Next departures from San Diego to Chicago on 7 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 8 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 9 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 10 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 11 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
Santa Fe Depot
Chicago (Union Station), IL
No tags
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
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 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
Last refresh of the prices: Today at 00:07 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 £143, it presents an excellent value for a comfortable ride.
Based on 5627 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 £143
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 vary at the time of your journey.
How much does a train ticket cost from San Diego to Chicago?
The cheapest train tickets from San Diego to Chicago start from £143. The average price for this train route is around £199. Busbud recommends booking your tickets in advance for the best chance of getting 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 1728 miles. The fastest 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 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
04/12
£568
05/12
£253
Today
£219
07/12
£219
08/12
£158
09/12
£253
10/12
£253
11/12
£953
The cheapest trip from San Diego, CA, US to Chicago was searched and found on 8 Dec 2025 with a price of £158
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 £158 to £2,265 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 £158, 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 £199 on average. If you're on a budget, you'll find cheap tickets from £143. 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!