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| 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 |
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Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from San Diego, CA, US to Chicago was searched and found on 9 Oct 2025 with a price of US$243To 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 US$243 to US$3,254 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 US$243, which is on 2025-10-09.
About Train Travel
Train Travel Tips
Taking the fastest trains allows you to travel at speeds greater than 300 km/h. Taking a trip from San Diego to Chicago is not only much quicker but more comfortable too! You can usually travel directly to the city centre and save time while you're at it.
Whether you take a regional or high-speed train to Chicago, you’ll help reduce the environmental impact and carbon footprint of your trip. As you watch the landscapes unfold before your eyes, you can tell yourself that with this choice, you are making sure they remain protected.
The train emits up to 30x less CO2 for a trip between San Diego and Chicago compared to the same trip made by plane or car. A truly ecological mode of transport that will allow you to easily reduce your carbon footprint.
Create your own real-life musical score by curating a personalised train travel playlist – the perfect accompaniment for your journey from San Diego to Chicago.
Did you know?
Railway companies played a major role as early as 1883 in the use of time zones as we know them today.
New York holds the record for the most platforms and track numbers in a single station. Grand Central Station in Manhattan is one of the largest rail terminals in the world with more than 44 platforms and 67 tracks to accommodate passengers.
Some trains in Sweden can recover more than a fifth of the energy they use by braking. This is especially true with ore trains as they descend from Narvik to Kiruna.
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