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
235 USD for flights from Boston to Chicago leaving on 8/6/2017 and returning on 8/25/2017
Low 116 USD
235 USD
High 393 USD
Choose my own dates
Best time to book
Cheapest time to buy a ticket for Boston — Chicago is approximately 49 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 August and August.
Impact on price
Cheapest airline
According to our data, Delta Air Lines, Spirit Airlines and US Airways are the cheapest airlines to fly this route.
momondo users most frequently choose to fly from Boston to Chicago with either Delta Air Lines, Spirit Airlines or US Airways.
Impact on price (additional fees may apply)
Delta Air Lines
+23%
Spirit Airlines
+26%
US Airways
+28%
Airtran Airways
+33%
American Airlines
+34%
Major US Carrier
+37%
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 44 booking sites supporting this and nearby routes.
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 35 minutes.
Direct flights available: 397 PER WEEK
Popular non-direct routes for this connection are Logan Intl - Baltimore - O'Hare Intl, Logan Intl - Port Columbus - Midway and Logan Intl - Nth Kentucky - O'Hare Intl.
Stop-off cities for indirect flights from Logan Intl to Chicago include Baltimore, Port Columbus and Nth Kentucky.
Direct flights available on
Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday

Get there quickly

Direct flights to Chicago from Boston
Return trip
Jun 27 - Nov 30
184 USD
OneTwoTripUS
BOS BOS
2h 54min
Direct
CHI CHI
CHI CHI
2h 23min
Direct
BOS BOS
Return trip
Jun 28 - Jul 4
207 USD
Smartfares
BOS BOS
2h 52min
Direct
CHI CHI
CHI CHI
2h 21min
Direct
BOS BOS
Return trip
Jun 27 - Jul 3
217 USD
CrystalTravelUS
BOS BOS
2h 45min
Direct
CHI CHI
CHI CHI
2h 15min
Direct
BOS BOS

Go right away

Last minute flights from Boston to Chicago
Return trip
Jun 28 - Jul 5
180 USD
FlightNetworkUS
BOS BOS
2h 47min
Direct
CHI CHI
CHI CHI
2h 15min
Direct
BOS BOS
Return trip
Jun 27 - Jul 5
185 USD
FlightNetworkUS
BOS BOS
2h 47min
Direct
CHI CHI
CHI CHI
9h 4min
1 stop
BOS BOS
Return trip
Jun 28 - Jul 12
191 USD
FlightNetworkUS
BOS BOS
2h 47min
Direct
CHI CHI
CHI CHI
2h 32min
Direct
BOS BOS

Go for less - experience more

Cheap flights from Boston to Chicago
Return trip
Jul 11 - Jul 19
131 USD
OmegaTravelUS
BOS BOS
2h 44min
Direct
CHI CHI
CHI CHI
2h 22min
Direct
BOS BOS
Return trip
Jul 11 - Jul 13
132 USD
KissAndFlyUS
BOS BOS
2h 44min
Direct
CHI CHI
CHI CHI
2h 20min
Direct
BOS BOS
Return trip
Jul 11 - Jul 18
171 USD
EDreamsUS
BOS BOS
2h 47min
Direct
CHI CHI
CHI CHI
9h 4min
1 stop
BOS BOS

Coming or going?

Cheap flights from Chicago to Boston
Return trip
Jun 27 - Jul 6
226 USD
CFLOLTravelUS
CHI CHI
5h 43min
1 stop
BOS BOS
BOS BOS
4h 2min
1 stop
CHI CHI
Return trip
Jun 27 - Jun 30
237 USD
Travel2beDE
CHI CHI
2h 20min
Direct
BOS BOS
BOS BOS
2h 42min
Direct
CHI CHI
Return trip
Jun 28 - Jul 5
249 USD
CrystalTravelUS
CHI CHI
2h 20min
Direct
BOS BOS
BOS BOS
2h 40min
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
3.91 USD
-1%
Chicago
3.95 USD
Cappuccino is 1.1% more expensive in Chicago than Boston
MEAL
Inexpensive
Boston
15.06 USD
%
Chicago
15.06 USD
Meal is 0% cheaper in Chicago than Boston
MILK
1 liter
Boston
3.13 USD
6%
Chicago
2.96 USD
Milk is 5.7% cheaper in Chicago than Boston
BUS
One-way ticket
Boston
2.51 USD
10%
Chicago
2.26 USD
Bus is 9.8% cheaper in Chicago than Boston
MOVIE THEATER
1 ticket
Boston
12.8 USD
6%
Chicago
12.05 USD
movie theater is 5.9% cheaper in Chicago than Boston
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