A Travel Price Comparison for United States of America Chicago vs. Oahu for Attractions, Food, Nightlife, and Music

Should you visit Chicago or Oahu?

Which is cheaper to visit? Which is more expensive for vacation?

Which city is more affordable and which is best for your travel style? If you're trying to figure out where to go next, comparing the travel costs between Chicago and Oahu can help you decide which place is right for you.

Chicago

Chicago is a vibrant, multicultural, and edgey city. With plenty of activities and things to do, it's a huge city that draws plenty of visitors. It's a beautiful place to visit, too. Visitors also love the live music, food, and beaches.

Oahu

Oahu is a historic, energetic, and vibrant island. Because this is such a big city, visitors will find many sights and attractions around town. The famous beauty of this place is one of the main draws. Other popular activities here include shopping, museums, and nightlife.

Chicago and Oahu: Pros and Cons

Is there more to do in Chicago or Oahu?

Both Oahu and Chicago have plenty of things to do for travelers. Both provide a wide variety of sights and activities for tourists. Chicago is more popular for its museums, theatre productions, food, nightlife, music, shopping, christmas markets, and big city activities, while Oahu is known for its resorts, scuba diving & snorkeling, beaches, hiking, and impressive beauty. Oahu is more touristy than Chicago and is popular for its unique blend of cultures, stunning beaches, vibrant energy, and world class water sports (including surfing). Chicago is popular for its thriving sports scene, its iconic local cuisine, and its world class shopping at the Magnificent Mile.

How is Chicago different from Oahu?

Which is Better for a Holiday?

Let's take a look at the differences and similarities between Oahu and Chicago. Then, you can decide for yourself which place is better for your next trip.

Are the Museums and Historical Sights Better in Chicago or Oahu?

Chicago is a world-class destination for its museums and history. Also, Oahu is not quite as popular, but is fairly good for its museums and landmarks.

The museums and tourist attractions in Chicago are world-renowned. There are countless landmarks, museums, and iconic sights in the area. Some of the most famous are the Art Institute of Chicago, Adler Planetarium, and the Museum of Science and Industry. Notable landmarks include the famous Willis Tower - formerly the Sears Tower, Buckingham Fountain, and the iconic Cloud Gate (the bean).

You'll find a good number of museums and monuments packed into Oahu. The USS Arizona Memorial & Pearl Harbor is a moving and special place to visit, but tickets should be purchased in advance. Other landmarks around the island include the Tour Iolani Palace and the Battleship Missouri Memorial.

Is Chicago or Oahu Better for Theater?

Chicago is a world-class destination for its theatre productions. However, Oahu is not a theatre destination.

Famous for its theaters and plays, you'll find world-renowned shows in Chicago. Theater is big here with many of the major Broadway productions visiting the city. There is also an endless list of smaller, local theaters to choose from.

Oahu is not a theatre destination.

Is the Food Better in Chicago or Oahu? Which Destination has the Best Restaurants?

Chicago is a world-class destination for its restaurants. Also, Oahu is not quite as popular, but is fairly good for its restaurant scene.

Known for it's food and restaurant scene, Chicago is always at the top of any foodie's travel list. With everything from award-winning luxury restaurants to local dives, this city has something for everyone. It also has very distinct local flavors and dishes that create an identity and bring great pride to the locals. While you're in town you have to try the famous deep dish pizza, Chicago style hot dogs, and Italian beef.

There are many up and coming restaurants in the Oahu area. Honolulu has a diversity of cuisines and a cosmopolitan vibe, giving it some of the best food in the Hawaiian Islands. The local restaurants are influenced by a number of countries and often incorporate Japanese, Chinese, Filipino, Korean, and Portuguese flavors. Dishes are often saucy, sweet, and starchy, but you'll also find fresh tropical fruits such as mango and coconut.

Is Chicago or Oahu Better for Nightlife?

Chicago is a world-class destination for nightlife and partying. Also, Oahu is not quite as popular, but is fairly good for its evening party scene.

