HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Boston

$59+ 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 7/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
May 22 — May 291
Thu 5/22
Thu 5/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Boston with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to Boston Logan Intl are usually found in September or August, booked 73 days in advance, depart on a Wednesday or Thursday 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 May 17, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$116
(Cheapflightsfares)

One-way from

$59
(American Airlines)

Popular in

April

Cheapest in

September

Average price

$253

Good round-trip deal

$141 or less

Good one-way deal

$58 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. 9% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2025
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

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 May 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 5/16. 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.
Tue 6/35:05 amORD - BOS
1 stop8h 39mSpirit Airlines
Tue 6/103:49 pmBOS - ORD
1 stop8h 15mSpirit Airlines
Deal found 5/16$116
This Delta deal was found by Cheapflights users on 5/15. 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 9/172:10 pmORD - BOS
Nonstop2h 34mDelta
Thu 9/2511:00 amBOS - ORD
Nonstop2h 52mDelta
Deal found 5/15$117
This Southwest deal was found by Cheapflights users on 5/16. 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 5/297:20 pmMDW - BOS
Nonstop2h 15mSouthwest
Mon 6/25:45 amBOS - MDW
Nonstop2h 35mSouthwest
Deal found 5/16$117
This JetBlue deal was found by Cheapflights users on 5/15. 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 5/307:31 pmORD - BOS
Nonstop2h 29mJetBlue
Mon 6/26:00 amBOS - ORD
Nonstop3h 00mJetBlue
Deal found 5/15$122
This American Airlines deal was found by Cheapflights users on 5/17. 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 5/246:35 pmORD - BOS
Nonstop2h 32mAmerican Airlines
Tue 5/273:51 pmBOS - ORD
Nonstop3h 02mAmerican Airlines
Deal found 5/17$138
This Gotogate deal was found by Cheapflights users on 5/16. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1012:41 pmORD - BOS
1 stop9h 48mMultiple Airlines
Sat 6/219:40 amBOS - ORD
1 stop22h 29mMultiple Airlines
Deal found 5/16$154
This Southwest deal was found by Cheapflights users on 5/17. 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 8/271:50 pmORD - BOS
1 stop4h 30mSouthwest
Sun 8/316:50 amBOS - ORD
1 stop8h 25mSouthwest
Deal found 5/17$157
This United Airlines deal was found by Cheapflights users on 5/16. 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 6/117:53 pmORD - BOS
Nonstop2h 27mUnited Airlines
Sat 6/146:05 amBOS - ORD
1 stop5h 34mUnited Airlines
Deal found 5/16$165
This CheapOair deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/144:06 pmMDW - BOS
1 stop7h 32mFrontier
Mon 8/189:40 amBOS - MDW
1 stop11h 42mFrontier
Deal found 5/16$166
This CheapOair deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/296:10 amORD - BOS
1 stop27h 56mFrontier
Fri 9/510:10 amBOS - ORD
1 stop6h 34mFrontier
Deal found 5/17$191
This Mytrip deal was found by Cheapflights users on 5/16. 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.
Fri 6/68:36 pmMDW - BOS
1 stop11h 36mAllegiant Air
Fri 6/139:02 amBOS - MDW
1 stop11h 44mAllegiant Air
Deal found 5/16$210
This Mytrip deal was found by Cheapflights users on 5/16. 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.
Fri 6/68:36 pmMDW - BOS
2 stops26h 11mMultiple Airlines
Fri 6/139:02 amBOS - MDW
1 stop11h 44mMultiple Airlines
Deal found 5/16$275

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 17, 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

