YOUR NEXT SAN ANTONIO ESCAPEBest fares checked Sep 27, 2026Seven-night round trip · one adult · USD · sampled fares
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Prices may change. Select and confirm the full itinerary with the booking provider. Dates can differ between airport cards.

CHICAGO → SAT

Cheap flights from
Chicago to San Antonio.

A great San Antonio trip starts with a fare worth finding. Compare the latest samples below, then join our upcoming free newsletter to get standout Chicago flight finds in your inbox.

Last checked Sep 27, 20261 adult · Economy · USDSources & coverage
Lowest recently sampled round trip
$258
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Same airports & dates. Each provider checks its own current prices.

ORD → SAT · Dec 2–Dec 9
Search fare; select your return flight to confirm.

A LOWER FARE. A BIGGER TRIP BUDGET.

What could a better fare change?

Spend more on being in San Antonio, and less on getting there. These are real examples from our research—the reason it pays to keep an eye on the fares.

FLEXIBLE TRAVEL DATES$255 less

49% below the priciest date sample

$258 for Dec 2–Dec 9, 2026, compared with $513 for Jun 27–Jul 4, 2027.

12 seven-night date pairs from ORD to the same arrival-airport set (SAT). Lowest returned fare per date pair; checks within 24 hours. Airlines, stops and ticket conditions can differ. A travel-date comparison, not a booking-time prediction.

Explore the cheaper date samples ↗
WHY WATCH THE PRICE?27% price gap

$83 between this search’s high and low

The same dated search ranged from $215 to $298 across 61 historical price observations.

ORD → SAT · Dec 2–Dec 9, 2026. Google Flights history covers Jul 29, 2026–Sep 27, 2026. The percentage is the low below the high. This does not prove when you should book or what subscribers will save.

See the price history ↗
OUR LOWEST RECORDED FARE$258

The lowest seven-night fare in our archive

ORD → SAT · Dec 2–Dec 9, 2026. Recorded Sep 27, 2026.

Our archive starts Sep 27, 2026 and contains 229 seven-night fare observations for this route. Search fare; return may require confirmation. This is our record, not an industry-wide all-time low or a current offer.

How we keep fare records ↗
START WITH THE RIGHT AIRPORT

O’Hare or Midway?

Same dates: Dec 2–Dec 9. Same arrival airports: SAT.

ORD
O’Hare International
$258

1 stop outbound

MDW
Midway International
$337

Nonstop outbound

$79 separates the lowest and highest airport sample for these dates. These are search-result fares for seven-night trips. Flight times, stops and baggage can differ. Ground transport is excluded.

Across 12 matched date pairs in this sample, ORD had the lowest airport fare 12 time(s); MDW had the lowest airport fare 2 time(s). Ties count for each airport. This describes the sampled dates only.

YOUR AIRPORT, YOUR MATH

Which airport wins for you?

A cheaper ticket can come with a pricier ride. Add your own round-trip transport estimate to the matched fares.

ORD

Flight sample $399

$399fare + transport
MDW

Flight sample $585

$585fare + transport

Add your transport estimates to compare your total.

One adult, economy, USD. The two fares use identical dates and arrival-airport sets, checked within 24 hours. Transport starts at $0 because we don’t know your starting point. Baggage and other extras are excluded. Prices and itineraries can differ.

A FEW NUMBERS TO TRAVEL BY

San Antonio, by the flight.

2h 45m

Fastest sampled outbound

MDW → SAT, Oct 11. Nonstop.

5

Airlines in the mix

Across 24 seven-night airport/date searches. Includes connecting carriers.

12

Travel windows sampled

Lowest: $258, Dec 2–Dec 9 from ORD.

2 / 2

Origins with nonstop samples

MDW, ORD in these outbound results. This is not a full schedule.

Derived from the current seven-night observations on this page. Outbound times describe the outbound journey only; fare amounts are round-trip search results. See sources and coverage.

A LITTLE FLEXIBILITY CAN HELP

Compare upcoming travel dates.

Lowest fare in each sampled departure month. Seven-night trips only.

Swipe to see more months →

Oct 26Nov 26Dec 26Jan 27Feb 27Mar 27Apr 27May 27Jun 27Jul 27

Tap a bar to see the dates, airports and check time behind that sample.

Read the chart as a data table
Departure monthLowest sampleDate pairs
2026-10$3991
2026-11$2841
2026-12$2582
2027-01$2851
2027-02$3121
2027-03$3981
2027-04$4171
2027-05$4171
2027-06$4172
2027-07$4571

Sampled dates, not a complete fare calendar. Each month can have different date coverage. This chart describes future travel dates, not past price movements.

THE DETAILS BEHIND THE PRICE

Find a fare worth your next trip.

