Southwest Airlines Chicago to Boston Flights

One way Round trip

Adults

Children under 12

Infants under 2 without place

Economy

Business

First

done

Return flight: Boston – Chicago

Page navigation

Best Airfare Price Calendar Flights Schedule

Cheapflightsplus.com will find cheap Southwest Airlines flights from Chicago to Boston. Compare airline ticket prices and book air tickets starting from $56 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 Chicago (IL) — Boston (MA) 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 march: one-way - $56, two-way – $96.

Direct flights

Check to choose departure date Check to choose departure date

Check prices for return flight

Find flights

Cheap Flights from Chicago to Boston 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 $56. The fastest nonstop flight takes 2h 5m. The fastest connecting flight — 3h 40m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $56 Find flight	9:30 pm Chicago Midway	0:35 am+1 день Boston Logan	2h 5m	Southwest Airlines	WN2387
from $77 Find flight	7:20 pm Chicago Midway	10:30 pm Boston Logan	2h 10m	Southwest Airlines	WN484
from $81 Find flight	7:40 am Chicago Midway	11:00 am Boston Logan	2h 20m	Southwest Airlines	WN376
from $100 Find flight	1:55 pm Chicago Midway	5:20 pm Boston Logan	2h 25m	Southwest Airlines	WN1665
from $120 Find flight	10:15 am Chicago Midway	1:35 pm Boston Logan	2h 20m	Southwest Airlines	WN451
from $58 Find flight	5:25 pm Chicago Midway	10:05 pm Boston Logan	3h 40m layover 0h 35m - Columbus	Southwest Airlines	WN1098 WN1098
from $62 Find flight	10:25 am Chicago Midway	5:10 pm Boston Logan	5h 45m layover 2h 30m - Baltimore	Southwest Airlines	WN352 WN6595
from $62 Find flight	6:00 pm Chicago Midway	0:35 am+1 день Boston Logan	5h 35m layover 1h 55m - Lake Saint Louis	Southwest Airlines	WN444 WN1941
from $80 Find flight	5:40 am Chicago Midway	12:30 pm Boston Logan	5h 50m layover 2h 45m - Baltimore	Southwest Airlines	WN2462 NK1020
from $83 Find flight	4:10 pm Chicago Midway	9:30 pm Boston Logan	4h 20m layover 0h 55m - Baltimore	Southwest Airlines	WN1668 WN2449
from $83 Find flight	10:25 pm Chicago Midway	7:31 am+1 день Boston Logan	8h 6m layover 4h 50m - Baltimore	Southwest Airlines	WN4754 NK1028
from $84 Find flight	1:25 pm Chicago Midway	6:55 pm Boston Logan	4h 30m layover 0h 50m - Lake Saint Louis	Southwest Airlines	WN1937 WN1937
from $87 Find flight	10:25 am Chicago Midway	5:05 pm Boston Logan	5h 40m layover 2h 25m - Baltimore	Southwest Airlines	WN352 WN1314
from $99 Find flight	9:00 am Chicago Midway	4:19 pm Boston Logan	6h 19m layover 2h 15m - Raleigh	Southwest Airlines	WN4521 DL3349
from $90 Find flight	9:00 am Chicago Midway	3:45 pm Boston Logan	5h 45m layover 0h 35m - Raleigh 0h 40m - Baltimore	Southwest Airlines	WN4521 WN5989 WN5989
from $127 Find flight	9:50 pm Chicago Midway	10:03 am+1 день Boston Logan	11h 13m layover 4h 50m - Raleigh 1h 45m - Washington D.C.	Southwest Airlines	WN358 AA1596 AA2169

