CHI - SAT

$111 Find Cheap Flights from Chicago to San Antonio

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to San Antonio departing on 9/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to San Antonio

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Antonio, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Antonio, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$270
Typical prices: $427-$331
Frontier
Fri 7/3Tue 7/7
ORD - SAT • 1 stop
Cheapest non-stop
$282
Typical prices: $425-$265
United Airlines
Tue 9/1Fri 9/4
ORD - SAT • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Southwest free carry-on helps value, but checked bags now cost extra.
United Economy Plus adds up to six inches of legroom over standard economy.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $270 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, Southwest and United Airlines. Average duration is 2h 52m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 1% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $138 (round-trip)
Shortest trip • 4h 20m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 52% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 34% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to San Antonio!
Flight Deals
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Expert advice
Flight Deals

Cheap Flights from Chicago to San Antonio (CHI-SAT)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to San Antonio that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to San Antonio

Fri, Jul 3 - Tue, Jul 7
Frontier Logo
9:48 pm - 6:56 pm
ORD
-
SAT
21h 08m
1 stop
Frontier Logo
9:32 pm - 5:37 am
SAT
-
ORD
8h 05m
1 stop
$270Frontier
Fri, Jul 3 - Tue, Jul 7
Frontier Logo
7:20 am - 8:11 pm
ORD
-
SAT
12h 51m
1 stop
Frontier Logo
9:32 pm - 5:37 am
SAT
-
ORD
8h 05m
1 stop
$271Frontier
Sat, Oct 31 - Wed, Nov 4
Southwest Logo
11:30 am - 2:10 pm
MDW
-
SAT
2h 40mnonstop
Southwest Logo
9:45 am - 5:10 pm
SAT
-
MDW
7h 25m
2 stops
$273Southwest
Thu, Sep 24 - Sun, Sep 27
Frontier Logo
1:02 pm - 9:39 pm
ORD
-
SAT
8h 37m
1 stop
Frontier Logo
7:49 pm - 10:01 am
SAT
-
ORD
14h 12m
1 stop
$274Frontier
Fri, Jul 10 - Sat, Jul 11
Frontier Logo
5:13 pm - 3:41 pm
ORD
-
SAT
22h 28m
1 stop
Frontier Logo
9:32 pm - 5:37 am
SAT
-
ORD
8h 05m
1 stop
$276Frontier
Sat, Sep 26 - Tue, Sep 29
Delta Logo
5:10 pm - 10:46 pm
ORD
-
SAT
5h 36m
1 stop
Delta Logo
1:31 pm - 8:55 pm
SAT
-
ORD
7h 24m
1 stop
$277Delta
Tue, Aug 4 - Sat, Aug 8
Delta Logo
6:05 am - 1:38 pm
MDW
-
SAT
7h 33m
1 stop
Delta Logo
6:30 am - 1:10 pm
SAT
-
MDW
6h 40m
1 stop
$277Delta
Thu, Aug 6 - Wed, Aug 12
Southwest Logo
7:30 am - 1:40 pm
MDW
-
SAT
6h 10m
1 stop
Southwest Logo
7:10 am - 1:55 pm
SAT
-
MDW
6h 45m
1 stop
$278Southwest
Sat, Oct 31 - Wed, Nov 4
Southwest Logo
2:30 pm - 8:40 pm
MDW
-
SAT
6h 10m
1 stop
Southwest Logo
9:45 am - 5:10 pm
SAT
-
MDW
7h 25m
2 stops
$283Southwest
Wed, Sep 9 - Mon, Sep 14
Southwest Logo
10:30 am - 4:50 pm
MDW
-
SAT
6h 20m
2 stops
Southwest Logo
11:10 am - 4:55 pm
SAT
-
MDW
5h 45m
2 stops
$288Southwest
Booking Insights

KAYAK's insights & trends for Chicago to San Antonio flights

Get data-powered insights and trends into flights from Chicago to San Antonio to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to San Antonio?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to San Antonio departing in July.

What is the cheapest Chicago to San Antonio flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The absolute cheapest return flight from Chicago to San Antonio costs $297 on the route between Chicago O'Hare Intl Airport (ORD) and San Antonio (SAT). However, over the past month, flights between Chicago Midway Airport (MDW) and San Antonio (SAT) were, on average, 1% cheaper than other Chicago-San Antonio routes. The most popular route is between Chicago O'Hare Intl Airport (ORD) and San Antonio (SAT).

What’s the cheapest day of the week to fly from Chicago to San Antonio?

The average price of all round-trip flights from Chicago to San Antonio clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to San Antonio on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Chicago to San Antonio. For your return ticket, we recommend flying on a Thursday and avoiding Sundays for the best deals.

What is the cheapest month to fly from Chicago to San Antonio?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to San Antonio, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to San Antonio is January, where tickets cost $88 (return) on average. On the other hand, the most expensive months are April and March, where the average cost of round-trip tickets is $207 and $186 respectively.

Can I save money by flying with a layover from Chicago to San Antonio?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $346 on average.

How far in advance should I book a flight from Chicago to San Antonio?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to San Antonio, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to San Antonio, you should book around 4 weeks before departure, which saves you about 52% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to San Antonio

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, ORD and MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Brandon Schultz

Brandon Schultz

Expert on SAT

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Good to know

Low seasonJanuary
Cheapest flight$111
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Chicago O'Hare Airport to San Antonio

When to book flights from Chicago to San Antonio

Are your dates flexible? Find out the best times to travel from Chicago to San Antonio based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to San Antonio

  • How can I get downtown from San Antonio International Airport?

