Southwest Airlines Boston to Chicago Flights

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Best Airfare Price Calendar Flights Schedule

Cheapflightsplus.com will find cheap Southwest Airlines flights from Boston to Chicago. Compare airline ticket prices and book air tickets starting from $127 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of Southwest Airlines, arrivals and departure details below.

Find Cheap Airfare Boston (MA) — Chicago (IL) by Southwest Airlines

To find cheap tickets choose a day of your departure with attractive price on the graph below and click «Find flights». For round trip flights please click «Check prices for return flight». The cheapest airfare is in may: one-way - $127, two-way – $218.

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Cheap Flights from Boston to Chicago by Southwest Airlines

Look at the list of plane tickets for the most popular direct and connecting flights by Southwest Airlines, their prices start from $127. The fastest nonstop flight takes 2h 45m. The fastest connecting flight — 4h 25m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $127 Find flight	5:30 am Boston Logan	7:15 am Chicago Midway	2h 45m	Southwest Airlines	WN1349
from $204 Find flight	7:40 am Boston Logan	9:30 am Chicago Midway	2h 50m	Southwest Airlines	WN780
from $204 Find flight	9:50 am Boston Logan	11:40 am Chicago Midway	2h 50m	Southwest Airlines	WN2508
from $204 Find flight	12:10 pm Boston Logan	2:00 pm Chicago Midway	2h 50m	Southwest Airlines	WN2235
from $204 Find flight	8:05 pm Boston Logan	9:50 pm Chicago Midway	2h 45m	Southwest Airlines	WN2100
from $207 Find flight	6:35 am Boston Logan	9:35 am Chicago Midway	4h 0m	Southwest Airlines	WN1071
from $146 Find flight	5:45 am Boston Logan	11:10 am Chicago Midway	6h 25m layover 1h 10m - Baltimore	Southwest Airlines	WN2371 WN2122
from $146 Find flight	8:30 am Boston Logan	2:40 pm Chicago Midway	7h 10m layover 1h 50m - Baltimore	Southwest Airlines	WN391 WN1600
from $146 Find flight	7:00 am Boston Logan	2:40 pm Chicago Midway	8h 40m layover 3h 20m - Baltimore	Southwest Airlines	WN2126 WN1600
from $163 Find flight	7:45 pm Boston Logan	11:10 pm Chicago Midway	4h 25m layover 0h 50m - Baltimore	Southwest Airlines	WN1937 WN1360
from $163 Find flight	7:30 am Boston Logan	1:05 pm Chicago Midway	6h 35m layover 1h 30m - Atlanta	Southwest Airlines	WN1385 WN1599
from $232 Find flight	3:40 pm Boston Logan	9:30 pm Chicago Midway	6h 50m layover 3h 30m - Columbus	Southwest Airlines	WN437 WN1083

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 04/26/2024

Southwest Airlines Flight Schedule Boston to Chicago

Below is a detailed 2024 flight schedule for today, tomorrow and all other days. It may vary depending on season and a day of the week of your desired trip. We recommend booking your itinerary at least 2 weeks prior your travel to get the best price and availability by the airline.

