SAT - CHI

$98 Find Cheap Flights from San Antonio to Chicago - Compare and Save

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Everything you should know

Cheapest round-trip
$306
Typical prices: $332-$525
Southwest
Mon 12/10Mon 12/17
SAT - MDW • 2 stops
Cheapest non-stop
$311
Typical prices: $347-$535
American Airlines
Tue 12/4Wed 12/5
SAT - ORD • Non-stop
Nonstop flights
You can fly direct with American Airlines, United Airlines and Southwest. Average duration is 2h 55m
Direct flights
+1
Direct flights
+1
Top routes
Cheapest • 1% average savings
Most popular
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 49% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 16% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $205 (round-trip)
Shortest trip • 5h 20m (one-way)
Insights
Insights
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Flight Deals
Booking Insights
Expert advice
Flight Deals

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

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from San Antonio to Chicago

Thu, Dec 10 - Thu, Dec 17
Southwest Logo
9:50 am - 5:15 pmSAT  San Antonio-MDW Chicago Midway
7h 25m2 stops Dallas Love Field Milwaukee-Mitchell
Southwest Logo
9:30 pm - 12:25 amMDW  Chicago Midway-SAT San Antonio
2h 55mnonstop
$306Southwest
Mon, Jan 11 - Sat, Jan 16
Frontier Logo
11:05 am - 11:50 amSAT  San Antonio-ORD Chicago O'Hare Intl
24h 45m2 stops Orlando Atlanta Hartsfield-Jackson
Frontier Logo
6:21 am - 7:27 pmORD  Chicago O'Hare Intl-SAT San Antonio
13h 06m1 stop Denver Intl
$310Frontier
Mon, Nov 23 - Fri, Nov 27
United Airlines Logo
6:34 am - 9:33 amSAT  San Antonio-ORD Chicago O'Hare Intl
2h 59mnonstop
United Airlines Logo
9:00 am - 12:08 pmORD  Chicago O'Hare Intl-SAT San Antonio
3h 08mnonstop
$311United Airlines
Thu, Nov 19 - Thu, Nov 26
United Airlines Logo
5:30 am - 10:11 amSAT  San Antonio-ORD Chicago O'Hare Intl
4h 41m1 stop Houston George Bush Intcntl
United Airlines Logo
6:55 am - 1:16 pmORD  Chicago O'Hare Intl-SAT San Antonio
6h 21m1 stop Houston George Bush Intcntl
$311United Airlines
Sat, Nov 21 - Wed, Nov 25
American Airlines Logo
4:34 pm - 12:20 amSAT  San Antonio-ORD Chicago O'Hare Intl
7h 46m1 stop Dallas/Fort Worth
American Airlines Logo
7:04 pm - 12:06 amORD  Chicago O'Hare Intl-SAT San Antonio
5h 02m1 stop Dallas/Fort Worth
$311American Airlines
Tue, Dec 1 - Tue, Dec 1
American Airlines Logo
7:00 am - 2:15 pmSAT  San Antonio-ORD Chicago O'Hare Intl
7h 15m1 stop Dallas/Fort Worth
American Airlines Logo
6:56 pm - 12:06 amORD  Chicago O'Hare Intl-SAT San Antonio
5h 10m1 stop Dallas/Fort Worth
$311American Airlines
Thu, Nov 19 - Mon, Nov 23
Delta Logo
6:40 am - 11:48 amSAT  San Antonio-ORD Chicago O'Hare Intl
5h 08m1 stop Minneapolis St Paul
Delta Logo
3:59 pm - 12:33 amORD  Chicago O'Hare Intl-SAT San Antonio
8h 34m1 stop Atlanta Hartsfield-Jackson
$311Delta
Sat, Nov 21 - Wed, Nov 25
Delta Logo
2:33 pm - 9:33 pmSAT  San Antonio-ORD Chicago O'Hare Intl
7h 00m1 stop Minneapolis St Paul
Delta Logo
2:44 pm - 10:54 pmORD  Chicago O'Hare Intl-SAT San Antonio
8h 10m1 stop Detroit Metropolitan Wayne County
$311Delta
Mon, Dec 7 - Thu, Dec 10
Southwest Logo
3:20 pm - 9:35 pmSAT  San Antonio-MDW Chicago Midway
6h 15m1 stop Lambert-St Louis
Southwest Logo
9:55 am - 4:20 pmMDW  Chicago Midway-SAT San Antonio
6h 25m1 stop Atlanta Hartsfield-Jackson
$311Southwest
Sat, Dec 19 - Tue, Dec 29
Frontier Logo
7:15 pm - 5:49 amSAT  San Antonio-ORD Chicago O'Hare Intl
10h 34m1 stop Las Vegas Harry Reid Intl
Frontier Logo
7:35 am - 10:53 amORD  Chicago O'Hare Intl-SAT San Antonio
27h 18m1 stop Las Vegas Harry Reid Intl
$311Frontier
Booking Insights

Price, demand and travel trends for San Antonio to Chicago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

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

Round-trip flights from San Antonio to Chicago typically range from $332 to $525. The lowest price found in the past 5 days was $306, on Southwest.

