Q: Can I fly back to Boston Logan Intl from Chicago?

Returning to Boston Logan Intl from Chicago COVID-19 testing requirements Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 1 day for RT-PCR (NAAT) and 1 day for Antigen (quick-test) before departing to Boston Logan Intl. Quarantine requirements Visitors from Chicago are not required to quarantine after entering Boston Logan Intl.

Question 1

What days are nonstop flights available from Boston to Chicago?

Accepted Answer

You can find nonstop flights on the following days: Sunday, Monday, Tuesday, Thursday, Friday, Saturday.

Question 2

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

Accepted Answer

16 flight departures from Boston to Chicago per day on average.
Early Morning (Midnight to 6am) - 25% of flight departures
Morning (6am - Noon) - 25% of flight departures
Afternoon (Noon - 6pm) - 25% of flight departures
Evening (6pm - Midnight) - 25% of flight departures

Question 3

How long is the flight from Boston to Chicago?

Accepted Answer

For as low as $150, JetBlue can have you in Chicago from Boston in 2h 54m. Airlines will cover a distance of 869 mi. This flight may include one or multiple stops.

Question 4

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

Accepted Answer

Our cheapest airline available from Boston to Chicago is JetBlue. Our recent data shows that you can find tickets from as low as $150 on this airline. Additional options worth looking into are American Airlines and Delta, starting at $159 and $168 round-trip.

Question 5

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

Accepted Answer

To fly one-way, consider booking your trip with JetBlue, which is currently one of the cheapest options available, starting at $75. United Airlines flights start at $76 while deals on Spirit Airlines start at $79 one-way.

Question 6

Can I fly to Chicago from Boston Logan Intl right now?

Accepted Answer

Information is based on travel restrictions for travel to Chicago within the United States

Most visitors from Boston Logan Intl need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Boston Logan Intl must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 1 day for RT-PCR (NAAT) and 1 day for Antigen (quick-test) before departing to Chicago.

Quarantine requirements
Visitors from Boston Logan Intl are not required to quarantine after entering Chicago.

Question 7

Can I fly back to Boston Logan Intl from Chicago?

Accepted Answer

Returning to Boston Logan Intl from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 1 day for RT-PCR (NAAT) and 1 day for Antigen (quick-test) before departing to Boston Logan Intl.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Boston Logan Intl.

Question 8

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

Accepted Answer

The most popular airlines flying from Boston to Chicago are Major Airline, American Airlines and Alaska Airlines. Something to consider prior to booking your flight.

Question 9

What are the most popular routes from Boston to Chicago?

Accepted Answer

Most travelers choose Boston Logan Intl - Chicago O'Hare Intl, Boston Logan Intl - Chicago Midway or Boston Logan Intl - Chicago Greater Rockford when deciding on the best route from Boston to Chicago.

Question 10

What are the cheapest flights from Boston to Chicago?

Accepted Answer

The cheapest flight price from Boston to Chicago is $75. On average you can expect to pay $359. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $150.

Question 11

What are the most reliable airlines from Boston to Chicago?

Accepted Answer

Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Boston to Chicago on time: ANA (96%), SkyWest Airlines (94%), Japan Airlines (92%).

Question 12

Can I find flights from Boston to Chicago for under $200 on Cheapflights?

Accepted Answer

Yes, there are multiple flights from Boston to Chicago for under $200. The cheapest flight booked recently is on JetBlue for just $150, but on average you can expect to pay $167.

Question 13

Are there nonstop flights from Boston to Chicago for under $200 on Cheapflights?

Accepted Answer

Cheapflights has at least 20 direct flights from Boston to Chicago under $200. A good price for a nonstop flight from Boston to Chicago is less than $186.

Question 14

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

Accepted Answer

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

Question 15

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

Accepted Answer

Located just 2.6 mi from the city center, Boston Logan Intl is the airport most travelers will use when flying to Chicago from Boston. Booking flights from Logan Intl (BOS) to Chicago should be relatively easy as there are 64 daily outbound flights to Chicago from 10 different airlines.

