Cheap flights from Chicago to Boston (CHI - BOS)

Know your dates, get live prices in seconds:

From
To
Depart
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime

We work with more than 300 partners to bring you better travel deals

The best prices from Chicago to Boston are usually found in August or July, booked 5 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)

All the information you need to plan the best CHI to BOS flight in 2021: compare Chicago to Boston flight prices with the expected peak season, weather and rainfall in Boston.
CHI - BOS
Price
$70 - $195
BOS
Temperature
39.2 - 84.2 °F
BOS
Rainfall
2.8 - 3.9 inches

Popular in

December

High demand for flights, 26% potential price rise

Cheapest in

August

Best time to find cheap flights, 51% potential price drop

Average price

$127

Average for round-trip flights in May 2021

Round-trip from

$70

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 25% 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 Chicago to Boston from $185 1-2 weeks out and tickets from $243 for flights departing within the next 72 hours.

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

Flights from Chicago to Boston lean towards being more expensive in December. Prices are generally better when you fly from Chicago to Boston in August, with the cheapest ticket starting at $50.

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

When flying from Chicago to Boston, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 32% versus a flight in the afternoon.

Cheap flights from Chicago to Boston in May, June 2021

The best prices found for CHI to BOS flights for May, June
9 Jun - 16 Jun
$94pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
15 Jun - 22 Jun
$97pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
22 Jun - 13 Jul
$98pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to Boston 2021 flight deals

Cheap flights to Boston from Chicago found for this year
18 Aug - 24 Aug
$58pp
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
18 Aug - 24 Aug
$61pp
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
22 Aug - 25 Aug
$70pp
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
18 Aug - 24 Aug
$58pp
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
18 Aug - 24 Aug
$61pp
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
22 Aug - 25 Aug
$70pp
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
24 May - 25 May
$142pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
26 May - 6 Jul
$144pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
26 May - 30 May
$150pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl

One-way flights to Boston from Chicago

The cheapest one-way flights from Chicago to Boston
2:00 am - 6:40 am
Frontier
1 Stop
27h 40m
ORD - BOS
Frontier
$78
Kiwi.com
4:35 pm - 7:54 pm
American Airlines
Nonstop
2h 19m
ORD - BOS
American Airlines
4:34 pm - 6:26 am
Spirit Airlines
1 Stop
12h 52m
ORD - BOS
Spirit Airlines
$85
Kiwi.com

Related info for your journey

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

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

American Airlines, United Airlines, and Spirit 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.

What airport do you fly into for flights to Boston from Chicago?

Boston Logan Intl (BOS) is the airport you will fly into if you book a flight from Chicago to Boston. You should not have trouble finding flights to Logan Intl from Chicago; the airport handles an average of 25 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 7 airlines have flights to the Boston airport from Chicago. It is only a 2.6 mi journey from Logan Intl (BOS) to Boston’s city center.

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 $58, but on average you can expect to pay $83.

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 $87.

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

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

What days are nonstop flights available from Chicago to Boston?

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

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

3 flight departures from Chicago to Boston Logan Intl per day on average.
Morning (6am - Noon) - 67% of flight departures
Evening (6pm - Midnight) - 33% 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.

How long is the flight from Chicago to Boston?

A quick flight from Chicago to Boston can take about 2h 18m. Spirit Airlines provides one of the quickest options available for as low as $58. Chicago and Boston are separated by a distance of 869 mi. Most flights are nonstop.

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

Flying on Spirit Airlines is currently your cheapest option to Boston, with prices starting at $58. You may be able to fly from Chicago to Boston for 59% less than the average price by searching for this airline.

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

The cheapest airlines for a one-way flight from Chicago to Boston are Spirit Airlines ($28), Delta ($58), and Allegiant Air ($74).

Alternative routes for Chicago to Boston

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

Destination information for Boston

Things to know before you go - useful duration and weather info for your trip from Chicago to Boston.
Flight duration
2h 30m
Average temperature for May in Boston
68.0 °F
Avg rainfall for May in Boston
3.7 ″

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Airports servicing Boston

Top 6 airlines flying from Chicago to Boston

The chart below displays the airlines Cheapflights users traveling from Chicago to Boston 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
$54 $132 No cancel fee 65%
JetBlue
$71 $202 No cancel fee 62%
American Airlines
$76 $208 No cancel fee 71%
United Airlines
$76 $247 No cancel fee 69%
Southwest
$189 $267 No cancel fee 63%
Delta
$48 $268 No cancel fee N/A

Hourly flight availability from Chicago to Boston

See what time of day planes typically take off from Chicago towards Boston.
Afternoon Noon to 6 PM 38% of CHI to BOS departures
Evening 6 PM to midnight 32% of CHI to BOS departures
Morning 6 AM to noon 29% 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
See how many times per day planes take to the skies headed from Chicago to Boston.
Sunday
33 daily flights
Monday
27 daily flights
Tuesday
16 daily flights
Wednesday
20 daily flights
Thursday
27 daily flights
Friday
33 daily flights
Saturday
20 daily flights
Home North America USA Massachusetts Boston Cheap flights from Chicago to Boston