6

6:25 pm-9:35 pm

Nonstop2h 10m

$158

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mié. 1/1

6:02 am-8:05 am

Nonstop3h 03m

Chicago O'Hare Intl

lun. 2/3

9:10 am-3:41 pm

1 stop5h 31m

$183

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mar. 12/31

6:45 am-8:49 am

Nonstop3h 04m

Chicago O'Hare Intl

dom. 1/5

8:30 pm-12:15 am

Nonstop2h 45m

$194

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 1/2

7:40 pm-9:41 pm

Nonstop3h 01m

Chicago O'Hare Intl

dom. 1/5

7:35 am-11:03 am

Nonstop2h 28m

$199

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

jue. 2/20

5:10 am-11:58 pm

1 stop19h 48m

Chicago Midway

dom. 2/23

6:38 pm-3:05 pm

1 stop19h 27m

$204

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 28 results
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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 November.
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*3 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.

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 November 15, 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, September is the cheapest month in which you can book a flight from Boston to Chicago (average of $232). Flying from Boston to Chicago in June is currently the most expensive (average of $308). 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 noviembre 20, 2024.

Unlike at noon, when flights are generally more expensive, you can save up to 16% 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 18, 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 noviembre 20, 2024.

The most flights from BOS to CHI are scheduled on a Monday (50 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 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 noviembre 20, 2024.
See what other customers who have flown with American Airlines, Frontier 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
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,461 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

JetBlue
7.5
Good
3,394 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 39 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 $124 on this airline. Additional options worth looking into are Spirit Airlines and JetBlue, starting at $134 and $157 round-trip. You may be able to fly from Boston to Chicago for 49% 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. JetBlue 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 (100%), Japan Airlines (96%), Republic Airways (93%).

  • What are the cheapest flights from Boston to Chicago?

    The cheapest flight price from Boston to Chicago is $75. On average you can expect to pay $909. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $101.

  • 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, September is the cheapest month in which you can book a flight from Boston to Chicago (average of $232). Flying from Boston to Chicago in June is currently the most expensive (average of $308). 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.
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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 2,629,791 searches. Data last updated noviembre 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$104FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$83Average$234FlexibilityNo cancel feeOn-time62%
DeltaCheapest$94Average$346FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$98Average$134FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$135Average$266FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$145Average$234FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$147Average$312FlexibilityNo cancel feeOn-time69%
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