It’s hard to imagine two more different places than Chicago, Illinois and the Hawaiian Islands. One is a Midwestern urban hub, famous for its architecture and its punishing winters, and the other is a Pacific paradise known for its laid-back lifestyle and sunny, palm-tree-lined beaches.

If you’re considering a move from Chicago to Hawaii (or vice versa), our guess is that you’re looking for a big change. Maybe you want to trade the leisurely pace of island life for that fast-paced city life—or perhaps you’ve endured one too many Chicago winters and you’re ready to ditch your coat in favor of an aloha shirt.

Whatever your reasons, we’d love to help you make a smooth relocation between Hawaii and Chicago. First, we’ll point out a few unexpected links between the two places to help you find a little bit of familiarity after you move. Then, we’ll give you a head start on your research by discussing a few great neighborhoods in both places. Finally, we’ll show you a few things you can do on your days off, whether your destination is Chicago or Hawaii.

Let’s get started!

4 Surprising Similarities Between Chicago and Hawaii

Although we started out by discussing the differences between the third-largest city in the U.S. and its 50th state, if you’re willing to think creatively, there are a few parallels between the two locations.

1. You’ll Discover a Shared Spirit of Friendliness

Chicago is one of those rare urban areas in the U.S. where strangers make eye contact and smile at each other when passing on the sidewalk. Chalk it up to that famous Midwestern friendliness, but, whatever the reason behind it, Chicago can be a downright pleasant city to live in. You’ll find a similarly pleasant attitude in Hawaii. Of course, as with any location, your mileage may vary, but we’ve found the Aloha Spirit alive and well in the Hawaiian Islands. By and large, Hawaii is a place where people stop to wave pedestrians across the crosswalks, one where smiles and warm greetings at the grocery store are still commonplace.

2. You’ll Need to Dress for the Weather

If you’re moving from Chicago to Hawaii, you might be relieved to ditch all of that winter gear you’ve accumulated over the years—the heavy coat, the warm hat and gloves, and the insulated boots. Trust us, you won’t need them in Hawaii, and downsizing your possessions is a great way to save some money on your move. You’ll still need to dress for the weather in Hawaii, though. Invest in some comfortable slippers (that’s what they call flip-flops in Hawaii) and some resort casual wear, because that’s pretty much as formal as it gets in the Hawaiian Islands.

Now, if you’re doing the reverse and moving from Hawaii to Chicago, you’re going to have to rethink a lot of your wardrobe. Winter in Chicago is no joke, and, if you’ve lived in Hawaii for a significant amount of time, you’ll need to adjust accordingly. Our advice? Invest in a good, warm winter coat once you get to Chicago. Think in layers, and get a set of long underwear. Finally, trade in those slippers for a sturdy pair of waterproof boots. The first time your foot breaks through the ice and you find yourself standing in a slushy black puddle, you’ll be grateful.

3. Your Neighborhood Will Impact Your Experience—Big Time

It’s said that Chicago has more than 200 neighborhoods. The city is formally divided into 77 community areas within nine districts, and each brings its own particular features, culture, and vibe to the table. Chicagoans take their neighborhood allegiances seriously, so choose your home with care since it will shape your experience of the city.

The same is true for Hawaii. If you haven’t visited the state, you might not be aware that your experiences can diverge widely, depending on where you decide to live. First of all, the four major inhabited islands—Oahu, Maui, Kauai, and the Big Island—all have their own distinct feel. Then, within your island of choice, you’ll also discover that where you choose to live makes a big difference. Would you prefer a hot, sunny area near the beach? Or would you rather a wetter, lush rainforest landscape to enjoy? Perhaps it’s your dream to live in a place where you’re surrounded by horses, cattle, and farmland? It’s all available in Hawaii, so make sure to do your research before you settle in.

While we’re on that topic, let’s talk about a few places you might want to add to your list as you research your neighborhood of choice.

What Are the Best Places to Live in Chicago and Hawaii?

If you’re moving from Chicago to Hawaii, the first question you’ll want to ask yourself is whether or not you want to retain that city-like feel, with easy access to innovative restaurants, tons of shopping, and arts and cultural events.

If the answer is yes, then Oahu is probably the island for you. You might even want to consider living close to or within Honolulu, which is the largest urban area in the Hawaiian Islands. If you’d to be close to all the restaurants, bars, shops, and activities that Honolulu offers but slightly removed from the day-to-day hustle-bustle of busy Waikiki, you might check out Manoa. The area is also home to the University of Hawaii at Manoa, and you’ll find plenty of amenities close by, plus easy access to downtown Honolulu when you want it.

If you’re looking for a big change with an eye toward a more local, small-town feel, consider Kauai. Consider the Princeville area on Kauai’s North Shore, which offers everything from studio condos to detached single-family homes to grand estates. You’ll have easy access to several of Kauai’s stunning beaches, as well as a recently repaved bike and pedestrian path so you can enjoy a stroll or a ride while taking in the gorgeous views.

