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$69+ Cheap flights from Chicago (CHI) to Boston (BOS)

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 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Aug 26 — Sep 21
Tue 8/26
Tue 9/2
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Boston Logan Intl are usually found in September or January, booked 73 days in advance, depart on a Thursday or Wednesday and return on a Friday

Cheap flight deals from Chicago to Boston

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Boston (BOS). 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

$127
(Southwest)

One-way from

$69
(United Airlines)

Popular in

April

Cheapest in

September

Average price

$220

Good round-trip deal

$99 or less

Good one-way deal

$98 or less
From Chicago (CHI) to Boston Logan Intl
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One-way flight from Chicago (CHI) to Boston Logan Intl
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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 ($5 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 Chicago (CHI) to Boston Logan Intl.
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Price to beat on a one-way flight from Chicago (CHI) to Boston Logan Intl.
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Find flight deals from Chicago to Boston

Cheapest flights from Chicago to Boston
Explore the most affordable flight options available from Chicago to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2025.

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.
Thu 9/47:00 amORD - BOS
Nonstop2h 30mDelta
Fri 9/57:55 pmBOS - ORD
Nonstop3h 01mDelta
Deal found 8/21$127
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 10/231:50 pmORD - BOS
1 stop6h 10mSouthwest
Mon 10/275:00 amBOS - ORD
1 stop12h 25mSouthwest
Deal found 8/20$132
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/511:25 amMDW - BOS
1 stop4h 55mSouthwest
Sun 11/96:50 amBOS - MDW
1 stop9h 50mSouthwest
Deal found 8/21$132
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/79:25 pmORD - BOS
Nonstop2h 20mUnited Airlines
Sun 11/97:30 amBOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 8/20$134
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.
Tue 9/1611:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Wed 9/246:10 amBOS - ORD
1 stop12h 29mSpirit Airlines
Deal found 8/19$135
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/511:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Wed 9/106:10 amBOS - ORD
1 stop12h 29mSpirit Airlines
Deal found 8/20$136
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/68:50 amORD - BOS
Nonstop2h 20mJetBlue
Mon 12/84:55 pmBOS - ORD
Nonstop3h 10mJetBlue
Deal found 8/20$137
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/276:55 amMDW - BOS
Nonstop2h 15mSouthwest
Wed 12/35:30 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 8/19$137
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2411:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Tue 9/3012:20 pmBOS - ORD
1 stop10h 38mSpirit Airlines
Deal found 8/21$138
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/131:50 pmMDW - BOS
1 stop8h 50mSouthwest
Sun 11/166:50 amBOS - MDW
1 stop9h 50mSouthwest
Deal found 8/19$138
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/226:00 amORD - BOS
1 stop6h 20mSpirit Airlines
Wed 10/223:00 pmBOS - ORD
1 stop9h 45mSpirit Airlines
Deal found 8/21$140
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/197:50 pmORD - BOS
Nonstop2h 35mJetBlue
Sat 9/277:00 amBOS - ORD
Nonstop2h 56mJetBlue
Deal found 8/20$142

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Boston 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 Chicago to Boston that are best for you.

Fly from

Chicago

Fly to

Boston

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 9/20

2:00 pm-5:39 pm

Nonstop2h 39m

Boston Logan Intl

Sun 9/21

7:25 am-9:15 am

Nonstop2h 50m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 9/8

1:50 pm-10:15 pm

1 stop7h 25m

Boston Logan Intl

Tue 9/9

5:20 am-12:45 pm

1 stop8h 25m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 9/4

7:00 am-10:30 am

Nonstop2h 30m

Boston Logan Intl

Fri 9/5

7:55 pm-9:56 pm

Nonstop3h 01m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 10/17

7:10 pm-10:45 pm

Nonstop2h 35m

Boston Logan Intl

Wed 10/22

4:10 pm-6:10 pm

Nonstop3h 00m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/3

7:00 am-10:30 am

Nonstop2h 30m

Boston Logan Intl

Fri 9/5

7:55 pm-9:56 pm

Nonstop3h 01m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 10/23

1:50 pm-9:00 pm

1 stop6h 10m

Boston Logan Intl

Mon 10/27

5:00 am-4:25 pm

1 stop12h 25m

$132

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 11/5

6:40 am-12:55 pm

1 stop5h 15m

Boston Logan Intl

Sun 11/9

6:50 am-3:40 pm

1 stop9h 50m

$132

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 11/7

6:45 am-6:10 pm

1 stop10h 25m

Boston Logan Intl

Mon 11/10

5:55 pm-11:00 pm

1 stop6h 05m

$132

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/17

7:30 am-11:01 am

Nonstop2h 31m

Boston Logan Intl

Sun 9/21

6:10 am-8:05 am

Nonstop2h 55m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 11/19

7:00 am-10:30 am

Nonstop2h 30m

Boston Logan Intl

Tue 12/2

8:10 pm-10:02 pm

Nonstop2h 52m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 37 results
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The best insider tips for Chicago to Boston 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 Chicago to Boston trip
Airlines
United Airlines

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


United's MileagePlus allows pooling miles, useful for family travel.

