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$68+ 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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
Aug 26 — Sep 21
Tue 8/26
Tue 9/2
1 adult, Economy
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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 Friday or Wednesday and return on a Thursday

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 August 21, 2025.

Round-trip from

$132
(Southwest)

One-way from

$68
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$223

Good round-trip deal

$194 or less

Good one-way deal

$146 or less
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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Highest demand for flights based on searches. 8% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Boston Logan Intl to Chicago (CHI).
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Price to beat on a 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 August 21, 2025.

This Southwest deal was found by Cheapflights users on 8/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/185:35 amBOS - MDW
1 stop4h 25mSouthwest
Mon 9/227:15 amMDW - BOS
1 stop8h 10mSouthwest
Deal found 8/18$132
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/17:20 amBOS - ORD
Nonstop2h 56mDelta
Wed 9/36:00 pmORD - BOS
Nonstop2h 38mDelta
Deal found 8/21$132
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Wed 9/1712:20 pmBOS - ORD
1 stop10h 38mSpirit Airlines
Wed 9/2411:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Deal found 8/19$135
This Cheapflightsfares deal was found by Cheapflights users on 8/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/86:10 amBOS - ORD
1 stop12h 29mSpirit Airlines
Tue 9/911:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Deal found 8/19$136
This Southwest deal was found by Cheapflights users on 8/20. 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.
Thu 9/1812:15 pmBOS - MDW
Nonstop2h 35mSouthwest
Sun 9/218:35 pmMDW - BOS
Nonstop2h 20mSouthwest
Deal found 8/20$137
This JetBlue deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/245:35 pmBOS - ORD
Nonstop3h 15mJetBlue
Thu 11/2712:28 pmORD - BOS
Nonstop2h 26mJetBlue
Deal found 8/21$137
This Southwest deal was found by Cheapflights users on 8/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/225:35 amBOS - MDW
2 stops8h 35mSouthwest
Wed 9/246:25 amMDW - BOS
1 stop8h 00mSouthwest
Deal found 8/18$138
This Kissandfly.com deal was found by Cheapflights users on 8/19. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/47:00 amBOS - ORD
Nonstop2h 56mJetBlue
Sun 9/76:30 amORD - BOS
Nonstop2h 26mJetBlue
Deal found 8/19$138
This Justfly.com deal was found by Cheapflights users on 8/19. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/78:47 amBOS - ORD
1 stop9h 04mMultiple Airlines
Wed 9/1011:57 amORD - BOS
1 stop11h 00mMultiple Airlines
Deal found 8/19$142
This Southwest deal was found by Cheapflights users on 8/20. 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.
Wed 12/35:35 pmBOS - MDW
1 stop4h 30mSouthwest
Sun 12/77:15 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 8/20$143
This Mytrip deal was found by Cheapflights users on 8/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/163:00 pmBOS - ORD
1 stop8h 48mSpirit Airlines
Wed 9/175:05 amORD - BOS
1 stop17h 52mSpirit Airlines
Deal found 8/20$145
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Wed 9/173:00 pmBOS - ORD
1 stop8h 48mSpirit Airlines
Sat 9/2011:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Deal found 8/19$146

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 August 21, 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 - MDW

BOSMDW

Boston Logan Intl

Thu 9/18

5:35 am-9:00 am

1 stop4h 25m

Chicago Midway

Mon 9/22

7:15 am-4:25 pm

1 stop8h 10m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/4

7:20 am-9:15 am

Nonstop2h 55m

Chicago O'Hare Intl

Sun 9/7

7:00 am-10:30 am

Nonstop2h 30m

$132

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 10/7

7:50 am-2:25 pm

1 stop7h 35m

Chicago Midway

Sun 10/12

6:05 am-9:20 am

Nonstop2h 15m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 9/1

7:20 am-9:16 am

Nonstop2h 56m

Chicago O'Hare Intl

Wed 9/3

6:00 pm-9:38 pm

Nonstop2h 38m

$132

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 9/22

5:35 am-9:00 am

1 stop4h 25m

Chicago Midway

Wed 9/24

6:25 am-3:25 pm

1 stop8h 00m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 10/17

5:35 am-12:45 pm

1 stop8h 10m

Chicago O'Hare Intl

Sat 10/18

1:30 pm-6:50 pm

1 stop4h 20m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 10/9

7:00 am-8:57 am

Nonstop2h 57m

Chicago O'Hare Intl

Sun 10/12

9:42 am-1:10 pm

Nonstop2h 28m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 8/28

6:00 am-7:55 am

Nonstop2h 55m

Chicago O'Hare Intl

Sun 8/31

5:36 pm-9:12 pm

Nonstop2h 36m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 10/25

5:20 am-7:00 am

Nonstop2h 40m

Chicago Midway

Wed 10/29

6:05 am-9:20 am

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 10/3

9:35 pm-11:15 pm

Nonstop2h 40m

Chicago Midway

Mon 10/6

9:20 pm-12:40 am

Nonstop2h 20m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 51 results
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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
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
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
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
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
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
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

Daniel Scheffler

Daniel Scheffler

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

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

Ramsey Qubein

Ramsey Qubein

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

Read more
Paul Rubio

Paul Rubio

Expert on BOS

Paul Rubio

Paul Rubio

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

Read more

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 August 8, 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, 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 August 21, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 23% 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 August 17, 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 August 21, 2025.

The most flights from BOS to CHI are scheduled on a Thursday (81 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (24 on average).

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

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.

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 August 21, 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
4,245 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,930 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,916 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 56 daily outbound flights to Chicago from 7 different airlines.

  • How long is the flight from Boston to Chicago?

    For as low as $132, Southwest can have you in Chicago from Boston in 2h 55m. Airlines will cover a distance of 864 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 Spirit Airlines. Our recent data shows that you can find tickets from as low as $32 on this airline. Additional options worth looking into are JetBlue and United Airlines, starting at $77 and $97 round-trip. You may be able to fly from Boston to Chicago for 86% less than the average price by searching for these airlines.

  • 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: Icelandair (91%), TAP AIR PORTUGAL (90%), Avianca (89%).

  • What are the cheapest flights from Boston to Chicago?

    The cheapest flight price from Boston to Chicago is $68. On average you can expect to pay $694. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $107.

  • 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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.
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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 2,558,603 searches. Data last updated August 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$32Average$173FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$77Average$204FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$97Average$235FlexibilityNo cancel feeOn-time69%
DeltaCheapest$99Average$295FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$100Average$107FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$120Average$228FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$137Average$254FlexibilityNo cancel feeOn-time71%

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