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
165 USD for flights from Boston to Chicago leaving on 12/3/2017 and returning on 12/22/2017
Low 104 USD
165 USD
High 408 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 October. Most expensive are February and December.
Currently the cheapest days to fly this route are between December and December.
Impact on price
Cheapest airline
According to our data, Finnair, Spirit Airlines and Delta Air Lines are the cheapest airlines to fly this route.
Popular airlines for this route are Finnair, Spirit Airlines and Delta Air Lines.
Impact on price (additional fees may apply)
Finnair
+3%
Spirit Airlines
+25%
Delta Air Lines
+27%
Major US Carrier
+28%
Air Canada Rouge
+45%
American Airlines
+47%
Best time to fly
Boston to Chicago flights are approximately 7% more expensive in the noon than in the evening.
It's generally cheaper to take evening 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 47 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 39 minutes.
Direct flights available: 401 PER WEEK
Popular non-direct routes for this connection are Logan Intl - Lambert - Midway, Logan Intl - Newark Liberty Intl - O'Hare Intl and Logan Intl - Port Columbus - Midway.
Stop-off cities for indirect flights from Logan Intl to Chicago include Lambert, Newark Liberty 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
Oct 24 - Oct 24
93 USD
KissAndFlyUS
BOS BOS
2h 44min
Direct
CHI CHI
CHI CHI
2h 23min
Direct
BOS BOS
Return trip
Oct 25 - Oct 30
101 USD
FlyingCOM
BOS BOS
2h 37min
Direct
CHI CHI
CHI CHI
2h 16min
Direct
BOS BOS
Return trip
Oct 24 - Oct 26
108 USD
ExploreTripDom
BOS BOS
2h 50min
Direct
CHI CHI
CHI CHI
2h 30min
Direct
BOS BOS

Go right away

Last minute flights from Boston to Chicago
Return trip
Oct 26 - Oct 28
92 USD
ExploreTripDom
BOS BOS
2h 50min
Direct
CHI CHI
CHI CHI
2h 30min
Direct
BOS BOS
Return trip
Oct 26 - Nov 2
102 USD
ExploreTripDom
BOS BOS
2h 50min
Direct
CHI CHI
CHI CHI
2h 30min
Direct
BOS BOS
Return trip
Oct 26 - Oct 29
196 USD
CFFlyFarUS
BOS BOS
2h 50min
Direct
CHI CHI
CHI CHI
2h 10min
Direct
BOS BOS

Go for less - experience more

Cheap flights from Boston to Chicago
Return trip
Nov 7 - Nov 11
90 USD
CrystalTravelUS
BOS BOS
2h 54min
Direct
CHI CHI
CHI CHI
2h 15min
Direct
BOS BOS
Return trip
Nov 7 - Nov 14
94 USD
CheapBestFares
BOS BOS
2h 58min
Direct
CHI CHI
CHI CHI
2h 12min
Direct
BOS BOS
Return trip
Nov 7 - Nov 10
105 USD
CrystalTravelUS
BOS BOS
2h 54min
Direct
CHI CHI
CHI CHI
2h 15min
Direct
BOS BOS

Coming or going?

Cheap flights from Chicago to Boston
Return trip
Oct 24 - Nov 7
91 USD
CheapestFareNow
CHI CHI
2h 16min
Direct
BOS BOS
BOS BOS
2h 57min
Direct
CHI CHI
Return trip
Oct 25 - Oct 28
93 USD
ExploreTripDom
CHI CHI
2h 30min
Direct
BOS BOS
BOS BOS
2h 50min
Direct
CHI CHI
Return trip
Oct 24 - Oct 27
102 USD
ExploreTripDom
CHI CHI
2h 30min
Direct
BOS BOS
BOS BOS
2h 50min
Direct
CHI CHI

Weather forecast for Chicago

Going soon? Be prepared for the weather in Chicago.

Wednesday, Wednesday, October 18, 2017

17°C
12°C

Thursday, Thursday, October 19, 2017

18°C
12°C

Friday, Friday, October 20, 2017

21°C
15°C

Saturday, Saturday, October 21, 2017

22°C
15°C

Sunday, Sunday, October 22, 2017

16°C
12°C

Monday, Monday, October 23, 2017

17°C
12°C

Tuesday, Tuesday, October 24, 2017

12°C
8°C

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
3.88 USD
-1%
Chicago
3.91 USD
Cappuccino is 0.91% more expensive in Chicago than Boston
MEAL
Inexpensive
Boston
15.01 USD
%
Chicago
15.02 USD
Meal is 0.078% more expensive in Chicago than Boston
MILK
1 liter
Boston
3.07 USD
2%
Chicago
3.03 USD
Milk is 1.5% cheaper in Chicago than Boston
BUS
One-way ticket
Boston
2.58 USD
13%
Chicago
2.25 USD
Bus is 13% cheaper in Chicago than Boston
MOVIE THEATER
1 ticket
Boston
13 USD
6%
Chicago
12.26 USD
movie theater is 5.7% cheaper in Chicago than Boston
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