Is it better to fly to O'Hare or Midway?

O'Hare is larger, but Midway is often closer to the downtown area.

How long is the flight?

Direct flights take about 3 hours and 10 minutes.

Yes, but it is a long journey requiring a transfer in a hub like Washington D.C.

What is the best time to visit?

Late spring through early autumn offers the best weather.

Is Chicago safe for tourists?

Major tourist areas are generally safe, but always practice standard urban caution.

Hollywood

Chicago

Train Flight

Hollywood to Chicago

Updated: 30 May 2026

The route from Hollywood, Florida to Chicago, Illinois covers approximately 2,200 kilometers. Flying from Fort Lauderdale-Hollywood International Airport (FLL) to O'Hare (ORD) or Midway (MDW) is the most practical option, taking about 3 hours. For a unique experience, you can take an Amtrak train, though it requires a transfer and takes over 30 hours. Driving takes roughly 22 hours via I-75 and I-65. Chicago is famous for its architecture, deep-dish pizza, and vibrant lakefront.

Total Distance: 2,200 km driving, 1,900 km air distance.

Fastest Way

Direct flight from FLL to ORD, taking approximately 3 hours.

Cheapest Way

Budget airline flight booked during the off-season.

Compare Hollywood to Chicago Routes

	Train Connecting	Flight Direct
Duration	32 hours	3 hours 10 mins
Avg Price	$200 - $500	$130 - $350
Operator	Amtrak	United Airlines
Route	Hollywood to Miami to Chicago	FLL to ORD
Tip	The City of New Orleans line is a classic American rail journey.	O'Hare is well-connected to the city via the Blue Line train.

Travel Tips

Public Transit
Use the 'L' train system to get around Chicago efficiently.
Airport Transit
The Blue Line connects O'Hare directly to downtown for a low fare.
Dining
Try authentic deep-dish pizza at local institutions like Lou Malnati's.
Weather
Chicago is known as the 'Windy City'; dress in layers regardless of the season.
Architecture
Take an architecture river cruise to see the city's famous skyline from the water.

Safety Tips

Neighborhood Awareness
Research neighborhoods before booking accommodation; stick to tourist-friendly areas.
Public Transit Safety
Stay alert on late-night trains and buses.
Pedestrian Safety
Use designated crosswalks in busy downtown areas.
Emergency Info
Keep the local emergency number saved in your contacts.