Southwest airlines flights — Chicago, IL
Last updated: September 24, 2026
What affects the price
Flight prices shift based on how far in advance you book and the flexibility of your travel dates. If you are flying during major holidays or peak vacation weeks, you will see higher rates due to high demand. Choosing mid-week flights or opting for less popular departure times can help keep your budget in check. Cabin class, baggage requirements, and last-minute changes also play a significant role in the final total. Your exact pricing is confirmed free on the call.
About this service
Southwest is known for its straightforward approach, often including two checked bags in your fare. This is a solid option if you are planning a family trip or need flexibility with your luggage. Exact pricing confirmed free on the call.
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Also serving nearby: Naperville · Aurora · Joliet · Elgin · Waukegan
More on this: DOT Aviation Consumer Protection — refund rights and the 24-hour rule.
Service area details
Serving all of Chicago — population 2,664,452; about 11,699 residents per square mile across 227.7 sq mi. ZIP codes covered include 60601, 60602, 60603, 60604, 60605, 60606, 60607, 60608.
Neighborhoods served in Chicago: Lincoln Park, Wicker Park, Lakeview, Gold Coast, Pilsen, Hyde Park — and every surrounding area.
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Areas we serve
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Arizona (4)
All of Arizona · Avondale · Chandler · Scottsdale · Tucson
Arkansas (1)
California (21)
All of California · Burbank · El Monte · Fairfield · Glendale · Huntington Beach · Irvine · Lancaster · Modesto · Murrieta · Ontario · Pasadena · Redding · Richmond · Salinas · San Diego · San Jose · Santa Clarita · Temecula · Tracy · Vallejo · Victorville
Colorado (2)
Florida (5)
All of Florida · Gainesville · Hollywood · Orlando · Pembroke Pines · Sunrise
Georgia (1)
Illinois (3)
All of Illinois · Chicago · Elgin · Joliet
Indiana (1)
Iowa (1)
Kansas (3)
Kentucky (1)
Louisiana (1)
Massachusetts (1)
Michigan (1)
Missouri (1)
New Jersey (1)
New York (1)
North Carolina (2)
Ohio (1)
Oklahoma (1)
Oregon (2)
Pennsylvania (1)
South Carolina (1)
South Dakota (1)
Texas (10)
All of Texas · Abilene · Carrollton · College Station · Edinburg · El Paso · Irving · League City · Plano · Sugar Land · Waco