- Must visit
Art Institute Of Chicago
One of the world’s leading art museums, famous for Impressionist masterpieces, American art, and major special exhibitions.
Cheapest price
$327
Average price
$887
Fastest journey
1 d 23 h 19 m
Average duration
2 d 11 h 45 m
Trains per day
6
Distance
2784 km
The best way to find a cheap train ticket from San Diego, CA to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from San Diego, CA to Chicago, IL will cost around $887 if you buy it on the day, but the cheapest tickets can be found for only $327.
It's difficult to get from San Diego, CA to Chicago, IL without transferring at least once.
581 Pacific Surfliner · 4 Southwest Chief
581 Pacific Surfliner · 4 Southwest Chief
785 Pacific Surfliner · 422 Texas Eagle
785 Pacific Surfliner · 422 Texas Eagle
785 Pacific Surfliner · 4785 AMTRAK · 6 California Zephyr
581 Pacific Surfliner · 4 Southwest Chief
581 Pacific Surfliner · 4 Southwest Chief
785 Pacific Surfliner · 422 Texas Eagle
785 Pacific Surfliner · 422 Texas Eagle
785 Pacific Surfliner · 4785 AMTRAK · 6 California ZephyrOmio recommends booking the train as it is the most popular option from San Diego, CA to Chicago, IL among Omio's users. If you are prioritising price take the flight with prices starting from $50. For those with little time consider booking a flight which can get you there in 4h 33m. In case you are seeking to minimise your carbon footprint the train is your best bet as it emits only 0.8 - 2.5kg. The ticket price range depends on the travel mode: a flight costs an average of $50, and a train costs an average of $200.
Distance: 1729 miles (2784 km)
Most popular Train | Flight | Bus | Driving |
|---|---|---|---|
$459 Average price | $324 Average price Cheapest | $355 Average price | $436 Average price (fuel + tolls) |
49h 31m Average total duration 49h 1m Onboard + 30m Additional time* | 7h 33m Average total duration Fastest 4h 33m Onboard + 3h 0m Additional time* | 49h 18m Average total duration 48h 48m Onboard + 30m Additional time* | 30h 1m Average total duration (door-to-door) |
0.8 - 2.5kg CO2 emissions Lowest | 8.4 - 16.7kg CO2 emissions | 2.8 - 7.0kg CO2 emissions | - CO2 emissions |
![]() Most popular train company | ![]() Most popular airline | ![]() Most popular bus company | Your own car or car rental |
Direct Options | Direct Options | Direct Options | Direct Options |
Additional time: Average total travel duration to departure point, security checks and transfers.
This is compared to other travel options from San Diego, CA to Chicago, IL:
A flight is $31 (€25) less than a bus for this route with tickets for a bus from San Diego, CA to Chicago, IL costing on average $355 (€286).
A flight is $135 (€109) less than a train for this route with tickets for a train from San Diego, CA to Chicago, IL costing on average $459 (€370).
Other travel options to Chicago, IL take longer:
Bus takes on average 48h 48m.
Train takes on average 49h 1m.
Tickets start at around $459 (€370) compared to roughly $436 (€351) in fuel and tolls — a saving of about $-23.02 (€-18.57). The journey takes 49h 1m versus 30h 1m by car, so you'll arrive a bit later, but you can work, read, or sleep along the way rather than spending the time behind the wheel. You'll also save the hassle of parking at the other end.
Driving is worth it if you're on a tight schedule, travelling as a group, or want to stop somewhere en route.
The table below shows live departures for San Diego, CA to Chicago, IL trains for today, Thursday, June 4. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
581 Pacific Surfliner · 4 Southwest Chief | 2:01 PM Santa Fe Depot, San Diego, CA | 47h28 | 3:29 PM Chicago Union Station, Chicago, IL | 1 transfer | |
581 Pacific Surfliner · 4 Southwest Chief | 2:10 PM Old Town Station, San Diego, CA | 47h19 | 3:29 PM Chicago Union Station, Chicago, IL | 1 transfer | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Compare train, bus, and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Trains from San Diego, CA to Chicago, IL run on average 4 times per day, taking around 49h 1m. Cheap train tickets for this journey start at $200 (€161) but you can travel from only $50 (€40) by flight.
The earliest train runs at 11:03, the last at 16:40. The fastest train covers the 1729 miles (2784 km) distance in 46h 32m.
Distance 1729 miles (2784 km) |
Average train duration 49h 1m |
Cheapest ticket price $200 (€161) |
Trains per day 4 |
Fastest train 46h 32m |
First train 11:03 AM |
Last train 4:40 PM |
Cheapest Month Oct |
Cheapest Day Tue |
High Season Jul - Sep |
Low Season Oct - Dec |
Busiest Day Tue |
Least Busy Day Tue |
Best time to book 56 days |
Discover the best of Chicago — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago trip today.
One of the world’s leading art museums, famous for Impressionist masterpieces, American art, and major special exhibitions.
Major natural history museum known for Sue the T. rex, ancient cultures, and large family-friendly science exhibits.
Large hands-on science museum in Hyde Park with a U-505 submarine, aviation exhibits, and immersive interactive displays.
Chicago’s signature public space, home to Cloud Gate and major events, with strong appeal for first-time visitors and photographers.
Scenic pedestrian route along the Chicago River, popular for architecture views, strolling, and social-media-friendly city scenes.
Famous stretch of North Michigan Avenue known for landmark architecture, flagship stores, and busy big-city energy.
Chicago’s iconic thick-crust pizza baked in a deep pan with layers of cheese, toppings, and chunky tomato sauce.
An all-beef hot dog on a poppy seed bun topped with mustard, onions, relish, tomato, pickle spear, sport peppers, and celery salt.
A classic Chicago sandwich of thin-sliced seasoned beef served on a roll, often dipped in jus and topped with giardiniera or sweet peppers.
A well-known Magnificent Mile restaurant serving Mediterranean-influenced small plates, charcuterie, and strong wine selections.
Chicago’s internationally acclaimed fine-dining restaurant known for inventive tasting menus and a polished, theatrical experience.
A legendary Chicago pizzeria best known for buttery-crust deep-dish pizza in a casual, family-friendly setting.
Moderate by U.S. big-city standards. Hotels can be pricey downtown, but food and transit offer good value.
Tip 18-20% at sit-down restaurants; 20%+ for great service. USD 1-2 per drink at bars, round up or 10-15% for taxis, and USD 1-2 per bag for hotel staff.
Find answers to the most common questions about traveling from San Diego, CA to Chicago, IL by train. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest train, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

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