$127 Cheap flight deals from Chicago (CHI) to Helotes (SAT)
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This Weekend's Flight Deals from Chicago to Helotes
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.
ORD
O'Hare Intl.
SAT
San Antonio Intl.
$723 Roundtrip, found 1 day ago
$723
Roundtrip
found 1 day ago
MDW
Midway Intl.
SAT
San Antonio Intl.
$957 Roundtrip, found 19 hours ago
$957
Roundtrip
found 19 hours ago
Airfares from $127 One Way, $236 Round Trip from Chicago to Helotes
Prices starting at $236 for return flights and $127 for one-way flights to Helotes were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
ORD
Chicago
SAT
San Antonio
$236 Roundtrip, found 12 hours ago
$236
Roundtrip
found 12 hours ago
ORD
Chicago
SAT
San Antonio
$249 Roundtrip, found 5 days ago
$249
Roundtrip
found 5 days ago
ORD
Chicago
SAT
San Antonio
$250 Roundtrip, found 1 day ago
$250
Roundtrip
found 1 day ago
ORD
Chicago
SAT
San Antonio
$255 Roundtrip, found 11 hours ago
$255
Roundtrip
found 11 hours ago
ORD
Chicago
SAT
San Antonio
$297 Roundtrip, found 5 days ago
$297
Roundtrip
found 5 days ago
Helotes economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Contessa
9/10 Wonderful! (3,593 reviews)
Jul 2 - Jul 5
3 night stay
Chicago (CHI) to San Antonio (SAT)
American Airlines • Non-stop • Coach
San Antonio (SAT) to Chicago (CHI)
Frontier Airlines • Non-stop • Coach
Price was $794, price is now $593 per person
$593
per person
found 1 day ago
Staff was accommodating.
Reviewed on Apr 11, 2026
4.0-star property
Signia by Hilton La Cantera Resort & Spa
9/10 Wonderful! (1,051 reviews)
Jul 2 - Jul 5
3 night stay
Chicago (CHI) to San Antonio (SAT)
American Airlines • Non-stop • Coach
San Antonio (SAT) to Chicago (CHI)
Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,025, price is now $680 per person
$680
per person
found 1 day ago
We had a great time.
Reviewed on Aug 5, 2025
4.5-star property
The St. Anthony, A Luxury Collection Hotel, San Antonio
8.8/10 Excellent! (1,002 reviews)
Jul 2 - Jul 5
3 night stay
Chicago (CHI) to San Antonio (SAT)
American Airlines • Non-stop • Coach
San Antonio (SAT) to Chicago (CHI)
Frontier Airlines • Non-stop • Coach
Price was $775, price is now $616 per person
$616
per person
found 1 day 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
Helotes first class flight packages
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Staybridge Suites San Antonio by IHG
8.4/10 Very Good! (1,000 reviews)
Jul 3 - Jul 6
3 night stay
Chicago (CHI) to San Antonio (SAT)
American Airlines • FirstClass
San Antonio (SAT) to Chicago (CHI)
Frontier Airlines • FirstClass
Price was $791, price is now $713 per person
$713
per person
found 1 day ago
Very nice staff! Floors were a little greasy. Soap handle was broken in the bathroom… bathrooms were very old.
Reviewed on May 11, 2026
3.5-star property
Hyatt Vacation Club at Wild Oak Ranch, San Antonio
9/10 Wonderful! (1,681 reviews)
Jul 3 - Jul 6
3 night stay
Chicago (CHI) to San Antonio (SAT)
American Airlines • FirstClass
San Antonio (SAT) to Chicago (CHI)
Frontier Airlines • FirstClass
Price was $1,129, price is now $975 per person
$975
per person
found 1 day ago
Location was very nice and well maintained nice amenities. Pool and hot tubes with lazy river were great.Only real issue was staffing at front desk needed better customer service skills . The gentleman on the front desk needs an attitude adjustment or a career change .He choose to work customer service and is not great at it . Pro tip if you need to extend your stay and you booked through a third party travel site contact or use the app you booked through to rebook a room. Hyatt vacation club will charge three times the cost you booked you room and not blink an eye at it and lie the they all booked up. Yet the rooms are available on the travel site for the same date you looking at and a third of the cost. when I confronted the gentleman at the desk, Diego and inquired about this later after her rebooking with Hyat. Diego “it is what it is. “slapped my receipt on the counter and turned and walked away from me. Not what I was expecting from Hyat vacation club Customer;service very unprofessional think twice before staying at that site !
Reviewed on May 6, 2026
4.5-star property
InterContinental San Antonio Riverwalk by IHG
9.2/10 Wonderful! (690 reviews)
Jul 3 - Jul 6
3 night stay
Chicago (CHI) to San Antonio (SAT)
American Airlines • FirstClass
San Antonio (SAT) to Chicago (CHI)
Frontier Airlines • FirstClass
Price was $852, price is now $744 per person
$744
per person
found 1 day ago
Newly renovated property with good design. Rooms are spacious and bathrooms are good. Only problem we had was the air conditioning had a hard time keeping up with the texas summer heat. Would recommend.
Reviewed on Jun 30, 2025
More About Flying To Helotes from Chicago
Route Information for Flights from Chicago to Helotes
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | SAT |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Helotes
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Get Package Savings by Booking Flights and Hotels at the Same Time
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- Hotels in Northwest San Antonio
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- Visit USAA Corporate Office Headquarters
- Hotels in San Antonio
- Hotels near Six Flags Fiesta Texas
- Hotels near The Rim Shopping Center
- Things to do in Northwest San Antonio
- Hotels near University of Texas at San Antonio
- Flights to San Antonio
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.