$70 Cheap flight deals from San Antonio (SAT) to Oak Brook (CHI)

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This Weekend's Flight Deals from San Antonio to Oak Brook

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.

Sun, Aug 10 - Sat, Aug 16
SAT
San Antonio Intl.
MDW
Midway Intl.
$241 Roundtrip, found 4 days ago
$241
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, Aug 10 from San Antonio Intl. to Midway Intl., returning Sat, Aug 16, priced at $241 found 4 days ago
Sun, Aug 10 - Tue, Aug 12
SAT
San Antonio Intl.
ORD
O'Hare Intl.
$354 Roundtrip, just found
$354
Roundtrip
just found
Select Spirit Airlines flight, departing Sun, Aug 10 from San Antonio Intl. to O'Hare Intl., returning Tue, Aug 12, priced at $354 just found

Airfares from $70 One Way, $139 Round Trip from San Antonio to Oak Brook

Prices starting at $139 for return flights and $70 for one-way flights to Oak Brook 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, Oct 8 - Sat, Oct 11
SAT
San Antonio
ORD
Chicago
$139 Roundtrip, found 1 hour ago
$139
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Oct 8 from San Antonio to Chicago, returning Sat, Oct 11, priced at $139 found 1 hour ago
Wed, Oct 8 - Sat, Oct 11
SAT
San Antonio
ORD
Chicago
$141 Roundtrip, found 1 hour ago
$141
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Oct 8 from San Antonio to Chicago, returning Sat, Oct 11, priced at $141 found 1 hour ago
Mon, Sep 15 - Wed, Sep 17
SAT
San Antonio
MDW
Chicago
$164 Roundtrip, found 2 days ago
$164
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, Sep 15 from San Antonio to Chicago, returning Wed, Sep 17, priced at $164 found 2 days ago
Wed, Oct 8 - Sat, Oct 11
SAT
San Antonio
ORD
Chicago
$165 Roundtrip, found 1 hour ago
$165
Roundtrip
found 1 hour ago
Select United flight, departing Wed, Oct 8 from San Antonio to Chicago, returning Sat, Oct 11, priced at $165 found 1 hour ago
Sat, Aug 30 - Wed, Sep 3
SAT
San Antonio
ORD
Chicago
$167 Roundtrip, just found
$167
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Aug 30 from San Antonio to Chicago, returning Wed, Sep 3, priced at $167 just found

Oak Brook economy flight packages

Price found within the past 48 hours. Click for updated prices.
Staypineapple, An Iconic Hotel, The Loop
4.0-star property

Staypineapple, An Iconic Hotel, The Loop

9.4/10 Exceptional! (1,035 reviews)

Oct 3 - Oct 6

3 night stay

San Antonio (SAT) to Chicago (ORD)

United • Coach

Chicago (ORD) to San Antonio (SAT)

American Airlines • Coach
per person
found 20 hours ago
Location was great near multiple lines using CTA in the loop. Also near several restaurants. Bathroom was nice & big. There is a safe in the room. Shower was in the back corner and open concept. There was a curtain to use. Previous reviews were correct about only a fitted sheet; no flat sheet. Only a duvet. Got hot & cold throughout the night; so I did not get good sleep for 3 nights. I do not think the controller on the air conditioner works. The controller was an old school dial that turns to adjust the temp setting because the temp felt the same all the time. Stayed 3 nights & no housekeeping. I made it work by alternating days with 2 towels; hanging the towel after each use. One of the workers was giving me a hard time about being a Cubs fan, & I did not initiate the conversation as I was checking out. Did not appreciate that since I was not a Sox fan. Wish I would have stayed @ the L7.

Reviewed on Jul 26, 2025

Canopy by Hilton Chicago Central Loop
4.0-star property

Canopy by Hilton Chicago Central Loop

9.4/10 Exceptional! (1,238 reviews)

Sep 26 - Sep 29

3 night stay

San Antonio (SAT) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach

Chicago (ORD) to San Antonio (SAT)

Southwest Airlines • Non-stop • Coach
per person
found 22 hours ago
Not the best Canopy I've stayed in but it was overall above an average hotel

Reviewed on Jul 19, 2025

Palmer House a Hilton Hotel
4.0-star property

Palmer House a Hilton Hotel

8.4/10 Very Good! (1,819 reviews)

Sep 26 - Sep 29

3 night stay

San Antonio (SAT) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach

Chicago (ORD) to San Antonio (SAT)

Southwest Airlines • Non-stop • Coach
per person
found 22 hours ago
We came to town for a wedding and loved the location of the Palmer House. We spent much of the day before the event walking the city and sightseeing. It is a beautiful hotel.

Reviewed on Jul 28, 2025

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More About Flying To Oak Brook from San Antonio

Route Information for Flights from San Antonio to Oak Brook

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

San Antonio to Oak Brook

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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.