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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 October, 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

$46

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 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 30% versus a flight in the afternoon.

Cheap flights from Chicago to Boston in October, November 2020

The best prices found for CHI to BOS flights for October, November
4 Nov - 10 Nov
$64pp
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
10 Nov - 12 Nov
$67pp
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
8 Nov - 16 Nov
$70pp
ORD
Chicago O'Hare Intl
United Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to Boston 2020 flight deals

Cheap flights to Boston from Chicago found for this year
5 Dec - 8 Dec
$48pp
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
2 Dec - 9 Dec
$49pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
5 Dec - 9 Dec
$50pp
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

Non-stop flights to Boston from Chicago

Save time with Chicago to Boston direct flight deals
4 Nov - 7 Nov
$89pp
ORD
Chicago O'Hare Intl
Major Airline
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Major Airline
Non-Stop
ORD
Chicago O'Hare Intl
4 Nov - 4 Nov
$91pp
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
13 Nov - 16 Nov
$93pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
United 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
4 Nov - 10 Nov
$64pp
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
3 Nov - 10 Nov
$72pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
3 Nov - 10 Nov
$84pp
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

One-way flights to Boston from Chicago

The cheapest one-way flights from Chicago to Boston
3:25 am - 6:47 am
Major Airline
Nonstop
2h 22m
ORD - BOS
Major Airline
$46
StudentUniverse
4:10 am - 7:22 am
United Airlines
Nonstop
2h 12m
ORD - BOS
United Airlines
$49
United
4:04 am - 7:13 am
JetBlue
Nonstop
2h 09m
ORD - BOS
JetBlue

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.

What safety measures are being taken by airlines flying from Chicago to Boston Logan Intl to control the spread of COVID-19?

Airlines globally have implemented additional safety measures to accommodate you. JetBlue, Southwest, and Delta are some of the many airlines that have done so. Some of the new policies that have been implemented to accommodate travelers flying from Chicago to Boston Logan Intl are improved sanitation, HEPA filters, mask requirements, social distance seating (for a limited time), and pre-flight testing for antibodies and symptoms. Policies will vary by airline.

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.

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 $48, but on average you can expect to pay $71.

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 $125.

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: Sunday, Tuesday, Wednesday, Thursday, Friday, Saturday.

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

60 flight departures from Chicago to Boston Logan Intl per day on average.
Morning (6am - Noon) - 35% of flight departures
Afternoon (Noon - 6pm) - 42% of flight departures
Evening (6pm - Midnight) - 23% 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 12m. United Airlines provides one of the quickest options available for as low as $93. Chicago and Boston are separated by a distance of 869 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

Flying on Spirit Airlines is currently your cheapest option to Boston, with prices starting at $48. Additional round-trip tickets that might be worth considering are offered by United Airlines and JetBlue, with the lowest prices starting at $70 and $97, respectively. You may be able to fly from Chicago to Boston for 73% less than the average price by searching for these airlines.

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 ($23), United Airlines ($41), and American Airlines ($45).

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 30m
Average temperature for October in Boston
64.4 °F
Avg rainfall for October in Boston
3.7 ″

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 38% of CHI to BOS departures
Evening 6 PM to midnight 11% 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
11 daily flights
Monday
23 daily flights
Tuesday
21 daily flights
Wednesday
12 daily flights
Thursday
18 daily flights
Friday
18 daily flights
Saturday
11 daily flights
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