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$79+ 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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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The best prices from Chicago to Boston Logan Intl are usually found in September or January, booked 83 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

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 November 20, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

April

Cheapest in

September

Round-trip from

$100
(Frontier)

One-way from

$79
(JetBlue)
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl flights.
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High demand for flights, 18% potential price rise
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Best time to find cheap flights, 21% potential price drop
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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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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 November 20, 2024.

This Frontier deal was found by Cheapflights users on 11/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1012:57 pmMDW - BOS
1 stop10h 33mFrontier
Wed 12/116:00 amBOS - MDW
1 stop6h 42mFrontier
Deal found 11/19$100
This eDestinos deal was found by Cheapflights users on 11/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/109:58 amORD - BOS
1 stop13h 40mSpirit Airlines
Wed 12/115:00 amBOS - ORD
1 stop12h 06mSpirit Airlines
Deal found 11/20$101
This Kiwi.com deal was found by Cheapflights users on 11/19. 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.
Mon 12/910:59 amORD - BOS
1 stop12h 31mMultiple Airlines
Tue 12/105:00 amBOS - ORD
1 stop12h 06mMultiple Airlines
Deal found 11/19$108
This CheapOair deal was found by Cheapflights users on 11/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/910:59 amORD - BOS
1 stop12h 31mFrontier
Wed 12/116:00 amBOS - ORD
1 stop27h 24mFrontier
Deal found 11/19$114
This United Airlines deal was found by Cheapflights users on 11/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/101:55 pmORD - BOS
Nonstop2h 21mUnited Airlines
Tue 12/1710:45 amBOS - ORD
Nonstop2h 56mUnited Airlines
Deal found 11/19$157
This Southwest deal was found by Cheapflights users on 11/19. 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.
Fri 12/138:00 amMDW - BOS
Nonstop2h 15mSouthwest
Sun 12/156:40 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 11/19$158
This JetBlue deal was found by Cheapflights users on 11/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1010:14 amORD - BOS
1 stop7h 31mJetBlue
Sun 12/156:00 amBOS - ORD
Nonstop3h 06mJetBlue
Deal found 11/19$166
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/156:30 amORD - BOS
Nonstop2h 30mDelta
Wed 12/187:25 amBOS - ORD
Nonstop3h 03mDelta
Deal found 11/19$177
This American Airlines deal was found by Cheapflights users on 11/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/197:19 amORD - BOS
Nonstop2h 31mAmerican Airlines
Mon 1/208:45 amBOS - ORD
Nonstop3h 00mAmerican Airlines
Deal found 11/20$182
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/61:30 pmMDW - BOS
1 stop5h 30mDelta
Mon 12/97:59 pmBOS - MDW
1 stop13h 59mDelta
Deal found 11/19$300

Find flights from Chicago to Boston within your budget

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 12/10

12:57 pm-12:30 am

1 stop10h 33m

Boston Logan Intl

Wed 12/11

6:00 am-11:42 am

1 stop6h 42m

$100

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 12/10

9:58 am-12:38 am

1 stop13h 40m

Boston Logan Intl

Wed 12/11

5:00 am-4:06 pm

1 stop12h 06m

$101

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/9

5:02 pm-12:30 am

1 stop6h 28m

Boston Logan Intl

Tue 1/14

6:00 am-1:34 pm

1 stop8h 34m

$108

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 12/10

9:58 am-12:38 am

1 stop13h 40m

Boston Logan Intl

Thu 12/12

6:00 am-9:54 am

1 stop28h 54m

$115

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 12/10

4:40 pm-8:02 pm

Nonstop2h 22m

Boston Logan Intl

Tue 12/17

1:59 pm-3:53 pm

Nonstop2h 54m

$157

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 12/13

8:30 pm-11:40 pm

Nonstop2h 10m

Boston Logan Intl

Tue 12/17

7:00 am-8:45 am

Nonstop2h 45m

$158

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 12/4

9:20 am-12:45 pm

Nonstop2h 25m

Boston Logan Intl

Sat 12/7

3:57 pm-8:07 pm

1 stop5h 10m

$167

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 12/15

6:30 am-10:00 am

Nonstop2h 30m

Boston Logan Intl

Wed 12/18

7:25 am-9:28 am

Nonstop3h 03m

$177

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 12/4

5:30 pm-10:09 pm

1 stop3h 39m

Boston Logan Intl

Sun 12/8

8:45 am-10:50 am

Nonstop3h 05m

$208

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 12/6

4:58 pm-1:22 am

1 stop7h 24m

Boston Logan Intl

Tue 12/10

8:50 am-5:01 pm

1 stop9h 11m

$300

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 23 results
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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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 star
CheapOairPrice Accuracy2 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 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.

Travel insights for flights from Chicago to Boston

Get recent, data-driven insights about flights from Chicago to Boston including ideal travel times, pricing trends, and more.

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 November 15, 2024.

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 79 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 November 20, 2024.

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 November 18, 2024.

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 November 20, 2024.

The most flights from CHI to BOS are scheduled on a Monday (63 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 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 November 20, 2024.
Peruse reviews from past customers who have flown with American Airlines, Frontier and Spirit 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
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

JetBlue
7.5
Good
3,394 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 45 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 $100. Other airlines that can offer you cheap pricing are Spirit Airlines, from $101, and Delta, from $157. These flights start at 58% 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 $79. Users have also found prices from $79 and $80 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: Envoy Air (96%), Avianca (95%), Royal Jordanian( 94%).

  • What are the cheapest flights from Chicago to Boston?

    On average you can expect to pay $439 for a flight from Chicago to Boston. The cheapest flight overall is $63 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 $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.

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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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$96FlexibilityNo cancel feeOn-time65%
DeltaCheapest$63Average$329FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$69Average$116FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$83Average$240FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$137Average$258FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$148Average$298FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$153Average$267FlexibilityNo cancel feeOn-time63%
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