Popular in | June |
---|---|
Cheapest in | January |
Round-trip from | $223 |
One-way from | $95 |
Travelers have found that booking a Monday departure is the best way to save up to 27% 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 52 days in advance, which can save you up to 36% on flights from Boston to Chicago compared to booking the week you need them. Waiting 52 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 $279. For sooner than that we have options available in the next 3 days from $328.
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 $273 on average during January, but can be found for as low as $106.
Unlike at noon, when flights are generally more expensive, you can save up to 12% 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 57% cheaper than other airlines traveling the same route. Flights from Spirit Airlines typically cost $93.90 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.
JetBlue is one of the most popular airlines used for those traveling from Boston to Chicago. Flights from JetBlue traveling this route typically cost $365.75 RT. This price is typically 48% more expensive than other airlines that offer Boston to Chicago flights. When booking this route, the cheapest RT price found was $98. 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 11% more popular than any other airline flying that same route.
Fly from
Fly to
Budget
$53 - $177
Route
Depart
Return
Price
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/4
1 stop8h 38m
Chicago O'Hare Intl
Wed 6/5
Nonstop2h 29m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/29
1 stop10h 08m
Chicago O'Hare Intl
Wed 6/5
Nonstop2h 29m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/4
1 stop6h 52m
Chicago O'Hare Intl
Wed 6/5
Nonstop2h 29m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Thu 8/22
Nonstop2h 33m
Chicago O'Hare Intl
Tue 8/27
Nonstop2h 18m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Thu 6/6
Nonstop2h 54m
Chicago O'Hare Intl
Thu 6/13
Nonstop2h 28m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/11
1 stop6h 05m
Chicago O'Hare Intl
Thu 6/13
Nonstop2h 28m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/29
1 stop10h 08m
Chicago O'Hare Intl
Tue 6/4
1 stop5h 12m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 6/5
1 stop6h 43m
Chicago Midway
Tue 6/11
1 stop7h 42m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Mon 6/3
Nonstop2h 54m
Chicago O'Hare Intl
Wed 6/5
Nonstop2h 26m
Currently, February is the cheapest month in which you can book a flight from Boston to Chicago (average of $244). Flying from Boston to Chicago in June is currently the most expensive (average of $342). 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
$244
March
$280
April
$258
May
$278
June
$342
July
$327
August
$274
September
$258
October
$248
November
$270
December
$248
CHI Temperature | 23 - 73.4 °F |
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Entertainment
Boarding
Comfort
Crew
Food
Overall
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Entertainment
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Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
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Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
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Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
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Overall
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Entertainment
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Overall
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
13%of flight departures | Early morningMidnight to 6 am |
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39%of flight departures | Morning6 am to noon |
42%of flight departures | AfternoonNoon to 6 pm |
6%of flight departures | Evening6 pm to midnight |
Sunday | 51daily flights |
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Monday | 66daily flights |
Tuesday | 46daily flights |
Wednesday | 52daily flights |
Thursday | 56daily flights |
Friday | 61daily flights |
Saturday | 31daily flights |
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