What is the cheapest San Antonio to Chicago flight route?

There's little price difference between San Antonio to Chicago routes. They average around $398 round-trip, based on KAYAK data over the past 12 months.

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

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from San Antonio to Chicago. It’s 6% cheaper than the average day, while Friday is the most expensive, with prices 11% higher.

What’s the cheapest month to fly from San Antonio to Chicago?

•February is the cheapest month to fly from San Antonio to Chicago at $332 round-trip.
•November ($439) and June ($424) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 32% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from San Antonio to Chicago the cheapest?

Flights from San Antonio to Chicago are cheapest 5 weeks before departure. Booking in this window typically costs about 49% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from San Antonio to Chicago

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Qatar Airways, 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.

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.

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.

Key details for San Antonio to Chicago flights

Low season

February

Cheapest flight

$98
Beat the crowds with an average 46% drop in travelers.
The most popular month to fly with an average 59% increase in travelers.
One-way flight from San Antonio to Chicago O'Hare Intl Airport

When to book flights from San Antonio to Chicago

Are your dates flexible? Find out the best times to travel from San Antonio to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your San Antonio to Chicago flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from San Antonio to Chicago?

    These are the earliest and latest flight times available from San Antonio to Chicago:

    • Earliest: departs at 5:00 am and lands at 7:55 am
    • Latest: departs at 7:09 pm and lands at 10:04 pm.

    The flight takes about 2h 55m.

  • What cabin classes can I book on flights from San Antonio to Chicago?

    Three cabin classes are available on flights from San Antonio to Chicago:

    • Economy Class
    • Business Class
    • First Class

  • How long is a flight from San Antonio to Chicago?

    A nonstop flight from San Antonio to Chicago takes 2h 55m, covering 1,045 miles.

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

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a San Antonio to Chicago flight?

    Round-trip flights from San Antonio to Chicago range from $332 to $525, with an average of $397 over the past 12 months. Anything below $332 counts as a good deal.

  • How expensive are last-minute San Antonio to Chicago flights?

    Last-minute fares on this route (booked within two weeks of departure) run 77% above the $397 route average. Book 5 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from San Antonio to Chicago?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $205 round-trip via Fort Lauderdale (FLL), compared to $407 for nonstop.

  • What is the standard checked-bag allowance on flights from San Antonio to Chicago?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • How are flight departures from San Antonio to Chicago spread across the day?

    Morning is the busiest departure period on San Antonio to Chicago flights, with 38% of flights leaving in that window. Afternoon departures account for 37%, evening flights for 25%, and night flights for 0%.

  • Have flight prices from San Antonio to Chicago changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $306 to $2,132. That means the highest observed fare was about 7x higher than the lowest one.

  • Which airlines offer Wi-Fi on San Antonio to Chicago flights?

    Two airlines offer in-flight Wi-Fi on San Antonio to Chicago flights:

    • American Airlines
    • JetBlue

    Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

  • How are flight prices from San Antonio to Chicago looking right now?

    One-way fares from San Antonio to Chicago are currently lower than usual. Average one-way flight prices are about $141, which is 45% below the typical average for this route.

  • What car rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates averaging $64:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Ace
    • Dollar

    Near Chicago Midway Airport (MDW) — daily rates averaging $84:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

    Near Chicago Greater Rockford Airport (RFD) — daily rates averaging $81:

    • Alamo
    • Enterprise Rent-A-Car
    • Budget
    • Avis
    • National

  • Which airports can I use when flying from San Antonio to Chicago?

    Flights from San Antonio to Chicago usually depart from San Antonio (SAT) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • Which airports do connecting flights from San Antonio to Chicago pass through?

    One-stop flights from San Antonio to Chicago most commonly connect through:

    • Denver Intl (DEN) - 29% of one-stop connections
    • Fort Lauderdale (FLL) - 20% of one-stop connections
    • Las Vegas Harry Reid Intl (LAS) - 17% of one-stop connections
    • Chicago O'Hare Intl (ORD) - 9% of one-stop connections

  • Can I save money by using flexible dates for flights from San Antonio to Chicago?

    Yes. Flexible dates can save you up to 15% on flights from San Antonio to Chicago. Wednesday is the cheapest departure day at $376 round-trip on average, while Friday is the most expensive at $441, a difference of $65.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from San Antonio to Chicago?

