Southwest Airlines to Chicago
Southwest Airlines to Chicago cheap flights
- One way
- Round-trip
- Sort: Price (Lowest)
- Sort: Departure (Earliest)
- DCA06:252hDirectMDW07:25Washington D.C. - Chicago|Wed, May 8|Southwest AirlinesS$ 77S$ 77
- BNA06:001h 35mDirectMDW07:35Nashville - Chicago|Sat, May 18|Southwest AirlinesS$ 81S$ 81
- DEN17:252h 30mDirectORD20:55Denver - Chicago|Sat, Apr 27|Southwest AirlinesS$ 85S$ 85
- LGA21:302h 25mDirectMDW22:55New York - Chicago|Tue, May 21|Southwest AirlinesS$ 86S$ 86
- LGA19:302h 30mDirectMDW21:00New York - Chicago|Wed, May 8|Southwest AirlinesS$ 88S$ 88
- DCA21:151h 55mDirectMDW22:10Washington D.C. - Chicago|Fri, Apr 26|Southwest AirlinesS$ 88S$ 88
- DCA12:402hDirectMDW13:40Washington D.C. - Chicago|Tue, Apr 30|Southwest AirlinesS$ 96S$ 96
- LGA21:402h 25mDirectMDW23:05New York - Chicago|Mon, Apr 29|Southwest AirlinesS$ 98S$ 98
- DCA12:402hDirectMDW13:40Washington D.C. - Chicago|Tue, May 7|Southwest AirlinesS$ 99S$ 99
- DCA06:252hDirectMDW07:25Washington D.C. - Chicago|Tue, May 14|Southwest AirlinesS$ 102S$ 102
- DEN08:252h 20mDirectMDW11:45Denver - Chicago|Sat, Apr 27|Southwest AirlinesS$ 102S$ 102
- DEN19:552h 20mDirectMDW23:15Denver - Chicago|Fri, Apr 26|Southwest AirlinesS$ 105S$ 105
- DEN06:002h 25mDirectORD09:25Denver - Chicago|Fri, Apr 26|Southwest AirlinesS$ 105S$ 105
- DEN08:252h 25mDirectORD11:50Denver - Chicago|Wed, May 15|Southwest AirlinesS$ 108S$ 108
- BNA21:301h 30mDirectMDW23:00Nashville - Chicago|Tue, May 21|Southwest AirlinesS$ 109S$ 109
- DEN16:302h 30mDirectORD20:00Denver - Chicago|Mon, May 6|Southwest AirlinesS$ 110S$ 110
- DEN17:552h 25mDirectMDW21:20Denver - Chicago|Mon, May 6|Southwest AirlinesS$ 110S$ 110
- DAL07:152h 5mDirectMDW09:20Dallas - Chicago|Sat, Apr 27|Southwest AirlinesS$ 110S$ 110
- DEN17:552h 25mDirectMDW21:20Denver - Chicago|Thu, May 9|Southwest AirlinesS$ 110S$ 110
- DEN06:002h 25mDirectORD09:25Denver - Chicago|Thu, May 9|Southwest AirlinesS$ 110S$ 110
- DEN08:252h 25mDirectORD11:50Denver - Chicago|Wed, May 8|Southwest AirlinesS$ 111S$ 111
- DEN20:052h 20mDirectMDW23:25Denver - Chicago|Wed, May 8|Southwest AirlinesS$ 111S$ 111
- DEN21:202h 20mDirectMDW00:40Denver - Chicago|Fri, May 10|Southwest AirlinesS$ 111S$ 111
- MIA07:353h 5mDirectMDW09:40Miami - Chicago|Tue, May 7|Southwest AirlinesS$ 111S$ 111
- LGA06:302h 25mDirectMDW07:55New York - Chicago|Tue, May 14|Southwest AirlinesS$ 113S$ 113
- LGA15:302h 30mDirectMDW17:00New York - Chicago|Tue, Apr 30|Southwest AirlinesS$ 114S$ 114
- DAL17:402h 20mDirectORD20:00Dallas - Chicago|Sat, Apr 27|Southwest AirlinesS$ 114S$ 114
- LGA21:302h 25mDirectMDW22:55New York - Chicago|Wed, May 15|Southwest AirlinesS$ 114S$ 114
- LGA19:552h 35mDirectMDW21:30New York - Chicago|Wed, Jun 5|Southwest AirlinesS$ 114S$ 114
- LGA06:302h 25mDirectMDW07:55New York - Chicago|Tue, May 7|Southwest AirlinesS$ 175S$ 175
- WAS13:003h 5mDirectCHI14:00Washington D.C. - Chicago|Fri, May 3|Southwest AirlinesFind More FlightsFind More Flights
Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
Southwest Airlines to Chicago Flight schedule
WN2078
Southwest Airlines
05:35
BNA
07:05
MDW
SMTWTFSWN3634
Southwest Airlines
06:00
DEN
09:25
ORD
SMTWT-SWN2636
Southwest Airlines
06:00
DEN
09:20
MDW
-MT--F-WN4920
Southwest Airlines
06:30
LGA
07:55
MDW
SMTWT-SWN3085
Southwest Airlines
06:55
DCA
08:00
MDW
SMTWTFSWN2119
Southwest Airlines
07:35
BNA
09:05
MDW
SMTWTFSWN692
Southwest Airlines
07:50
DEN
11:10
MDW
S--WTF-WN941
Southwest Airlines
08:25
DEN
11:50
ORD
SMTWT--WN3086
Southwest Airlines
09:30
DCA
10:35
MDW
SMTWTFSWN719
Southwest Airlines
10:40
DEN
15:35
MDW
SMTWTFSWN2503
Southwest Airlines
11:10
DEN
14:30
MDW
SMTWTFSWN3087
Southwest Airlines
12:00
DCA
13:00
MDW
SMTWT-SWN1130
Southwest Airlines
13:30
DEN
17:00
ORD
-----FSWN3624
Southwest Airlines
14:40
BNA
16:25
ORD
SMTWTFSWN1603
Southwest Airlines
17:55
DEN
21:20
MDW
SMTWT--WN6141
Southwest Airlines
19:00
DCA
20:00
MDW
SMTWTFSWN3625
Southwest Airlines
19:45
BNA
21:30
ORD
SMTWT--WN2302
Southwest Airlines
21:15
DCA
22:10
MDW
SMTWT-SWN3100
Southwest Airlines
21:20
DEN
00:40
MDW
S--WT--WN4967
Southwest Airlines
21:40
LGA
23:05
MDW
SMTWT-S
Hotels in Chicago
Hotels near Chicago
Site Operator: Trip.com Travel Singapore Pte. Ltd. Travel License No. 02943