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$179+ Cheap flights from San Antonio (SAT) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — CHI
Jan 21 — Jan 281
Tue 1/21
Tue 1/28
1 adult, Economy
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The best prices from San Antonio to Chicago are usually found in April or February, booked 52 days in advance, depart on a Tuesday or Saturday and return on a Tuesday

Cheap flight deals from San Antonio to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from San Antonio (SAT) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$309
(Mytrip)

One-way from

$179
(Mytrip)

Popular in

December

Cheapest in

April

Average price

$407
Provider with most accurate pricing for San Antonio-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for San Antonio-Chicago (CHI) flights.
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From San Antonio to Chicago (CHI)
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One-way flight from San Antonio to Chicago (CHI)
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High demand for flights, 9% potential price rise
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Best time to find cheap flights, 1% potential price drop
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Average for round-trip flights in January 2025
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Find flight deals from San Antonio to Chicago

Cheapest flights from San Antonio to Chicago
Explore the most affordable flight options available from San Antonio to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 16, 2025.

This Mytrip deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/211:17 amSAT - ORD
3 stops23h 48mSpirit Airlines
Sun 3/97:42 pmORD - SAT
1 stop14h 21mSpirit Airlines
Deal found 1/16$309
This Frontier deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/215:58 pmSAT - MDW
1 stop11h 23mFrontier
Sun 2/236:40 amMDW - SAT
1 stop6h 38mFrontier
Deal found 1/16$310
This American Airlines deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/86:00 amSAT - ORD
Nonstop2h 51mAmerican Airlines
Mon 2/108:45 pmORD - SAT
Nonstop3h 06mAmerican Airlines
Deal found 1/16$317
This Southwest deal was found by Cheapflights users on 1/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/63:35 pmSAT - MDW
Nonstop2h 35mSouthwest
Mon 2/106:45 pmMDW - SAT
Nonstop3h 05mSouthwest
Deal found 1/15$317
This FlightHub deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/2910:30 pmSAT - ORD
1 stop12h 54mMultiple Airlines
Tue 4/16:45 amORD - SAT
1 stop6h 32mMultiple Airlines
Deal found 1/16$319
This Delta deal was found by Cheapflights users on 1/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/105:30 amSAT - MDW
1 stop6h 29mDelta
Wed 2/125:05 pmMDW - SAT
1 stop7h 22mDelta
Deal found 1/15$337
This Southwest deal was found by Cheapflights users on 1/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/107:45 amSAT - ORD
1 stop7h 15mSouthwest
Wed 2/121:45 pmORD - SAT
2 stops7h 55mSouthwest
Deal found 1/15$342
This United Airlines deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/157:00 amSAT - ORD
Nonstop2h 51mUnited Airlines
Sun 2/169:05 amORD - SAT
Nonstop3h 16mUnited Airlines
Deal found 1/16$372
This Frontier deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/2910:25 amSAT - ORD
1 stop5h 35mFrontier
Fri 1/3112:48 amORD - SAT
1 stop10h 08mFrontier
Deal found 1/16$431
This Delta deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/245:20 amSAT - ORD
1 stop7h 19mDelta
Mon 5/265:20 pmORD - SAT
1 stop5h 40mDelta
Deal found 1/16$447
This Alaska Airlines deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/253:03 pmSAT - ORD
2 stops22h 01mAlaska Airlines
Tue 3/45:54 pmORD - SAT
1 stop20h 13mAlaska Airlines
Deal found 1/16$544

Find flights from San Antonio to Chicago within your budget

Customize your flight search to find flights from San Antonio to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 16, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Sun 3/2

