Cheap flights from San Antonio to Chicago from $107
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San Antonio to Chicago departing on 10/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Fly from
Fly to
Route
Depart
Return
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Tue 11/3
9:50 am-5:10 pm
2 stops7h 20m
Chicago Midway
Mon 11/9
9:30 pm-12:25 am
Nonstop2h 55m
San AntonioChicago
SAT San Antonio - ORD Chicago O'Hare Intl
SATORD
San Antonio
Thu 11/5
8:20 pm-12:21 am
1 stop28h 01m
Chicago O'Hare Intl
Mon 11/9
6:30 am-7:25 pm
1 stop12h 55m
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Tue 11/10
3:00 pm-5:35 pm
Nonstop2h 35m
Chicago Midway
Wed 11/11
1:15 pm-9:25 pm
2 stops8h 10m
San AntonioChicago
SAT San Antonio - ORD Chicago O'Hare Intl
SATORD
San Antonio
Sat 11/21
1:31 pm-12:53 am
1 stop11h 22m
Chicago O'Hare Intl
Thu 11/26
5:15 am-3:18 pm
1 stop10h 03m
San AntonioChicago
SAT San Antonio - ORD Chicago O'Hare Intl
SATORD
San Antonio
Tue 11/10
6:30 pm-11:54 pm
1 stop5h 24m
Chicago O'Hare Intl
Wed 11/11
3:59 pm-10:06 pm
1 stop6h 07m
San AntonioChicago
SAT San Antonio - ORD Chicago O'Hare Intl
SATORD
San Antonio
Mon 11/9
11:04 am-5:05 pm
1 stop6h 01m
Chicago O'Hare Intl
Tue 11/10
9:59 am-5:40 pm
1 stop7h 41m
San AntonioChicago
SAT San Antonio - ORD Chicago O'Hare Intl
SATORD
San Antonio
Thu 12/3
6:35 am-9:32 am
Nonstop2h 57m
Chicago O'Hare Intl
Mon 12/7
7:45 pm-10:52 pm
Nonstop3h 07m
San AntonioChicago
SAT San Antonio - ORD Chicago O'Hare Intl
SATORD
San Antonio
Thu 10/22
7:10 am-10:10 am
Nonstop3h 00m
Chicago O'Hare Intl
Mon 10/26
8:59 pm-11:57 pm
Nonstop2h 58m
San AntonioChicago
SAT San Antonio - ORD Chicago O'Hare Intl
SATORD
San Antonio
Tue 10/27
7:10 am-10:10 am
Nonstop3h 00m
Chicago O'Hare Intl
Thu 10/29
8:59 pm-11:57 pm
Nonstop2h 58m
San AntonioChicago
SAT San Antonio - ORD Chicago O'Hare Intl
SATORD
San Antonio
Tue 10/27
6:37 am-9:36 am
Nonstop2h 59m
Chicago O'Hare Intl
Tue 10/27
2:22 pm-9:26 pm
1 stop7h 04m
See travel insights to Chicago from
How to get the cheapest flight ticket from San Antonio to Chicago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between San Antonio and Chicago?
Prices are currently low for flights on this route.
Typical prices usually range from $360 to $549.The lowest price recently found on this route was $278.
What is the cheapest month to fly to Chicago?
The month of February is, on average, the cheapest month to fly to Chicago from San Antonio, with most prices found around $344. If you’re not able to fly to Chicago in February, then April is your next best option. Flight prices from San Antonio to Chicago during April average around $363.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $481. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from San Antonio to Chicago for around $811.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from San Antonio to Chicago during this time can be as low as $408. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $762.
What is the cheapest San Antonio to Chicago flight route?
Fly from San Antonio to Chicago Midway for the best San Antonio - Chicago flight prices
How far in advance should I book a flight from San Antonio to Chicago?
You are more likely to see cheaper flights to Chicago from San Antonio when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $407 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from San Antonio for as low as $297 on momondo.
What cabin class options are available on San Antonio to Chicago flights?
There are 4 cabin classes available to choose from on San Antonio to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on San Antonio to Chicago flights?
