Is there a train to Chicago?

Yes, Amtrak's City of New Orleans and other lines go to Chicago.

Yes, there are many tolls on the roads leading into Chicago.

What is the best time to visit?

Summer and early fall are the best times.

Yes, there are many flights from TPA to Chicago airports.

Odessa

Chicago

Flight Driving

Odessa to Chicago

Updated: 28 May 2026

The drive from Odessa to Chicago is approximately 1,200 miles and takes about 19 hours via I-65 North. This is a long-distance journey that crosses through several states, including Georgia, Tennessee, Kentucky, and Indiana. You will pass through major cities like Nashville and Indianapolis. Flying is highly recommended for this distance.

Total Distance: 1930 km driving distance and 1700 km straight-line air distance.

Fastest Way

Flying from TPA to ORD is the fastest method, taking 2.75 hours in the air.

Cheapest Way

Flying is often cheaper than the total cost of fuel, tolls, and hotels for driving.

Compare Odessa to Chicago Routes

	Flight Direct	Driving Direct
Duration	2 hours 45 mins	18 hours 30 mins
Avg Price	$150-$400	$160-$260 in fuel
Operator	United Airlines	Personal Vehicle
Route	TPA to ORD/MDW	Take SR 54 to I-75 N, merge onto I-65 N in Nashville.
Tip	Flying is significantly faster and often cheaper than driving.	This is a multi-day drive; plan for at least one overnight stop.

Travel Tips

Traffic
Avoid driving in downtown Chicago; use the 'L' train system.
Local Transit
The CTA 'L' train system is the most efficient way to get around.
Dining
Try the famous Chicago-style deep-dish pizza.
Parking
Parking in Chicago is expensive; use public transit.
Events
Check for events at the United Center.

Safety Tips

Road Safety
Be prepared for heavy traffic and aggressive drivers on I-65.
Weather
Chicago can experience extreme cold and snow in winter; check road conditions.
Emergency
Keep a roadside emergency kit in your vehicle.
Personal Safety
Stay aware of your surroundings in crowded tourist areas.