Chicago → San Antonio

1 a dayfastest 32h36AmtrakNight train

Direct trains · no change

14:10 → 22:46⁺¹
Texas Eagle 21 Night train
Chicago Union Station → San Antonio Amtrak Station · via St. Louis, Little Rock, Dallas, Fort Worth
32h3627 stops
Runs: Daily, not Sun 8 NovAmtrak ↗

Local times at each station. Times from official open data: Amtrak (file of 26 Oct 2026). Checked Mon 26 Oct 2026; they cover 26 Oct to 22 Nov 2026. Timetables change, so check with the operator before you travel. How we build this.

Door to door vs flying

Overnight: leave 14:10, arrive 22:46

The plane is 25h47 quicker on paper, but the night train uses your night instead of a day and saves a hotel.

Train · fastest direct32h47

To Chicago Union Station1 min
Before departure10 min
Texas Eagle 2132h36

Plane · nonstop MDW to SAT7h00

To Midway (MDW)40 min
Check-in & security2h00
Flight MDW to SAT3h05
Landing to exit35 min
From SAT40 min

From city centre to city centre unless you pick otherwise. Getting to stations and airports: typical public-transport times (estimates). Airport: check-in & security 2h before, 35 min to get out after landing. Flight time is typical for the distance.

Flying instead? Chicago → San Antonio

3 airlines fly it nonstop. Book direct on the airline's own site:

American AirlinesORD→SATBook direct ↗
Southwest AirlinesMDW→SATBook direct ↗
United AirlinesORD→SATBook direct ↗

Compare on picktheflight ↗