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

BOS — CHI
May 17 — May 244

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.

BOS - CHI

Price

$56 - $206

CHI

Temperature

23 - 73.4 °F

CHI

Rainfall

1.7 - 4.9 inches

Popular inDecemberHigh demand for flights, 29% potential price rise
Cheapest inAugustBest time to find cheap flights, 62% potential price drop
Average price$127Average for round-trip flights in May 2022
Round-trip from$56From 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 29% 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 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.

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

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.

Cheap flights from Boston to Chicago in May, June 2022

The best prices found for BOS to CHI flights for May, June
May 25 - May 29
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 55m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

Nonstop

2h 22m
$150

JetBlue

View Deal

Deal found 9/5/22

Jun 8 - Jun 8
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 50m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

1 stop

7h 41m
$155

Multiple Airlines

View Deal

Deal found 9/5/22

Jun 8 - Jun 8
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 50m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

1 stop

7h 41m
$157

Multiple Airlines

View Deal

Deal found 11/5/22

Boston to Chicago 2022 flight deals

Cheap flights to Chicago from Boston found for this year
Sep 15 - Sep 17
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 54m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

Nonstop

2h 21m
$150

JetBlue

View Deal

Deal found 10/5/22

Jun 8 - Jun 8
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 50m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

1 stop

7h 41m
$155

Multiple Airlines

View Deal

Deal found 9/5/22

Jun 8 - Jun 8
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 50m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

1 stop

7h 41m
$157

Multiple Airlines

View Deal

Deal found 11/5/22

Cheap American Airlines flights from Boston to Chicago

Aug 23 - Aug 30
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 57m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

1 stop

5h 33m
$159

American Airlines

View Deal

Deal found 9/5/22

Aug 10 - Aug 10
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

1 stop

4h 45m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

1 stop

5h 02m
$162

American Airlines

View Deal

Deal found 11/5/22

Sep 6 - Sep 13
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

1 stop

5h 05m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

1 stop

4h 43m
$166

American Airlines

View Deal

Deal found 11/5/22

Cheap Spirit Airlines flights from Boston to Chicago

May 19 - Jun 8
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

1 stop

8h 41m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

1 stop

7h 41m
$194

Spirit Airlines

View Deal

Deal found 9/5/22

May 17 - May 24
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

1 stop

26h 10m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

2 stops

20h 14m
$222

Spirit Airlines

View Deal

Deal found 9/5/22

Non-stop flights to Chicago from Boston

Save time with Boston to Chicago direct flight deals
Sep 15 - Sep 20
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 54m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

Nonstop

2h 24m
$150

JetBlue

View Deal

Deal found 11/5/22

Aug 24 - Aug 29
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 57m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

Nonstop

2h 15m
$160

JetBlue

View Deal

Deal found 11/5/22

Jul 13 - Jul 19
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 50m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

Nonstop

2h 17m
$165

Multiple Airlines

View Deal

Deal found 9/5/22

Last minute flights from Boston to Chicago

Late deals on return flights to Chicago from Boston, departing today and this week
May 19 - Jun 8
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 59m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

1 stop

7h 41m
$166

Multiple Airlines

View Deal

Deal found 9/5/22

May 17 - May 28
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 57m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

1 stop

5h 00m
$174

Delta

View Deal

Deal found 10/5/22

May 18 - May 20
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 55m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

Nonstop

2h 23m
$180

JetBlue

View Deal

Deal found 10/5/22

One-way flights to Chicago All airports from Boston

The cheapest one-way flights from Boston to Chicago
May 25
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 56m
$75

JetBlue

View Deal

Deal found 11/5/22

Jun 8
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 50m
$76

United Airlines

View Deal

Deal found 10/5/22

Jun 6
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

1 stop

6h 27m
$79

Spirit Airlines

View Deal

Deal found 10/5/22

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 64 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?

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.

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

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.

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

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.

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

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

What days are nonstop flights available from Boston to Chicago?

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

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

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

How long is the flight from Boston to Chicago?

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.

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

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.

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 $75. United Airlines flights start at $76 while deals on Spirit Airlines start at $79 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 Major Airline, 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: ANA (96%), SkyWest Airlines (94%), Japan Airlines (92%).

What are the cheapest flights from Boston to Chicago?

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.

Alternative routes for Boston to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Quincyfrom $224 pp
Boston to Marionfrom $334 pp
Boston to Peoriafrom $355 pp
Boston to Molinefrom $626 pp

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.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$14Average$22FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
Spirit AirlinesCheapest$49Average$138FlexibilityNo cancel feeOn-time65%COVID-19 safety
Search Spirit Airlines flights
JetBlueCheapest$58Average$225FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search JetBlue flights
DeltaCheapest$71Average$263FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
United AirlinesCheapest$82Average$218FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights

Hourly flight availability from Boston to Chicago

See what time of day planes typically take off from Boston to Chicago
8%of flight departuresEarly morningMidnight to 6 am
43%of flight departuresMorning6 am to noon
42%of flight departuresAfternoonNoon to 6 pm
7%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
Sunday65daily flights
Monday74daily flights
Tuesday64daily flights
Wednesday75daily flights
Thursday68daily flights
Friday68daily flights
Saturday37daily flights