Tue 6/3

5:05 am-2:44 pm

1 stop8h 39m

Boston Logan Intl

Tue 6/10

3:49 pm-11:04 pm

1 stop8h 15m

$116

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/17

2:10 pm-5:44 pm

Nonstop2h 34m

Boston Logan Intl

Thu 9/25

11:00 am-12:52 pm

Nonstop2h 52m

$117

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 5/29

7:20 pm-10:35 pm

Nonstop2h 15m

Boston Logan Intl

Mon 6/2

5:45 am-7:20 am

Nonstop2h 35m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 5/30

7:31 pm-11:00 pm

Nonstop2h 29m

Boston Logan Intl

Mon 6/2

6:00 am-8:00 am

Nonstop3h 00m

$122

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 5/28

1:22 pm-4:48 pm

Nonstop2h 26m

Boston Logan Intl

Sat 5/31

8:51 pm-10:52 pm

Nonstop3h 01m

$138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 6/10

12:41 pm-11:29 pm

1 stop9h 48m

Boston Logan Intl

Sat 6/21

9:40 am-7:09 am

1 stop22h 29m

$154

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 8/27

1:50 pm-7:20 pm

1 stop4h 30m

Boston Logan Intl

Sun 8/31

6:50 am-2:15 pm

1 stop8h 25m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 6/11

7:53 pm-11:20 pm

Nonstop2h 27m

Boston Logan Intl

Sat 6/14

6:05 am-10:39 am

1 stop5h 34m

$165

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 8/14

4:06 pm-12:38 am

1 stop7h 32m

Boston Logan Intl

Mon 8/18

9:40 am-8:22 pm

1 stop11h 42m

$166

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 8/29

6:10 am-11:06 am

1 stop27h 56m

Boston Logan Intl

Fri 9/5

10:10 am-3:44 pm

1 stop6h 34m

$191

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/15

Showing 1-10 of 28 results
1
2
3

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*2 stars
PricelinePrice Accuracy2 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 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 Chicago-Boston flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Chicago-Boston flight deals on Cheapflights vs. CheapOair >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 CheapOair the most. CheapOair 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.

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 May 16, 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 $308). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from 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 17, 2025.

It’s typically best to fly out from Chicago to Boston in the evening. Doing so could potentially save you 33% on the flight price compared to flying in the afternoon, 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 11, 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 afternoons 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 17, 2025.

The most flights from CHI to BOS are scheduled on a Sunday (73 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (61 on average).

Rainfall in Boston by month

Plan your trip to Boston by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Boston ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Boston when rainfall is around 3.1 in.

Temperature in Boston by month

Plan your trip to Boston by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Boston, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

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 17, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and United Airlines from Chicago to Boston to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,291 reviews

Entertainment

7.6

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,291 reviews
Southwest
8.0
Very good
4,291 reviews

Entertainment

7.6

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,949 reviews
Southwest
8.0
Very good
4,291 reviews

Entertainment

7.6

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,731 reviews
Southwest
8.0
Very good
4,291 reviews

Entertainment

7.6

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,927 reviews
Southwest
8.0
Very good
4,291 reviews

Entertainment

7.6

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Allegiant Air
7.3
Good
732 reviews
Southwest
8.0
Very good
4,291 reviews

Entertainment

7.6

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 65 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.

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

    Cheapflights users have booked flights from Chicago to Boston round-trip from $116. Other airlines that can offer you cheap pricing are Delta, from $117, and Southwest, from $117. These flights start at 49% 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 American Airlines. According to our data, you can fly for as low as $59. Users have also found prices from $59 and $60 on Southwest and Spirit 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: Air France (100%), Iberia (90%), TAP AIR PORTUGAL( 86%).

  • What are the cheapest flights from Chicago to Boston?

    On average you can expect to pay $400 for a flight from Chicago to Boston. The cheapest flight overall is $58 while the most popular route, (Chicago O'Hare Intl - Boston Logan Intl) is currently priced at $107.

  • 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 $308). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Cambridge
Warwick
Marlborough
Medford
Watertown
Waltham
Framingham
Brockton
Chestnut Hill
Cranston
Randolph
Lowell
Woburn
York Beach
Saco
Seabrook
Burlington
West Yarmouth
Smithfield
Somerville

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.

Alternative routes for Chicago to Boston

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Boston flights
Midway to Boston flights
St. Louis to Boston flights
O'Hare Intl to Albany flights
O'Hare Intl to Hartford flights
Midway to Albany flights
Midway to Hartford flights
O'Hare Intl to Nantucket flights
O'Hare Intl to West Tisbury flights
Peoria to Hartford flights
Moline to Boston flights
Midway to Nantucket flights
St. Louis to Hartford flights
St. Louis to Albany flights
O'Hare Intl to Worcester flights
Peoria to Albany flights
O'Hare Intl to Hyannis flights
Peoria to Boston flights
Bloomington to Boston flights
Moline to Albany flights
Moline to Hartford flights
Decatur to Boston flights
Evansville to Boston flights
St. Louis to West Tisbury flights
Bloomington to Albany flights
Springfield to Boston flights
O'Hare Intl to Provincetown flights
Dubuque to Boston flights
Champaign to Boston flights
Bloomington to Hartford flights
Springfield to Hartford flights
Champaign to Hartford flights
O'Hare Intl to New Bedford flights
Evansville to Hartford flights
Dubuque to Hartford flights
Champaign to Albany flights

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 May 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$93FlexibilityNo cancel feeOn-time65%
FrontierCheapest$69Average$111FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$78Average$201FlexibilityNo cancel feeOn-time62%
DeltaCheapest$88Average$297FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$134Average$292FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$136Average$238FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$157Average$292FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
Privacy Preferences©2025 Cheapflights
OSZAR »