Next departures from San Diego to Chicago on 20 November
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
Santa Fe Depot
Chicago (Union Station), IL
No tags
Next departures from San Diego to Chicago on 21 November
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
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 22 November
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 23 November
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 24 November
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
Santa Fe Depot
Chicago (Union Station), IL
No tags
Next departures from San Diego to Chicago on 25 November
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
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 26 November
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: Today at 21:00 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 £145, it presents an excellent value for a comfortable ride.
Based on 5593 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 £145
Frequently asked questions about travelling from San Diego, CA, US to Chicago by train
How much does a cheap train ticket from San Diego to Chicago cost?
The average train ticket price from San Diego to Chicago is £198. The best way to find cheap train tickets from San Diego to Chicago is to book your tickets as early as possible. Prices tend to rise as your travel date approaches, so book in advance to secure the best prices!
How long is the train trip from San Diego to Chicago?
A train trip between San Diego and Chicago is around 1d 22h, although the fastest train will take about 1d 22h. This is the time it takes to travel the 1729 miles that separates the two cities.
How many daily train are there between San Diego and Chicago?
The number of trains from San Diego to Chicago can differ depending on the day of the week. On average, there are 2. Some trains are direct while others include transferring trains. Simplify your train trip from San Diego to Chicago by comparing and selecting the train that fits your travel style and budget on Busbud.
Which train companies travel from San Diego to Chicago?
When taking the train from San Diego to Chicago, you can travel comfortably and safely with Amtrak.
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
16/11
£261
17/11
£256
Today
£261
19/11
£371
20/11
£1,239
21/11
£312
22/11
£312
23/11
£409
The cheapest trip from San Diego, CA, US to Chicago was searched and found on 17 Nov 2025 with a price of £256
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 £256 to £1,784 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 £312, which is on 2025-11-21.