If you’re moving from Hawaii to Chicago, you’ll have a plentiful selection of neighborhoods to choose from. One we particularly like is Lakeview, which you’ll find on Chicago’s North Side. You’ll find some of Chicago’s signature architecture, a ton of restaurants and bars to frequent, and a convenient L train stop for easy access to the rest of the city. As a bonus, you’ll also be walking distance from Wrigley Field, home of the Chicago Cubs, so you can enjoy a pastime that’s just not available in Hawaii: professional baseball. And if you haven’t been to a baseball game in a long time, you’re in for a pleasant surprise: Ballpark food has gotten a serious upgrade. (Don’t miss the short rib disco fries!)

Now that you’ve gotten a head start on where to live in both locations, let’s talk about a few ways to spend your days off.

4 Ways to Enjoy Your Time in Both Chicago and Hawaii

1. Hop a Boat Tour to Get a New Perspective

In Hawaii, this is probably a no-brainer. Taking a day-long snorkel cruise or a sunset sail is a great way to experience another side of the Hawaiian islands—and to take in some views you wouldn’t be able to get otherwise. For example, in Kauai, a sunset sail can deliver unforgettable views of the island’s famous Na Pali coast bathed in the light of the golden hour. In Chicago, consider one of the city’s architecture cruises along the Chicago River. As you motor through the birthplace of the skyscraper, you’ll discover the fascinating history of 50+ of the city’s most iconic buildings. You’ll never look at these feats of engineering the same way again.

2. Go to Town on the Local Food

While the signature dishes in these two locations are markedly different, they still offer plenty of opportunities to chow down and immerse yourself in the area’s unique specialties.

In Hawaii, don’t miss:

  • Loco moco – Two scoops of rice, two hamburger patties, and two fried eggs, all topped with gravy. It’s the kind of breakfast that will keep you going all day.
  • Shave ice – Credited to Japanese immigrants who brought this concept with them to Hawaii, it’s become a quintessential Hawaiian specialty. Locally made syrups elevate this treat to a new level.
  • Poke – Don’t overlook this specialty just because it’s available in most grocery stores. Look for the varieties with fresh (not frozen) ahi, and you’ll see what we mean.

In Chicago, make sure to try:

  • Deep dish pizza – Arrive hungry. A slice is pretty much a meal in and of itself!
  • Chicago dogs – We don’t know which is our favorite part: the poppy seed bun, the mustard, the relish, the chopped onions and tomatoes, the pickle, the peppers, or the celery salt. If you need an on-the-go snack to replace your spam musubi, the Chicago dog is a great candidate.
  • Pierogis – Like Hawaii, Chicago’s food scene is heavily influenced by its immigrant population. A large Polish contingent means you’ll find plenty of fluffy pierogis lovingly wrapped in a light dough—the perfect pierogi.
3. Get Lost in Nature

You’ll find this relatively easy in Hawaii, whether you’re strolling down a long beach, paddling out for a few waves, or hiking Hawaii’s striking landscape. But did you know that you’ll have similar options right outside the Windy City? The Chicago Outerbelt is a continuous 170-mile hike that circles the city. The maps from the Chicago Outerbelt Alliance make it easy to plan an excursion for a day. (Or, if you’re more of a completist, start planning your quest to hike every mile during your time in Chicago.) If you’re worried about missing those outdoor adventures you loved in Hawaii, let the Outerbelt offer you a new mission.

4. Take a Road Trip

If you’re moving to the mainland from Hawaii, you’ve probably already considered how amazing it’ll be to access the United States by car. Want to pop over to Milwaukee for a weekend? You can be there in an hour and a half (no plane ride required)! However, maybe you haven’t considered road tripping in Hawaii. The sheer size of each of the Hawaiian Islands mean that you’ll find plenty of opportunities for road tripping, right within your island. For example, if you take our advice and settle in Manoa on Oahu, plan a road trip to the laid-back North Shore of the island, which offers a completely different feel. On Maui, a road trip to Hana, paired with an overnight stay, can be a mini-vacation in and of itself. So if you’re worried about “island fever” or finding enough to do in the Hawaiian Islands, don’t forget those road trip opportunities right in your backyard.

Making the Big Move from Chicago to Hawaii (or Vice Versa!)

No matter whether you’re moving from Chicago to Hawaii or relocating from Hawaii to Chicago, it’s going to mean a pretty big change for you and any other family members who will be making the transition with you. That said, you’ll find a few similarities between the two places, and some of your favorite hobbies may even translate from location to location. These little touchstones will give you a base of familiarity to ease into the transition, so you can start your life off right in your new home.




Moving between Chicago and Hawaii? We’ve helped tens of thousands of families and individuals make the transition—in both directions! We’d be happy to help you make a safe, easy, and affordable move. It all starts with a free quote from one of our experts.


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