People head to Chicago just to party. It has a wide range of activities at night, with everything from theater and comedy clubs to dance venues, sporting events, and local bars. It's easy to fill many evenings with whatever activity appeals to you. Popular bars and clubs include the Smart Bar, Beauty Bar, and Le Nocturne.

Oahu is a popular destination for visitors looking to party into the night. Honolulu, and Oahu, have some of the best nightlife in the Hawaiian islands. There are tiki bars and posh nightclubs that keep buzzing late into the night. Head to Waikiki for some of the island's best nightlife. In Honolulu you'll find some local bars and clubs, but many resorts also offer a great nightlife scene and a fun atmosphere that caters specifically to tourists.

Is Chicago or Oahu Better for Music?

Chicago is a world-class destination for its live music scene. However, Oahu is lacking in good options for its music scene.

With so many music venues, you're guaranteed a show any night of the week in Chicago. The city is the birthplace of such interesting styles as modern gospel and the Chicago style blues.

For those who seek it out, Oahu has several music venues. There are a few good venues that offer live music on Oahu.

Is Chicago or Oahu Better for Resorts?

Oahu is a great destination for its resorts. However, Chicago is not a resort destination.

Vacationers can choose from a number of terrific resorts in Oahu. The island has a diversity of resorts, from luxury 5 star accommodation to family-friendly resorts that are fun for all ages. Ko Olina is where you'll find Aulani, the Disney Resort. Waikiki is one of the most famous tourist areas on the island and you'll find high rise hotels and condos along the beach.

Chicago is not a resort destination.

Is Chicago or Oahu Better for Scuba Diving and Snorkeling?

Oahu is a great destination for snorkeling and scuba diving. However, Chicago is not a scuba or snorkeling destination.

There is a nice variety of marine life that makes scuba diving and snorkeling great in Oahu. Snorkeling and diving on the island is among the best in the world. There are 3 marine life conservation parks and miles of coastline to explore.

Chicago is not a scuba or snorkeling destination.

Is Chicago or Oahu Better for Beaches?

Oahu is renowned for the beach. Also, Chicago is still popular, but not quite as popular for its beaches.

With world-famous beaches, Oahu is a very popular vacation destination. From the energetic Waikiki Beach to the family-friendly Ko Olina, Oahu has some of the most famous beaches in the world. The beaches are lined with sand and some areas offer better swimming conditions than others. You'll also find beaches with snorkeling or sea turtles, and some with world class surfing waves.

Chicago has a beach worth visiting. While you don't immediately think of beaches when you think of Chicago, there are some nice beaches by the lake. If the weather is nice, it's a great area to spend some time.

Is Chicago or Oahu Better for Hiking?

Oahu is renowned for its hiking experiences. However, Chicago is not a hiking destination.

Many people visit Oahu specifically for its hiking. World famous hikes on the island include Diamond Head and Koko Crater Railroad Trailhead. There are hikes ranging from easy to challenging and views that will take your breath away.

Chicago is not a hiking destination.

Is the Shopping Better in Chicago or Oahu?

Chicago is a world-class destination for its shopping opportunities. Also, Oahu is not quite as popular, but is fairly good for its shopping areas.

Known for shopping, Chicago draws large crowds to its stores. There are countless neighborhoods that are filled with boutiques, local vendors, and art galleries. The city has some of the country's best shopping opportunities, and the most notable area is the famous Michigan Avenue and the Magnificent Mile.

Browsing through shops is a popular activity in Oahu. There are shopping centers and malls in Honolulu that have major department stores as well as island favorites. For a local experience head to the Aloha Stadium Swap Meet or wander along the Waikiki Beach Walk with its many boutique shops. Also worth a visit is the Honolulu Chinatown market.

Is Chicago or Oahu Better for Christmas?

Chicago is a very popular place for its Christmas holiday experiences. However, Oahu does not offer Christmas activities.

Since it has plenty to do, Chicago is a very popular place to visit during Christmas. There's a number of seasonal celebrations, ice skating, and excellent shopping.

