Cheap flights from Boston to Chicago (BOS - CHI)

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

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 2021: 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
Precipitation
1.7 - 4.9 inches

Popular in

December

High demand for flights, 29% potential price rise

Cheapest in

August

Best time to find cheap flights, 62% potential price drop

Round-trip from

$56

From Boston Logan Intl to Chicago (CHI)

One-way from

$36

One-way flight from Boston Logan Intl to Chicago (CHI)

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Boston to Chicago?

Travelers have found that booking a Friday departure is the best way to save up to 20% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

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 36% on flights from Boston to Chicago by exploring options for tickets at noon.

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.

Cheap flights from Boston to Chicago in October, November 2021

The best prices found for BOS to CHI flights for October, November
2 Nov - 3 Nov
$79pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
10 Nov - 16 Nov
$86pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
2 Nov - 4 Nov
$89pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl

Boston Logan Intl to Chicago 2021 flight deals

Cheap flights to Chicago from Boston found for this year
2 Nov - 3 Nov
$79pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
10 Nov - 16 Nov
$86pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
2 Nov - 4 Nov
$89pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl

Non-stop flights to Chicago from Boston

Save time with Boston to Chicago direct flight deals
9 Nov - 13 Nov
$125pp
BOS
Boston Logan Intl
Major Airline
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Major Airline
Non-Stop
BOS
Boston Logan Intl
8 Nov - 8 Nov
$136pp
BOS
Boston Logan Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
BOS
Boston Logan Intl
2 Nov - 3 Nov
$138pp
BOS
Boston Logan Intl
Major Airline
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Major Airline
Non-Stop
BOS
Boston Logan Intl

Last minute flights from Boston to Chicago

Late deals on round-trip flights to Chicago from Boston, departing today and this week
26 Oct - 2 Nov
$91pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
26 Oct - 30 Oct
$98pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
27 Oct - 1 Nov
$101pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl

One-way flights to Chicago from Boston

The cheapest one-way flights from Boston to Chicago
12:03 am - 2:06 am
JetBlue
Nonstop
3h 03m
BOS - ORD
JetBlue
1:00 am - 1:59 am
JetBlue
Nonstop
2h 59m
BOS - ORD
JetBlue
1:00 am - 12:38 pm
Spirit Airlines
1 Stop
12h 38m
BOS - ORD
Spirit Airlines
$36
mytrip.com

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Boston</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From Boston to Chicago

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 56 daily outbound flights to Chicago from 7 different airlines.

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

United Airlines, American 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 Spirit Airlines for just $79, but on average you can expect to pay $102.

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 $149.

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: Sunday, Friday, Saturday.

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

24 flight departures from Boston to Chicago per day on average.
Early Morning (Midnight to 6am) - 29% of flight departures
Morning (6am - Noon) - 38% of flight departures
Afternoon (Noon - 6pm) - 4% of flight departures
Evening (6pm - Midnight) - 29% of flight departures

How long is the flight from Boston to Chicago?

For as low as $79, Spirit Airlines can have you in Chicago from Boston in 13h 31m. Airlines will cover a distance of 869 mi.

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

Our cheapest airline available from Boston to Chicago is Spirit Airlines. Our recent data shows that you can find tickets from as low as $79 on this airline. You may be able to fly from Boston to Chicago for 45% less than the average price by searching for this airline.

What are the cheapest flights from Boston to Chicago?

The cheapest flight price from Boston to Chicago is $52. On average you can expect to pay $341. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $98.

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 JetBlue. 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: Cathay Pacific (100%), ANA (98%), Iberia (95%).

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from Boston?

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 72 hours before departing to Chicago.

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

Do I need a test to fly back to Boston 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 72 hours before departing to Boston Logan Intl.

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

Hide COVID Travel Restrictions for Chicago, IL

Alternative routes for Boston to Chicago

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

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Boston to Chicago.
Average temperature for October in Chicago
64.4 °F
Avg rainfall for October in Chicago
2.6 ″

Airports servicing Boston

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Top 6 airlines flying from Boston Logan Intl 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.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Spirit Airlines
$56 $168 No cancel fee 65%
Delta
$68 $270 No cancel fee N/A
JetBlue
$71 $250 No cancel fee 62%
American Airlines
$77 $241 No cancel fee 71%
United Airlines
$80 $237 No cancel fee 69%
Southwest
$185 $387 No cancel fee 63%

Hourly flight availability from Boston to Chicago

See what time of day planes typically take off from Boston towards Chicago.
Morning 6 AM to noon 39% of BOS to CHI departures
Afternoon Noon to 6 PM 32% of BOS to CHI departures
Early morning Midnight to 6 AM 28% of BOS to CHI departures
Evening 6 PM to midnight 1% of BOS to CHI departures
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.
Sunday
44 daily flights
Monday
57 daily flights
Tuesday
56 daily flights
Wednesday
71 daily flights
Thursday
66 daily flights
Friday
65 daily flights
Saturday
33 daily flights
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