CHI

Find cheap Southwest flights to Chicago from $80

1 adult
1 adult, Economy, 0 bags

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Flight Deals

Cheap Southwest Flight Deals to Chicago

 
Here are some of the best deals found on KAYAK recently from Southwest to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip Southwest flight deals to Chicago

Wed, Feb 18 - Sat, Feb 21
Southwest Logo
6:45 am - 1:00 pm
DEN
-
ORD
5h 15m1 stop
Southwest Logo
5:15 pm - 7:05 pm
ORD
-
DEN
2h 50mnonstop
$178Southwest
Wed, Feb 11 - Sat, Feb 14
Southwest Logo
12:35 pm - 10:35 pm
DEN
-
ORD
9h 00m1 stop
Southwest Logo
5:15 pm - 7:05 pm
ORD
-
DEN
2h 50mnonstop
$186Southwest
Fri, Jan 16 - Tue, Jan 20
Southwest Logo
6:25 am - 1:00 pm
DEN
-
ORD
5h 35m1 stop
Southwest Logo
2:15 pm - 9:05 pm
ORD
-
DEN
7h 50m1 stop
$197Southwest
Wed, Feb 18 - Sat, Feb 21
Southwest Logo
6:00 am - 1:30 pm
DEN
-
ORD
6h 30m1 stop
Southwest Logo
3:45 pm - 10:20 pm
ORD
-
DEN
7h 35m2 stops
$201Southwest
Fri, Jan 16 - Tue, Jan 20
Southwest Logo
6:25 am - 1:00 pm
DEN
-
ORD
5h 35m1 stop
Southwest Logo
2:15 pm - 10:40 pm
ORD
-
DEN
9h 25m2 stops
$202Southwest
Thu, Jan 8 - Sat, Jan 10
Southwest Logo
6:20 am - 3:25 pm
DEN
-
ORD
8h 05m1 stop
Southwest Logo
3:05 pm - 7:45 pm
ORD
-
DEN
5h 40m1 stop
$215Southwest
Wed, Jan 21 - Sun, Jan 25
Southwest Logo
12:35 pm - 10:35 pm
DEN
-
ORD
9h 00m1 stop
Southwest Logo
2:15 pm - 8:35 pm
ORD
-
DEN
7h 20m1 stop
$216Southwest
Fri, Jan 16 - Sun, Jan 18
Southwest Logo
6:25 am - 1:00 pm
DEN
-
ORD
5h 35m1 stop
Southwest Logo
2:15 pm - 9:05 pm
ORD
-
DEN
7h 50m1 stop
$217Southwest
Thu, Jan 15 - Mon, Jan 19
Southwest Logo
6:25 am - 1:00 pm
DEN
-
ORD
5h 35m1 stop
Southwest Logo
1:45 pm - 10:10 pm
ORD
-
DEN
9h 25m2 stops
$220Southwest
Fri, Jan 16 - Mon, Jan 19
Southwest Logo
6:25 am - 1:00 pm
DEN
-
ORD
5h 35m1 stop
Southwest Logo
1:45 pm - 10:10 pm
ORD
-
DEN
9h 25m2 stops
$221Southwest
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$80
Average price round-trip$360
Good deal one-way$238
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Los Angeles to Chicago Midway Airport
(avg. price over the last 2 weeks)
or less

When to book flights with Southwest to Chicago

Average price per month
Flight prices as travel date approaches

FAQs for flying to Chicago with Southwest

  • Which other airlines fly to Chicago?

    Along with Southwest, you can also fly to Chicago with United Airlines, United Airlines, Allegiant Air, American Airlines, Contour, Frontier, Denver Air Connection, Frontier, Delta, Avelo Airlines, Avelo Airlines and Alaska Airlines.

  • How much is a flight to Chicago with Southwest?

    On average, Southwest flights to Chicago cost $264 one-way.

  • Which airport do Southwest flights to Chicago fly into?

    Southwest flights to Chicago will fly into either Chicago O'Hare Airport, Chicago Midway Airport and Chicago Greater Rockford.

Top tips for your flights to Chicago with Southwest

  • The cheapest flight to Chicago with Southwest found on KAYAK in the last 2 weeks departed from Rochester and cost $58.
  • If you’re intending to fly with Southwest, book your flight to Chicago at least 2 weeks before departure to ensure a below-average price.
  • High season for flights to Chicago with Southwest is May and prices are highest at this time. The cheapest month to fly is January.

Southwest customer reviews

7.9
Good4,249 verified ratings
8.0Comfort
7.0Food
8.6Crew
7.5Entertainment
8.1Boarding
Pros +
  • Flights were on time and crew was great. (in 567 reviews)
  • Really funny flight attendant. (in 563 reviews)
Cons -
  • WiFi was terrible. (in 156 reviews)
  • Left on time and got in ten minutes early. (in 42 reviews)
Show reviews that mention
Traveler rating:
Sort by:
M
10.0 Wonderful
Excellent
R
8.0 Very good
The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.
P
2.0 Poor
2 hour delay
A
10.0 Wonderful
The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.
A
10.0 Wonderful
Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.
T
2.0 Poor
Multiple delays, canceled flights, and flight reroutes.
D
10.0 Wonderful
Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!
D
10.0 Wonderful
Excellent experience, no complaints.
I
10.0 Wonderful
No delays and arrived to destination 30 min early. Staff was super friendly.
G
10.0 Wonderful
San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.
Read more about Southwest

Everything you need to know for your flight to Chicago

Other airlines flying to Chicago

Flights from the other most popular airlines that fly to Chicago according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Frontier flights to Chicago
Spirit Airlines flights to Chicago
Delta flights to Chicago
American Airlines flights to Chicago
United Airlines flights to Chicago