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
210 USD for flights from Boston to Chicago leaving on 3/31/2017 and returning on 4/21/2017
Low 96 USD
210 USD
High 344 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 March and April.
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.
Noon flights tend to be the most expensive.
Impact on price
Cheapest day
Friday is normally the most expensive day to fly, whilst Tuesday tends to be the cheapest.
Cheapest day of week is typically Tuesday and the most expensive is typically Friday.
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.
Logan Intl - O'Hare Intl tends to be 0% cheaper than Logan Intl - Midway.
We scan 41 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
+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: 433 PER WEEK
Popular non-direct routes for this connection are Logan Intl - Indianapolis Intl - Midway, 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 Indianapolis Intl, 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
Feb 25 - Feb 28
181 USD
OneTwoTripUS
BOS BOS
2h 50min
Direct
CHI CHI
CHI CHI
2h 15min
Direct
BOS BOS
Return trip
Feb 24 - Feb 28
195 USD
CheapTicketsDeal
BOS BOS
2h 58min
Direct
CHI CHI
CHI CHI
2h 14min
Direct
BOS BOS
Return trip
Feb 25 - Mar 27
212 USD
OneTwoTripUS
BOS BOS
2h 50min
Direct
CHI CHI
CHI CHI
2h 10min
Direct
BOS BOS

Go right away

Last minute flights from Boston to Chicago
Return trip
Feb 21 - Feb 23
210 USD
VayamaDom
BOS BOS
6h 38min
1 stop
CHI CHI
CHI CHI
5h 15min
1 stop
BOS BOS
Return trip
Feb 21 - Feb 21
227 USD
VayamaDom
BOS BOS
6h 38min
1 stop
CHI CHI
CHI CHI
5h 3min
1 stop
BOS BOS
Return trip
Feb 21 - Feb 24
292 USD
GoToGateUS
BOS BOS
4h 28min
1 stop
CHI CHI
CHI CHI
4h 30min
1 stop
BOS BOS

Go for less - experience more

Cheap flights from Boston to Chicago
Return trip
Mar 7 - Mar 9
84 USD
OmegaTravelUS
BOS BOS
2h 52min
Direct
CHI CHI
CHI CHI
2h 17min
Direct
BOS BOS
Return trip
Mar 6 - Mar 7
120 USD
KiwiUS
BOS BOS
2h 55min
Direct
CHI CHI
CHI CHI
2h 14min
Direct
BOS BOS
Return trip
Mar 6 - Mar 6
121 USD
OneTwoTripUS
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
Feb 22 - Feb 24
120 USD
KiwiUS
CHI CHI
2h 13min
Direct
BOS BOS
BOS BOS
2h 55min
Direct
CHI CHI
Return trip
Feb 23 - Feb 27
139 USD
CheapTicketsDeal
CHI CHI
2h 14min
Direct
BOS BOS
BOS BOS
2h 58min
Direct
CHI CHI
Return trip
Feb 21 - Feb 22
168 USD
OmegaTravelUS
CHI CHI
2h 13min
Direct
BOS BOS
BOS BOS
2h 52min
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
3.9 USD
-3%
Chicago
3.99 USD
Cappuccino is 2.5% more expensive in Chicago than Boston
MEAL
Inexpensive
Boston
15.01 USD
%
Chicago
15.01 USD
Meal is 0% cheaper in Chicago than Boston
MILK
1 liter
Boston
3.36 USD
12%
Chicago
2.96 USD
Milk is 12% cheaper in Chicago than Boston
BUS
One-way ticket
Boston
2.58 USD
3%
Chicago
2.51 USD
Bus is 2.9% cheaper in Chicago than Boston
MOVIE THEATER
1 ticket
Boston
12.26 USD
2%
Chicago
12 USD
movie theater is 2.1% cheaper in Chicago than Boston
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