Next departures for San Diego to Chicago on February 3
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Price and booking link
Old Town San Diego
Chicago (Union Station), IL
CheapestFastest
Old Town San Diego
Chicago (Union Station), IL
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Old Town San Diego
Chicago (Union Station), IL
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Old Town San Diego
Chicago (Union Station), IL
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Old Town San Diego
Chicago (Union Station), IL
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Next departures for San Diego to Chicago on February 4
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Vehicle type
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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
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Old Town San Diego
Chicago (Union Station), IL
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Old Town San Diego
Chicago (Union Station), IL
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Next departures for San Diego to Chicago on February 5
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Departure time
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Price and booking link
Old Town San Diego
Chicago (Union Station), IL
CheapestFastest
Old Town San Diego
Chicago (Union Station), IL
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Old Town San Diego
Chicago (Union Station), IL
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Old Town San Diego
Chicago (Union Station), IL
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Old Town San Diego
Chicago (Union Station), IL
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Next departures for San Diego to Chicago on February 6
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Departure 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
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Old Town San Diego
Chicago (Union Station), IL
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Old Town San Diego
Chicago (Union Station), IL
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Next departures for San Diego to Chicago on February 7
Operated by
Vehicle type
Departure 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
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Old Town San Diego
Chicago (Union Station), IL
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Old Town San Diego
Chicago (Union Station), IL
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Next departures for San Diego to Chicago on February 8
Operated by
Vehicle type
Departure time
Departure location
Trip duration
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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
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Old Town San Diego
Chicago (Union Station), IL
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Old Town San Diego
Chicago (Union Station), IL
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Next departures for San Diego to Chicago on February 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
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
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Old Town San Diego
Chicago (Union Station), IL
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Last refresh of the prices: Yesterday at 6:54 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 a good way to reach Chicago. The journey takes about 1 day, 22 hours 41 minutes, and with fares starting at just $261, it presents an excellent value for a comfortable ride.
Based on 5754 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 $261
Frequently asked questions about travelling 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 at $261. The average price for this train route is around $306. Busbud recommends booking your tickets in advance to increase your chances of getting the lowest possible price.
How long is the train ride from San Diego to Chicago?
The average train trip from San Diego to Chicago takes 1d 22h and covers 2787 km. The quickest train gets you there in 1d 22h and is operated by Amtrak.
Which train operators serve the San Diego to Chicago route?
Several major train operators serve 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 2:01pm. 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
01-31
$400
02-01
$347
Today
$400
02-03
$400
02-04
$400
02-05
$400
02-06
$341
02-07
$341
The cheapest trip from San Diego, CA, US to Chicago was searched and found on Feb 6, 2026 with a price of $341
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 $341 to $2,095 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 $341 which is on 2026-02-06.