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
222 USD for flights from Boston to Chicago leaving on 7/4/2017 and returning on 7/28/2017
Low 114 USD
222 USD
High 394 USD
Choose my own dates
Best time to book
Cheapest time to buy a ticket for Boston — Chicago is approximately 59 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 September. Most expensive are February and December.
The cheapest flights from Boston to Chicago are currently available between July and July.
Impact on price
Cheapest airline
According to our data, Delta Air Lines, Spirit Airlines and American Airlines are the cheapest airlines to fly this route.
Delta Air Lines, Spirit Airlines and American Airlines are the most popular choices flying from Boston to Chicago.
Impact on price (additional fees may apply)
Delta Air Lines
+19%
Spirit Airlines
+19%
American Airlines
+26%
US Airways
+27%
Major US Carrier
+30%
Airtran Airways
+32%
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 - Midway for the best Boston to Chicago flight prices saving up to 0% on average.
Logan Intl - Midway tends to be 0% cheaper than Logan Intl - O'Hare Intl.
We scan 44 sites offering flights from Boston to Chicago to find all the best options.
Impact on price
Logan Intl-Midway
+0%
Logan Intl-O'Hare Intl
+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: 400 PER WEEK
Popular non-direct routes for this connection are Logan Intl - Baltimore - O'Hare Intl, Logan Intl - Indianapolis Intl - Midway and Logan Intl - Port Columbus - Midway.
You can fly from Logan Intl to Chicago indirect via Baltimore, Indianapolis Intl or Port Columbus.
Direct flights available on
Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday

Get there quickly

Direct flights to Chicago from Boston
Return trip
May 25 - Aug 28
146 USD
Smartfares
BOS BOS
2h 46min
Direct
CHI CHI
CHI CHI
2h 32min
Direct
BOS BOS
Return trip
May 25 - Jun 5
155 USD
OmegaTravelUS
BOS BOS
2h 50min
Direct
CHI CHI
CHI CHI
2h 15min
Direct
BOS BOS
Return trip
May 25 - Jun 6
188 USD
SkyToursUS
BOS BOS
2h 40min
Direct
CHI CHI
CHI CHI
2h 15min
Direct
BOS BOS

Go right away

Last minute flights from Boston to Chicago
Return trip
May 25 - Jun 6
188 USD
SkyToursUS
BOS BOS
2h 40min
Direct
CHI CHI
CHI CHI
2h 15min
Direct
BOS BOS
Return trip
May 25 - May 30
208 USD
FaregeekUS
BOS BOS
2h 50min
Direct
CHI CHI
CHI CHI
2h 15min
Direct
BOS BOS
Return trip
May 25 - May 29
234 USD
EDreamsUS
BOS BOS
2h 46min
Direct
CHI CHI
CHI CHI
2h 19min
Direct
BOS BOS

Go for less - experience more

Cheap flights from Boston to Chicago
Return trip
Jun 7 - Jun 14
111 USD
Smartfares
BOS BOS
2h 46min
Direct
CHI CHI
CHI CHI
2h 31min
Direct
BOS BOS
Return trip
Jun 7 - Jun 20
140 USD
Smartfares
BOS BOS
2h 46min
Direct
CHI CHI
CHI CHI
2h 32min
Direct
BOS BOS
Return trip
Jun 7 - Jun 21
140 USD
Smartfares
BOS BOS
2h 46min
Direct
CHI CHI
CHI CHI
2h 32min
Direct
BOS BOS

Coming or going?

Cheap flights from Chicago to Boston
Return trip
May 25 - May 30
257 USD
OneTwoTripUS
CHI CHI
4h 41min
1 stop
BOS BOS
BOS BOS
2h 50min
Direct
CHI CHI
Return trip
May 25 - Jun 1
271 USD
CFEDreamsUS
CHI CHI
2h 31min
Direct
BOS BOS
BOS BOS
2h 46min
Direct
CHI CHI
Return trip
May 25 - May 27
276 USD
AmericanAirlines
CHI CHI
4h 15min
1 stop
BOS BOS
BOS BOS
3h 4min
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
3.85 USD
-2%
Chicago
3.93 USD
Cappuccino is 2% more expensive in Chicago than Boston
MEAL
Inexpensive
Boston
14.97 USD
%
Chicago
14.97 USD
Meal is 0% cheaper in Chicago than Boston
MILK
1 liter
Boston
3.23 USD
8%
Chicago
2.96 USD
Milk is 8.3% cheaper in Chicago than Boston
BUS
One-way ticket
Boston
2.49 USD
%
Chicago
2.49 USD
Bus is 0% cheaper in Chicago than Boston
MOVIE THEATER
1 ticket
Boston
12.48 USD
4%
Chicago
11.98 USD
movie theater is 4% cheaper in Chicago than Boston
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