$129 Cheap flight deals from San Antonio (SAT) to Highland Park (CHI)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

This Weekend's Flight Deals from San Antonio to Highland Park

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, Oct 9 - Mon, Oct 12
SAT
San Antonio Intl.
ORD
O'Hare Intl.
$619 Roundtrip, found 12 hours ago
$619
Roundtrip
found 12 hours ago
Select United flight, departing Fri, Oct 9 from San Antonio Intl. to O'Hare Intl., returning Mon, Oct 12, priced at $619 found 12 hours ago
Fri, Oct 9 - Mon, Oct 12
SAT
San Antonio Intl.
MDW
Midway Intl.
$640 Roundtrip, just found
$640
Roundtrip
just found
Select Southwest Airlines flight, departing Fri, Oct 9 from San Antonio Intl. to Midway Intl., returning Mon, Oct 12, priced at $640 just found

Airfares from $129 One Way, $258 Round Trip from San Antonio to Highland Park

Prices starting at $258 for return flights and $129 for one-way flights to Highland Park were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Dec 12 - Tue, Dec 15
SAT
San Antonio
ORD
Chicago
$258 Roundtrip, just found
$258
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Dec 12 from San Antonio to Chicago, returning Tue, Dec 15, priced at $258 just found
Tue, Dec 1 - Tue, Dec 8
SAT
San Antonio
ORD
Chicago
$262 Roundtrip, just found
$262
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Dec 1 from San Antonio to Chicago, returning Tue, Dec 8, priced at $262 just found
Tue, Dec 22 - Tue, Dec 29
SAT
San Antonio
ORD
Chicago
$268 Roundtrip, just found
$268
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Dec 22 from San Antonio to Chicago, returning Tue, Dec 29, priced at $268 just found
Fri, Dec 4 - Mon, Dec 7
SAT
San Antonio
ORD
Chicago
$281 Roundtrip, just found
$281
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Dec 4 from San Antonio to Chicago, returning Mon, Dec 7, priced at $281 just found
Sat, Dec 12 - Tue, Dec 15
SAT
San Antonio
ORD
Chicago
$285 Roundtrip, just found
$285
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Dec 12 from San Antonio to Chicago, returning Tue, Dec 15, priced at $285 just found

Highland Park economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

8.2/10 Very Good! (3,084 reviews)

Nov 12 - Nov 16

4 night stay

San Antonio (SAT) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to San Antonio (SAT)

Frontier Airlines • Coach
Price was $842, price is now $603 per person
$603
per person
found 1 day ago
Room was clean, bed was comfortable. The location is great but the room was tiny. There was only about 2 1/2 feet between the king bed and the walls so it was very cramped. No refrigerator, microwave or coffee maker in the room (there was a clothing steamer, which we didn't use, and a hair dryer in bathroom). Shower, not a tub, and new/extra towels were delivered on request. There are 3 elevators, but only one appeared to be working for the 3 nights we stayed. Coffee was available downstairs in the morning. There was a lot of street noise and sirens at night, but that may just be the city since we are used to a quieter neighborhood.

Reviewed on Oct 1, 2026

Kimpton Gray Hotel by IHG
4.5-star property

Kimpton Gray Hotel by IHG

9.4/10 Exceptional! (1,007 reviews)

Nov 12 - Nov 16

4 night stay

San Antonio (SAT) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to San Antonio (SAT)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,149, price is now $824 per person
$824
per person
found 1 day ago
I stayed in a room at the back, every morning at 5:30 am trucks and dumpsters were moved, noise so loud it woke me up. Was charged an amenity fee and there were really mo amenities. Breakfast sucked both days in first floor restaurant. Won't stay again.

Reviewed on Oct 1, 2026

Fairmont Chicago at Millennium Park
4.5-star property

Fairmont Chicago at Millennium Park

8.8/10 Excellent! (2,309 reviews)

Nov 12 - Nov 16

4 night stay

San Antonio (SAT) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to San Antonio (SAT)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,067, price is now $769 per person
$769
per person
found 1 day ago

Don't see what you're looking for?
See all available trips from San Antonio to Highland Park
View all trips

Highland Park first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile
4.0-star property

Hotel Saint Clair- Magnificent Mile

8.6/10 Excellent! (2,240 reviews)

Nov 13 - Nov 15

2 night stay

San Antonio (SAT) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,042, price is now $944 per person
$944
per person
found 8 hours ago

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.6/10 Exceptional! (2,035 reviews)

Nov 13 - Nov 15

2 night stay

San Antonio (SAT) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,556, price is now $1,254 per person
$1,254
per person
found 8 hours ago
This is an elegant and high class facility with warm service and hospitality stuff Centrally located on North River north bank. The room is big and spacious overlooking the river. We loved our stay. The concierge gave us a great tips and services Recommend by all means.

Reviewed on Oct 2, 2026

Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

9.2/10 Wonderful! (527 reviews)

Nov 13 - Nov 15

2 night stay

San Antonio (SAT) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,260, price is now $1,089 per person
$1,089
per person
found 8 hours ago
The location is perfect and the building is quite nice. The rooms are also comfortable. This is not a hotel, but rather occupies several floors in a large apartment building. We had a couple issues with our room (malfunctioning, smoke alarm and empty body wash) and neither were dealt with despite a asking multiple times.

Reviewed on Sep 27, 2026

Don't see what you're looking for?
See all available trips from San Antonio to Highland Park
View all trips

More About Flying To Highland Park from San Antonio

Route Information for Flights from San Antonio to Highland Park

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

San Antonio to Highland Park

Orbitz gives you great deals on your flights from San Antonio to Highland Park. If you also need a discount car rental or a cheap hotel room after you arrived at your destination, Orbitz has you covered.

We Offer Great Travel Deals and Discounts

When you book flights from San Antonio to Highland Park with Orbitz for, you can be assured that you are getting the lowest price possible. Orbitz works constantly with our airline partners to ensure guaranteed low prices on San Antonio to Highland Park flights for your trip—whether you are traveling for business or for fun with your family.

Enjoy Savings on Last-Minute Flights

If you are looking for a discount price on last-minute flights from San Antonio to Highland Park, chances are that Orbitz can offer you a deal that will save you lots of money. Whether you just want to get away for the weekend or go on a vacation lasting weeks, Orbitz can help you find the best deals on San Antonio to Highland Park flights that fit your budget and your itinerary for the perfect trip.

Full-Service Mobile Apps

Need more mobility when it comes to travel planning? Orbitz has easy-to-use mobile apps for iPhone, iPad, and Android, to help the traveler on the go. Not only can use the apps to find huge savings on San Antonio to Highland Park flights wherever you are, but you can also check out and book discount hotel rooms too. The apps will also keep you up-to-date when it’s time to fly. Get easy access to your itinerary for flights from San Antonio to Highland Park and review gate and baggage claim details too.

More Destinations

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.