Question 16

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

Accepted Answer

United Airlines, JetBlue, and American Airlines 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.

Question 17

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

Accepted Answer

Travelers have found that booking a Monday departure is the best way to save up to 29% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

Question 18

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

Accepted Answer

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, August can be a great choice for travel to Chicago. Flights to Chicago from Boston in August are about $146 on average during August, but can be found for as low as $34.

Question 19

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

Accepted Answer

Unlike in the afternoon, when flights are generally more expensive, you can save up to 19% on flights from Boston to Chicago by exploring options for tickets in the evening.

Popular in	December	High demand for flights, 29% potential price rise
Cheapest in	August	Best time to find cheap flights, 62% potential price drop
Average price	$127	Average for round-trip flights in May 2022
Round-trip from	$56	From Boston Logan Intl to Chicago (CHI)

Airline	Cheapest	Average	Flexibility	On-time	COVID-19 safety
Juneyao Airlines	Cheapest$14	Average$22	FlexibilityNo cancel fee	On-time66%	COVID-19 safety	Search Juneyao Airlines flights
Spirit Airlines	Cheapest$49	Average$138	FlexibilityNo cancel fee	On-time65%	COVID-19 safety	Search Spirit Airlines flights
JetBlue	Cheapest$58	Average$225	FlexibilityNo cancel fee	On-time62%	COVID-19 safety	Search JetBlue flights
Delta	Cheapest$71	Average$263	FlexibilityNo cancel fee	On-timeN/A	COVID-19 safety	Search Delta flights
United Airlines	Cheapest$82	Average$218	FlexibilityNo cancel fee	On-time69%	COVID-19 safety	Search United Airlines flights

8%of flight departures	Early morningMidnight to 6 am
43%of flight departures	Morning6 am to noon
42%of flight departures	AfternoonNoon to 6 pm
7%of flight departures	Evening6 pm to midnight

Sunday	65daily flights
Monday	74daily flights
Tuesday	64daily flights
Wednesday	75daily flights
Thursday	68daily flights
Friday	68daily flights
Saturday	37daily flights

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

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

How to find the cheapest flight from Boston to Chicago

All the information you need to plan the best BOS to CHI flight in 2022: compare Boston to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.

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

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

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

Cheap flights from Boston to Chicago in May, June 2022

The best prices found for BOS to CHI flights for May, June

Boston to Chicago 2022 flight deals

Cheap flights to Chicago from Boston found for this year

Cheap American Airlines flights from Boston to Chicago

Cheap Spirit Airlines flights from Boston to Chicago

Non-stop flights to Chicago from Boston

Save time with Boston to Chicago direct flight deals

Last minute flights from Boston to Chicago

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

One-way flights to Chicago All airports from Boston

The cheapest one-way flights from Boston to Chicago

Related info for your journey

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

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

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

Can I find flights from Boston to Chicago for under $200 on Cheapflights?

Are there nonstop flights from Boston to Chicago for under $200 on Cheapflights?

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

What days are nonstop flights available from Boston to Chicago?

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

How long is the flight 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 popular routes from Boston to Chicago?

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

What are the most reliable airlines from Boston to Chicago?

What are the cheapest flights from Boston to Chicago?

Other flights from Boston

Other flights to Chicago

Flights to Chicago from Boston

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COVID Restrictions

Can I fly to Chicago from Boston Logan Intl right now?

Can I fly back to Boston Logan Intl from Chicago?

Alternative routes for Boston to Chicago

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

Top 5 airlines flying from Boston to Chicago

The chart below displays the airlines Cheapflights users traveling from Boston to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.

Popular flight searches

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Hourly flight availability from Boston to Chicago

See what time of day planes typically take off from Boston to Chicago

Weekly flight availability from Boston to Chicago

See how many times per day planes take to the skies headed from Boston to Chicago