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

BOS — CHI
Feb 12 — Feb 191

The best prices from Boston Logan Intl to Chicago are usually found in February or January, booked 0 days in advance, depart on a Tuesday or Saturday and return on a Tuesday

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

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

BOS - CHI

Price

$152 - $328

CHI

Temperature

23 - 73.4 °F

CHI

Rainfall

1.7 - 4.9 inches

Popular inJuneHigh demand for flights, 25% potential price rise
Cheapest inFebruaryBest time to find cheap flights, 39% potential price drop
Round-trip from$152From Boston Logan Intl to Chicago (CHI)
One-way from$59One-way flight from Boston Logan Intl to Chicago (CHI)

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

Travelers have found that booking a Monday departure is the best way to save up to 30% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

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

Due to multiple factors, expect to potentially pay more when booking in June. For low rates, February can be a great choice for travel to Chicago. Flights to Chicago from Boston in February are about $247 on average during February, but can be found for as low as $97.

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

Unlike at noon, when flights are generally more expensive, you can save up to 18% on flights from Boston to Chicago by exploring options for tickets in the evening.

Cheap flights from Boston to Chicago in February, March 2023

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

Boston to Chicago 2023 flight deals

Cheap flights to Chicago from Boston found for this year

Cheap United Airlines flights from Boston to Chicago

  • If you’re traveling from Boston to Chicago, one of the more common airlines traveling that route is United Airlines. Flights from United Airlines traveling this route typically cost $372.30 RT. This price is typically 24% more expensive than other airlines that offer Boston to Chicago flights. When booking this route, the cheapest RT price found was $307. The most popular departure airport in Boston when flying to Chicago is Boston Logan Intl Airport. The most popular airport to fly into when visiting Chicago is Chicago O'Hare Intl Airport. When flying from Boston to Chicago, United Airlines flights are 23% more popular than any other airline flying that same route.

Cheap JetBlue flights from Boston to Chicago

  • JetBlue is one of the most popular airlines used for those traveling from Boston to Chicago. Flights from JetBlue traveling this route typically cost $316.64 RT. This price is typically 34% more expensive than other airlines that offer Boston to Chicago flights. When booking this route, the cheapest RT price found was $79. The most popular departure airport in Boston when flying to Chicago is Boston Logan Intl Airport. The most popular airport to fly into when visiting Chicago is Chicago O'Hare Intl Airport. When flying from Boston to Chicago, JetBlue flights are 22% more popular than any other airline flying that same route.

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 from Boston

The cheapest one-way flights from Boston to Chicago

Reviews of Airlines Servicing Chicago

Delta
7.9
Good
2,079 reviews

Food

7.2

Overall

7.9

Comfort

7.9

Boarding

8.0

Entertainment

7.8

Crew

8.5

Reviews

1 / 10

There wasn't a meal from San Diego to JFK.

Delta
7.9
Good
2,079 reviews
Delta
7.9
Good
2,079 reviews

Food

7.2

Overall

7.9

Comfort

7.9

Boarding

8.0

Entertainment

7.8

Crew

8.5

Reviews

1 / 10

There wasn't a meal from San Diego to JFK.

JetBlue
7.7
Good
387 reviews
Delta
7.9
Good
2,079 reviews

Food

7.2

Overall

7.9

Comfort

7.9

Boarding

8.0

Entertainment

7.8

Crew

8.5

Reviews

1 / 10

There wasn't a meal from San Diego to JFK.

United Airlines
7.6
Good
1,217 reviews
Delta
7.9
Good
2,079 reviews

Food

7.2

Overall

7.9

Comfort

7.9

Boarding

8.0

Entertainment

7.8

Crew

8.5

Reviews

1 / 10

There wasn't a meal from San Diego to JFK.

Southwest
7.5
Good
961 reviews
Delta
7.9
Good
2,079 reviews

Food

7.2

Overall

7.9

Comfort

7.9

Boarding

8.0

Entertainment

7.8

Crew

8.5

Reviews

1 / 10

There wasn't a meal from San Diego to JFK.

Allegiant Air
7.5
Good
95 reviews
Delta
7.9
Good
2,079 reviews

Food

7.2

Overall

7.9

Comfort

7.9

Boarding

8.0

Entertainment

7.8

Crew

8.5

Reviews

1 / 10

There wasn't a meal from San Diego to JFK.

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?

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 51 daily outbound flights to Chicago from 10 different airlines.

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

American Airlines, United Airlines, and JetBlue 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 Boston to Chicago for under $100 on Cheapflights?

Yes, there are multiple flights from Boston to Chicago for under $100. The cheapest flight booked recently is on United Airlines for just $90, but on average you can expect to pay $128.

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

Cheapflights has at least 20 direct flights from Boston to Chicago under $100. A good price for a nonstop flight from Boston to Chicago is less than $143.

Are there last-minute flights available from Boston to Chicago for under $100?

There are currently 20+ open flights from Boston to Chicago within the next 7 days for less than $100.

What days are nonstop flights available from Boston to Chicago?

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

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

41 flight departures from Boston to Chicago per day on average.
Early Morning (Midnight to 6am) - 5% of flight departures
Morning (6am - Noon) - 78% of flight departures
Afternoon (Noon - 6pm) - 17% of flight departures

How long is the flight from Boston to Chicago?

For as low as $90, United Airlines 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.

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

Our cheapest airline available from Boston to Chicago is United Airlines. Our recent data shows that you can find tickets from as low as $90 on this airline. Additional options worth looking into are JetBlue and Spirit Airlines, starting at $109 and $120 round-trip. You may be able to fly from Boston to Chicago for 63% less than the average price by searching for these airlines.

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

To fly one-way, consider booking your trip with JetBlue, which is currently one of the cheapest options available, starting at $45. United Airlines flights start at $49 while deals on Delta start at $58 one-way.

What are the most popular routes from Boston to Chicago?

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.

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

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

What are the most reliable airlines from Boston to Chicago?

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: Republic Airways (90%), ANA (89%), Royal Jordanian (87%).

What are the cheapest flights from Boston to Chicago?

The cheapest flight price from Boston to Chicago is $59. On average you can expect to pay $977. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $94.

Alternative routes for Boston to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Peoriafrom $264 pp
Boston to Quincyfrom $354 pp
Boston to Decaturfrom $357 pp
Boston to Molinefrom $716 pp

Top 7 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.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$15Average$23FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
JetBlueCheapest$69Average$224FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search JetBlue flights
United AirlinesCheapest$79Average$259FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
DeltaCheapest$79Average$317FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
American AirlinesCheapest$114Average$287FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
Spirit AirlinesCheapest$114Average$233FlexibilityNo cancel feeOn-time65%COVID-19 safety
Search Spirit Airlines flights
Alaska AirlinesCheapest$307Average$372FlexibilityNo cancel feeOn-time75%COVID-19 safety
Search Alaska Airlines flights

Hourly flight availability from Boston to Chicago

See what time of day planes typically take off from Boston to Chicago
24%of flight departuresEarly morningMidnight to 6 am
36%of flight departuresMorning6 am to noon
40%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Boston to Chicago

See how many times per day planes take to the skies headed from Boston to Chicago
Sunday56daily flights
Monday62daily flights
Tuesday44daily flights
Wednesday51daily flights
Thursday53daily flights
Friday60daily flights
Saturday31daily flights
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