Show All Flights

*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 03/14/2025

Southwest Airlines Flight Schedule Chicago to Boston

Below is a detailed 2025 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
10:15 am — 1:35 pm	10:15 am — 1:35 pm WN451 Southwest Airlines Chicago — Boston	2h 20m	Find flight from$120
1:55 pm — 5:20 pm	1:55 pm — 5:20 pm WN1665 Southwest Airlines Chicago — Boston	2h 25m	Find flight from$100
1:55 pm — 5:20 pm	1:55 pm — 5:20 pm WN1217 Southwest Airlines Chicago — Boston	2h 25m	Find flight from$138
7:20 pm — 10:30 pm	7:20 pm — 10:30 pm WN484 Southwest Airlines Chicago — Boston	2h 10m	Find flight from$77
7:40 am — 11:00 am	7:40 am — 11:00 am WN376 Southwest Airlines Chicago — Boston	2h 20m	Find flight from$81
9:30 pm — 0:35 am +1 day	9:30 pm — 0:35 am WN2387 Southwest Airlines Chicago — Boston	2h 5m	Find flight from$56
10:25 am — 5:10 pm	10:25 am — 1:10 pm WN352 Southwest Airlines Chicago — Baltimore 2h 30m stop 3:40 pm — 5:10 pm WN6595 Southwest Airlines Baltimore — Boston	5h 45m including layover	Find flight from$62
10:25 pm — 7:31 am +1 day	10:25 pm — 1:10 am WN4754 Southwest Airlines Chicago — Baltimore 4h 50m stop 6:00 am — 7:31 am NK1028 Spirit Airlines Baltimore — Boston	8h 6m including layover	Find flight from$83
11:50 am — 6:55 pm	11:50 am — 1:00 pm WN2122 Southwest Airlines Chicago — Lake Saint Louis 2h 20m stop 3:20 pm — 6:55 pm WN1937 Southwest Airlines Lake Saint Louis — Boston	6h 5m including layover	Find flight from$126
12:45 pm — 8:58 pm	12:45 pm — 3:25 pm WN1376 Southwest Airlines Chicago — Baltimore 4h stop 7:25 pm — 8:58 pm NK2030 Spirit Airlines Baltimore — Boston	7h 13m including layover	Find flight from$113
1:25 pm — 6:55 pm	1:25 pm — 2:30 pm WN1937 Southwest Airlines Chicago — Lake Saint Louis 50m stop 3:20 pm — 6:55 pm WN1937 Southwest Airlines Lake Saint Louis — Boston	4h 30m including layover	Find flight from$84
2:05 pm — 8:56 pm	2:05 pm — 5:10 pm WN1210 Southwest Airlines Chicago — Newark 2h 20m stop 7:30 pm — 8:56 pm UA2323 United Airlines Newark — Boston	5h 51m including layover	Find flight from$142
2:10 pm — 8:52 pm	2:10 pm — 5:15 pm WN1151 Southwest Airlines Chicago — Newark 2h 15m stop 7:30 pm — 8:52 pm UA2323 United Airlines Newark — Boston	5h 42m including layover	Find flight from$155
4:10 pm — 9:30 pm	4:10 pm — 7:00 pm WN1668 Southwest Airlines Chicago — Baltimore 55m stop 7:55 pm — 9:30 pm WN2449 Southwest Airlines Baltimore — Boston	4h 20m including layover	Find flight from$83
5:25 pm — 10:05 pm	5:25 pm — 7:35 pm WN1098 Southwest Airlines Chicago — Columbus 35m stop 8:10 pm — 10:05 pm WN1098 Southwest Airlines Columbus — Boston	3h 40m including layover	Find flight from$58
5:40 am — 12:30 pm	5:40 am — 8:15 am WN2462 Southwest Airlines Chicago — Baltimore 2h 45m stop 11:00 am — 12:30 pm NK1020 Spirit Airlines Baltimore — Boston	5h 50m including layover	Find flight from$80
6:00 pm — 0:35 am +1 day	6:00 pm — 7:05 pm WN444 Southwest Airlines Chicago — Lake Saint Louis 1h 55m stop 9:00 pm — 0:35 am WN1941 Southwest Airlines Lake Saint Louis — Boston	5h 35m including layover	Find flight from$62
6:10 am — 1:20 pm	6:10 am — 7:15 am WN4891 Southwest Airlines Chicago — Lake Saint Louis 2h 30m stop 9:45 am — 1:20 pm WN2328 Southwest Airlines Lake Saint Louis — Boston	6h 10m including layover	Find flight from$137
9:50 pm — 8:01 pm +1 day	9:50 pm — 0:45 am WN358 Southwest Airlines Chicago — Raleigh 17h 15m stop 6:00 pm — 8:01 pm NK716 Spirit Airlines Raleigh — Boston	21h 11m including layover	Find flight from$80

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

*Departure and arrival times are local. Last updated on 03/14/2025

Flight Information

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

Departures start from 10:15 am to 9:50 pm. Nonstop flight is 2h 5m. The time difference between Chicago and Boston is 1h.

The fastest flight 2h 5m
Average flight time 2h 20m
The earliest flight 10:15 am
The latest flight 9:50 pm
Distance 852 ml

The cheapest flight by Southwest Airlines that our users were able to find is $56. This airfare is economy class on one-way WN2387 flight for October 7, 2019 leaving Midway in Chicago at 9:30 pm, it includes all taxes and additional fees.

Find same flight?

Southwest Airlines Airplanes on the Route

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

Other Popular Airlines on the Route

Besides Southwest Airlines there are other 17 airline carriers between Chicago and Boston. Please review schedules and prices from the most popular airlines to find the best airfare deals from Chicago to Boston.

Nonstop flights

There are 39 direct flights every day from Chicago. Airlines and fares are below:

B6 - JetBlue

from $98

Find
DL - Delta Air Lines Inc.

from $83

Find
UA - United Airlines

from $70

Find
NK - Spirit Airlines

from $43

Find
AA - American Airlines

from $74

Find

See more direct flights

Connecting Flights

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

DL - Delta Air Lines Inc.

from $168

Find
UA - United Airlines

from $111

Find
B6 - JetBlue

from $101

Find
NK - Spirit Airlines

from $69

Find
AA - American Airlines

from $145

Find
EI - Aer Lingus

from $1346

Find
SY - Sun Country Airlines

from $328

Find
LX - SWISS International Air Lines

from $6580

Find
G4 - Allegiant Air

from $501

Find
AS - Alaska Airlines

from $244

Find
F9 - Frontier Airlines

from $62

Find

See more connecting flights

How to book an air ticket yourself?

Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
Click «Buy» when you are ready — our system will redirect you to the site that sells the selected airfare.
Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.
To find a plane ticket, please select dates.