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$96+ 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 7/28. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
Aug 10 — Aug 171
Mon 8/10
Mon 8/17
1 adult, Economy
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Find cheap flights from Boston to Chicago with Cheapflights

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Cheapflights Tip: The best prices from Boston Logan Intl to Chicago are usually found in January or September, booked 90 days in advance, depart on a Friday or Thursday and return on a Saturday

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 July 11, 2026.

This Southwest deal was found by Cheapflights users on 7/10. 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 10/16:45 pm
BOS
-
MDW
1 stop5h 20m
Southwest
Mon 10/52:50 pm
MDW
-
BOS
2 stops5h 30m
Southwest
Deal found 7/10$162
This Southwest deal was found by Cheapflights users on 7/8. 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 8/136:40 pm
BOS
-
MDW
Nonstop2h 40m
Southwest
Mon 8/175:55 am
MDW
-
BOS
1 stop6h 40m
Southwest
Deal found 7/8$163
This Cheapflightsfares deal was found by Cheapflights users on 7/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:15 am
BOS
-
ORD
Nonstop2h 56m
JetBlue
Sun 8/308:20 pm
ORD
-
BOS
Nonstop2h 31m
JetBlue
Deal found 7/10$163
This Southwest deal was found by Cheapflights users on 7/9. 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.
Wed 8/127:30 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Tue 8/2511:55 am
MDW
-
BOS
2 stops5h 40m
Southwest
Deal found 7/9$164
This United Airlines deal was found by Cheapflights users on 7/9. 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.
Sat 8/157:05 am
BOS
-
ORD
Nonstop2h 59m
United Airlines
Sun 8/169:40 pm
ORD
-
BOS
Nonstop2h 31m
United Airlines
Deal found 7/9$164
This Southwest deal was found by Cheapflights users on 7/8. 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.
Fri 8/216:40 pm
BOS
-
MDW
Nonstop2h 40m
Southwest
Sun 8/236:00 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Deal found 7/8$165
This United Airlines deal was found by Cheapflights users on 7/8. 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 8/147:05 am
BOS
-
ORD
Nonstop2h 59m
United Airlines
Sun 8/169:40 pm
ORD
-
BOS
Nonstop2h 31m
United Airlines
Deal found 7/8$165
This Southwest deal was found by Cheapflights users on 7/10. 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 8/245:25 am
BOS
-
MDW
1 stop6h 35m
Southwest
Mon 8/317:55 am
MDW
-
BOS
2 stops7h 15m
Southwest
Deal found 7/10$166
This Delta deal was found by Cheapflights users on 7/8. 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.
Tue 7/288:45 pm
BOS
-
ORD
Nonstop2h 54m
Delta
Wed 8/57:30 pm
ORD
-
BOS
Nonstop2h 30m
Delta
Deal found 7/8$166
This Southwest deal was found by Cheapflights users on 7/9. 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 8/185:25 am
BOS
-
MDW
1 stop4h 35m
Southwest
Tue 8/252:00 pm
MDW
-
BOS
2 stops7h 10m
Southwest
Deal found 7/9$167
This Southwest deal was found by Cheapflights users on 7/9. 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 8/248:20 pm
BOS
-
MDW
Nonstop2h 40m
Southwest
Wed 8/2611:55 am
MDW
-
BOS
2 stops5h 40m
Southwest
Deal found 7/9$168
This United Airlines deal was found by Cheapflights users on 7/8. 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 8/56:00 am
BOS
-
ORD
Nonstop2h 58m
United Airlines
Tue 8/1112:16 pm
ORD
-
BOS
1 stop4h 36m
United Airlines
Deal found 7/8$168

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 July 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$162
(Southwest)

One-way from

$96
(Southwest)

Popular in

June

Cheapest in

January

Average price

$240

Good round-trip deal

$237 or less

Good one-way deal

$139 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. 7% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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 July 11, 2026.
Use the filters below to find and compare flights from Boston to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 8/11

