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$83+ 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 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Jun 4 — Jun 111
Thu 6/4
Thu 6/11
1 adult, Economy
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Find cheap flights from Chicago to Boston with Cheapflights

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Cheapflights Tip: The best prices from Chicago to Boston Logan Intl are usually found in January or September, booked 86 days in advance, depart on a Wednesday or Thursday and return on a Friday

Cheap 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 May 5, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 5/278:30 pm
ORD
-
BOS
Nonstop2h 29m
JetBlue
Wed 6/36:00 am
BOS
-
ORD
Nonstop3h 00m
JetBlue
Deal found 4/30$162
This Super.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/58:20 pm
ORD
-
BOS
Nonstop2h 31m
JetBlue
Wed 8/128:10 am
BOS
-
ORD
Nonstop2h 56m
JetBlue
Deal found 5/2$164
This Super.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/110:56 am
ORD
-
BOS
Nonstop2h 26m
JetBlue
Wed 7/158:10 am
BOS
-
ORD
Nonstop2h 56m
JetBlue
Deal found 5/2$165
This flygcity.se deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/231:56 pm
ORD
-
BOS
Nonstop2h 31m
JetBlue
Sun 5/246:00 am
BOS
-
ORD
Nonstop3h 00m
JetBlue
Deal found 5/2$166
This Delta deal was found by Cheapflights users on 4/30. 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.
Sat 5/307:00 am
ORD
-
BOS
Nonstop2h 35m
Delta
Sat 5/305:30 pm
BOS
-
ORD
Nonstop3h 03m
Delta
Deal found 4/30$167
This Southwest deal was found by Cheapflights users on 4/30. 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 6/166:05 pm
MDW
-
BOS
Nonstop2h 15m
Southwest
Wed 6/175:35 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Deal found 4/30$167
This American Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/306:00 am
ORD
-
BOS
Nonstop2h 27m
American Airlines
Sat 6/67:46 pm
BOS
-
ORD
Nonstop3h 14m
American Airlines
Deal found 5/2$168
This Priceline deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/209:49 am
ORD
-
BOS
Nonstop2h 31m
Multiple Airlines
Tue 5/269:12 am
BOS
-
ORD
1 stop11h 29m
Multiple Airlines
Deal found 5/4$169
This Super.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:30 pm
ORD
-
BOS
Nonstop2h 29m
JetBlue
Sun 5/316:00 am
BOS
-
ORD
Nonstop3h 00m
JetBlue
Deal found 5/2$170
This Delta deal was found by Cheapflights users on 5/1. 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.
Wed 6/37:16 pm
ORD
-
BOS
Nonstop2h 34m
Delta
Mon 6/84:15 pm
BOS
-
ORD
Nonstop3h 05m
Delta
Deal found 5/1$172
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/107:40 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Mon 6/155:25 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Deal found 5/4$172
This American Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:20 pm
ORD
-
BOS
Nonstop2h 34m
American Airlines
Sun 5/247:00 am
BOS
-
ORD
Nonstop3h 04m
American Airlines
Deal found 4/30$173

Find 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 May 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$162
(Cheapflightsfares)

One-way from

$83
(Cheapflightsfares)

Popular in

April

Cheapest in

January

Average price

$227

Good round-trip deal

$208 or less

Good one-way deal

$108 or less
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl flights.
Search Deals
From Chicago (CHI) to Boston Logan Intl
Search Deals
One-way flight from Chicago (CHI) to Boston Logan Intl
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Boston Logan Intl.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Boston Logan Intl.
Search Deals

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 May 5, 2026.
Use the filters below to find and compare flights from Chicago to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 6/10

