$86 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.

Fri, Jan 30 - Sat, Feb 7
ORD
O'Hare Intl.
SAT
San Antonio Intl.
$296 Roundtrip, found 1 hour ago
$296
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Jan 30 from O'Hare Intl. to San Antonio Intl., returning Sat, Feb 7, priced at $296 found 1 hour ago

Airfares from $86 One Way, $159 Round Trip from Chicago to Southside

Prices starting at $159 for return flights and $86 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.

Mon, Feb 23 - Tue, Mar 3
ORD
Chicago
SAT
San Antonio
$159 Roundtrip, found 5 hours ago
$159
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Mon, Feb 23 from Chicago to San Antonio, returning Tue, Mar 3, priced at $159 found 5 hours ago
Wed, Apr 8 - Mon, Apr 13
ORD
Chicago
SAT
San Antonio
$180 Roundtrip, found 1 day ago
$180
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Apr 8 from Chicago to San Antonio, returning Mon, Apr 13, priced at $180 found 1 day ago
Wed, Feb 25 - Sat, Feb 28
ORD
Chicago
SAT
San Antonio
$271 Roundtrip, found 5 days ago
$271
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Feb 25 from Chicago to San Antonio, returning Sat, Feb 28, priced at $271 found 5 days ago
Sat, Mar 21 - Tue, Mar 24
MDW
Chicago
SAT
San Antonio
$273 Roundtrip, found 5 days ago
$273
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Mar 21 from Chicago to San Antonio, returning Tue, Mar 24, priced at $273 found 5 days ago
Wed, Feb 25 - Sat, Feb 28
ORD
Chicago
SAT
San Antonio
$295 Roundtrip, found 5 days ago
$295
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Feb 25 from Chicago to San Antonio, returning Sat, Feb 28, priced at $295 found 5 days ago

Southside economy flight packages

Price found within the past 48 hours. Click for updated prices.
La Luz
3.0-star property

La Luz

9.8/10 Exceptional! (47 reviews)

Mar 12 - Mar 16

4 night stay

Chicago (ORD) to San Antonio (SAT)

American Airlines • Coach

San Antonio (SAT) to Chicago (ORD)

Frontier Airlines • Coach
Price was $765, price is now $622 per person
$622
per person
found 1 day ago
Hotel Contessa
4.0-star property

Hotel Contessa

9/10 Wonderful! (3,372 reviews)

Feb 24 - Feb 27

3 night stay

Chicago (CHI) to San Antonio (SAT)

American Airlines • Coach

San Antonio (SAT) to Chicago (CHI)

Southwest Airlines • Coach
Price was $1,191, price is now $957 per person
$957
per person
found 2 hours ago
Fire alarms going off multiple times. The entire hallway had an extremely strong smell of marijuana. Then before checkout I found another 11 dollar bill due. This is for all their hidden fees such as the pool, the WiFi and so on. I will not be staying in this hotel again. Very disappointed

Reviewed on Nov 26, 2025

The St. Anthony, A Luxury Collection Hotel, San Antonio
4.5-star property

The St. Anthony, A Luxury Collection Hotel, San Antonio

8.8/10 Excellent! (1,000 reviews)

Feb 27 - Mar 1

2 night stay

Chicago (CHI) to San Antonio (SAT)

Southwest Airlines • Coach

San Antonio (SAT) to Chicago (CHI)

Frontier Airlines • Coach
Price was $771, price is now $633 per person
$633
per person
found 11 hours ago
The service was excellent, beautiful property. Only downside was the smell - reminded me of very old European properties with a vague sewer smell in the room like the drains do not have proper traps. Common areas smelled fine. Valet was overpriced, the bar was excellent!

Reviewed on Sep 14, 2025

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Southside packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites San Antonio Medical-Six Flags by IHG
2.5-star property

Holiday Inn Express & Suites San Antonio Medical-Six Flags by IHG

7.8/10 Good! (1,027 reviews)

Mar 6 - Mar 9

3 night stay

Chicago (ORD) to San Antonio (SAT)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $760, price is now $699 per person
$699
per person
found 1 day ago
Room was clean, and accommodating.

Reviewed on Nov 5, 2025

Downtown San Antonio Apartments by Landing
4.0-star property

Downtown San Antonio Apartments by Landing

No reviews

Mar 6 - Mar 9

3 night stay

Chicago (ORD) to San Antonio (SAT)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,134, price is now $995 per person
$995
per person
found 1 day ago
Best Western Premier Historic Travelers Hotel Alamo Riverwalk
3.0-star property

Best Western Premier Historic Travelers Hotel Alamo Riverwalk

7.6/10 Good! (1,004 reviews)

Mar 6 - Mar 9

3 night stay

Chicago (ORD) to San Antonio (SAT)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $854, price is now $782 per person
$782
per person
found 1 day ago
The young lady at the front desk on the morning of 01/18/26 was very attentive and she was helpful. She was very nice and friendly.

Reviewed on Jan 19, 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.