Question 1

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

Accepted Answer

Currently priced at £101, JetBlue will fly you from Boston to Chicago and back. In addition to JetBlue, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and Southwest - these airlines can fly you to your destination from £102 and £104, respectively. These flights start at 41% lower than the current average price 3 months from now.

Question 2

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

Accepted Answer

The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as £51. However, be on the lookout for offers from Southwest and Delta, as they are both options that can get you from Boston to Chicago for a low price.

Question 3

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

Accepted Answer

The best time to book flights from Boston to Chicago is 90 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

Question 4

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

Accepted Answer

Currently, January is the cheapest month in which you can book a flight from Boston to Chicago (average of £595). Flying from Boston to Chicago in July is currently the most expensive (average of £843). 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 Boston to Chicago?

Accepted Answer

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

Question 6

Weekly flight availability from Boston to Chicago

Accepted Answer

The most flights from BOS to CHI are scheduled on a Thursday (84 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 on average).

Question 7

E

Accepted Answer

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 inches per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Question 8

E

Accepted Answer

If weather is an important factor for your trip to Chicago, 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 -5.0 C).

Question 9

What are the cheapest flights from Boston to Chicago?

Accepted Answer

The cheapest flight price from Boston to Chicago is £72. On average you can expect to pay £322. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for £93.

Question 10

What are the most reliable airlines from Boston to Chicago?

Accepted Answer

No one likes to see their flight delayed. When booking a flight from Boston to Chicago consider choosing Avianca (95%), TAP AIR PORTUGAL (95%) or Cathay Pacific (95%) 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 Boston to Chicago?

Accepted Answer

It’s generally more expensive to depart on a Tuesday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

Question 12

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

Accepted Answer

Travelers have found it’s best to book a flight 50 days in advance to save up to 63% 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 50 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 Boston to Chicago 1-2 weeks in advance for as low as £149, or £261 for flights within the next 24 hours.

Question 13

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

Accepted Answer

Flights from Boston to Chicago lean towards being more expensive in March. Prices are generally better when you fly from Boston to Chicago in September, with the cheapest ticket starting at £43.

Question 14

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

Accepted Answer

When flying from Boston to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 66% versus a flight at midday.

Question 15

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

Accepted Answer

Boston Logan Intl (BOS) is the airport you will fly out of if you book a flight from Boston to Chicago. You should not have trouble finding flights to Chicago from Logan Intl; the airport handles an average of 60 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 1 airline has flights from the Boston airport to Chicago. It is only a 2.6 mi journey to Logan Intl (BOS) from Boston’s city center.

Question 16

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

Accepted Answer

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

Question 17

How can I find direct flights from Boston to Chicago?

Accepted Answer

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

Question 18

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

Accepted Answer

Yes. Cheapflights offers flight deals from Boston to Chicago 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 Boston to Chicago?

Accepted Answer

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago from Boston today with Cheapflights!

Question 20

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

Accepted Answer

Cheapflights helps you find that perfect flight to Chicago from Boston by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Question 21

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

Accepted Answer

Users can book flights with no change fees policies with our dedicated filters. Book flights from Boston to Chicago flexibly with Cheapflights today.

Question 22

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

Accepted Answer

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from Boston today and book when prices fit your budget.

Round-trip from	£101
One-way from	£51
Popular in	March
Cheapest in	September
Average price	£164
Good round-trip deal	£435 or less
Good one-way deal	£72 or less

Cheap flights from Boston to Chicago 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 23/7. Fares are subject to change and may not be available on all flights or dates of travel.

Cheapflights Tip: The best prices from Boston Logan Intl to Chicago are usually found in September or January, booked 90 days in advance, depart on a Wednesday or Thursday and return on a Saturday

Cheap flight deals from Boston to Chicago

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Boston to Chicago

Cheapest flights from Boston to ChicagoExplore the most affordable flight options available from Boston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 10 July 2025.

Explore the most affordable flight options available from Boston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 10 July 2025.

Cheapflights Fare Finder

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

Best time to book a flight from Boston to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Boston with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Boston to Chicago

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

Use this chart to determine the optimal time to book a return flight from Boston to Chicago. Price data was last updated on 27 June 2025.

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

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

Find hourly flight availability from Boston to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 10 July 2025.

Weekly flight availability from Boston to Chicago

Explore weekly flight availability from Boston to Chicago. 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 10 July 2025.

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with Southwest, Delta, andUnited Airlines from Boston to Chicago by reading reviews from past customers. Users have also rated airlines 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 Boston to Chicago. 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 from for flights from Boston to Chicago?

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

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

What are the most reliable airlines from Boston to Chicago?

What are the cheapest flights from Boston to Chicago?

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

How can I find direct flights from Boston to Chicago?

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

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

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 Boston to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top airline flying from Boston to Chicago

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 Boston to Chicago?

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

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

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

100% Free

Book with Flexibility

Travel Smart

Cheapest flights from Boston to Chicago
Explore the most affordable flight options available from Boston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 10 July 2025.