Is Chicago safe for tourists?

Yes, tourist areas like the Loop and Magnificent Mile are generally safe.

Do I need a car in Chicago?

No, public transit is excellent and parking is very expensive.

How cold does it get?

Winters can drop well below freezing with significant wind chill.

What is the best way to get from O'Hare to downtown?

The CTA Blue Line train is the fastest and cheapest option.

Is there a direct train from Florida?

No, Amtrak requires a transfer and takes over 30 hours.

Longwood

Chicago

Flight Driving

Longwood to Chicago

Updated: 01 Jun 2026

Traveling from Longwood to Chicago covers roughly 1,900 kilometers. Flying is the most practical method, with direct flights from Orlando International Airport (MCO) to O'Hare (ORD) or Midway (MDW) taking about 2.5 hours. Driving is a significant undertaking, requiring nearly 19 hours of road time via I-75 and I-65. Chicago is a major hub for culture, architecture, and deep-dish pizza. Plan your trip according to the seasonal weather shifts in the Midwest.

Total Distance: 1,900 km driving distance; 1,650 km straight-line air distance.

Fastest Way

Direct flight from MCO to ORD.

Cheapest Way

Flying is often cheaper than the cost of fuel and overnight hotels for driving.

Compare Longwood to Chicago Routes

	Flight Direct	Driving Direct
Duration	2 hours 40 mins	19 hours
Avg Price	$180-$400	$250-$350 in fuel
Operator	United Airlines	Personal Vehicle
Route	MCO to ORD.	I-75 N to I-65 N.
Tip	O'Hare is better connected to the city via the Blue Line train.	Expect heavy traffic through Indianapolis and Louisville.

Travel Tips

Public Transit
Use the CTA 'L' train system; it is the most efficient way to navigate the city.
Weather
Always pack layers, as Chicago weather changes rapidly near Lake Michigan.
Dining
Try authentic deep-dish pizza at Lou Malnati's or Giordano's.
Airport Access
The Blue Line runs 24/7 from O'Hare to downtown.
Walking
Chicago is a very walkable city, so bring comfortable shoes.

Safety Tips

Urban Awareness
Stay in well-populated areas and avoid walking alone in unfamiliar neighborhoods at night.
Winter Safety
If driving in winter, ensure your vehicle has snow tires and an emergency kit.
Personal Belongings
Keep your bag in front of you on crowded public transit.
Emergency
Dial 911 for any immediate assistance needed in the city.