Is it better to fly or take the train?

Flying is much faster, but the train offers a unique cross-country experience.

How long is the flight?

Connecting flights typically take 6 to 8 hours total.

Do I need a car in Chicago?

No, public transportation is excellent and a car is often a burden.

What is the best time to visit?

Late spring and early fall offer the most comfortable weather.

Are there direct trains?

No, you must transfer in Los Angeles to reach Chicago by rail.

Templeton

Chicago

Train Flight

Templeton to Chicago

Updated: 29 May 2026

Traveling from Templeton to Chicago is a major cross-country journey of over 2,100 miles. The most practical way is to fly from San Luis Obispo (SBP) to Chicago O'Hare (ORD) with a connection. Alternatively, you can take a train from Paso Robles to Los Angeles and connect to the Amtrak Southwest Chief for a classic cross-country rail experience.

Total Distance: 3,380 km driving distance; 2,800 km straight-line air distance.

Fastest Way

Flying is the fastest, taking only a few hours.

Cheapest Way

Flying is generally cheaper and faster than the train.

Compare Templeton to Chicago Routes

	Train Connecting	Flight Connecting
Duration	50 hours	6 hours
Avg Price	$300-$700	$300-$600
Operator	Amtrak	United Airlines
Route	Paso Robles to LA Union Station to Chicago Union Station.	SBP to ORD
Tip	The Southwest Chief route is legendary for its scenery.	Book flights with a single connection to minimize travel time.

Travel Tips

Public Transit
The 'L' train system is the best way to navigate the city.
Weather
Chicago is known for its windy weather; dress accordingly.
Dining
Try the famous deep-dish pizza at one of the local iconic pizzerias.
Architecture
Take an architecture river cruise to see the city's famous skyline.
Walking
Chicago is very walkable, especially along the Magnificent Mile.

Safety Tips

Urban Awareness
Stay in well-populated areas, especially when using public transit at night.
Weather Safety
Be prepared for extreme cold if visiting during the winter months.
Navigation
Use reliable transit apps to track train and bus schedules.
Personal Belongings
Keep your belongings secure in crowded tourist areas.