Next departures for San Diego to Chicago on November 20
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 for San Diego to Chicago on November 21
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 for San Diego to Chicago on November 22
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 for San Diego to Chicago on November 23
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 for San Diego to Chicago on November 24
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 for San Diego to Chicago on November 25
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 for San Diego to Chicago on November 26
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 9:00 PM PST.
Compare 2 ways to go from San Diego to Chicago
We recommend taking the train
Among the sustainable travel choices, the train stands out as the good way to reach Chicago. The journey takes about 1 day, 22 hours 41 minutes and with fares starting at just $186, it presents an excellent value for a comfortable ride.
Based on 5593 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at $186
Frequently asked questions about traveling from San Diego, CA, US to Chicago by train
How much does a train ticket from San Diego to Chicago cost?
The average train ticket price from San Diego to Chicago is $253. The best way to find 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 trains 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 have layovers. 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.
What are the best sights and things to do in Chicago?
Once in Chicago, you can explore the city. The top sights and things to do are Museum of Contemporary Art, Willis Tower (Sears Tower), Chicago Shakespeare Theater on Navy Pier, Navy Pier, Lincoln Park Zoo.
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
11/16
$334
11/17
$328
Today
$334
11/19
$475
11/20
$1,588
11/21
$399
11/22
$399
11/23
$524
The cheapest trip from San Diego, CA, US to Chicago was searched and found on Nov 17, 2025 with a price of $328
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 $328 to $2,286 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 $399 which is on 2025-11-21.