No. A direct flight is the cheapest option for a flight between San Antonio to Chicago.
How have San Antonio to Chicago flight prices changed over time?
As of October 2026, prices for San Antonio to Chicago flights are approximately 10% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from San Antonio to Chicago?
United Airlines, Delta, and Southwest are the most popular carriers operating from San Antonio to Chicago
What airlines fly to Chicago?
American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Chicago from San Antonio according to our data. American Airlines is the first choice among our users, with 40% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
Which airport is the most popular layover for flights between San Antonio and Chicago?
Atlanta (ATL) was the most common stop: 67% of momondo users choosing 1-stop flights on this route connected there.
Which layover airport offers the lowest fares from San Antonio to Chicago?
Flights via Atlanta (ATL) offer the lowest average round-trip price of $173.
Which layover airport has the shortest travel time from San Antonio to Chicago?
Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 6h 01m.
Which layover airport has the shortest connection time from San Antonio to Chicago?
Detroit (DTW) has the shortest average layover time for this route: 1h 48m.
How many flights depart from San Antonio to Chicago on average per day?
As of October 2026, 17 flights take off from San Antonio and land in Chicago each day. The most common flight departure time for this route is 2:00PM, with 61% of daily flights taking off in the afternoon.
How many flights depart from San Antonio to Chicago on average per week?
122 flights are operational weekly from San Antonio to Chicago as of October 2026. The most popular departure day for this route is Fri, with 22% of flights per week taking off on this day.
When to book flights from San Antonio to Chicago
Cheap San Antonio to Chicago (SAT to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from San Antonio to Chicago
Frequently asked questions about flying from San Antonio to Chicago
How far is San Antonio to Chicago by plane?
There are 1052.0 mi between San Antonio and Chicago. Flights usually cover this in 2h 30m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from San Antonio Airport to Chicago?
Prices for flights from San Antonio Airport to Chicago refresh daily.
How many operators does momondo search for flights from San Antonio Airport to Chicago?
The number of operators available for flights from San Antonio Airport to Chicago is 4 as of October 2026.
How old do you have to be to fly from San Antonio Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San Antonio Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from San Antonio to Chicago?
Based on momondo bookings for flights between San Antonio and Chicago, the leading plane model is Airbus A319, making up 26.82% of the total bookings. Other popular models include Embraer 175 with 20.97%, Boeing 737-700 with 13.35%, and Boeing 737-800 with 9.45%.
What is the most popular airline from San Antonio to Chicago?
Based on momondo bookings for flights between San Antonio and Chicago, the leading airline is United Airlines, making up 36% of the total bookings. Other popular airlines include American Airlines with 35%, Southwest with 22%, and Frontier with 7%.
Best airlines flying from San Antonio to Chicago
Compare and see reviews for airlines that fly from San Antonio to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $114 | Free Cancellation | Rating 5.5 2,550 reviews | |||
| PriceFrom $237 | Free Cancellation | Rating 7.0 12,127 reviews | |||
| PriceFrom $289 | Free Cancellation | Rating 7.4 10,285 reviews | |||
| PriceFrom $313 | Free Cancellation | Rating 7.9 4,212 reviews |
Southwest Flights From San Antonio to Chicago
Southwest operates around 11 flights from San Antonio to Chicago every week. The average price of these flights found in the last 72 hours has been $493, but momondo users have found Southwest deals from San Antonio to Chicago from as low as $313 round-trip. Southwest has been scored 7.9/10 in 4,212 reviews.
United Airlines Flights From San Antonio to Chicago
The best United Airlines deal for San Antonio to Chicago flight tickets found on momondo in the last 72 hours was $289, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $454 round-trip. United Airlines operates 21 flights out of San Antonio into Chicago in an average week, so prices vary by time and availability. 10,286 United Airlines reviews by users on momondo have scored the airline at 7.4/10.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from San Antonio to Chicago?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from San Antonio to Chicago. momondo saves you time and could save you money on your trip.
Can I find flights from San Antonio to Chicago with flexible booking policies on momondo?
Flights from San Antonio to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from San Antonio to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from San Antonio. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from San Antonio to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from San Antonio are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.