Popular in | June |
---|---|
Cheapest in | January |
Round-trip from | $207 |
One-way from | $54 |
BOS - CHI Price | $207 - $364 |
---|---|
CHI Temperature | 23 - 73.4 °F |
CHI Rainfall | 1.7 - 4.9 inches |
Travelers have found that booking a Friday departure is the best way to save up to 32% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.
Due to multiple factors, expect to potentially pay more when booking in June. For low rates, January can be a great choice for travel to Chicago. Flights to Chicago from Boston in January are about $251 on average during January, but can be found for as low as $118.
Unlike at noon, when flights are generally more expensive, you can save up to 16% on flights from Boston to Chicago by exploring options for tickets in the evening.
If you’re traveling from Boston to Chicago, one of the more common airlines traveling that route is American Airlines. Flights from American Airlines traveling this route typically cost $299.40 RT. This price is typically 30% more expensive than other airlines that offer Boston to Chicago flights. When booking this route, the cheapest RT price found was $49. The most popular departure airport in Boston when flying to Chicago is Boston Logan Intl Airport. The most popular airport to fly into when visiting Chicago is Chicago O'Hare Intl Airport. When flying from Boston to Chicago, American Airlines flights are 10% more popular than any other airline flying that same route.
JetBlue is one of the most popular airlines used for those traveling from Boston to Chicago. Flights from JetBlue traveling this route typically cost $325.83 RT. This price is typically 27% more expensive than other airlines that offer Boston to Chicago flights. When booking this route, the cheapest RT price found was $94. The most popular departure airport in Boston when flying to Chicago is Boston Logan Intl Airport. The most popular airport to fly into when visiting Chicago is Chicago O'Hare Intl Airport. When flying from Boston to Chicago, JetBlue flights are 8% more popular than any other airline flying that same route.
Fly from
Fly to
Budget
$78 - $156
Route
Depart
Return
Price
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 10/24
1 stop5h 05m
Chicago Midway
Wed 10/25
1 stop10h 26m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 10/24
1 stop5h 05m
Chicago Midway
Sat 10/28
1 stop14h 33m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Sat 11/4
Nonstop3h 00m
Chicago O'Hare Intl
Wed 11/8
Nonstop2h 17m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Sat 11/11
Nonstop2h 48m
Chicago O'Hare Intl
Tue 11/14
Nonstop2h 13m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 11/7
1 stop6h 43m
Chicago O'Hare Intl
Tue 11/7
Nonstop2h 17m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 10/31
1 stop8h 59m
Chicago Midway
Sat 11/4
1 stop11h 16m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Sat 11/4
Nonstop2h 57m
Chicago O'Hare Intl
Sat 11/4
Nonstop2h 21m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Wed 10/18
1 stop16h 34m
Chicago O'Hare Intl
Tue 10/24
1 stop11h 09m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Thu 11/2
Nonstop2h 49m
Chicago O'Hare Intl
Wed 11/8
Nonstop2h 25m
Food
Comfort
Boarding
Crew
Entertainment
Overall
Reviews
It was weird that we had to check after security and go to a corral which had no bathroom or other services about an hour before boarding. Had to check out of the corral to leave and check back in.
Food
Comfort
Boarding
Crew
Entertainment
Overall
Reviews
It was weird that we had to check after security and go to a corral which had no bathroom or other services about an hour before boarding. Had to check out of the corral to leave and check back in.
Food
Comfort
Boarding
Crew
Entertainment
Overall
Reviews
It was weird that we had to check after security and go to a corral which had no bathroom or other services about an hour before boarding. Had to check out of the corral to leave and check back in.
Food
Comfort
Boarding
Crew
Entertainment
Overall
Reviews
It was weird that we had to check after security and go to a corral which had no bathroom or other services about an hour before boarding. Had to check out of the corral to leave and check back in.
Food
Comfort
Boarding
Crew
Entertainment
Overall
Reviews
It was weird that we had to check after security and go to a corral which had no bathroom or other services about an hour before boarding. Had to check out of the corral to leave and check back in.
Food
Comfort
Boarding
Crew
Entertainment
Overall
Reviews
It was weird that we had to check after security and go to a corral which had no bathroom or other services about an hour before boarding. Had to check out of the corral to leave and check back in.
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 51 daily outbound flights to Chicago from 7 different airlines.
Yes, there are multiple flights from Boston to Chicago for under $100. The cheapest flight booked recently is on Frontier for just $78, but on average you can expect to pay $99.
Cheapflights has at least 20 direct flights from Boston to Chicago under $100. A good price for a nonstop flight from Boston to Chicago is less than $126.
There are currently 20+ open flights from Boston to Chicago within the next 7 days for less than $200.
You can find nonstop flights on the following days: Sunday, Monday, Tuesday, Thursday, Friday, Saturday.
82 flight departures from Boston to Chicago per day on average.
Early Morning (Midnight to 6am) - 7% of flight departures
Morning (6am - Noon) - 33% of flight departures
Afternoon (Noon - 6pm) - 51% of flight departures
Evening (6pm - Midnight) - 9% of flight departures
For as low as $78, Frontier can have you in Chicago from Boston in 2h 48m. Airlines will cover a distance of 869 mi. This flight may include one or multiple stops.
Our cheapest airline available from Boston to Chicago is Frontier. Our recent data shows that you can find tickets from as low as $78 on this airline. Additional options worth looking into are JetBlue and American Airlines, starting at $88 and $90 round-trip. You may be able to fly from Boston to Chicago for 68% less than the average price by searching for these airlines.
To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $39. JetBlue flights start at $44 while deals on Spirit Airlines start at $51 one-way.
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.
The most popular airlines flying from Boston to Chicago are Undisclosed Carrier, American Airlines and Alaska Airlines. Something to consider prior to booking your flight.
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: Japan Airlines (90%), ANA (88%), SkyWest Airlines (82%).
The cheapest flight price from Boston to Chicago is $79. On average you can expect to pay $600. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $88.
BOS and ORD are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. BOS to ORD refers to a flight route from Boston Logan Intl Airport to Chicago O'Hare Intl Airport. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.
20%of flight departures | Early morningMidnight to 6 am |
---|---|
34%of flight departures | Morning6 am to noon |
43%of flight departures | AfternoonNoon to 6 pm |
3%of flight departures | Evening6 pm to midnight |
Sunday | 51daily flights |
---|---|
Monday | 66daily flights |
Tuesday | 46daily flights |
Wednesday | 52daily flights |
Thursday | 56daily flights |
Friday | 61daily flights |
Saturday | 31daily flights |
Cheapflights makes it easy to find Boston to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.
Millions of users choose and trust Cheapflights to book the best flight deals from Boston to Chicago for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.
Yes, we can. To see specific flights from Boston to Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.
Yes! Start tracking prices for Boston to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, navigate to the search form above to perform a search, which will then prompt you for a valid email address to use the tool.