Departure	Flight Details	Flight Time	Price
12:10 pm — 2:00 pm	12:10 pm — 2:00 pm WN2235 Southwest Airlines Boston — Chicago	2h 50m	Find flight from$204
3:40 pm — 9:30 pm	3:40 pm — 5:50 pm WN437 Southwest Airlines Boston — Columbus 3h 30m stop 9:20 pm — 9:30 pm WN1083 Southwest Airlines Columbus — Chicago	6h 50m including layover	Find flight from$232
3:40 pm — 7:15 pm	3:40 pm — 5:50 pm WN437 Southwest Airlines Boston — Columbus 1h 15m stop 7:05 pm — 7:15 pm WN2054 Southwest Airlines Columbus — Chicago	4h 35m including layover	Find flight from$239
4:55 pm — 9:30 pm	4:55 pm — 7:10 pm WN1517 Southwest Airlines Boston — Lake Saint Louis 1h 20m stop 8:30 pm — 9:30 pm WN2237 Southwest Airlines Lake Saint Louis — Chicago	5h 35m including layover	Find flight from$357
5:30 am — 7:15 am	5:30 am — 7:15 am WN1349 Southwest Airlines Boston — Chicago	2h 45m	Find flight from$127
5:45 am — 11:10 am	5:45 am — 7:15 am WN2371 Southwest Airlines Boston — Baltimore 1h 10m stop 8:25 am — 11:10 am WN2122 Southwest Airlines Baltimore — Chicago	6h 25m including layover	Find flight from$146
6:35 am — 9:35 am	6:35 am — 9:35 am WN1071 Southwest Airlines Boston — Chicago	4h	Find flight from$207
7:00 am — 2:40 pm	7:00 am — 8:45 am WN2126 Southwest Airlines Boston — Baltimore 3h 20m stop 12:05 pm — 2:40 pm WN1600 Southwest Airlines Baltimore — Chicago	8h 40m including layover	Find flight from$146
7:30 am — 1:05 pm	7:30 am — 10:35 am WN1385 Southwest Airlines Boston — Atlanta 1h 30m stop 12:05 pm — 1:05 pm WN1599 Southwest Airlines Atlanta — Chicago	6h 35m including layover	Find flight from$163
7:40 am — 9:30 am	7:40 am — 9:30 am WN780 Southwest Airlines Boston — Chicago	2h 50m	Find flight from$204
7:45 pm — 11:10 pm	7:45 pm — 9:25 pm WN1937 Southwest Airlines Boston — Baltimore 50m stop 10:15 pm — 11:10 pm WN1360 Southwest Airlines Baltimore — Chicago	4h 25m including layover	Find flight from$163
8:05 pm — 9:50 pm	8:05 pm — 9:50 pm WN2100 Southwest Airlines Boston — Chicago	2h 45m	Find flight from$204
8:30 am — 2:40 pm	8:30 am — 10:15 am WN391 Southwest Airlines Boston — Baltimore 1h 50m stop 12:05 pm — 2:40 pm WN1600 Southwest Airlines Baltimore — Chicago	7h 10m including layover	Find flight from$146
9:50 am — 11:40 am	9:50 am — 11:40 am WN2508 Southwest Airlines Boston — Chicago	2h 50m	Find flight from$204

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times are local. Last updated on 04/26/2024

Flight Information

There are 6 flights by Southwest Airlines from Boston to Chicago every week with departures from Logan, Boston City Heliport, Boston RT128 Rail, Boston South Rail. All flights arrive at Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee.

Departures start from 12:10 pm to 9:50 am. Nonstop flight is 2h 45m. The time difference between Boston and Chicago is 1h.

The fastest flight 2h 45m
Average flight time 2h 50m
The earliest flight 12:10 pm
The latest flight 9:50 am
Distance 852 ml

The cheapest flight by Southwest Airlines that our users were able to find is $127. This airfare is economy class on one-way WN1349 flight for October 11, 2019 leaving Logan in Boston at 5:30 am, it includes all taxes and additional fees.

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Southwest Airlines Airplanes on the Route

List of the most popular Southwest Airlines airplanes flying from Boston to Chicago:

Boeing 737 MAX 8

from $127

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Boeing 737-700

from $146

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Boeing 737-800

from $146

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Other Popular Airlines on the Route

Besides Southwest Airlines there are other 1 airline carriers between Boston and Chicago. Please review schedules and prices from the most popular airlines to find the best airfare deals from Boston to Chicago.

Nonstop flights

There are 8 direct flights every day from Boston. Airlines and fares are below:

B6 - JetBlue

from $76

Find

See more direct flights

Connecting Flights

List of flights with layovers (1 and more stops):

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How to book an air ticket yourself?

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