Prices checked within seven days. Use the filters to find a trip that fits.

Round-trip search fares · 36 representative results · return verification marked individually
Dates / airportsAirline / outboundRound tripCheck price
Dec 2–Dec 9ORD → SAT · 7 nightsFrontier1 stop · 7h 7m$258Select return to confirmChecked Sep 27Google Skyscanner ↗
Nov 6–Nov 13ORD → SAT · 7 nightsFrontier1 stop · 12h 44m$284Select return to confirmChecked Sep 27Google Skyscanner ↗
Jan 23–Jan 30ORD → SAT · 7 nightsFrontier1 stop · 13h 6m$285Select return to confirmChecked Sep 27Google Skyscanner ↗
Feb 18–Feb 25ORD → SAT · 7 nightsFrontier1 stop · 13h 6m$312Select return to confirmChecked Sep 27Google Skyscanner ↗
Oct 25–Oct 28ORD → SAT · 3 nightsFrontier1 stop · 12h 56m$318Select return to confirmChecked Sep 27Google Skyscanner ↗
Dec 2–Dec 9ORD → SAT · 7 nightsUnitedNonstop · 3h 15m$337Return also checkedChecked Sep 27Google Skyscanner ↗
Itinerary

ORD → SAT
UA 1036 · 2026-12-02 9:5

SAT → ORD
UA 1332 · 2026-12-09 6:45

Dec 2–Dec 9MDW → SAT · 7 nightsSouthwestNonstop · 2h 55m$337Return also checkedChecked Sep 27Google Skyscanner ↗
Itinerary

MDW → SAT
WN 3276 · 2026-12-02 10

SAT → MDW
WN 2348 · 2026-12-09 9:50

Jan 23–Jan 30MDW → SAT · 7 nightsSouthwestNonstop · 3h 0m$337Select return to confirmChecked Sep 27Google Skyscanner ↗
Dec 2–Dec 9ORD → SAT · 7 nightsAmericanNonstop · 3h 14m$337Select return to confirmChecked Sep 27Google Skyscanner ↗
Jan 23–Jan 30ORD → SAT · 7 nightsUnitedNonstop · 3h 14m$337Select return to confirmChecked Sep 27Google Skyscanner ↗
Jan 23–Jan 30ORD → SAT · 7 nightsAmericanNonstop · 3h 10m$337Select return to confirmChecked Sep 27Google Skyscanner ↗
Feb 18–Feb 25ORD → SAT · 7 nightsUnitedNonstop · 3h 12m$337Select return to confirmChecked Sep 27Google Skyscanner ↗
Feb 18–Feb 25ORD → SAT · 7 nightsAmericanNonstop · 2h 56m$337Select return to confirmChecked Sep 27Google Skyscanner ↗
Feb 18–Feb 25MDW → SAT · 7 nightsSouthwestNonstop · 2h 55m$347Select return to confirmChecked Sep 27Google Skyscanner ↗
Dec 2–Dec 9MDW → SAT · 7 nightsSouthwest1 stop · 4h 40m$347Select return to confirmChecked Sep 27Google Skyscanner ↗
Dec 2–Dec 9ORD → SAT · 7 nightsAmerican1 stop · 4h 43m$347Select return to confirmChecked Sep 27Google Skyscanner ↗
Jan 23–Jan 30MDW → SAT · 7 nightsSouthwest1 stop · 5h 30m$347Select return to confirmChecked Sep 27Google Skyscanner ↗
Jan 23–Jan 30ORD → SAT · 7 nightsAmerican1 stop · 4h 55m$347Select return to confirmChecked Sep 27Google Skyscanner ↗
Dec 28–Jan 4ORD → SAT · 7 nightsFrontier1 stop · 14h 15m$349Select return to confirmChecked Sep 27Google Skyscanner ↗
Nov 6–Nov 13MDW → SAT · 7 nightsSouthwestNonstop · 2h 55m$363Select return to confirmChecked Sep 27Google Skyscanner ↗
Mar 15–Mar 22ORD → SAT · 7 nightsAmericanNonstop · 2h 56m$398Select return to confirmChecked Sep 27Google Skyscanner ↗
Oct 11–Oct 18ORD → SAT · 7 nightsFrontier1 stop · 12h 56m$399Select return to confirmChecked Sep 27Google Skyscanner ↗
Apr 10–Apr 17MDW → SAT · 7 nightsSouthwestNonstop · 3h 0m$417Select return to confirmChecked Sep 27Google Skyscanner ↗
Apr 10–Apr 17ORD → SAT · 7 nightsUnitedNonstop · 2h 53m$417Select return to confirmChecked Sep 27Google Skyscanner ↗
May 6–May 13MDW → SAT · 7 nightsSouthwestNonstop · 3h 0m$417Select return to confirmChecked Sep 27Google Skyscanner ↗
May 6–May 13ORD → SAT · 7 nightsUnitedNonstop · 2h 53m$417Select return to confirmChecked Sep 27Google Skyscanner ↗
Jun 1–Jun 8ORD → SAT · 7 nightsUnitedNonstop · 2h 53m$417Select return to confirmChecked Sep 27Google Skyscanner ↗
Jun 1–Jun 8MDW → SAT · 7 nightsSouthwestNonstop · 3h 0m$428Select return to confirmChecked Sep 27Google Skyscanner ↗
Mar 15–Mar 22MDW → SAT · 7 nightsDelta1 stop · 5h 21m$437Select return to confirmChecked Sep 27Google Skyscanner ↗
Oct 25–Oct 28MDW → SAT · 3 nightsSouthwestNonstop · 2h 50m$452Select return to confirmChecked Sep 27Google Skyscanner ↗
Dec 28–Jan 4MDW → SAT · 7 nightsSouthwestNonstop · 2h 55m$455Select return to confirmChecked Sep 27Google Skyscanner ↗
Jul 23–Jul 30ORD → SAT · 7 nightsUnitedNonstop · 2h 53m$457Select return to confirmChecked Sep 27Google Skyscanner ↗
Jul 23–Jul 30MDW → SAT · 7 nightsDelta1 stop · 5h 40m$477Select return to confirmChecked Sep 27Google Skyscanner ↗
Jun 27–Jul 4ORD → SAT · 7 nightsAmericanNonstop · 3h 0m$513Select return to confirmChecked Sep 27Google Skyscanner ↗
Oct 11–Oct 18MDW → SAT · 7 nightsSouthwestNonstop · 2h 50m$585Select return to confirmChecked Sep 27Google Skyscanner ↗
Jun 27–Jul 4MDW → SAT · 7 nightsDelta1 stop · 5h 26m$606Select return to confirmChecked Sep 27Google Skyscanner ↗

