Question 1

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

Accepted Answer

Flying on JetBlue is currently your cheapest option to Boston, with prices starting at £102. Additional return tickets that might be worth considering are offered by Spirit Airlines and Southwest, with the lowest prices starting at £103 and £105, respectively. You may be able to fly from Chicago to Boston for 39% less than the average price by searching for these airlines.

Question 2

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

Accepted Answer

One-way options have recently been found by users for as low as £51 on JetBlue. Other airlines that offer cheap prices include Delta from £55 and Southwest from £58 one-way.

Question 3

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

Accepted Answer

Booking 73 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Boston. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

Question 4

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

Accepted Answer

Currently, October is the cheapest month in which you can book a flight from Chicago to Boston (average of £10). Flying from Chicago to Boston in July is currently the most expensive (average of £724). 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.

Question 5

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

Accepted Answer

Travellers seeking maximum savings on their Chicago to Boston flight should consider departing on Saturday mornings when fares are most often at their lowest. Wednesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Question 6

Weekly flight availability from Chicago to Boston

Accepted Answer

The most flights from CHI to BOS are scheduled on a Monday (86 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (46 on average).

Question 7

E

Accepted Answer

In terms of precipitation, rainfall in Boston ranges from 78.0 - 101.0 inches per month. March is typically the wettest month, when rainfall can reach 101.0 mm. July is typically the driest time to visit Boston when rainfall is around 78.0 mm.

Question 8

E

Accepted Answer

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 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -1.0 C).

Question 9

What are the cheapest flights from Chicago to Boston?

Accepted Answer

The cheapest flight price from Chicago to Boston is £77. On average you can expect to pay £453. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for £94.

Question 10

What are the most reliable airlines from Chicago to Boston?

Accepted Answer

No one likes to see their flight delayed. When booking a flight from Chicago to Boston consider choosing Etihad Airways (92%), Royal Jordanian (83%) or EL AL (80%) as they are the most reliable in getting you off to your destination on time.

Question 11

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

Accepted Answer

Departing on a Friday is a good option for securing a great price. You can expect to save up to 521% when planning your travel around this day of the week.

Question 12

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

Accepted Answer

Travelers have found it’s best to book a flight 48 days in advance to save up to 76% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 48 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago to Boston 1-2 weeks in advance for as low as £153, or £275 for flights within the next 24 hours.

Question 13

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

Accepted Answer

Flights from Chicago to Boston lean towards being more expensive in April. Prices are generally better when you fly from Chicago to Boston in September, with the cheapest ticket starting at £47.

Question 14

What is the cheapest time of day to fly from CHI to BOS?

Accepted Answer

When flying from Chicago to Boston, the time of day you fly usually plays a role in the price. Save by searching for a flight at midday, which can drop the price by up to 68% versus a flight in the afternoon.

Question 15

What airport do you fly into for flights to Boston from Chicago?

Accepted Answer

Most people fly into Boston Logan Intl (BOS) if they book a flight to Boston from Chicago. On average, Logan Intl has 69 inbound flights from Chicago per day from 0 airlines. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

Question 16

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

Accepted Answer

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

Question 17

How can I find direct flights from Chicago to Boston?

Accepted Answer

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

Question 18

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

Accepted Answer

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.

Question 19

How does Cheapflights help users find flights from Chicago to Boston?

Accepted Answer

Deals for Chicago to Boston flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Question 20

Why should you use Cheapflights to find cheap flight tickets from Chicago to Boston?

Accepted Answer

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago to Boston.

Question 21

Can Cheapflights find flights from Chicago to Boston with no change fees?

Accepted Answer

Cheapflights does show flights with no change fees to all users. To see these options for flights from Chicago to Boston, users can toggle the no change fees filter when performing a flight search.

Question 22

Can Cheapflights notify me if prices for flights from Chicago to Boston become cheaper?

Accepted Answer

Yes! Start tracking prices for Chicago to Boston flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

Round-trip from	£102
One-way from	£51
Popular in	April
Cheapest in	September
Average price	£166
Good round-trip deal	£282 or less
Good one-way deal	£178 or less

Cheap flights from Chicago to Boston from £51

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 6/8. Fares are subject to change and may not be available on all flights or dates of travel.

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 Saturday or Monday and return on a Thursday

Cheap flight deals from Chicago to Boston

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Chicago to Boston

Cheapest flights from Chicago to BostonExplore 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 15 July 2025.

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 15 July 2025.

Cheapflights Fare Finder

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

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.

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 return flight from Chicago to Boston. Price data was last updated on 11 July 2025.

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

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 15 July 2025.

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 15 July 2025.

How much does it cost for a return flight 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 15 July 2025.

Read reviews from past customers who have flown with Southwest, Delta, andUnited Airlines from Chicago to Boston. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

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?

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

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

What are the most reliable airlines from Chicago to Boston?

What are the cheapest flights from Chicago to Boston?

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

How can I find direct flights from Chicago to Boston?

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

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

Travelling to a place near Boston?

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.

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Chicago to Boston?

Why should you use Cheapflights to find cheap flight tickets from Chicago to Boston?

Can Cheapflights find flights from Chicago to Boston with no change fees?

Can Cheapflights notify me if prices for flights from Chicago to Boston become cheaper?

100% Free

Book with Flexibility

Travel Smart

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 15 July 2025.