$116 Cheap flight deals from Chicago (CHI) to Southside (SAT)

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This Weekend's Flight Deals from Chicago to Southside

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Jul 11 - Sun, Jul 12
ORD
O'Hare Intl.
SAT
San Antonio Intl.
$448 Roundtrip, found 10 hours ago
$448
Roundtrip
found 10 hours ago
Select Delta flight, departing Sat, Jul 11 from O'Hare Intl. to San Antonio Intl., returning Sun, Jul 12, priced at $448 found 10 hours ago
Fri, Jul 10 - Tue, Aug 25
MDW
Midway Intl.
SAT
San Antonio Intl.
$474 Roundtrip, found 16 hours ago
$474
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Fri, Jul 10 from Midway Intl. to San Antonio Intl., returning Tue, Aug 25, priced at $474 found 16 hours ago

Airfares from $116 One Way, $236 Round Trip from Chicago to Southside

Prices starting at $236 for return flights and $116 for one-way flights to Southside were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Jul 29 - Tue, Aug 4
ORD
Chicago
SAT
San Antonio
$236 Roundtrip, found 6 hours ago
$236
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, Jul 29 from Chicago to San Antonio, returning Tue, Aug 4, priced at $236 found 6 hours ago
Wed, Sep 16 - Sat, Sep 19
ORD
Chicago
SAT
San Antonio
$239 Roundtrip, found 1 day ago
$239
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Sep 16 from Chicago to San Antonio, returning Sat, Sep 19, priced at $239 found 1 day ago
Wed, Aug 12 - Sat, Aug 15
ORD
Chicago
SAT
San Antonio
$245 Roundtrip, found 6 hours ago
$245
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Chicago to San Antonio, returning Sat, Aug 15, priced at $245 found 6 hours ago
Thu, Sep 17 - Sat, Sep 19
ORD
Chicago
SAT
San Antonio
$245 Roundtrip, found 4 days ago
$245
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Sep 17 from Chicago to San Antonio, returning Sat, Sep 19, priced at $245 found 4 days ago
Mon, Sep 14 - Sat, Sep 19
MDW
Chicago
SAT
San Antonio
$291 Roundtrip, found 4 days ago
$291
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Mon, Sep 14 from Chicago to San Antonio, returning Sat, Sep 19, priced at $291 found 4 days ago

Southside economy flight packages

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham San Antonio Medical Ctr NW
3.0-star property

La Quinta Inn & Suites by Wyndham San Antonio Medical Ctr NW

8.4/10 Very Good! (3,429 reviews)

Aug 20 - Aug 24

4 night stay

Chicago (CHI) to San Antonio (SAT)

Southwest Airlines • Coach

San Antonio (SAT) to Chicago (CHI)

Frontier Airlines • Coach
Price was $572, price is now $472 per person
$472
per person
found 23 hours ago
I booked three rooms for my family through Hotels.com. As a Silver member, my reservation explicitly included free parking, and the front desk staff confirmed upon arrival that my two vehicles would not be charged. I am also a 100% Disabled Veteran with a trained service dog that alerts me for medication. I explained her specific ADA task and provided my VA paperwork. I filled out their required animal agreement, and my service dog was never left unattended during our stay. After checking out on the 5th, I found unauthorized charges for both parking and a 'pet fee' on my card, even though my rooms were fully prepaid. When I called to resolve this, the lady even remembered me, and said I should not have been charged for either fee and blamed a new employee for the mistake. But then she also stated a refund 'might' be approved with no clear timeline of how long it would take. This is completely unacceptable for a hotel to charge these fees, especially when the free parking was part of hotels.com agreement.

Reviewed on Jul 7, 2026

Hotel Contessa
4.0-star property

Hotel Contessa

9/10 Wonderful! (3,680 reviews)

Aug 20 - Aug 24

4 night stay

Chicago (CHI) to San Antonio (SAT)

Southwest Airlines • Coach

San Antonio (SAT) to Chicago (CHI)

Frontier Airlines • Coach
Price was $803, price is now $646 per person
$646
per person
found 23 hours ago
No microwave made it difficult to fine a place to reheat food

Reviewed on Jul 6, 2026

Joshua Creek Ranch
4.0-star property

Joshua Creek Ranch

9/10 Wonderful! (73 reviews)

Aug 29 - Sep 2

4 night stay

Chicago (ORD) to San Antonio (SAT)

American Airlines • Roundtrip • Coach
Price was $858, price is now $714 per person
$714
per person
found 4 hours ago
Great place to stay---beautiful setting---nice pool. Bed was comfortable---towels smelled fresh. In the room were snacks and bottles of water. Can't get over how nice it was---will stay again!!!!

Reviewed on Jul 6, 2026

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More About Flying To Southside from Chicago

Route Information for Flights from Chicago to Southside

Origin Airport IATA Code
CHI
Destination Airport IATA Code
SAT
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Southside

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.