Prices can change. Cabin baggage and checked bags are not assumed included. Confirm the complete itinerary, airline fare rules and final price on the booking site.

ONE SEARCH, OVER TIME

How this search’s price moved.

ORD → SAT · Dec 2–Dec 9, 2026

Jul 29, 2026$215–$298Sep 27, 2026
Read the historical observations
Observation datePrice
Jul 29, 2026$285
Jul 30, 2026$285
Jul 31, 2026$258
Aug 1, 2026$258
Aug 2, 2026$258
Aug 3, 2026$258
Aug 4, 2026$258
Aug 5, 2026$258
Aug 6, 2026$258
Aug 7, 2026$258
Aug 8, 2026$258
Aug 9, 2026$258
Aug 10, 2026$237
Aug 11, 2026$237
Aug 12, 2026$237
Aug 13, 2026$237
Aug 14, 2026$237
Aug 15, 2026$257
Aug 16, 2026$257
Aug 17, 2026$257
Aug 18, 2026$257
Aug 19, 2026$257
Aug 20, 2026$257
Aug 21, 2026$257
Aug 22, 2026$257
Aug 23, 2026$297
Aug 24, 2026$297
Aug 25, 2026$297
Aug 26, 2026$297
Aug 27, 2026$297
Aug 28, 2026$297
Aug 29, 2026$278
Aug 30, 2026$278
Aug 31, 2026$278
Sep 1, 2026$278
Sep 2, 2026$258
Sep 3, 2026$258
Sep 4, 2026$258
Sep 5, 2026$258
Sep 6, 2026$258
Sep 7, 2026$258
Sep 8, 2026$258
Sep 9, 2026$258
Sep 10, 2026$258
Sep 11, 2026$258
Sep 12, 2026$278
Sep 13, 2026$298
Sep 14, 2026$261
Sep 15, 2026$261
Sep 16, 2026$215
Sep 17, 2026$222
Sep 18, 2026$232
Sep 19, 2026$244
Sep 20, 2026$244
Sep 21, 2026$250
Sep 22, 2026$249
Sep 23, 2026$249
Sep 24, 2026$249
Sep 25, 2026$249
Sep 26, 2026$258
Sep 27, 2026$258

Google Flights price history returned through Scrapingdog for the dates and settings above. It is not a destination-wide average or a prediction. Source checked Sep 27, 2026.

THE FLIGHT IS ONLY PART OF THE TRIP

Arriving in San Antonio.

Airport context and source-backed details to help you compare the whole journey.

SAT · San Antonio International Airport

San Antonio, United States · Airport coordinates 29.534, -98.470

Lowest sample to SAT: $258 round trip from ORD, Dec 2–Dec 9. Different arrival airports may use different dates.

