SAT → ORD

Find and Compare the Cheapest Ways to Fly from San Antonio to Chicago

Compare one-way, round-trip and flight + hotel packages from San Antonio to Chicago, a nonstop flight of about 2h 35m, with fares from around 160.

San Antonio to Chicago flight facts

San Antonio to Chicago is a domestic route covering about 1,042 miles, arriving at O'Hare International Airport (ORD) in United States. Peak travel season in Chicago runs June–August (warm, lakefront festivals), while November–April is usually the quietest and best-value time to visit. The cheapest fares we've tracked on this route include at least one stop.

Key facts for flights from San Antonio to Chicago
Departing fromSan Antonio International Airport (SAT)
Arriving atO'Hare International Airport (ORD)
Distance1,042 miles (1,678 km)
Nonstop flight timeAbout 2h 35m
Nonstop airlines seenNone in recent fares, expect 1 stop
Round-trip fares from$160 (estimate)
Cheapest monthsFebruary, September, January
Peak season in ChicagoJune–August
Cheapest hotel months in ChicagoNovember–April
Best time to book1 to 3 months ahead
Route info updatedOctober 16, 2026

When to visit Chicago

  • Peak season

    June–August

    Warm, lakefront festivals

  • Shoulder season

    May & September–October

    Mild and comfortable

  • Off-peak season

    November–April

    Cold, windy and snowy

Estimated round-trip fares by month, San Antonio to Chicago

Estimated lowest round-trip fare per month
MonthFares from
January$175
February$160
March$225
April$205
May$180
June$245
July$270
August$220
September$170
October$205
November$220
December$265

Flying from San Antonio to Chicago

Airlines Flying this Route

The cheapest fares we've tracked on this route include at least one stop. Ducoffs.com compares full-service and low-cost airlines flying between San Antonio and Chicago in a single search, including nonstop and one-stop options, so you can weigh price against total travel time.

Best Time to Book Flights from San Antonio to Chicago

Fares on this route tend to be lowest in February, September, and January. For the best selection, book about 1 to 3 months before departure and stay flexible by a day or two.

Average Travel Duration

San Antonio and Chicago are about 1,042 miles apart. A nonstop flight takes roughly 2h 35m; connecting itineraries usually add 2 to 5 hours.

San Antonio to Chicago flight questions

How can I find the absolute cheapest flight from San Antonio to Chicago?

The best way to secure budget rates is by comparing multiple airlines simultaneously and checking flexible dates. Ducoffs.com scans available partner networks to bring you real-time pricing options.

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

Based on typical seasonal demand, February, September, and January tend to offer the lowest fares on this route, with estimated round-trip prices starting around $160. Live prices change daily, so run a search for your exact dates.

How long is the flight from San Antonio to Chicago?

San Antonio and Chicago are about 1,042 miles apart. A nonstop flight takes roughly 2h 35m, while connecting itineraries usually add 2 to 5 hours depending on the layover.

Which airlines fly nonstop from San Antonio to Chicago?

The cheapest fares we've tracked recently on this route include at least one stop. Your live search shows any nonstop options available for your dates.

When are hotels cheapest in Chicago?

Hotel rates in Chicago are usually lowest in November–April, when demand is quieter, and highest during peak season (June–August). Booking your flight and hotel together can save up to 30%.

Which airport do I fly into for Chicago?

This route arrives at O'Hare International Airport (ORD). Your search results also show nearby airports when they offer a cheaper or faster option.

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

For this route, booking about 1 to 3 months before departure usually gives the best balance of price and seat selection. Mid-week departures are often cheaper than weekend flights.

Is it cheaper to bundle flights and hotels together?

Yes. Bundling your travel components can save you up to 30% compared to booking flights and hotels separately, as airlines and properties offer exclusive package discounts.