Question 1

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Accepted Answer

Flying to Chicago O'Hare Intl Airport from Boston in the evening is the least expensive time of day to depart. momondo users have found prices as low as $271 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $362. Of course, these prices can vary depending on the time of year and what airport you fly to.

Question 2

How many flights depart from Boston to Chicago O'Hare Intl Airport on average per week?

Accepted Answer

As of December 2025, there are 269 flights per week flying from Boston to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Mon, with 21% of flights taking off on this day.

Question 3

What is the cheapest Boston Logan Intl to Chicago O'Hare Intl flight route?

Accepted Answer

Fly from Boston Logan Intl to Chicago O'Hare Intl for the best Boston Logan Intl - Chicago O'Hare Intl flight prices

Question 4

What cabin class options are available on Boston Logan Intl to Chicago O'Hare Intl flights?

Accepted Answer

There are 4 cabin classes available to choose from on Boston Logan Intl to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Question 5

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

Accepted Answer

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $321. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Boston because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $420.

Question 6

What airlines fly to Chicago O'Hare Intl Airport?

Accepted Answer

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Boston according to our data. American Airlines is the first choice among our users, with 44% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 6 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

Question 7

What is the cheapest airline that flies from Boston Logan Intl to Chicago O'Hare Intl?

Accepted Answer

United Airlines, Southwest, and JetBlue are the most popular carriers operating from Boston Logan Intl to Chicago O'Hare Intl

Question 8

What day of the week experiences the fewest flight delays on this route?

Accepted Answer

Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Thursday has historically seen more delays on average compared to the rest of the week.

Question 9

What is the most punctual flight time for Boston to Chicago flights?

Accepted Answer

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Question 10

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

Accepted Answer

The month of January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Boston averaging around $216.

Question 11

How often are flights from Boston to Chicago delayed?

Accepted Answer

Historically, on average around 13% of flights between Boston and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 168 minutes.

Question 12

How many flights depart from Boston to Chicago O'Hare Intl Airport on average per day?

Accepted Answer

The number of flights available between Boston and Chicago O'Hare Intl Airport is 38 per day as of December 2025. The most frequent departure time is 4:00PM, with 49% of daily flights leaving in the afternoon.

Question 13

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

Accepted Answer

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $251 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Boston for as low as $207 on momondo.

Question 14

Which airline has the best punctuality record on Boston to Chicago flights?

Accepted Answer

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 10% of their flights experiencing any sort of delay.

Question 15

How have Boston to Chicago O'Hare Intl Airport flight prices changed over time?

Accepted Answer

As of December 2025, prices for Boston to Chicago O'Hare Intl Airport flights are approximately 20% cheaper when compared to flights at the same time last year.

Question 16

Which airlines fly direct from Boston to Chicago?

Accepted Answer

If you want one-way flights from Boston to Chicago, several airlines fly this route that offer direct flights. JetBlue offers a nonstop flight from Boston Logan International Airport (BOS) to Chicago O'Hare International Airport (ORD), a flight that takes about 3h. United Airlines also offers flights from Boston Logan International Airport to O'Hare International Airport, taking about 2h and 45min. Another option includes flights by Delta Airlines on this route, which takes up to 2h and 48min. American Airlines also offers cheap flights from Boston to Chicago International Airport to O'Hare International Airport on a flight that takes a little over 3h. To use Spirit Airlines for Boston to Chicago flights on this route, the flight includes a layover at Fort Lauderdale-Hollywood International Airport (FLL). This flight takes longer than nonstop flights, at around 8h. A faster option with one layover is a flight by American Airlines that stops at Charlotte Douglas International Airport (CLT), which takes about 5h and 28min.

Question 17

What is the best way to get in and out of airports in Boston and Chicago?

Accepted Answer

There are several options if you want to move into and out of Boston Logan International Airport. If you prefer an affordable option, you can use the MBTA, which offers Blue Line Subway services and a rapid transit that runs between the airport and downtown Boston. Ground transportation options to and from the airport include the bus service, which serves New Hampshire communities and nearby areas of Salem, Manchester, and Londonderry. Particularly, the Cape Bus provides express luxury service between the airport and Cape Cod with connections to Nantucket ferry service and Martha’s Vineyard. If you’re in Chicago, there are plenty of options to and from O'Hare International Airport. Some several regional buses and shuttles serve the O'Hare International Airport, which makes it easy for passengers in the region to get to and from the airport. You can also use a taxi service or a rental car. Other public transportation options that ease airport accessibility include the Chicago Transit Authority, which is an economical choice. This offers train and bus service throughout Chicago and nearby suburbs.

Which cities can you get to from O'Hare International Airport?

From O'Hare International Airport, you can access different nearby cities, including Bensenville, Schiller Park, Franklin Park, Elk Grove Village, Wood Dale, and Northlake. The airport is also near Mount Prospect, Niles, and Melrose Park. All these cities are within driving distance of the airport. If you want to visit major cities from O'Hare International Airport, there are several options nearby, including Chicago and Milwaukee. The airport offers flights to most major cities.

