Popular in | June |
---|---|
Cheapest in | January |
Round-trip from | $223 |
One-way from | $73 |
Travelers have found that booking a Monday departure is the best way to save up to 31% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.
When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 55 days in advance, which can save you up to 24% on flights from Boston to Chicago compared to booking the week you need them. Waiting 55 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $237. For sooner than that we have options available in the next 3 days from $310.
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 $260 on average during January, but can be found for as low as $79.
Unlike at noon, when flights are generally more expensive, you can save up to 14% 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 Spirit Airlines. Boston to Chicago flights are typically 118% cheaper than other airlines traveling the same route. Flights from Spirit Airlines typically cost $96.40 RT. The cheapest Spirit Airlines flight found for this route was $39. When traveling from Boston to Chicago on Spirit Airlines, the most popular airport to depart from is Boston Logan Intl Airport and the most popular airport to arrive at is Chicago O'Hare Intl Airport. When flying from Boston to Chicago, Spirit Airlines flights are 11% more popular than any other airline flying that same route.
One of the most popular airlines traveling from Boston to Chicago is Delta. Flights from Delta traveling this route typically cost $363.21 RT. This price is typically 35% cheaper than other airlines that offer Boston to Chicago flights. When booking this route, the cheapest RT price found was $94. Boston Logan Intl Airport is the most common Boston airport to take off from when flying to Chicago. Chicago O'Hare Intl Airport is the most popular arrival airport in Chicago. When flying from Boston to Chicago, Delta flights are 10% more popular than any other airline flying that same route.
Fly from
Fly to
Budget
$96 - $165
Route
Depart
Return
Price
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Mon 4/29
1 stop11h 49m
Chicago Midway
Sat 5/4
1 stop10h 51m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 4/9
1 stop9h 40m
Chicago Midway
Sat 4/13
1 stop10h 51m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/1
1 stop27h 26m
Chicago O'Hare Intl
Thu 5/2
1 stop13h 17m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Thu 4/4
1 stop13h 36m
Chicago O'Hare Intl
Tue 4/9
1 stop8h 20m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Mon 5/6
1 stop27h 26m
Chicago O'Hare Intl
Thu 5/9
1 stop13h 02m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 5/7
Nonstop2h 54m
Chicago O'Hare Intl
Tue 5/14
Nonstop2h 35m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/4
Nonstop2h 53m
Chicago O'Hare Intl
Wed 5/8
Nonstop2h 26m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/29
Nonstop2h 50m
Chicago O'Hare Intl
Wed 6/5
Nonstop2h 20m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 4/9
Nonstop3h 11m
Chicago O'Hare Intl
Wed 4/10
Nonstop2h 14m
Currently, February is the cheapest month in which you can book a flight from Boston to Chicago (average of $245). Flying from Boston to Chicago in June is currently the most expensive (average of $361). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
January
$248
February
$245
March
$280
April
$288
May
$292
June
$361
July
$338
August
$276
September
$258
October
$248
November
$271
December
$248
CHI Temperature | 23 - 73.4 °F |
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Overall
Comfort
Boarding
Crew
Entertainment
Food
Reviews
No tray tables for food or drink not convenient nor comfortable
Overall
Comfort
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No tray tables for food or drink not convenient nor comfortable
Overall
Comfort
Boarding
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Entertainment
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No tray tables for food or drink not convenient nor comfortable
Overall
Comfort
Boarding
Crew
Entertainment
Food
Reviews
No tray tables for food or drink not convenient nor comfortable
Overall
Comfort
Boarding
Crew
Entertainment
Food
Reviews
No tray tables for food or drink not convenient nor comfortable
Overall
Comfort
Boarding
Crew
Entertainment
Food
Reviews
No tray tables for food or drink not convenient nor comfortable
31%of flight departures | Early morningMidnight to 6 am |
---|---|
28%of flight departures | Morning6 am to noon |
36%of flight departures | AfternoonNoon to 6 pm |
5%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 |
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