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If you’ve ever wondered exactly how far those beautiful Hawaiian islands are from the Windy City of Chicago, you’re not alone. Many travelers contemplating a trip to Hawaii want to know just how long it will take them to get there from the Midwest.

If you’re short on time, here’s a quick answer to your question: Hawaii is about 4,400 miles from Chicago as the crow flies.

In this comprehensive guide, we’ll look at the exact distance and travel times between Chicago and the major Hawaiian islands by plane, share driving routes and times, and compare the mileage to other major U.S. cities.

Flight Distance and Travel Times from Chicago to Hawaii

Nonstop Flights

As of December 2023, there are no direct flights available from Chicago O’Hare International Airport (ORD) to any of the major Hawaiian islands. The great circle flight distance from Chicago to Honolulu is approximately 4,436 miles (7,138 km).

This lengthy journey across the Pacific Ocean makes nonstop service unfeasible given current aircraft capabilities and ticket costs.

However, United Airlines does offer seasonal nonstop flights from ORD to Kahului Airport (OGG) on Maui. This seasonal service typically operates from December through March using Boeing 767 aircraft. The flying distance from Chicago to Kahului is approximately 4,452 miles and the total travel time is around 9 hours.

Connecting Flights Through Los Angeles or San Francisco

Most major airlines including United, Delta, American, and Hawaiian offer daily connecting flights from Chicago to the Hawaiian Islands with one stopover on the West Coast. Typical routes include trips with connections at Los Angeles International Airport (LAX) or San Francisco International Airport (SFO).

The total travel time and mileage varies depending on your specific itinerary, but some sample stats are:

  • Chicago ORD to Honolulu HNL via LAX: 4,714 miles – flying time is around 8-9 hours including connection
  • Chicago ORD to Honolulu HNL via SFO: 4,806 miles – flying time is around 8-10 hours including connection
  • Chicago ORD to Kahului, Maui OGG via LAX: 4,730 miles – flying time is around 9-10 hours including connection

As you can see, adding the extra stop only adds 1-2 hours onto your total travel time compared to the hypothetical nonstop flights. The connections are typically about 2 hours through LAX or SFO which provides you adequate time to change planes.

Some benefits of the connecting flights are much more flexibility in terms of flight schedules and times. There are multiple daily flight options to choose from out of Los Angeles and San Francisco. Plus avoiding the long 9+ hour nonstop overwater flight out of windy Chicago in winter may actually feel like a plus during turbulent weather!

Driving Distance and Route from Chicago to Hawaii

Driving from Chicago, Illinois to Hawaii is not possible without taking a ferry or transporting your vehicle. This is because Hawaii is an island state located in the Pacific Ocean, about 4,400 miles from Chicago.

However, here is an overview of the route and distance if it was possible to drive the entire way.

Total Driving Distance

The total driving distance from Chicago to Hawaii would be approximately 4,928 miles. This factors in the driving routes through multiple states to get to the west coast from the Midwest. It does not account for any ferry transportation.

General Route

The route would start by driving southwest from Chicago through Missouri, Kansas, Colorado, Utah, Nevada and into California. Once on the west coast, the drive would continue from San Diego to Port Hueneme where the vehicle would need to loaded onto a ferry ship to Hawaii.

The last leg would be sailing across the Pacific Ocean to the island of Oahu. From there, it’s just a short drive to Honolulu or other Hawaiian destinations.

  • Drive approx. 2,448 miles from Chicago to Port Hueneme, CA
  • Transport vehicle via ferry from California to Oahu, HI
  • Complete the trip by driving 30-50 miles (depending on destination) once in Hawaii

Alternatives to Driving

Instead of attempting the long drive, most people opt to fly from Chicago to Hawaii. There are many nonstop flights available that take about 8 hours. This is significantly faster and more realistic than driving or shipping your car.

Some other options include:

  • Take a road trip to the west coast, then fly to Hawaii from there
  • Book a Hawaii cruise departing from San Diego or other port cities
  • Ship your vehicle via container instead of taking it on a ferry

No matter which option you choose, Hawaii is an amazing and beautiful destination to visit from the Midwest region.

Hawaii’s Distance from Other Major U.S. Cities

New York City

Hawaii is located nearly 5,000 miles from New York City. To put that into perspective, you could fly from New York to London about 3 times in the distance it takes to reach Hawaii! Specifically, Hawaii is 4,980 miles away from the Big Apple if you travel in a straight line from Honolulu to the Empire State Building.

If you wanted to drive it, it would take about 71 hours of nonstop driving to go from NYC to Hawaii, according to Google Maps. Of course, unless you’ve converted your car into an amphibious vehicle, you’ll have to load your car onto a ship for a good portion of that trip!

Washington, D.C.

From America’s capital city, Honolulu is 4,931 miles away as the crow flies. That’s over 80 hours just to drive there, without stopping! To compare, you could drive from DC to Los Angeles 3 times in about that same distance.

Interestingly, Hawaii is actually closer to the equator than Washington, DC. So while Hawaii enjoys fairly consistent warm tropical weather year-round, Washington sees all 4 seasons and even gets the occasional snowstorm during winter.


The distance between Dallas and Hawaii is 3,935 miles if you could travel in a straight line over the Pacific Ocean. Driving-wise, Google Maps estimates it would take about 56 hours of nonstop driving to go from big D to the Big Island.

Because Dallas is much closer to the mainland than coastal cities like DC or NYC, Hawaii feels exceptionally far away in comparison. In fact, you could drive from Dallas to Juneau, Alaska *and back* in around the same mileage it takes just to get to Hawaii!


We’ve covered a lot of ground exploring the distance between Chicago and glorious Hawaii. Whether you’re flying or sailing, it’s quite a haul to make it from the Midwest to those sun-soaked Pacific islands.

But the beautiful beaches, lush rainforests, and aloha spirit make it all worthwhile. The journey itself builds the anticipation for a Hawaiian vacation like no other. Now that you know precisely what you’re getting into mileage-wise, you can start planning your Chicago-to-Hawaii adventure!

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