Maitland
Maitland
Chicago
Chicago
Flight Driving

Maitland to Chicago

Updated: 28 May 2026

The journey from Maitland to Chicago is 1,900 kilometers. Driving via I-65 North takes about 19 hours. Flying from Orlando to O'Hare or Midway is the most practical option.

Total Distance: 1,900 km driving, 1,600 km air.
Fastest Way
Flight from MCO to Chicago is the fastest.
Cheapest Way
Driving is cheaper for groups.
Compare Maitland to Chicago Routes
Flight
Direct
Driving
Direct
Duration 3 hours 19 hours
Avg Price $150-$400 $200-$300 in fuel
Operator United Airlines Personal Vehicle
Route MCO to ORD/MDW. I-75 N to I-65 N.
Tip Direct flights are very frequent. Plan for overnight stops.
Travel Tips
  • Traffic
    Avoid driving in Chicago.
  • Parking
    Parking is very expensive.
  • Weather
    Be prepared for cold winters.
  • Booking
    Book attractions in advance.
  • Navigation
    Use the L train.
Safety Tips
  • Driving
    Be careful on I-65.
  • Sun
    Wear sunscreen.
  • Water
    Stay hydrated.
  • Emergency
    Keep your phone charged.
People Also Ask
  • Is the flight worth it?
    Yes, it saves a lot of time.
  • How long is the drive?
    About 19 hours.
  • Is Chicago safe?
    Yes, in tourist areas.
  • What is the best route?
    I-65 North.
  • Are there tolls?
    Yes, many tolls on I-65.
Quick Info
  • From Maitland, Florida, United States
  • To Chicago, Illinois, United States
  • Modes
Best Time to Travel

Summer for festivals.

Things to Do in Chicago
1
Millennium Park
See the Bean. It is iconic.
2
Navy Pier
Enjoy the lakefront. It is fun.
3
Art Institute
Explore the museum. It is world-class.
4
Willis Tower
See the city views. It is amazing.
Tags
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