Find cheap Southwest flights to Chicago O'Hare Intl Airport
DSM — ORD
Aug 26 — Sep 21
Round-trip
1 adult, Economy
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Cheapest Southwest flights from USA to O'Hare IntlExplore the most affordable Southwest flight options available from USA to O'Hare Intl. Find the lowest fares with prices last updated on July 27, 2026.
Explore the most affordable Southwest flight options available from USA to O'Hare Intl. 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 O'Hare IntlDiscover carefully curated Southwest flight deals from USA to O'Hare Intl 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 O'Hare Intl 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 O'Hare IntlDiscover last-minute Southwest flight deals from USA to O'Hare Intl. Data last updated July 27, 2026 and is based on user searches.
Discover last-minute Southwest flight deals from USA to O'Hare Intl. 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 O'Hare Intl Airport with Southwest at a glance
Find detailed information about Southwest flights from USA to O'Hare Intl. Explore the options provided by Southwest to plan your journey from USA to O'Hare Intl. Data last updated July 27, 2026.
Cheapflights Insights
Find cheap Southwest flights to Chicago O'Hare Intl Airport
US0-ORD
BOS-ORD
How long is the flight to Chicago O'Hare Intl Airport with Southwest?
On average, Southwest flights from the United States to Chicago O'Hare Intl Airport take 2 hours 43 minutes. Flights to Chicago O'Hare Intl Airport from other popular cities in the United States will vary in length. Below are a few examples of popular routes and their flight times.
When is the cheapest time to fly to Chicago O'Hare Intl Airport with Southwest?
Users looking for the cheapest Southwest fares to Chicago O'Hare Intl Airport should consider flying on Saturday evenings, 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 O'Hare Intl Airport with Southwest
Reviews of Southwest
See what Cheapflights users have to say about their Southwest experience.
Overview
Reviews
Southwest
4,229 reviews
Overview
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
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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