    SAT is connected to the public bus system, and VIA bus route 5 provides regular services between the airport and downtown San Antonio. SuperShuttle also offers door-to-door shuttle services from SAT to downtown San Antonio and the surrounding neighborhoods. You can get tickets from Terminal A's baggage claim area. Taxis are also available at SAT, and you'll find them on the lower levels of Terminals A and B, around baggage claim. If you wish to self-drive, take a rental car from Terminal A's baggage claim area.

  • Does San Antonio International Airport offer accessible services?

    SAT is a fully accessible airport. The airport has provided ramps and elevators for barrier-free access. PRM also get accessible restrooms, wheelchair services, fast-track services, and reserved parking spots. Low-vision passengers at ORD will have free Air services, braille signage, and tactile guide paths. TTY telephones and visual paging services are available for the hard-of-hearing.

  • Which family services are offered at Chicago Midway International Airport?

    MDW has provided private spaces for nursing mothers to feed their babies. These rooms include a sink, a wash area, and comfortable seating. You'll find the nursing rooms on Concourse C beside the yoga room. Also available at MDW are the baby changing facilities, which are provided in all washrooms. The airport has provided a special family lane for parents traveling with kids for quicker transition. Additionally, most airport restaurants offer kid menus and high chairs for babies.

  • Which airlines have lounges at Chicago O'Hare International Airport?

    Air France, American Airlines, Swiss Air, Delta, and United Airlines have lounges at ORD. You can access these lounges by paying at the door, except for the Delta lounge, which is a members-only lounge. The Swiss Air and Air France lounges are in Terminal 5 airside. American Airlines has several locations, Concourses G, L, and H/K. The Delta lounge is in Terminal 2 near Gate E6, while United Club has several locations around Concourses B, C, and F.

  • What is the cheapest flight from Chicago to San Antonio?

    In the last 5 days, the lowest price for a flight from Chicago to San Antonio was $111 for a one-way ticket and $270 for a round-trip.

  • Do I need a passport to fly between Chicago and San Antonio?

    No, a passport isn't needed to fly from Chicago to San Antonio. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Chicago to San Antonio?

    Chicago is served by 2 major airports and there is only 1 main airport in San Antonio. You will leave Chicago from one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be arriving at San Antonio.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to San Antonio?

    American Airlines, JetBlue, and Alaska Airlines offer inflight Wi-Fi service on the Chicago to San Antonio flight route.

  • Which aircraft models fly most regularly from Chicago to San Antonio?

    The Embraer 175 is the aircraft model that flies most regularly on the Chicago to San Antonio flight route.

  • Which airline alliances offer flights from Chicago to San Antonio?

    Star Alliance, and oneworld are the airline alliances operating flights between Chicago and San Antonio, with Star Alliance being the most commonly used for this route.

  • On which days can I fly direct from Chicago to San Antonio?

    There are nonstop flights from Chicago to San Antonio on a daily basis.

  • Which is the best airline for flights from Chicago to San Antonio, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to San Antonio are Southwest and United Airlines. With an average price for the route of $396 and an overall rating of 7.9, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $413 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago to San Antonio?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to San Antonio.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to San Antonio?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San Antonio from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to San Antonio?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to San Antonio with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to San Antonio?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to San Antonio from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to San Antonio

  • Looking for a cheap flight? 25% of our users found flights on this route for $184 or less one-way and $336 or less round-trip.
  • Chicago O'Hare International Airport (ORD) has nine concourses in four terminals. The airport has provided an automated people mover running every 5-10min for easy movement between terminals and around the airport complex.
  • Around 532 kg of carbon is emitted on flights from Chicago to San Antonio. You can fly more sustainably with Southwest Airlines, which emits 43% less carbon per passenger on this route.
  • Are you traveling with your pet? San Antonio International Airport (SAT) is a pet-friendly airport with designated spaces for your furry friend's potty needs. You'll find pet relief areas in Terminal B near the west exit and airside in both terminals.
  • Are you nervous before your flight? Chicago Midway International Airport (MDW) has a yoga room where you can relax with a few stretches. The yoga room is airside on Concourse C, and it comes with a wall-mounted TV that shows the poses to follow.
  • Seaway National Bank runs a full-service branch at ORD if you're looking for banking services at ORD. The bank offers banking, currency exchange, and copying services and has two locations at ORD. The first is in Terminal 2 near the main hall landside, and the other in Terminal 5 on the lower level.

Prefer to fly direct from Chicago to San Antonio?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to San Antonio.
Find which airlines fly direct from Chicago to San Antonio Airport, which days they fly and book direct flights.

Direct departures

Chicago to San Antonio

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Direct returns

San Antonio to Chicago

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Reviews of the top 4 airlines serving from Chicago to San Antonio

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San Antonio. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to San Antonio? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4232 reviews
8.0Comfort
7.5Entertainment
8.6Crew
7.0Food
8.1Boarding
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

The seat was not comfortable. 1D. My back was sore all night and the next day.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

Snacks are always pretzels. Why can't you also offer peanuts ?

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

The gate experience at LAX was abysmal (same for the arrival experience two days prior). Despite the LAX -> SAT schedule of two flights daily, our departure gate was at a smaller hub that we had to be bussed to from Terminal 4. Fortunately, I arrived at LAX extra early and had time to spare, but if I had not known, I might have missed my flight. I looked at the LAX airport map in the AA app and there was no indication of the additional boarding process. Lastly the gate area we were bussed to was crowded with limited food and beverage options. On flight, the fight attendant was hospitable and attentive, the flight was smooth, and AA's free (and working) wifi for AA members were all on the positive side.

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

Got home at 3am after deboarding the plane. No compensation offered by American

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

Everything you need to know for your flight from Chicago to San Antonio

Information on your arrival and departure airports