Airport information

Which San Antonio airports are included?

This page searches SAT — San Antonio International Airport. Airport coverage follows the destination city market in the passenger dataset, with minor airports excluded. Always check the airport code on both legs: a city search can include different arrival airports, and the cheapest option may not be closest to where you are staying.

Read the source

Why this route is in our research

BTS recorded 269,356 scheduled passengers departing O’Hare and Midway for this destination city market from 2025-07 to 2026-06. That puts it at number 47 in our selected ranking. These are historical on-flight market passengers, not unique travelers, current flight frequencies or a measure of search popularity.

Read the source

Plan the connection from SAT

Once you have an arrival time, use the airport’s business information to plan the journey onward. Compare the arrival airport, your accommodation location and the return flight’s departure time before choosing a fare. We link to the operator so you can check current services directly; transport prices are not included in the airfare comparisons.

Read the source
FLIGHT FOUND. ADVENTURE NEXT.

Make a trip of San Antonio.

Keep an eye on the whole travel budget, from your first night to your last mile.

A good stay. A happy budget.

Compare places to stay in San Antonio. Add your dates, check the location, and compare the final total and cancellation terms.

Explore San Antonio stays ↗Booking.com · choose your travel dates

A little freedom to roam.

Planning a drive beyond San Antonio? Compare rental cars, mileage, deposits and pickup hours. City-only trip? Public transit may suit you better.

Compare rental cars ↗Discover Cars · enter SAT and your dates

These are planning links, not priced offers. Hotel and car availability is checked by the provider. We currently receive no commission from these links.

GOOD QUESTIONS. STRAIGHT ANSWERS.

Before you take off for San Antonio.

How can I get Chicago to San Antonio flight deals in my inbox?

Let us do the fare hunting. Our upcoming free newsletter will bring standout Chicago flight finds to your inbox, with travel dates and booking links so you can check the deal quickly. Use the signup panel near the top of this page when signup opens. It's free, and you'll be able to unsubscribe at any time.

What is the cheapest flight to San Antonio you have recorded?

The lowest seven-night round-trip search fare in our archive is $258, recorded Sep 27, 2026 for ORD to SAT, Dec 2–Dec 9, 2026. Our route archive starts Sep 27, 2026. This is our observed record, not an industry-wide all-time low, a verified booking price or a current offer.

How much are cheap flights from Chicago to San Antonio?

Our lowest current seven-night sample is $258 round trip for one adult in economy, from ORD to SAT, Dec 2–Dec 9, 2026. It was checked Sep 27, 2026. This is a dated search result, not a guaranteed ticket price; confirm the return and full fare conditions before paying.

Is O’Hare or Midway cheaper for San Antonio?

For the matched Dec 2–Dec 9, 2026 search, ORD had the lowest sample at $258. The highest and lowest airport fares were $79 apart. That applies to those dates and settings only. Try other matched dates and add your own ground transport cost in the airport calculator above.

Can I fly nonstop from Chicago to San Antonio?

The current sample includes a nonstop outbound from MDW to SAT on Dec 2, 2026, with a round-trip search fare of $337. Check the return direction separately: a nonstop outbound does not guarantee a nonstop return.

What is the cheapest month to fly to San Antonio?

The travel-period chart compares only the dates we sampled. It cannot establish the cheapest month of the year. Start with a promising sampled period, then check nearby dates with the same trip length. The separate history chart tracks one specific search over time; it is not a travel calendar.

Which San Antonio airport should I choose?

This destination market includes San Antonio International Airport (SAT). Check the exact arrival code on the fare you choose, then compare the onward journey to your accommodation. The arrival section links airport information and our source-backed planning notes.

Will Skyscanner show the same price as Google Flights?

Not necessarily. The buttons open separate searches with matching airports and dates when a dated sample is available. Providers can show different airlines, sellers, baggage rules and live prices. The sampled Google Flights price is never a Skyscanner quote.

Are bags, hotels and rental cars included?

Do not assume bags are included unless the provider explicitly confirms them. Our research shows flight search fares; the accommodation and rental-car links are separate planning tools. Compare the final total, cancellation terms and location before booking any part of the trip.

Answers use the dated research and sources on this page. Read our flight-saving field notes for a broader planning checklist.

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OPEN ABOUT THE NUMBERS

Sources, coverage & limitations.

This page contains 249 current search-result observations across 26 airport/date searches. Route research is compiled by the Chicago Flight Research desk from the sources below.

Destination photography: photographer, source and reuse license. Airline logos identify the carriers shown in results; no partnership is implied.

BTS demand period: 2025-07 to 2026-06. Searches use one adult, economy, USD and the US market. We do not sell tickets, guarantee fares, or infer baggage inclusions. Read the full methodology