Cheap flights from Chicago (CHI) to Boston (BOS)

CHI — BOS
Feb 12 — Feb 191

The best prices from Chicago to Boston Logan Intl are usually found in February or January, booked 3 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

How to find the cheapest flight from Chicago (CHI) to Boston (BOS)

All the information you need to plan the best CHI to BOS flight in 2023: compare Chicago to Boston flight prices with the expected peak season, weather and rainfall in Boston.

CHI - BOS

Price

$131 - $313

BOS

Temperature

30.2 - 73.4 °F

BOS

Rainfall

3.1 - 4 inches

Popular inJuneHigh demand for flights, 26% potential price rise
Cheapest inFebruaryBest time to find cheap flights, 43% potential price drop
Round-trip from$131From Chicago (CHI) to Boston Logan Intl
One-way from$49One-way flight from Chicago (CHI) to Boston Logan Intl

What is the cheapest day to fly round-trip from Chicago to Boston?

Flying to your destination on a Saturday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Boston. Check prices with Cheapflights to find a great deal for your trip.

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

February is one of the best times of the year to fly to Boston from Chicago. Prices for February average $232 per person but you can even find prices for as low as $97. The most expensive prices can be found in the month of June. Opting for a February flight can save you 35% on your journey compared to booking in June

When is the cheapest time to fly from Chicago to Boston (CHI - BOS)?

It’s typically best to fly out from Chicago to Boston in the evening. Doing so could potentially save you 17% on the flight price compared to flying at noon, which is usually more expensive.

Cheap flights from Chicago to Boston in February, March 2023

The best prices found for CHI to BOS flights for February, March

Chicago to Boston 2023 flight deals

Cheap flights to Boston from Chicago found for this year

Cheap JetBlue flights from Chicago to Boston

  • JetBlue is one of the most popular airlines used for those traveling from Chicago to Boston. Flights from JetBlue traveling this route typically cost $349.10 RT. This price is typically 26% more expensive than other airlines that offer Chicago to Boston flights. When booking this route, the cheapest RT price found was $239. The most popular departure airport in Chicago when flying to Boston is Chicago O'Hare Intl Airport. The most popular airport to fly into when visiting Boston is Boston Logan Intl Airport. When flying from Chicago to Boston, JetBlue flights are 23% more popular than any other airline flying that same route.

Cheap United Airlines flights from Chicago to Boston

  • If you’re traveling from Chicago to Boston, one of the more common airlines traveling that route is United Airlines. Flights from United Airlines traveling this route typically cost $314.76 RT. This price is typically 36% more expensive than other airlines that offer Chicago to Boston flights. When booking this route, the cheapest RT price found was $89. The most popular departure airport in Chicago when flying to Boston is Chicago O'Hare Intl Airport. The most popular airport to fly into when visiting Boston is Boston Logan Intl Airport. When flying from Chicago to Boston, United Airlines flights are 22% more popular than any other airline flying that same route.

Non-stop flights to Boston from Chicago

Save time with Chicago to Boston direct flight deals

Last minute flights from Chicago to Boston

Late deals on return flights to Boston from Chicago, departing today and this week

One-way flights to Boston from Chicago

The cheapest one-way flights from Chicago to Boston

Reviews of Airlines Servicing Boston

Delta
7.9
Good
2,091 reviews

Boarding

8.1

Overall

7.9

Comfort

7.9

Food

7.2

Crew

8.5

Entertainment

7.8

Reviews

1 / 10

Great airline. Will always flight with Delta. The flight attendant are so professional friendly and caring. Wifi was great. The tv selection to watch movies was perfect also. No complain.

Delta
7.9
Good
2,091 reviews
Delta
7.9
Good
2,091 reviews

Boarding

8.1

Overall

7.9

Comfort

7.9

Food

7.2

Crew

8.5

Entertainment

7.8

Reviews

1 / 10

Great airline. Will always flight with Delta. The flight attendant are so professional friendly and caring. Wifi was great. The tv selection to watch movies was perfect also. No complain.

JetBlue
7.7
Good
387 reviews
Delta
7.9
Good
2,091 reviews

Boarding

8.1

Overall

7.9

Comfort

7.9

Food

7.2

Crew

8.5

Entertainment

7.8

Reviews

1 / 10

Great airline. Will always flight with Delta. The flight attendant are so professional friendly and caring. Wifi was great. The tv selection to watch movies was perfect also. No complain.

