Flights from Boston to Chicago

Search and find cheap flights from Boston to Chicago (United States, North America)
Search and find cheap flights from Boston to Chicago (United States, North America)

Looking for the best tickets for Boston to Chicago?

Look no more. We’ve gone through the latest 5,765,685 fares to bring you all the insights you could possibly want.
Expect to pay
196 USD for flights from Boston to Chicago leaving on 5/3/2017 and returning on 5/26/2017
Low 102 USD
196 USD
High 356 USD
Choose my own dates
Best time to book
Cheapest time to buy a ticket for Boston — Chicago is approximately 52 days to departure.
Boston to Chicago flights are usually cheapest between 1 and 2 months before departure.
Days before departure
Best month
Cheapest time of year to fly to Chicago from Boston is January and February. Most expensive are November and December.
Currently the cheapest days to fly this route are between May and May.
Impact on price
Cheapest airline
According to our data, Spirit Airlines, Delta Air Lines and Mesa Airlines are the cheapest airlines to fly this route.
Popular airlines for this route are Spirit Airlines, Delta Air Lines and Mesa Airlines.
Impact on price (additional fees may apply)
Spirit Airlines
+5%
Delta Air Lines
+19%
Mesa Airlines
+20%
American Airlines
+21%
Major US Carrier
+21%
Southwest Airlines
+28%
Best time to fly
Boston to Chicago flights are approximately 5% more expensive in the noon than in the morning.
It's generally cheaper to take morning flights from Boston to Chicago.
Impact on price
Cheapest day
Cheapest day of week is typically Tuesday and the most expensive is typically Friday.
Friday is normally the most expensive day to fly, whilst Tuesday tends to be the cheapest.
Impact on price
Cheapest route
Fly Logan Intl - O'Hare Intl for the best Boston to Chicago flight prices saving up to 0% on average.
Of the possible routes between Boston and Chicago best prices tend to be found on Logan Intl - O'Hare Intl.
We've got 40 booking sites supporting this and nearby routes.
Impact on price
Logan Intl-O'Hare Intl
+0%
Logan Intl-Midway
+1%
Direct flights
There are direct flights from Logan Intl to Chicago all week with a flight time of 2 hours 33 minutes.
Direct flights available: 408 PER WEEK
Popular non-direct routes for this connection are Logan Intl - Baltimore - O'Hare Intl, Logan Intl - Indianapolis Intl - Midway and Logan Intl - Port Columbus - Midway.
Stop-off cities for indirect flights from Logan Intl to Chicago include Baltimore, Indianapolis Intl and Port Columbus.
Direct flights available on
Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday

Get there quickly

Direct flights to Chicago from Boston
Return trip
Mar 26 - Mar 31
154 USD
OmegaTravelUS
BOS BOS
2h 50min
Direct
CHI CHI
CHI CHI
2h 17min
Direct
BOS BOS
Return trip
Mar 27 - Apr 4
165 USD
OneTwoTripUS
BOS BOS
2h 45min
Direct
CHI CHI
CHI CHI
2h 15min
Direct
BOS BOS
Return trip
Mar 27 - Mar 27
205 USD
KiwiUS
BOS BOS
2h 45min
Direct
CHI CHI
CHI CHI
2h 10min
Direct
BOS BOS

Go right away

Last minute flights from Boston to Chicago
Return trip
Mar 27 - Apr 4
165 USD
OneTwoTripUS
BOS BOS
2h 45min
Direct
CHI CHI
CHI CHI
2h 15min
Direct
BOS BOS
Return trip
Mar 28 - Apr 17
189 USD
OmegaTravelUS
BOS BOS
2h 46min
Direct
CHI CHI
CHI CHI
2h 15min
Direct
BOS BOS
Return trip
Mar 27 - Mar 27
205 USD
KiwiUS
BOS BOS
2h 45min
Direct
CHI CHI
CHI CHI
2h 10min
Direct
BOS BOS

Go for less - experience more

Cheap flights from Boston to Chicago
Return trip
Apr 9 - Apr 18
195 USD
OneTwoTripUS
BOS BOS
2h 50min
Direct
CHI CHI
CHI CHI
2h 10min
Direct
BOS BOS
Return trip
Apr 9 - Apr 10
223 USD
OneTwoTripUS
BOS BOS
2h 50min
Direct
CHI CHI
CHI CHI
2h 10min
Direct
BOS BOS
Return trip
Apr 9 - Apr 16
237 USD
CheapTicketsDeal
BOS BOS
2h 55min
Direct
CHI CHI
CHI CHI
2h 15min
Direct
BOS BOS

Coming or going?

Cheap flights from Chicago to Boston
Return trip
Mar 26 - Mar 27
258 USD
OmegaTravelUS
CHI CHI
2h 16min
Direct
BOS BOS
BOS BOS
2h 46min
Direct
CHI CHI
Return trip
Mar 26 - May 28
301 USD
KiwiUS
CHI CHI
2h 10min
Direct
BOS BOS
BOS BOS
2h 46min
Direct
CHI CHI
Return trip
Mar 26 - Mar 31
399 USD
KiwiUS
CHI CHI
2h 15min
Direct
BOS BOS
BOS BOS
2h 45min
Direct
CHI CHI

Weather forecast for Chicago

Going soon? Be prepared for the weather in Chicago.

So what's it going to cost once you're in Chicago

Compare the costs of everyday items in Boston and Chicago
CAPPUCCINO
Regular
Boston
3.95 USD
%
Chicago
3.96 USD
Cappuccino is 0.27% more expensive in Chicago than Boston
MEAL
Inexpensive
Boston
15.05 USD
%
Chicago
15.05 USD
Meal is 0% cheaper in Chicago than Boston
MILK
1 liter
Boston
3.4 USD
15%
Chicago
2.88 USD
Milk is 15% cheaper in Chicago than Boston
BUS
One-way ticket
Boston
2.61 USD
14%
Chicago
2.25 USD
Bus is 14% cheaper in Chicago than Boston
MOVIE THEATER
1 ticket
Boston
12.04 USD
%
Chicago
12.04 USD
movie theater is 0% cheaper in Chicago than Boston
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