Next departures from San Diego to Chicago on 12 December
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Old Town San Diego
Chicago (Union Station), IL
Cheapest
Old Town San Diego
Chicago (Union Station), IL
Fastest
Old Town San Diego
Chicago (Union Station), IL
No tags
Santa Fe Depot
Chicago (Union Station), IL
No tags
Santa Fe Depot
Chicago (Union Station), IL
No tags
Next departures from San Diego to Chicago on 13 December
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Old Town San Diego
Chicago (Union Station), IL
CheapestFastest
Old Town San Diego
Chicago (Union Station), IL
No tags
Old Town San Diego
Chicago (Union Station), IL
No tags
Old Town San Diego
Chicago (Union Station), IL
No tags
Old Town San Diego
Chicago (Union Station), IL
No tags
Next departures from San Diego to Chicago on 14 December
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Old Town San Diego
Chicago (Union Station), IL
Cheapest
Old Town San Diego
Chicago (Union Station), IL
Fastest
Old Town San Diego
Chicago (Union Station), IL
No tags
Old Town San Diego
Chicago (Union Station), IL
No tags
Old Town San Diego
Chicago (Union Station), IL
No tags
Next departures from San Diego to Chicago on 15 December
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Old Town San Diego
Chicago (Union Station), IL
Cheapest
Old Town San Diego
Chicago (Union Station), IL
Fastest
Old Town San Diego
Chicago (Union Station), IL
No tags
Old Town San Diego
Chicago (Union Station), IL
No tags
Santa Fe Depot
Chicago (Union Station), IL
No tags
Next departures from San Diego to Chicago on 16 December
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Old Town San Diego
Chicago (Union Station), IL
Cheapest
Old Town San Diego
Chicago (Union Station), IL
Fastest
Old Town San Diego
Chicago (Union Station), IL
No tags
Old Town San Diego
Chicago (Union Station), IL
No tags
Santa Fe Depot
Chicago (Union Station), IL
No tags
Next departures from San Diego to Chicago on 17 December
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Old Town San Diego
Chicago (Union Station), IL
Cheapest
Old Town San Diego
Chicago (Union Station), IL
Fastest
Old Town San Diego
Chicago (Union Station), IL
No tags
Old Town San Diego
Chicago (Union Station), IL
No tags
Old Town San Diego
Chicago (Union Station), IL
No tags
Next departures from San Diego to Chicago on 18 December
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Old Town San Diego
Chicago (Union Station), IL
CheapestFastest
Old Town San Diego
Chicago (Union Station), IL
No tags
Santa Fe Depot
Chicago (Union Station), IL
No tags
Santa Fe Depot
Chicago (Union Station), IL
No tags
Last refresh of the prices: Last Tuesday at 8:08 PM PST.
Compare 2 ways to travel from San Diego to Chicago
We recommend taking the train
Among the sustainable travel choices, the train stands out as a good way to reach Chicago. The journey takes about 1 day, 22 hours 41 minutes and with fares starting at just R 3 207, it presents an excellent value for a comfortable ride.
Based on 5637 reviews, the company was rated 4.1 stars on Busbud. Travellers were especially satisfied with the seats and the ticket access but often complained with the Wi-Fi. Amtrak ticket prices on this trip start at R 3 207
Frequently asked questions about travelling from San Diego, CA, US to Chicago by train
Please note that timetables, routes, or operator details shown here may be updated or differ at the time of your trip.
How much is the train ticket from San Diego to Chicago?
The cheapest train tickets from San Diego to Chicago start from R 3 207. The average price for this train route is around R 5 123. Busbud recommends booking your tickets in advance for a better chance to secure the lowest possible price.
How long is the train journey from San Diego to Chicago?
The average train journey time from San Diego to Chicago is 1d 22h, covering a distance of 2787 km. The quickest train can get you there in 1d 22h and is operated by Amtrak.
Which train operators serve the San Diego to Chicago route?
Several major train operators run on this route, with 2 trains available per day.
What are the earliest and latest departure times for the train from San Diego to Chicago?
The earliest train from San Diego to Chicago departs at 14:01. And the latest train departs at 16:10.
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
09/12
R 5 673
10/12
R 6 970
Today
R 21 445
12/12
R 5 846
13/12
R 5 777
14/12
R 5 673
15/12
R 5 673
16/12
R 6 538
The cheapest trip from San Diego, CA, US to Chicago was searched and found on 09 Dec 2025 with a price of R 5 673
To save money and be sure you have the best seat, it's a good idea to buy your train tickets from San Diego, CA, US to Chicago as early as possible.
You can expect to pay from R 5 673 to R 24 212 for a train ticket from San Diego, CA, US to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at R 5 673, which is on 2025-12-14.