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Cheap flights from Chicago to Boston (CHI - BOS)

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The best prices from Chicago to Boston are usually found in September or January, booked 60 days in advance, depart on a Wednesday or Saturday and return on a Saturday

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

CHI - BOS
Price
$153 - $219
BOS
Temperature
39.2 - 84.2 °F
BOS
Rainfall
2.8 - 3.9 inches
Popular in July High demand for flights, 18% potential price rise
Cheapest in September Best time to find cheap flights, 15% potential price drop
Round-trip from $153 From Chicago to Boston
One-way from $51 One-way flight from Chicago to Boston
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 Chicago to Boston?

Saturday flights are generally found to be more expensive for flights from Chicago to Boston. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Boston.

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

To save up to 23% on this flight, we recommend booking at least 26 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago to Boston from $270 1-2 weeks out and tickets from $316 for flights departing within the next 72 hours.

Cheap flights from Chicago to Boston in July, August 2020

The best prices found for CHI to BOS flights for July, August
14 Jul - 28 Jul
$32pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
14 Jul - 15 Jul
$34pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
28 Jul - 4 Aug
$35pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Chicago to Boston 2020 flight deals

Cheap flights to Boston from Chicago found for this year
14 Jul - 28 Jul
$32pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
14 Jul - 15 Jul
$34pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
28 Jul - 4 Aug
$35pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Non-stop flights to Boston from Chicago

Save time with Chicago to Boston direct flight deals
14 Jul - 28 Jul
$32pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
14 Jul - 15 Jul
$34pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
28 Jul - 29 Jul
$35pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Boston

Late deals on round-trip flights to Boston from Chicago, departing today and this week
27 Jun - 11 Jul
$95pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
25 Jun - 11 Jul
$96pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
27 Jun - 12 Jul
$104pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl

One-way flights to Boston from Chicago

The cheapest one-way flights from Chicago to Boston
2:45 pm - 6:17 pm
British Airways
Nonstop
2h 32m
ORD - BOS
British Airways
$51
Ovago
2:16 pm - 5:33 pm
JetBlue
Nonstop
2h 17m
ORD - BOS
JetBlue
1:10 pm - 4:36 pm
Major Airline
Nonstop
2h 26m
ORD - BOS
Major Airline
$64
StudentUniverse

Related info for your journey

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

Flight FAQs

From Chicago to Boston

Are flight prices decreasing from Chicago to Boston 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 Chicago and Boston 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.

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

Yes, there are multiple flights from Chicago to Boston for under $100. The cheapest flight booked recently is on Spirit Airlines for just $32, but on average you can expect to pay $45.

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

Cheapflights has at least 20 direct flights from Chicago to Boston under $100. A good price for a nonstop flight from Chicago to Boston is less than $47.

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

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

What days are nonstop flights available from Chicago to Boston?

Nonstop flights can be found on the following days: Monday, Saturday.

How popular is this flight route?

Flights from Chicago to Boston Logan Intl have been viewed 207 times in the past calendar month.

What is the cheapest airline for this route?

While looking for the best option consider American Airlines Inc., our data currently shows that they have the cheapest flight available for the flight path. When traveling from Chicago to Boston, generally 206 flights depart for this route daily.

How long does the flight from Chicago to Boston take?

Your journey will take you approximately 3 hours. Your flight will cover a distance of about 540 miles.

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

4 flight departures from Chicago to Boston Logan Intl per day on average.
Morning (6am - Noon) - 50% of flight departures
Evening (6pm - Midnight) - 50% of flight departures

Is Chicago weather warmer or cooler than Boston?

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

Alternative routes for Chicago to Boston

Destination information for Boston

Things to know before you go. Useful info for your trip from Chicago to Boston
Flight duration
2h 36m
Average temperature for July in Boston
84.2 °F
Avg rainfall for July in Boston
3.2 ″

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Airports servicing Boston

Hourly flight availability from Chicago to Boston

Afternoon Noon to 6 PM 50% of CHI to BOS departures
Morning 6 AM to noon 40% of CHI to BOS departures
Evening 6 PM to midnight 9% of CHI to BOS departures
Early morning Midnight to 6 AM 1% of CHI to BOS departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Chicago to Boston
Sunday
29 daily flights
Monday
33 daily flights
Tuesday
21 daily flights
Wednesday
30 daily flights
Thursday
37 daily flights
Friday
31 daily flights
Saturday
19 daily flights