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 5,507,576 fares to bring you all the insights you could possibly want.
Expect to pay
170 USD for flights from Boston to Chicago leaving on 3/1/2017 and returning on 3/24/2017
Low 96 USD
170 USD
High 344 USD
Choose my own dates
Best time to book
Cheapest time to buy a ticket for Boston — Chicago is approximately 58 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 February. Most expensive are November and December.
Boston to Chicago flights are currently cheapest between March and March.
Impact on price
Cheapest airline
According to our data, Spirit Airlines, Mesa Airlines and Major US Carrier are the cheapest airlines to fly this route.
momondo users most frequently choose to fly from Boston to Chicago with either Spirit Airlines, Mesa Airlines or Major US Carrier.
Impact on price (additional fees may apply)
Spirit Airlines
+5%
Mesa Airlines
+20%
Major US Carrier
+21%
Delta Air Lines
+21%
American Airlines
+22%
Southwest Airlines
+29%
Best time to fly
Boston to Chicago flights are approximately 6% more expensive in the noon than in the morning.
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.
momondo compares flights to Chicago from Boston from 38 different sites.
Impact on price
Logan Intl-O'Hare Intl
+1%
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: 413 PER WEEK
Popular non-direct routes for this connection are Logan Intl - Indianapolis Intl - Midway, Logan Intl - Port Columbus - Midway and Logan Intl - Detroit Metro - O'Hare Intl.
You can fly from Logan Intl to Chicago indirect via Indianapolis Intl, Port Columbus or Detroit Metro.
Direct flights available on
Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday

Get there quickly

Direct flights to Chicago from Boston
Return trip
Jan 23 - Jan 26
187 USD
CheapTicketsDeal
BOS BOS
2h 58min
Direct
CHI CHI
CHI CHI
2h 10min
Direct
BOS BOS
Return trip
Jan 22 - Jan 28
197 USD
CheapBestFares
BOS BOS
2h 54min
Direct
CHI CHI
CHI CHI
2h 13min
Direct
BOS BOS
Return trip
Jan 23 - Jan 28
210 USD
OneTwoTripUS
BOS BOS
2h 55min
Direct
CHI CHI
CHI CHI
2h 15min
Direct
BOS BOS

Go right away

Last minute flights from Boston to Chicago
Return trip
Jan 23 - Jan 26
187 USD
CheapTicketsDeal
BOS BOS
2h 58min
Direct
CHI CHI
CHI CHI
2h 10min
Direct
BOS BOS
Return trip
Jan 22 - Jan 28
197 USD
CheapBestFares
BOS BOS
2h 54min
Direct
CHI CHI
CHI CHI
2h 13min
Direct
BOS BOS
Return trip
Jan 23 - Jan 28
210 USD
OneTwoTripUS
BOS BOS
2h 55min
Direct
CHI CHI
CHI CHI
2h 15min
Direct
BOS BOS

Go for less - experience more

Cheap flights from Boston to Chicago
Return trip
Feb 7 - Feb 13
96 USD
OneTravel
BOS BOS
2h 58min
Direct
CHI CHI
CHI CHI
2h 14min
Direct
BOS BOS
Return trip
Feb 5 - Feb 10
108 USD
OneTwoTripUS
BOS BOS
2h 55min
Direct
CHI CHI
CHI CHI
2h 15min
Direct
BOS BOS
Return trip
Feb 7 - Feb 7
129 USD
KiwiUS
BOS BOS
2h 58min
Direct
CHI CHI
CHI CHI
4h 35min
Direct
BOS BOS

Coming or going?

Cheap flights from Chicago to Boston
Return trip
Jan 23 - Jan 23
123 USD
FlyFarUS
CHI CHI
2h 15min
Direct
BOS BOS
BOS BOS
5h 40min
Direct
CHI CHI
Return trip
Jan 22 - Jan 25
127 USD
KiwiUS
CHI CHI
2h 10min
Direct
BOS BOS
BOS BOS
2h 55min
Direct
CHI CHI
Return trip
Jan 22 - Jan 24
237 USD
VayamaDom
CHI CHI
4h 11min
1 stop
BOS BOS
BOS BOS
4h 49min
1 stop
CHI CHI

Weather forecast for Chicago

Going soon? Be prepared for the weather in Chicago.

Saturday, Saturday, January 21, 2017

12°C
4°C

Sunday, Sunday, January 22, 2017

8°C
-4°C

Monday, Monday, January 23, 2017

5°C
2°C

Tuesday, Tuesday, January 24, 2017

4°C
-4°C

Wednesday, Wednesday, January 25, 2017

6°C
0°C

Thursday, Thursday, January 26, 2017

3°C
-3°C

Friday, Friday, January 27, 2017

1°C
-2°C

Saturday, Saturday, January 28, 2017

1°C
-3°C

Sunday, Sunday, January 29, 2017

0°C
-8°C

Monday, Monday, January 30, 2017

0°C
-3°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
3.94 USD
-1%
Chicago
3.96 USD
Cappuccino is 0.54% more expensive in Chicago than Boston
MEAL
Inexpensive
Boston
17.05 USD
12%
Chicago
15.04 USD
Meal is 12% cheaper in Chicago than Boston
MILK
1 liter
Boston
3.38 USD
12%
Chicago
2.98 USD
Milk is 12% cheaper in Chicago than Boston
BUS
One-way ticket
Boston
2.51 USD
10%
Chicago
2.25 USD
Bus is 10% cheaper in Chicago than Boston
MOVIE THEATER
1 ticket
Boston
12.03 USD
%
Chicago
12.03 USD
movie theater is 0% cheaper in Chicago than Boston
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