Next departures for San Diego to Chicago on December 7
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
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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 December 8
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 December 9
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 December 10
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 December 11
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 December 12
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 for San Diego to Chicago on December 13
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
Last refresh of the prices: Today at 12:07 AM 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 5627 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
Please note that schedules, routes, or operator details shown here may be updated or vary 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 $186. The average price for this train route is around $258. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.
How long is the train journey from San Diego to Chicago?
The average train ride duration from San Diego to Chicago is 1d 22h, covering a distance of 1728 miles (2787 km). The quickest train can get you there in 1d 22h and is operated by Amtrak.
Which train operators service the San Diego to Chicago route?
Several major train operators operate on this route with 2 trains available per day.
What is the earliest and latest departure time for the train from San Diego to Chicago?
The earliest train departs from San Diego to Chicago at 2:01pm. And the latest train departs at 4:10pm.
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
12/04
$738
12/05
$328
Today
$285
12/07
$285
12/08
$205
12/09
$328
12/10
$328
12/11
$1,240
The cheapest trip from San Diego, CA, US to Chicago was searched and found on Dec 8, 2025 with a price of $205
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 $205 to $2,947 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 $205 which is on 2025-12-08.
What's the cheapest way to go from San Diego, CA, US to Chicago?
The train is the cheapest travel choice for this destination
The best way to travel between San Diego, CA, US and Chicago is by train. By choosing the train, you'll get to save some money as you travel to your destination, as ticket prices cost $258 on average. If you're on a budget, you'll find cheap tickets from $186. If you're looking for the fastest way to get to Chicago, choose the train, as it will take you from San Diego, CA, US to Chicago in about 1d 22h - that's the fastest way to get there!