Cheap flights from Logan Intl to Chicago (BOS - CHI)

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The best prices from 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
Logan Intl (BOS) to Chicago (CHI)

All the information you need to plan the best BOS to CHI flight in 2021: compare Logan Intl to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
BOS - CHI
Price
$56 - $206
CHI
Temperature
33.8 - 84.2 °F
CHI
Rainfall
0.7 - 4.3 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

Average price

$127

Average for round-trip flights in May 2021

Round-trip from

$56

From Logan Intl to Chicago

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 Logan Intl to Chicago?

It’s generally more expensive to depart on a Friday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

How far in advance should I book a flight from Logan Intl to Chicago?

To save up to 10% on this flight, we recommend booking at least 20 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Logan Intl to Chicago from $137 1-2 weeks out and tickets from $157 for flights departing within the next 72 hours.

What is the cheapest month to fly from Logan Intl to Chicago?

April is one of the best times of the year to fly to Chicago from Logan Intl. Prices for April average $135 per person but you can even find prices for as low as $33. The most expensive prices can be found in the month of December. Opting for a April flight can save you 49% on your journey compared to booking in April

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

A simple way to save on the total cost of your ticket is to fly from Logan Intl to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 36% on your trip compared to booking a flight in the afternoon.

Cheap flights from Logan Intl to Chicago in May, June 2021

The best prices found for BOS to CHI flights for May, June
29 Jun - 10 Aug
$81pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
8 Jun - 9 Jun
$96pp
BOS
Boston Logan Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
9 Jun - 22 Jun
$97pp
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

Logan Intl to Chicago 2021 flight deals

Cheap flights to Chicago from Logan Intl found for this year
24 Aug - 31 Aug
$58pp
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
24 Aug - 31 Aug
$61pp
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
4 Aug - 9 Aug
$70pp
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl

Non-stop flights to Chicago from Logan Intl

Save time with Logan Intl to Chicago direct flight deals
24 Aug - 31 Aug
$58pp
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
24 Aug - 31 Aug
$61pp
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
4 Aug - 9 Aug
$70pp
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl

Last minute flights from Logan Intl to Chicago

Late deals on round-trip flights to Chicago from Logan Intl, departing today and this week
25 May - 2 Jun
$144pp
BOS
Boston Logan Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
25 May - 16 Jun
$147pp
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
25 May - 26 May
$151pp
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 Logan Intl

The cheapest one-way flights from Logan Intl to Chicago
2:45 am - 4:48 am
JetBlue
Nonstop
3h 03m
BOS - ORD
JetBlue
4:00 am - 5:51 am
United Airlines
Nonstop
2h 51m
BOS - ORD
United Airlines
$71
United
2:52 pm - 7:57 pm
American Airlines
1 Stop
6h 05m
BOS - ORD
American Airlines

Related info for your journey

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

Flight FAQs

From Logan Intl to Chicago

Are flight prices decreasing from Boston to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Boston and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

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.

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 25 daily outbound flights to Chicago from 7 different airlines.

Can I find flights from Logan Intl to Chicago for under $100 on Cheapflights?

Yes, there are multiple flights from Logan Intl to Chicago for under $100. The cheapest flight booked recently is on Spirit Airlines for just $58, but on average you can expect to pay $84.

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

Cheapflights has at least 20 direct flights from Logan Intl to Chicago under $100. A good price for a nonstop flight from Logan Intl to Chicago is less than $88.

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

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

What days are nonstop flights available from Boston to Chicago?

Days when nonstop flights are available for this flight are: Monday, Tuesday, Friday.

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

On average, you can expect to see 6 flights from Boston Logan Intl to Chicago a day.
Morning (6am - Noon) - 83% of flight departures
Afternoon (Noon - 6pm) - 17% of flight departures

Is Boston weather warmer or cooler than Chicago?

We forecast the temperature to be around the 84 °F's in July, on average. The temperature in Chicago is generally the same as in Boston. Book flights in a timely manner in correlation to your departure date.

How long is the flight from Logan Intl to Chicago?

Airlines like Spirit Airlines and Delta fly from Logan Intl to Chicago in about 2h 33m. The time it takes to get you to your destination is usually consistent. The distance from Logan Intl to Chicago is about 869 mi. Generally, flights for this route are nonstop.

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

Our cheapest airline available from Logan Intl to Chicago is Spirit Airlines. Our recent data shows that you can find tickets from as low as $58 on this airline. An additional option worth looking into is Delta, starting at $106. Users have found that Spirit Airlines is 60% cheaper than the other options available to this destination.

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

The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $28. However, be on the lookout for offers from United Airlines and Delta, as they are both options that can get you from Logan Intl to Chicago for a low price.

Alternative routes for Logan Intl 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 Logan Intl to Chicago.
Flight duration
2h 27m
Average temperature for May in Chicago
71.6 °F
Avg rainfall for May in Chicago
4.3 ″

Airports servicing Boston

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 6 airlines flying from Logan Intl to Chicago

The chart below displays the airlines Cheapflights users traveling from Logan Intl 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%
United Airlines
$80 $237 No cancel fee 69%
American Airlines
$77 $241 No cancel fee 71%
JetBlue
$71 $250 No cancel fee 62%
Delta
$68 $270 No cancel fee N/A
Southwest
$185 $387 No cancel fee 63%

Hourly flight availability from Logan Intl to Chicago

See what time of day planes typically take off from Logan Intl towards Chicago.
Early morning Midnight to 6 AM 39% of BOS to CHI departures
Morning 6 AM to noon 34% of BOS to CHI departures
Afternoon Noon to 6 PM 27% of BOS to CHI departures
Evening 6 PM to midnight 0% of BOS to CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Logan Intl to Chicago
See how many times per day planes take to the skies headed from Logan Intl to Chicago.
Sunday
34 daily flights
Monday
26 daily flights
Tuesday
19 daily flights
Wednesday
17 daily flights
Thursday
24 daily flights
Friday
33 daily flights
Saturday
27 daily flights
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