Oahu does not offer Christmas activities.

Is Chicago or Oahu Better for Christmas Markets?

Chicago is a nice place to visit for visiting Christmas markets. However, Oahu does not offer Christmas markets.

Chicago has Christmas markets worth visiting. Shopping is a highlight of a trip to the city, and the Christkindlmarkt is not to be missed.

Oahu does not offer Christmas markets.

Is Chicago or Oahu Better for Families?

You'll find terrific kid-friendly activities in either Chicago or Oahu.

Chicago is one of the most popular family destinations. The city has a large number of activities for kids, including zoos, Shedd Aquarium, impressive children's museums, and large and elaborate playgrounds in Millennium Park. It's easy to keep kids entertained in this very kid-focused city.

Oahu is an amazing family-friendly city to visit. There are plenty of outdoor activities, places to learn about Hawaiian culture, and world class beaches. The most popular family-friendly area is Ko Olina, which is where you'll find the Disney Resort, Aulani. Kids will also enjoy the area's snorkeling and kayaking. Surfing lessons are a fun activity for the whole family as well.

Is Chicago or Oahu Better for Couples?

Oahu is renowned for couples. Also, Chicago is still popular, but not quite as popular for romance.

For those traveling as a couple, Oahu has plenty to offer. The island offers a beautiful and adventurous honeymoon destination that is perfect for anniversaries and other romantic getaways. It's an island paradise with world class beaches, stunning vistas, and countless water sports.

Chicago is a nice destination for couples. Couples will enjoy exploring the city's vibrant theater scene and diverse neighborhoods. There are many varied restaurants and entertainment options that make for a great date night. There are also sporting events, parks, and gardens where couples can explore.

Is Chicago or Oahu Better for Backpackers and Budget Travelers?

Chicago and Oahu are good places to visit for backpackers and budget travelers.

Chicago is popular with backpackers and budget travelers. The city doesn't have a huge backpacker vibe, but it does have a number of hostels that help keep costs in check.

It's common for backpackers to visit Oahu. There are a couple of hostels on the island. Public transportation is also a bit better than the other islands, so it is one of the better Hawaiian islands for backpackers.

Is Chicago or Oahu Better for Students?

Chicago is a world-class destination for its student-friendly activities. However, Oahu is not popular with students.

Chicago is a great destination for students. The city has a large number of universities that bring in students from around the country and around the globe. It's a huge international city with economic ties and many opportunities connected to the universities.

Oahu is not popular with students.

Is Chicago or Oahu Better for Public Transit? Which Is Easier to Get Around Without a Car?

Chicago is a world-class destination for times when you don't have a car. However, Oahu is lacking in good options for its public transit.

With a huge network, the transit system in Chicago can get you around easily. There's a subway (the "L"), a commuter well, as well as buses and countless taxis available.

Public transit is generally limited in Oahu. Honolulu has a fairly good bus system, but once you're out of the city, public transportation is limited.

Is Chicago or Oahu a more walkable city?

Chicago is a very popular place for its high level of walkability. However, Oahu is lacking in good options for its ease of walking around.

Chicago is a very walkable city. The city has many restaurants, sights, and hotels that are easily accessible on foot.

Oahu is generally not very walkable. There are some walkable neighborhoods in Honolulu, but if you really want to explore the island, you'll want to have a car.

For even more information, also check out Is Chicago Worth Visiting? and Is Oahu Worth Visiting?.

Should I spend more time in Oahu or Chicago?

How long in Chicago or Oahu?

Both Chicago and Oahu have a number of activities to choose from. With generally more activities and things to do, visitors tend to spend more time in Oahu than in Chicago. Usually, 3-5 days is a good amount of time for Chicago, and 3-7 days is enough time in Oahu.

Families should spend more time in Chicago than Oahu. Because of the many family-friendly attractions and fun things to do for kids in Chicago, it's a great place to visit with the whole family.