7:40 am-10:55 am

Nonstop2h 15m

Boston Logan Intl

Tue 6/16

5:35 am-7:10 am

Nonstop2h 35m

$167

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 7/29

2:40 pm-6:00 pm

Nonstop2h 20m

Boston Logan Intl

Mon 8/10

8:20 pm-10:00 pm

Nonstop2h 40m

$172

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 5/20

6:00 am-9:25 am

Nonstop2h 25m

Boston Logan Intl

Sat 5/23

3:08 pm-5:00 pm

Nonstop2h 52m

$177

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 8/15

6:00 am-11:17 am

1 stop4h 17m

Boston Logan Intl

Tue 8/18

8:22 pm-10:19 pm

Nonstop2h 57m

$182

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 8/11

9:30 pm-1:05 am

Nonstop2h 35m

Boston Logan Intl

Thu 8/20

5:45 am-9:33 am

1 stop4h 48m

$182

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 6/29

9:41 pm-1:14 am

Nonstop2h 33m

Boston Logan Intl

Sun 7/5

6:00 am-7:58 am

Nonstop2h 58m

$191

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 7/13

7:35 pm-10:50 pm

Nonstop2h 15m

Boston Logan Intl

Thu 7/16

8:00 pm-12:15 am

1 stop5h 15m

$197

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 5/30

2:15 pm-11:40 pm

2 stops8h 25m

Boston Logan Intl

Sun 5/31

5:40 am-12:10 pm

1 stop7h 30m

$197

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 5/15

9:30 pm-12:59 am

Nonstop2h 29m

Boston Logan Intl

Mon 5/18

6:39 pm-8:40 pm

Nonstop3h 01m

$197

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 8/7

9:41 pm-1:14 am

Nonstop2h 33m

Boston Logan Intl

Thu 8/13

5:45 am-9:33 am

1 stop4h 48m

$201

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/3

Showing 1-10 of 46 resultsSorted by cheapest first
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Compare providers for flights from Chicago to Boston

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 Chicago to Boston in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
OvagoPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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 Chicago-Boston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Boston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Boston flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Boston 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 Chicago-Boston 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 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?

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 71 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, November is the cheapest month in which you can book a flight from Chicago to Boston (average of $182). Flying from Chicago to Boston in December is currently the most expensive (average of $283). 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 May 5, 2026.

It’s typically best to fly out from Chicago to Boston in the evening. Doing so could potentially save you 16% 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 May 2, 2026.

Travelers seeking maximum savings on their Chicago to Boston flight should consider departing on Thursday afternoons 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 May 5, 2026.

The most flights from CHI to BOS are scheduled on a Monday (77 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (41 on average).

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

How often are flights from Chicago to Boston delayed?

About 25% of weekly flights between Chicago and Boston have experienced delays in the past year, with the average delay time being 147 minutes.

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

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

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

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

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

Over the last year, JetBlue have had the lowest number of delays on this route, with just 21% of flights being delayed.

The best insider tips for Chicago to Boston 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 Chicago to Boston trip
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

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 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

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 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 May 5, 2026.
See what other customers who have flown with Southwest,Delta, andUnited 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
7.9
Good
4,305 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,305 reviews
Southwest
7.9
Good
4,305 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,460 reviews
Southwest
7.9
Good
4,305 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,683 reviews
Southwest
7.9
Good
4,305 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.2
Good
2,977 reviews
Southwest
7.9
Good
4,305 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,667 reviews
Southwest
7.9
Good
4,305 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 55 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 6 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 15m. Southwest provides one of the quickest options available for as low as $167. Airlines will cover a distance of 857 mi. Generally, flights for this route are nonstop.

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

    Cheapflights users have booked flights from Chicago to Boston round-trip from $67. Other airlines that can offer you cheap pricing are Spirit Airlines, from $79, and Delta, from $87. These flights start at 70% 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 $60. Users have also found prices from $63 and $66 on Spirit Airlines 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: Avianca (94%), Icelandair (86%), TAP AIR PORTUGAL( 81%).

  • What are the cheapest flights from Chicago to Boston?

    On average you can expect to pay $421 for a flight from Chicago to Boston. The cheapest flight overall is $83 while the most popular route, (Chicago O'Hare Intl - Boston Logan Intl) is currently priced at $160.

  • 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, November is the cheapest month in which you can book a flight from Chicago to Boston (average of $182). Flying from Chicago to Boston in December is currently the most expensive (average of $283). 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
Medford
Cambridge
Concord
Hampton Beach
Watertown
Brockton
Seekonk
Cranston
Chelsea
Warwick
Peabody
Seabrook
York Beach
Londonderry
Swansea
Old Orchard Beach
Quincy
Waltham
Lowell
Braintree

Browse thousands of different options on Cheapflights for your next trip

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

Top 6 airlines flying from Chicago to Boston

Discover the top 6 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 May 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$67Average$168FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$79Average$166FlexibilityNo cancel feeOn-time65%
DeltaCheapest$87Average$228FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$120Average$257FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$121Average$231FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$126Average$250FlexibilityNo cancel feeOn-time63%

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