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
151 USD for flights from Boston to Chicago leaving on 10/3/2017 and returning on 10/27/2017
Low 123 USD
151 USD
High 417 USD
Choose my own dates
Best time to book
Cheapest time to buy a ticket for Boston — Chicago is approximately 56 days to departure.
Normally the best deals on Boston to Chicago flights are available 1 to 2 months prior to departure.
Days before departure
Best month
Cheapest time of year to fly to Chicago from Boston is January and September. Most expensive are February and December.
Boston to Chicago flights are currently cheapest between October and October.
Impact on price
Cheapest airline
According to our data, US Airways, Delta Air Lines and Spirit Airlines are the cheapest airlines to fly this route.
momondo users most frequently choose to fly from Boston to Chicago with either US Airways, Delta Air Lines or Spirit Airlines.
Impact on price (additional fees may apply)
US Airways
+33%
Delta Air Lines
+33%
Spirit Airlines
+34%
American Airlines
+44%
Major US Carrier
+48%
Southwest Airlines
+54%
Best time to fly
Boston to Chicago flights are approximately 8% more expensive in the noon than in the evening.
Noon flights tend to be the most expensive.
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 scan 49 sites offering flights from Boston to Chicago to find all the best options.
Impact on price
Logan Intl-O'Hare Intl
+0%
Logan Intl-Midway
+0%
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: 408 PER WEEK
Popular non-direct routes for this connection are Logan Intl - Baltimore - O'Hare Intl, Logan Intl - Port Columbus - Midway and Logan Intl - Lambert - Midway.
Stop-off cities for indirect flights from Logan Intl to Chicago include Baltimore, Port Columbus and Lambert.
Direct flights available on
Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday

Get there quickly

Direct flights to Chicago from Boston
Return trip
Aug 23 - Sep 5
117 USD
FlyingCOM
BOS BOS
2h 43min
Direct
CHI CHI
CHI CHI
2h 20min
Direct
BOS BOS
Return trip
Aug 23 - Aug 30
118 USD
ExploreTripDom
BOS BOS
2h 51min
Direct
CHI CHI
CHI CHI
2h 32min
Direct
BOS BOS
Return trip
Aug 23 - Aug 31
139 USD
EDreamsIN
BOS BOS
2h 47min
Direct
CHI CHI
CHI CHI
2h 32min
Direct
BOS BOS

Go right away

Last minute flights from Boston to Chicago
Return trip
Aug 23 - Aug 28
152 USD
EDreamsUS
BOS BOS
2h 47min
Direct
CHI CHI
CHI CHI
9h 4min
1 stop
BOS BOS
Return trip
Aug 24 - Aug 27
217 USD
KissAndFlyUS
BOS BOS
2h 46min
Direct
CHI CHI
CHI CHI
2h 17min
Direct
BOS BOS
Return trip
Aug 23 - Aug 23
219 USD
EDreamsUS
BOS BOS
2h 47min
Direct
CHI CHI
CHI CHI
9h 4min
1 stop
BOS BOS

Go for less - experience more

Cheap flights from Boston to Chicago
Return trip
Sep 6 - Sep 6
100 USD
KissAndFlyUS
BOS BOS
2h 47min
Direct
CHI CHI
CHI CHI
2h 19min
Direct
BOS BOS
Return trip
Sep 6 - Sep 13
112 USD
FaregeekUSDOM
BOS BOS
2h 47min
Direct
CHI CHI
CHI CHI
2h 30min
Direct
BOS BOS
Return trip
Sep 6 - Sep 7
124 USD
Smartfares
BOS BOS
2h 47min
Direct
CHI CHI
CHI CHI
2h 33min
Direct
BOS BOS

Coming or going?

Cheap flights from Chicago to Boston
Return trip
Aug 23 - Aug 28
114 USD
EDreamsUS
CHI CHI
2h 32min
Direct
BOS BOS
BOS BOS
2h 47min
Direct
CHI CHI
Return trip
Aug 23 - Aug 30
124 USD
CFEDreamsUS
CHI CHI
9h 4min
1 stop
BOS BOS
BOS BOS
2h 47min
Direct
CHI CHI
Return trip
Aug 23 - Sep 3
126 USD
Smartfares
CHI CHI
2h 32min
Direct
BOS BOS
BOS BOS
2h 47min
Direct
CHI CHI

Weather forecast for Chicago

Going soon? Be prepared for the weather in Chicago.

Thursday, Thursday, August 17, 2017

29°C
19°C

Friday, Friday, August 18, 2017

28°C
18°C

Saturday, Saturday, August 19, 2017

26°C
21°C

Sunday, Sunday, August 20, 2017

29°C
22°C

Monday, Monday, August 21, 2017

30°C
23°C

Tuesday, Tuesday, August 22, 2017

31°C
23°C

Wednesday, Wednesday, August 23, 2017

29°C
22°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
3.84 USD
-3%
Chicago
3.94 USD
Cappuccino is 2.8% more expensive in Chicago than Boston
MEAL
Inexpensive
Boston
14.95 USD
%
Chicago
14.95 USD
Meal is 0% cheaper in Chicago than Boston
MILK
1 liter
Boston
3.1 USD
4%
Chicago
2.98 USD
Milk is 3.8% cheaper in Chicago than Boston
BUS
One-way ticket
Boston
2.56 USD
12%
Chicago
2.25 USD
Bus is 12% cheaper in Chicago than Boston
MOVIE THEATER
1 ticket
Boston
12.96 USD
4%
Chicago
12.47 USD
movie theater is 3.8% cheaper in Chicago than Boston
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