Read more about United Airlinesby Harriet Baskas
Spirit Airlines

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


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

Read more about Spirit Airlinesby Daniel Scheffler
Airports
ORD

Avoid long walks at ORD by using the free shuttle train between terminals outside of security.

Read more about ORDby Ramsey Qubein
MDW

Use the airport’s mobile system to order food directly to your gate, saving time and ensuring you don't miss boarding.

Read more about MDWby Ramsey Qubein
BOS

Take the MBTA Silver Line 1 bus for a free ride from BOS to South Station in downtown Boston.

Read more about BOSby Paul Rubio
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

Daniel Scheffler

Daniel Scheffler

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

Read more
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 Chicago to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston from Chicago 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 Chicago to Boston

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Boston. Price data was last updated on August 8, 2025.

The price you pay for your flight from Chicago to Boston may vary depending on when you book. For the best chance of a lower fare, look to book 73 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Boston (average of $218). Flying from Chicago to Boston in July is currently the most expensive (average of $311). 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 CHI to BOS?

Find hourly flight availability from Chicago to Boston. 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.

It’s typically best to fly out from Chicago to Boston in the evening. Doing so could potentially save you 21% on the flight price compared to flying at noon, which is usually more expensive.

What is the cheapest day to fly from Chicago to Boston?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Boston. Price data was last updated on August 17, 2025.

Travelers seeking maximum savings on their Chicago to Boston 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 Chicago to Boston

Explore weekly flight availability from Chicago to Boston. 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 CHI to BOS 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 (31 on average).

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

Reviews of airlines servicing Boston

Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated August 21, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines from Chicago to Boston have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,245 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

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

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

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

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

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

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

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

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

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

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

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 Chicago to Boston. 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 into for flights to Boston from Chicago?

    Boston Logan Intl (BOS) is the airport you will fly into if you book a flight from Chicago to Boston. You should not have trouble finding flights to Logan Intl from Chicago; the airport handles an average of 58 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 7 airlines have flights to the Boston airport from Chicago. It is only a 2.6 mi journey from Logan Intl (BOS) to Boston’s city center.

  • How long is the flight from Chicago to Boston?

    A quick flight from Chicago to Boston can take about 2h 39m. Delta provides one of the quickest options available for as low as $127. Airlines will cover a distance of 864 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Chicago to Boston round-trip?

    Cheapflights users have booked flights from Chicago to Boston round-trip from $31. Other airlines that can offer you cheap pricing are JetBlue, from $77, and Delta, from $92. These flights start at 86% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Boston one-way?

    For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $69. Users have also found prices from $69 and $69 on Delta and American Airlines, respectively.

  • What are the most reliable airlines from Chicago to Boston?

    Before booking your flight to Boston from Chicago, check out the most reliable airlines to get you to your destination on time: Envoy Air (95%), Etihad Airways (83%), Alaska Airlines( 76%).

  • What are the cheapest flights from Chicago to Boston?

    On average you can expect to pay $394 for a flight from Chicago to Boston. The cheapest flight overall is $68 while the most popular route, (Chicago O'Hare Intl - Boston Logan Intl) is currently priced at $87.

  • Can I find deals for flights from Chicago to Boston that include hotel bookings?

    Yes. In addition to deals on Chicago to Boston flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Boston?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Boston.

  • Can I find deals for business class flights from Chicago to Boston?

    Yes. Cheapflights offers flight deals from Chicago to Boston 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 Chicago to Boston?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Boston (average of $218). Flying from Chicago to Boston in July is currently the most expensive (average of $311). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Cambridge
Medford
Watertown
Hampton Beach
Waltham
Seabrook
Lowell
Lincoln
Smithfield
Cranston
Chestnut Hill
Warwick
Peabody
Quincy
York Beach
Chelsea
Swansea
Saugus
Burlington
Braintree

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Boston

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Chicago to Boston

Discover the top 7 airlines that operate flights from Chicago to Boston. 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$31Average$109FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$77Average$186FlexibilityNo cancel feeOn-time62%
DeltaCheapest$92Average$221FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$100Average$115FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$119Average$232FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$131Average$289FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$149Average$261FlexibilityNo cancel feeOn-time63%

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