Find cheap Southwest flights to Chicago
RDU — CHI
Aug 26 — Sep 21
Round-trip
1 adult, Economy
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Cheapest Southwest flights from USA to ChicagoExplore the most affordable Southwest flight options available from USA to Chicago. Find the lowest fares with prices last updated on July 27, 2026.
Explore the most affordable Southwest flight options available from USA to Chicago. Find the lowest fares with prices last updated on July 27, 2026.
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/118:30 am
BOS
- ORD
1 stop5h 30m
Southwest
Wed 8/124:20 pm
ORD
- BOS
1 stop4h 50m
Southwest
Deal found 7/24![Southwest logo]()
$245
Best Southwest flights from USA to ChicagoDiscover carefully curated Southwest flight deals from USA to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 27, 2026.
Discover carefully curated Southwest flight deals from USA to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 27, 2026.
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/118:30 am
BOS
- ORD
1 stop5h 30m
Southwest
Wed 8/124:20 pm
ORD
- BOS
1 stop4h 50m
Southwest
Deal found 7/24![Southwest logo]()
$245
Last-minute Southwest flights from USA to ChicagoDiscover last-minute Southwest flight deals from USA to Chicago. Data last updated July 27, 2026 and is based on user searches.
Discover last-minute Southwest flight deals from USA to Chicago. Data last updated July 27, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/118:30 am
BOS
- ORD
1 stop5h 30m
Southwest
Wed 8/124:20 pm
ORD
- BOS
1 stop4h 50m
Southwest
Deal found 7/24![Southwest logo]()
$245
Flights to Chicago with Southwest at a glance
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 July 27, 2026.
Popular in | July |
|---|---|
Cheapest in | September |
Average price | $324 |
Round-trip from | $245 |
Good one-way deal | $165 or less |
Cheapflights Insights
Find cheap Southwest flights to Chicago
US0-CHI
BOS-ORD
How long is the flight to Chicago with Southwest?
On average, Southwest flights from the United States to Chicago take 2 hours 10 minutes. Flights to Chicago from other popular cities in the United States will vary in length. Below are a few examples of popular routes and their flight times.
Southwest weekly flight availability to Chicago
The most flights to Chicago operated by Southwest are scheduled on a Monday (239 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (188 on average).
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 29 days before departure. On average, fares are higher if you book on the same day as 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
4,229 reviews
Overview
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Recent reviews
10.0
|Jul 2026Good
8.0
|Jun 2026One delay in a 2 layover flight=a good trip. The crew was great.
6.0
|Jun 2026The seats were super cramped and couldn’t move without hitting other passengers
8.0
|Jun 2026The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
10.0
|Jun 2026On time and no problems
1 out of 1410
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