Amtrak's City of New Orleans line connects the South to Chicago, but it is a long journey.

How long is the flight?

It typically takes about 3 hours.

Which airport is best?

ORD is larger, but MDW is often closer to downtown.

Yes, Chicago is generally safe for pedestrians.

What is the best time to visit?

Summer is the most popular time to visit.

Winter Park

Chicago

Flight

Winter Park to Chicago

Updated: 28 May 2026

The journey from Winter Park to Chicago is approximately 1,150 miles. Flying is the most practical and efficient mode of transport, with direct flights from Orlando International Airport (MCO) to O'Hare (ORD) or Midway (MDW) taking about 3 hours. Driving is a long, multi-day journey via I-65 North, which is generally not recommended unless you enjoy road trips. Chicago is a major hub for business, culture, and architecture in the Midwest.

Total Distance: 1,850 km driving distance; 1,600 km straight-line air distance.

Fastest Way

Flying is the fastest method, taking just 3 hours in the air.

Cheapest Way

Flying is the most cost-effective and time-efficient way to reach Chicago.

Compare Winter Park to Chicago Routes

Flight

Direct

Duration

3 hours

Avg Price

$150-$400

Operator

United Airlines

Route

MCO to ORD/MDW.

O'Hare is a major hub; allow extra time for connections.

Travel Tips

Airport Transit
The 'L' train connects O'Hare and Midway airports to downtown Chicago.
Public Transit
The 'L' train is the most efficient way to get around the city.
Walking
Chicago is a very walkable city; wear comfortable shoes.
Dining
Explore the diverse food scene in neighborhoods like Lincoln Park.
Weather
Chicago has four distinct seasons; pack accordingly.

Safety Tips

Personal Safety
Stay aware of your surroundings, especially in crowded tourist areas.
Public Transit Safety
Stay in well-lit areas on 'L' platforms at night.
Scams
Be wary of street performers or vendors asking for money.
Emergency
Dial 911 for any immediate safety concerns.