United Airlines
7.6
Good
1,217 reviews
Delta
7.9
Good
2,091 reviews

Boarding

8.1

Overall

7.9

Comfort

7.9

Food

7.2

Crew

8.5

Entertainment

7.8

Reviews

1 / 10

Great airline. Will always flight with Delta. The flight attendant are so professional friendly and caring. Wifi was great. The tv selection to watch movies was perfect also. No complain.

Southwest
7.5
Good
963 reviews
Delta
7.9
Good
2,091 reviews

Boarding

8.1

Overall

7.9

Comfort

7.9

Food

7.2

Crew

8.5

Entertainment

7.8

Reviews

1 / 10

Great airline. Will always flight with Delta. The flight attendant are so professional friendly and caring. Wifi was great. The tv selection to watch movies was perfect also. No complain.

American Airlines
7.4
Good
1,684 reviews
Delta
7.9
Good
2,091 reviews

Boarding

8.1

Overall

7.9

Comfort

7.9

Food

7.2

Crew

8.5

Entertainment

7.8

Reviews

1 / 10

Great airline. Will always flight with Delta. The flight attendant are so professional friendly and caring. Wifi was great. The tv selection to watch movies was perfect also. No complain.

Related info for your journey

Useful info, stats and facts about Chicago to Boston flights.

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 49 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 9 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.

Which airlines flying from Chicago to Boston Logan Intl have flexible cancellations due to COVID-19?

American Airlines, United Airlines, and Delta are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Can I find flights from Chicago to Boston for under $100 on Cheapflights?

Yes, there are multiple flights from Chicago to Boston for under $100. The cheapest flight booked recently is on JetBlue for just $90, but on average you can expect to pay $120.

Are there nonstop flights from Chicago to Boston for under $100 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Boston under $100. A good price for a nonstop flight from Chicago to Boston is less than $133.

Are there last-minute flights available from Chicago to Boston for under $200?

There are currently 20+ open flights from Chicago to Boston within the next 7 days for less than $200.

What days are nonstop flights available from Chicago to Boston?

Days when nonstop flights are available for this flight are: Sunday, Wednesday, Thursday, Friday, Saturday.

How many flights depart from Chicago to Boston on average per day?

On average, you can expect to see 40 flights from Chicago to Boston a day.
Morning (6am - Noon) - 60% of flight departures
Afternoon (Noon - 6pm) - 28% of flight departures
Evening (6pm - Midnight) - 13% of flight departures

How long is the flight from Chicago to Boston?

A quick flight from Chicago to Boston can take about 2h 14m. JetBlue provides one of the quickest options available for as low as $90. Airlines will cover a distance of 869 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 $90. Other airlines that can offer you cheap pricing are United Airlines, from $114, and Spirit Airlines, from $120. These flights start at 61% 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 $45. Users have also found prices from $49 and $58 on United Airlines and Spirit Airlines, respectively.

What are the most popular airlines that fly from Chicago to Boston?

Before booking your flight from Chicago to Boston check out the most popular airlines for this route: Undisclosed Carrier, American Airlines or Alaska Airlines.

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: Azul (84%), Republic Airways (82%), Icelandair( 81%).

What are the cheapest flights from Chicago to Boston?

On average you can expect to pay $857 for a flight from Chicago to Boston. The cheapest flight overall is $59 while the most popular route, (Chicago O'Hare Intl - Boston Logan Intl) is currently priced at $90.

Alternative routes for Chicago to Boston

See prices for flight routes from nearby airports that may be better suited for you.
Moline to Bostonfrom $254 pp
Peoria to Bostonfrom $265 pp

Top 7 airlines flying from Chicago to Boston

The chart below displays the airlines Cheapflights users traveling from Chicago to Boston choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$14Average$20FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
JetBlueCheapest$71Average$202FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search JetBlue flights
United AirlinesCheapest$88Average$216FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
DeltaCheapest$89Average$315FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
Spirit AirlinesCheapest$98Average$237FlexibilityNo cancel feeOn-time65%COVID-19 safety
Search Spirit Airlines flights
American AirlinesCheapest$115Average$268FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
Alaska AirlinesCheapest$239Average$349FlexibilityNo cancel feeOn-time75%COVID-19 safety
Search Alaska Airlines flights

Hourly flight availability from Chicago to Boston

See what time of day planes typically take off from Chicago to Boston
1%of flight departuresEarly morningMidnight to 6 am
69%of flight departuresMorning6 am to noon
19%of flight departuresAfternoonNoon to 6 pm
11%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Chicago to Boston

See how many times per day planes take to the skies headed from Chicago to Boston
Sunday47daily flights
Monday62daily flights
Tuesday44daily flights
Wednesday52daily flights
Thursday54daily flights
Friday57daily flights
Saturday33daily flights
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