AUS - CHI

$76 Find Cheap Southwest Flights from Austin to Chicago

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Flight Deals

Cheap Southwest Flight Deals from Austin to Chicago

 
Here are some of the best deals found on KAYAK recently from Southwest for round-trip flights from Austin 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 from Austin to Chicago

Tue, Nov 4 - Sat, Nov 8
Southwest Logo
6:15 am - 8:50 amAUS-MDW
2h 35mnonstop
Southwest Logo
7:30 pm - 10:15 pmMDW-AUS
2h 45mnonstop
$149Southwest
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Fri, Oct 31 - Tue, Nov 4
Southwest Logo
5:00 pm - 7:30 pmAUS-MDW
2h 30mnonstop
Southwest Logo
12:55 pm - 3:40 pmMDW-AUS
2h 45mnonstop
$150Southwest
Find Deal
Sat, Nov 1 - Tue, Nov 4
Southwest Logo
2:15 pm - 4:45 pmAUS-MDW
2h 30mnonstop
Southwest Logo
8:20 pm - 11:05 pmMDW-AUS
2h 45mnonstop
$159Southwest
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Fri, Oct 31 - Tue, Nov 4
Southwest Logo
12:40 pm - 6:50 pmAUS-MDW
6h 10m1 stop
Southwest Logo
8:15 am - 11:05 amMDW-AUS
2h 50mnonstop
$160Southwest
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Fri, Oct 31 - Tue, Nov 4
Southwest Logo
6:05 am - 11:55 amAUS-MDW
5h 50m2 stops
Southwest Logo
12:55 pm - 3:40 pmMDW-AUS
2h 45mnonstop
$165Southwest
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Tue, Nov 11 - Fri, Nov 14
Southwest Logo
6:15 am - 8:50 amAUS-MDW
2h 35mnonstop
Southwest Logo
9:50 pm - 12:35 amMDW-AUS
2h 45mnonstop
$174Southwest
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Wed, Dec 17 - Thu, Jan 1
Southwest Logo
2:25 pm - 9:00 pmAUS-MDW
6h 35m1 stop
Southwest Logo
8:20 pm - 11:05 pmMDW-AUS
2h 45mnonstop
$179Southwest
Find Deal
Tue, Nov 4 - Sat, Nov 8
Southwest Logo
9:30 am - 2:30 pmAUS-MDW
5h 00m1 stop
Southwest Logo
8:25 am - 11:15 amMDW-AUS
2h 50mnonstop
$180Southwest
Find Deal
Wed, Oct 22 - Fri, Oct 31
Southwest Logo
9:05 pm - 11:35 pmAUS-MDW
2h 30mnonstop
Southwest Logo
9:40 am - 1:40 pmMDW-AUS
4h 00m1 stop
$181Southwest
Find Deal
Wed, Oct 29 - Sat, Nov 1
Southwest Logo
12:15 pm - 2:50 pmAUS-MDW
2h 35mnonstop
Southwest Logo
2:10 pm - 4:50 pmMDW-AUS
2h 40mnonstop
$184Southwest
Find Deal
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Good to know

Low seasonJanuary
Cheapest flight$76
Average price round-trip$288
Good deal one-way$185
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly and prices are also 16% lower on average.
Flight from Austin to Chicago Midway Airport
(avg. price over the last 2 weeks)
or less

When to Book Flights with Southwest from Austin to Chicago

Average price per month
Flight prices as travel date approaches

FAQs for flying to Chicago with Southwest

  • How far in advance should I book tickets for a flight with Southwest from Austin to Chicago?

    Generally, when trying to get a below average price for your ticket, try to book around 8 days before departure. For the cheapest possible price, our data suggests booking 43 days before departure.

  • Is Southwest the cheapest airline to fly with from Austin to Chicago?

    With an average price of $327 return, Southwest is not the cheapest airline to fly from Austin to Chicago with. Instead, for the lowest price, our data suggests flying with Frontier, where a return flight costs $227 on average.

  • What is the cheapest Southwest flight from Austin to Chicago?

    In the last 3 days, the lowest price for a flight with Southwest from Austin to Chicago was $138 for a return flight and $70 for a one-way flight.

  • Does Southwest fly direct to Chicago from Austin?

    Yes, Southwest does offer direct flights for the route, with around 38 flights per week.

  • What’s the cheapest day of the week to fly from Austin to Chicago with Southwest?

    On average, the cheapest day of the week to fly from Austin to Chicago with Southwest is Friday, when prices are around $70. The most expensive day is generally Saturday, where the average price is around $136.

  • What’s the cheapest month to fly from Austin to Chicago with Southwest?

    The cheapest month for Southwest flights to Chicago from Austin is generally October, where plane tickets cost $145 on average. If possible, try to avoid the most expensive months of August and December, where tickets cost $228 and $279 respectively.

Southwest Customer Reviews

8.0
Very good4,237 verified ratings
8.0Comfort
7.0Food
7.5Entertainment
8.6Crew
8.1Boarding
Pros +
Cons -
Show reviews that mention
Traveler rating:
Sort by:
G
10.0 Wonderful
SJC-PDX
Boarding quick & efficient. Crew was friendly. Arrived early
H
6.0 Okay
PHX-ABQ
mandatory demand customer to check their carry on because not enough people check bags.
A
8.0 Very good
MCI-LGA
Good non stop is always good
G
10.0 Wonderful
DEN-SMF
Connecting flight is on time and boarding was a breeze!
G
10.0 Wonderful
LGA-DEN
Easy boarding process. No delays!
M
10.0 Wonderful
MDW-DTW
Excellent
M
10.0 Wonderful
MSY-MDW
Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience
R
10.0 Wonderful
RNO-LAS
As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.
A
4.0 Mediocre
PHX-OGG
Southwest airlines boarding process is the worst. Period.
V
8.0 Very good
LAS-DTW
Good

Everything you need to know for your flight from Austin to Chicago

Cabin class types available on flights to Chicago

Cabin classes available on flights to Austin. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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