7:15 pm-8:50 pm

Nonstop2h 35m

Chicago Midway

Mon 8/17

3:20 pm-10:20 pm

1 stop6h 00m

$163

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 8/21

6:40 pm-8:20 pm

Nonstop2h 40m

Chicago Midway

Sun 8/23

6:00 am-9:15 am

Nonstop2h 15m

$165

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 9/8

7:30 am-9:24 am

Nonstop2h 54m

Chicago O'Hare Intl

Thu 9/17

7:35 am-11:08 am

Nonstop2h 33m

$169

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 9/12

5:45 am-9:38 am

1 stop4h 53m

Chicago O'Hare Intl

Mon 9/14

9:40 pm-1:10 am

Nonstop2h 30m

$169

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 9/4

8:05 am-10:04 am

Nonstop2h 59m

Chicago O'Hare Intl

Fri 9/4

7:59 pm-11:34 pm

Nonstop2h 35m

$170

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 8/22

11:05 am-12:59 pm

Nonstop2h 54m

Chicago O'Hare Intl

Mon 8/24

9:40 am-6:27 pm

1 stop7h 47m

$171

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 9/8

8:10 am-10:06 am

Nonstop2h 56m

Chicago O'Hare Intl

Tue 9/15

1:00 pm-8:49 pm

1 stop6h 49m

$171

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 8/24

5:25 am-11:00 am

1 stop6h 35m

Chicago Midway

Mon 8/24

2:35 pm-10:10 pm

2 stops6h 35m

$178

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 9/5

6:42 pm-8:40 pm

Nonstop2h 58m

Chicago O'Hare Intl

Mon 9/7

6:15 am-9:36 am

Nonstop2h 21m

$183

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 8/1

7:19 am-9:17 am

Nonstop2h 58m

Chicago O'Hare Intl

Mon 8/31

1:55 pm-5:36 pm

Nonstop2h 41m

$183

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/7

Showing 1-10 of 56 resultsSorted by cheapest first
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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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
Trip.comPrice Accuracy1 starTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust 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 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.

Cheapflights Insights

Everything you need to know about your flight from Boston to Chicago

What is the cheapest month to book a flight from Boston to Chicago?

Currently, February is the cheapest month in which you can book a flight from Boston to Chicago (average of $202). Flying from Boston to Chicago in July is currently the most expensive (average of $292). 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 July 11, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 22% on flights from Boston to Chicago by exploring options for tickets in the evening.

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 July 11, 2026.

The most flights from BOS to CHI are scheduled on a Friday (79 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 on average).

How much does it cost to fly round-trip from Boston to Chicago?

How often are flights from Boston to Chicago delayed?

About 15% of weekly flights between Boston and Chicago have experienced delays in the past year, with the average delay time being 173 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?

Wednesday tends to have the lowest number of delays on this route, whereas Sunday 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, United Airlines have had the lowest number of delays on this route, with just 11% of flights being delayed.

How far ahead should I book a flight from Boston to Chicago?

The best time to book flights from Boston to Chicago is 77 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 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 July 4, 2026.

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

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
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

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

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 July 11, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited 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
7.9
Good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
7.9
Good
4,248 reviews
Southwest
7.9
Good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Delta
7.8
Good
8,458 reviews
Southwest
7.9
Good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
9,978 reviews
Southwest
7.9
Good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,805 reviews
Southwest
7.9
Good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
JetBlue
7.1
Good
3,014 reviews
Southwest
7.9
Good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

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 62 daily outbound flights to Chicago from 5 different airlines.

  • How long is the flight from Boston to Chicago?

    For as low as $163, Southwest can have you in Chicago from Boston in 2h 35m. 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 United Airlines, starting at $88 and $125 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 United Airlines, which is currently one of the cheapest options available, starting at $63. American Airlines flights start at $65 while deals on JetBlue start at $66 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: Japan Airlines (93%), Cathay Pacific (89%), Royal Jordanian (86%).

  • What are the cheapest flights from Boston to Chicago?

    The cheapest flight price from Boston to Chicago is $97. On average you can expect to pay $775. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $136.

  • 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, February is the cheapest month in which you can book a flight from Boston to Chicago (average of $202). Flying from Boston to Chicago in July is currently the most expensive (average of $292). 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
Benton Harbor
Hammond
Lansing
Merrillville
Valparaiso
Porter

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Top 5 airlines flying from Boston to Chicago

Discover the top 5 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 July 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$68Average$185FlexibilityNo cancel feeOn-time62%
DeltaCheapest$88Average$323FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$125Average$274FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$134Average$219FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$137Average$266FlexibilityNo cancel feeOn-time71%

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