Popular in | June |
---|---|
Cheapest in | January |
Round-trip from | $222 |
One-way from | $29 |
Travelers have found that booking a Monday departure is the best way to save up to 28% 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 38% 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 $271 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 15% 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 35% 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.
One of the most popular airlines traveling from Boston to Chicago is Delta. Flights from Delta traveling this route typically cost $366.20 RT. This price is typically 40% 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 11% more popular than any other airline flying that same route.
Fly from
Fly to
Budget
$33 - $137
Route
Depart
Return
Price
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Di 6/11
Nonstop2h 54m
Chicago O'Hare Intl
Mi 6/12
Nonstop2h 29m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Di 6/11
Nonstop2h 54m
Chicago O'Hare Intl
Mi 6/12
Nonstop2h 29m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Di 6/11
Nonstop2h 54m
Chicago O'Hare Intl
Mi 6/12
Nonstop2h 29m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Di 6/11
Nonstop2h 54m
Chicago O'Hare Intl
Mi 6/12
1 stop12h 02m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Di 6/11
Nonstop2h 54m
Chicago O'Hare Intl
Mi 6/12
1 stop12h 02m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Di 6/11
Nonstop2h 54m
Chicago O'Hare Intl
Di 6/18
Nonstop2h 28m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Di 8/20
1 stop7h 37m
Chicago Midway
Mi 8/21
1 stop10h 26m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Mi 6/12
1 stop16h 52m
Chicago O'Hare Intl
Mo 6/17
1 stop11h 52m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Di 8/20
Nonstop2h 54m
Chicago O'Hare Intl
Di 8/20
Nonstop2h 26m
CHI Temperature | 23 - 73.4 °F |
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Boarding
Comfort
Crew
Overall
Entertainment
Food
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Boarding
Comfort
Crew
Overall
Entertainment
Food
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Boarding
Comfort
Crew
Overall
Entertainment
Food
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Boarding
Comfort
Crew
Overall
Entertainment
Food
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Boarding
Comfort
Crew
Overall
Entertainment
Food
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Boarding
Comfort
Crew
Overall
Entertainment
Food
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
7%of flight departures | Early morningMidnight to 6 am |
---|---|
38%of flight departures | Morning6 am to noon |
51%of flight departures | AfternoonNoon to 6 pm |
4%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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