Question 18

What are the benefits of the different airports in Boston and Chicago?

Accepted Answer

Boston Logan International Airport offers numerous amenities, making this one of the most preferred airports for people traveling to and from Boston. If you want something to eat, there are many dining options, including restaurants and food stores at the terminals. For families traveling with kids, there’s a children’s play area named Kidport, which is equipped with fun features to keep your kid busy. Besides, there’s a Wings for Autism Program, which is designed for autistic kids to make flying less stressful. While at the Boston Logan Airport, you can find places to stay, including the Hyatt Regency Boston Harbor Hotel and the Hilton Logan Airport Hotel. In Terminal C, pre-security, there’s a chapel to use if you want a quiet space. At O'Hare International Airport, you can enjoy different amenities, including a yoga room, a space that invites you to relax and unwind, especially after a flight. For traveling mothers, the O'Hare International Airport offers the Mother’s Rooms in each terminal, which are cleanrooms for mothers to nurse and care for the young. In addition, the airport offers easy access to downtown Chicago and nearby areas.

Question 19

When did momondo last update prices for flights from Boston Logan Intl Airport to Chicago O'Hare Intl Airport?

Accepted Answer

Prices for flights from Boston Logan Intl Airport to Chicago O'Hare Intl Airport are updated daily.

Question 20

How many operators does momondo search for flights from Boston Logan Intl Airport to Chicago O'Hare Intl Airport?

Accepted Answer

There are 6 operators available for flights from Boston Logan Intl Airport to Chicago O'Hare Intl Airport as of December 2025.

Question 21

How old do you have to be to fly from Boston Logan Intl Airport to Chicago O'Hare Intl Airport?

Accepted Answer

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Boston Logan Intl Airport to Chicago O'Hare Intl Airport.

Question 22

What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

Accepted Answer

The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best Price Found	$137
Fastest flight time	2h 44m
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Airline	Rating	Free Cancellation	Price
JetBlue	PriceFrom $75	Free Cancellation	Rating 7.2 2,897 reviews	Search JetBlue flights
Spirit Airlines	PriceFrom $83	Free Cancellation	Rating 6.3 8,196 reviews	Search Spirit Airlines flights
Delta	PriceFrom $114	Free Cancellation	Rating 7.9 8,014 reviews	Search Delta flights
United Airlines	PriceFrom $123	Free Cancellation	Rating 7.4 9,105 reviews	Search United Airlines flights
American Airlines	PriceFrom $129	Free Cancellation	Rating 7.2 11,054 reviews	Search American Airlines flights
Southwest	PriceFrom $156	Free Cancellation	Rating 8.0 4,253 reviews	Search Southwest flights

Cheap flights from Boston to Chicago from $64

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How to get the cheapest flight ticket from Boston to Chicago O'Hare Intl Airport

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Boston averaging around $216.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

What is the cheapest Boston Logan Intl to Chicago O'Hare Intl flight route?

Fly from Boston Logan Intl to Chicago O'Hare Intl for the best Boston Logan Intl - Chicago O'Hare Intl flight prices

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

What cabin class options are available on Boston Logan Intl to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Boston Logan Intl to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Boston to Chicago O'Hare Intl Airport flight prices changed over time?

As of December 2025, prices for Boston to Chicago O'Hare Intl Airport flights are approximately 20% cheaper when compared to flights at the same time last year.

What is the cheapest airline that flies from Boston Logan Intl to Chicago O'Hare Intl?

United Airlines, Southwest, and JetBlue are the most popular carriers operating from Boston Logan Intl to Chicago O'Hare Intl

What airlines fly to Chicago O'Hare Intl Airport?

How often are flights from Boston to Chicago delayed?

Historically, on average around 13% of flights between Boston and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 168 minutes.

What is the most punctual flight time for Boston to Chicago flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Thursday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Boston to Chicago flights?

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 10% of their flights experiencing any sort of delay.

How many flights depart from Boston to Chicago O'Hare Intl Airport on average per day?

The number of flights available between Boston and Chicago O'Hare Intl Airport is 38 per day as of December 2025. The most frequent departure time is 4:00PM, with 49% of daily flights leaving in the afternoon.

How many flights depart from Boston to Chicago O'Hare Intl Airport on average per week?

As of December 2025, there are 269 flights per week flying from Boston to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Mon, with 21% of flights taking off on this day.

When to book flights from Boston to Chicago O'Hare Intl Airport

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When did momondo last update prices for flights from Boston Logan Intl Airport to Chicago O'Hare Intl Airport?

How many operators does momondo search for flights from Boston Logan Intl Airport to Chicago O'Hare Intl Airport?

How old do you have to be to fly from Boston Logan Intl Airport to Chicago O'Hare Intl Airport?

What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

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