    3 airlines operate flights between San Antonio and Chicago. The airlines offering nonstop flights on this route include:

    • American Airlines
    • United Airlines
    • Southwest

  • How much time can I save by choosing a different layover airport from San Antonio to Chicago?

    Flying via Dallas Love Field (DAL) gives the shortest average 1-stop total travel time at 5h 20m, compared with 5h 51m via Dallas/Fort Worth (DFW) and 5h 51m via Detroit Metropolitan Wayne County (DTW).

  • What popular places can I visit in Chicago?

    Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago on KAYAK.

  • Which airlines offer extra legroom and free seat selection on San Antonio to Chicago flights?

    Among airlines operating San Antonio to Chicago flights:

    • American Airlines: offers extra legroom; offers free seat selection
    • United Airlines: offers extra legroom; offers free seat selection
    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on San Antonio to Chicago flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • American Airlines: a cabin bag and a checked bag in Economy Class
    • United Airlines: a cabin bag and a checked bag in Economy Class
    • Southwest: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

  • Where can I sleep at Chicago O'Hare International Airport?

    If you want to stay at the airport, book your stay at the Hilton Chicago O'Hare Airport Hotel. The establishment is across from terminal 2 and is connected to all domestic terminals via a walkway. The hotel also offers a free shuttle service to and from terminal 5. This hotel offers day rooms between 10 am and 6 pm and overnight stays.

  • Is Chicago O'Hare International Airport an accessible airport?

    ORD is an ADA-compliant airport. ORD has provided passengers with limited mobility with ramps and elevators as stair-free options to all levels of the terminals. They also have accessible restrooms, reserved parking spots, accessible public transportation, and wheelchair assistance at ORD (organized through the airline). Low-vision passengers traveling through ORD can access Aira services and the airport has tactile guide paths and braille signage. Hard-of-hearing passengers will find TDD telephones, visual paging services, and closed captioning on video announcements at ORD.

  • What are the transport options leaving from Chicago Midway Airport (MDW)?

    MDW is served by public transportation and the CTA Orange Line runs from MDW to downtown Chicago with a total trip time of around 20 minutes. The airport is also well-served by the public bus system, nine CTA bus routes serve MDW offering transportation to various Chicago hubs. Also, there are seven PACE bus routes from MDW to the surrounding areas. Go Airport Express offers door-to-door services from MDW, they depart every 15 minutes from the arrivals hall on the lower level outside door 3. Taxis are available 24/7 in front of all terminals and are metered.

  • Does Chicago Midway Airport offer family services?

    MDW has provided a baby care room where nursing parents can feed and care for their babies. The baby care facility includes a sink, seating, and power outlets. You'll find the nursing room on concourse C beside the yoga room. MDW also has family bathrooms and almost all bathrooms at the airport offer baby changing facilities. The airport also has a family lane for passengers with kids. Most restaurants at MDW include kids' menus and high chairs for infants.

Your guide to booking San Antonio to Chicago flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Wednesday departure and avoid flying on Friday. On this route, Wednesday flights average $376, about $65 less than Friday fares (15% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 5 weeks before you fly. On this route, that window historically saves about 49% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your San Antonio to Chicago trip for February. Fares historically average $332 round-trip in that month - typically $107 less than the most expensive month, which is November (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Fort Lauderdale Airport (FLL) can be cheaper than flying direct. The cheapest layover option averages $205 round-trip on this route - about $202 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel Chicago Midway Airport
  • Chicago O'Hare International Airport (ORD) has four terminals and nine concourses. The airport has an automated shuttle that provides inter-terminal transportation every 5-10 minutes.
  • San Antonio International Airport (SAT) welcomes pets to their facility. However, the airport requires all pets to remain within their carriers while at SAT. SAT has four pet relief areas, two inside security in both terminals, one in terminal B next to the west exit, and another around the baggage claim area.
  • Only United Airlines has a lounge at SAT. You can access this lounge by paying at the door and showing your United Airlines flight ticket. The lounge is in terminal B between gates B3 and B5.
  • Around 615 kg of carbon is emitted on flights from San Antonio to Chicago. You can lower your carbon footprint by flying with American Airlines. AA offers an eco-friendly flight emitting 62% less carbon per passenger on this route.
  • If you're stranded and need guidance at SAT, approach the information desk in terminal A. The airport also has friendly ambassadors dressed in blue vests with cowboy hats who will help you out.

Prefer to fly direct from San Antonio to Chicago?

 
Find which airlines fly direct from San Antonio Airport to Chicago, which days they fly and book direct flights.

Direct departures

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

Direct returns

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

More options for your flight from San Antonio to Chicago

Complete your trip to Chicago with a hotel stay or car rental