Southwest Airlines Chicago to Boston Flights
Cheapflightsplus.com will find cheap Southwest Airlines flights from Chicago to Boston. Compare airline ticket prices and book air tickets starting from $53 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
Cheap Flights from Chicago to Boston by Southwest Airlines
Price | Departure | Arrival | Flight Time | Airline | Flight |
---|---|---|---|---|---|
from $53 | 9:30 pm Chicago Midway | 0:35 am+1 день Boston Logan | 2h 5m | Southwest Airlines | WN2387 |
from $73 | 7:20 pm Chicago Midway | 10:30 pm Boston Logan | 2h 10m | Southwest Airlines | WN484 |
from $77 | 7:40 am Chicago Midway | 11:00 am Boston Logan | 2h 20m | Southwest Airlines | WN376 |
from $95 | 1:55 pm Chicago Midway | 5:20 pm Boston Logan | 2h 25m | Southwest Airlines | WN1665 |
from $114 | 10:15 am Chicago Midway | 1:35 pm Boston Logan | 2h 20m | Southwest Airlines | WN451 |
from $131 | 1:55 pm Chicago Midway | 5:20 pm Boston Logan | 2h 25m | Southwest Airlines | WN1217 |
from $56 | 5:25 pm Chicago Midway | 10:05 pm Boston Logan | 3h 40m layover 0h 35m - Columbus | Southwest Airlines | WN1098 WN1098 |
from $59 | 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 $59 | 10:25 am Chicago Midway | 5:10 pm Boston Logan | 5h 45m layover 2h 30m - Baltimore | Southwest Airlines | WN352 WN6595 |
from $76 | 5:40 am Chicago Midway | 12:30 pm Boston Logan | 5h 50m layover 2h 45m - Baltimore | Southwest Airlines | WN2462 NK1020 |
from $79 | 4:10 pm Chicago Midway | 9:30 pm Boston Logan | 4h 20m layover 0h 55m - Baltimore | Southwest Airlines | WN1668 WN2449 |
from $79 | 5:40 am Chicago Midway | 11:35 am Boston Logan | 4h 55m layover 1h 45m - Baltimore | Southwest Airlines | WN2462 WN2235 |
Southwest Airlines Flight Schedule Chicago to Boston
Departure | Arrival | Flight Details | Flight Time | Price |
---|---|---|---|---|
10:15 am — 1:35 pm
|
10:15 am — 1:35 pm
WN451
Southwest Airlines
Chicago — Boston
|
2h 20m |
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from$114 |
|
1:55 pm — 5:20 pm
|
1:55 pm — 5:20 pm
WN1665
Southwest Airlines
Chicago — Boston
|
2h 25m |
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from$95 |
|
1:55 pm — 5:20 pm
|
1:55 pm — 5:20 pm
WN1217
Southwest Airlines
Chicago — Boston
|
2h 25m |
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from$131 |
|
7:20 pm — 10:30 pm
|
7:20 pm — 10:30 pm
WN484
Southwest Airlines
Chicago — Boston
|
2h 10m |
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from$73 |
|
7:40 am — 11:00 am
|
7:40 am — 11:00 am
WN376
Southwest Airlines
Chicago — Boston
|
2h 20m |
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from$77 |
|
9:30 pm — 0:35 am
+1 day
|
9:30 pm — 0:35 am
WN2387
Southwest Airlines
Chicago — Boston
|
2h 5m |
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from$53 |
|
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 |
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from$59 |
|
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 |
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from$79 |
|
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 |
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from$120 |
|
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 |
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from$108 |
|
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 |
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from$80 |
|
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 |
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from$135 |
|
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 |
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from$148 |
|
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 |
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from$79 |
|
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 |
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from$56 |
|
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$76 |
|
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$59 |
|
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$130 |
|
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$77 |
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 $53. 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.
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 2 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 9 direct flights every day from Chicago. Airlines and fares are below:
- from $143Find
- from $203Find
Connecting Flights
List of flights with layovers (1 and more stops):
- from $178Find
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