Find cheap Southwest flights to Chicago
RDU — CHI
Nov 12 — Nov 191
Round-trip
1 adult, Economy
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Find detailed information about Southwest flights from USA to Chicago. Explore the options provided by Southwest to plan your journey from USA to Chicago. Data last updated October 13, 2026.
Popular in | July |
|---|---|
Cheapest in | February |
Average price | $348 |
Good one-way deal | $138 or less |
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When is the best time to book a flight to Chicago with Southwest?
The best time to book a flight to Chicago with Southwest is 35 days before departure. On average, fares are higher if you book 2 days before departure.
When is the cheapest time to fly to Chicago with Southwest?
Users looking for the cheapest Southwest fares to Chicago should consider flying on Wednesday at noon, when prices are typically cheapest. Budget-minded travellers will want to avoid Sunday at noon, when prices are usually at their highest.
FAQs about flights to Chicago with Southwest
Reviews of Southwest
See what Cheapflights users have to say about their Southwest experience.
Overview
Reviews
Southwest
4,216 reviews
Overview
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Recent reviews
8.0
|Oct 2026I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.
10.0
|Sep 2026Changed flight which was easy. Gate Agent booked me from extra leg room seat on original flight to row 15 on new flight that did not have extra leg room - even though it was an exit row. The row in front of me with extra leg room had an empty seat.
4.0
|Sep 2026It was a red eye overnight which I prefer. But this time the seat was SOOOO uncomfortable that sleeping was difficult and painful
10.0
|Sep 2026I still think the aircraft should load from the back and window seats first for all passengers. It's so much easier and efficient to board when you do not have to worry about hitting Anyone already seated.
10.0
|Aug 2026great
1 out of 1406
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