11:17 am-11:05 am

3 stops23h 48m

Chicago O'Hare Intl

Sun 3/9

7:42 pm-10:03 am

1 stop14h 21m

$309

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 2/21

5:58 pm-5:21 am

1 stop11h 23m

Chicago Midway

Sun 2/23

6:40 am-1:18 pm

1 stop6h 38m

$310

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Sat 2/8

6:00 am-8:51 am

Nonstop2h 51m

Chicago O'Hare Intl

Mon 2/10

8:45 pm-11:51 pm

Nonstop3h 06m

$317

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Thu 2/6

5:40 am-8:10 am

Nonstop2h 30m

Chicago Midway

Mon 2/10

6:45 pm-9:50 pm

Nonstop3h 05m

$317

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Sat 3/29

10:30 pm-11:24 am

1 stop12h 54m

Chicago O'Hare Intl

Tue 4/1

6:45 am-1:17 pm

1 stop6h 32m

$319

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Mon 2/10

5:30 am-11:59 am

1 stop6h 29m

Chicago Midway

Wed 2/12

5:05 pm-12:27 am

1 stop7h 22m

$337

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Mon 2/10

7:45 am-3:00 pm

1 stop7h 15m

Chicago O'Hare Intl

Wed 2/12

1:45 pm-9:40 pm

2 stops7h 55m

$342

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Sat 2/15

7:00 am-9:51 am

Nonstop2h 51m

Chicago O'Hare Intl

Sun 2/16

9:05 am-12:21 pm

Nonstop3h 16m

$372

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Wed 3/12

11:23 am-5:00 pm

1 stop5h 37m

Chicago O'Hare Intl

Fri 3/14

1:48 am-11:56 am

1 stop10h 08m

$428

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Sat 5/24

5:20 am-12:39 pm

1 stop7h 19m

Chicago O'Hare Intl

Mon 5/26

5:20 pm-11:00 pm

1 stop5h 40m

$447

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

Showing 1-10 of 22 results
1
2
3

Compare providers for flights from San Antonio to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from San Antonio to Chicago in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 starsTrust Score*3 stars
CheapOairPrice Accuracy2 starsTrust Score*2 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on San Antonio-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Antonio-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Antonio-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San Antonio-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San Antonio-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from San Antonio to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from San Antonio with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from San Antonio to Chicago

Get recent, data-driven insights about flights from San Antonio to Chicago including ideal travel times, pricing trends, and more.

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

Use this chart to determine the optimal time to book a round-trip flight from San Antonio to Chicago. Price data was last updated on January 10, 2025.

To ensure you get the cheapest price possible for a flight from San Antonio to Chicago, you should look to book at least 35 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from San Antonio to Chicago?

Currently, August is the cheapest month in which you can book a flight from San Antonio to Chicago (average of $245). Flying from San Antonio to Chicago in March is currently the most expensive (average of $320). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from SAT to CHI?

Find hourly flight availability from San Antonio to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 16, 2025.

When flying from San Antonio to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 30% versus a flight at noon.

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

Use this chart to determine the cheapest time to fly round-trip from San Antonio to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their San Antonio to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from San Antonio to Chicago

Explore weekly flight availability from San Antonio to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 16, 2025.

The most flights from SAT to CHI are scheduled on a Thursday (16 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated January 16, 2025.
Read reviews from past customers who have flown Spirit Airlines, United Airlines and Southwest from San Antonio to Chicago. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Alaska Airlines
8.0
Very good
9,681 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Delta
8.0
Very good
8,511 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

United Airlines
7.4
Good
8,964 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Related info for your journey

Find useful and relevant information for your journey from San Antonio to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from San Antonio to Chicago?

    If you book a flight to Chicago from San Antonio, you will be flying from San Antonio, which is the city’s only airport. San Antonio (SAT) is located 7.6 mi from the center of San Antonio. There are 9 flights from San Antonio to Chicago per day from 6 different airlines.

  • What are the cheapest airlines flying from San Antonio to Chicago round-trip?

    Cheapflights users have booked flights from San Antonio to Chicago round-trip from $309. Other airlines that can offer you cheap pricing are Frontier, from $310, and American Airlines, from $317. These flights start at 17% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from San Antonio to Chicago one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $179. However, be on the lookout for offers from Frontier and United Airlines, as they are both options that can get you from San Antonio to Chicago for a low price.

  • What are the most popular routes from San Antonio to Chicago?

    When deciding which route to take from San Antonio to Chicago consider San Antonio - Chicago O'Hare Intl, San Antonio - Chicago Midway or San Antonio - Chicago Greater Rockford as they are the most popular.

  • What are the most reliable airlines from San Antonio to Chicago?

    The top 3 most reliable airlines when flying from San Antonio to Chicago are Iberia (98%), Japan Airlines (97%) and Royal Jordanian (92%).

  • What are the cheapest flights from San Antonio to Chicago?

    On average you can expect to pay $1,121 for a flight from San Antonio to Chicago. The cheapest flight overall is $183 while the most popular route, (San Antonio - Chicago O'Hare Intl) is currently priced at $167.

  • Can I find deals for flights from San Antonio to Chicago that include hotel bookings?

    Yes. In addition to deals on San Antonio to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Antonio to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Antonio to Chicago.

  • Can I find deals for business class flights from San Antonio to Chicago?

    Yes. Cheapflights offers flight deals from San Antonio to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, August is the cheapest month in which you can book a flight from San Antonio to Chicago (average of $245). Flying from San Antonio to Chicago in March is currently the most expensive (average of $320). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near San Antonio?

Book flights to San Antonio if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for San Antonio to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from San Antonio to Chicago

Discover the top 6 airlines that operate flights from San Antonio to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$111Average$222FlexibilityNo cancel feeOn-time65%
FrontierCheapest$112Average$189FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$190Average$390FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$222Average$428FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$248Average$465FlexibilityNo cancel feeOn-time69%
DeltaCheapest$297Average$415FlexibilityNo cancel feeOn-timeN/A
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