Couples should spend more time in Chicago than Oahu. You'll find plenty of romantic sights and fun activities in Chicago that are great for a weekend getaway or a longer couple's trip.

Backpackers and budget travelers should spend more time in Chicago than Oahu if your budget allows for it. With a larger number of budget-friendly sights, good nightlife, and active things to do, anyone traveling on a budget would have a good time in Chicago.

One day in Chicago or Oahu?

Chicago is a big city destination where you can fill many days. Take your pick from the many activities offered here. With so much to do, one day is probably not enough time to see everything.

In Oahu, you'll find shopping and museums. Travelers enjoy the resorts in the area as well. This island offers something for everyone. One day is usually not enough time for a trip here as there is plenty to do.

A weekend in Chicago or Oahu?

Chicago is a fun place to experience. But since there are so many activities, you'll likely want to spend more than a weekend exploring. The entire region has so many activities, and you'll want time to do everything.

In Oahu, you'll find museums and nightlife. The length of your trip often depends on your style of travel. Hiking can easily take up a good amount of your time here, too. Since there is so much to do in the area, a weekend is probably not enough for all of it.

Five days in Chicago or Oahu?

Chicago is a edgey big city where you can fill many days. This city offers something for everyone. Plenty of people spend five days in the area when traveling. Five days is often enough time to do most activities.

Oahu is a great place to explore. It is common to spend five days here. You can also relax and pamper yourself at one of the resorts. Five days is a great amount of time to relax and see the many things that Oahu has to offer. Anyone can find something fun to do here.

A week in Chicago or Oahu?

The cosmopolitan city of Chicago offers food and shopping. The length of your trip often depends on your style of travel. One week is usually plenty of time to spend here with extra days to spare. With this much time, visitors often visit nearby destinations or take day trips.

It's hard to know how much time to spend in Oahu. In Oahu, you'll find food and scuba diving and snorkeling. It's also a relaxing resort destination. With all of its activities, you can easily fill one week here.

For some great organized tour ideas, see The Best Family-Friendly Tours to United States of America, The Best Wildlife Tours to United States of America, The Best Hiking & Trekking Tours in United States of America, and The Best Historical Tours in United States of America.

When comparing the travel costs between Chicago and Oahu, we can see that Oahu is more expensive. However, the two cities are actually relatively comparable in price, as the difference is somewhat minimal. Generally, this means that you could travel with generally the same travel style and level of luxury in each place. Since both cities are in North America, it's no surprise that their costs are relatively close, as many destinations here have somewhat similar travel prices overall.

If you're trying to decide if either of these two destinations are within your price range, also see Is Chicago Expensive? and Is Oahu Expensive?.

When is the best time to visit Chicago or Oahu?

Both places have a temperate climate with four distinct seasons. As both cities are in the northern hemisphere, summer is in July and winter is in January.

Should I visit Chicago or Oahu in the Summer?

The summer brings many poeple to Chicago as well as Oahu. The beaches, the city activities, the music scene, and the family-friendly experiences are the main draw to Chicago this time of year. Also, many travelers come to Oahu for the beaches, snorkeling, the hiking, the city activities, the music scene, and the family-friendly experiences.

In July, Chicago is generally around the same temperature as Oahu. Daily temperatures in Chicago average around 77°F (25°C), and Oahu fluctuates around 81°F (27°C).

The sun comes out a lot this time of the year in Oahu. People are often attracted to the plentiful sunshine in Chicago this time of the year. In the summer, Chicago often gets around the same amount of sunshine as Oahu. Chicago gets 326 hours of sunny skies this time of year, while Oahu receives 303 hours of full sun.

Chicago receives a lot of rain in the summer. Chicago usually gets more rain in July than Oahu. Chicago gets 3.9 inches (100 mm) of rain, while Oahu receives 0.6 inches (15 mm) of rain this time of the year.

Should I visit Chicago or Oahu in the Autumn?

Both Oahu and Chicago are popular destinations to visit in the autumn with plenty of activities. Many travelers come to Chicago for the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area. Also, many visitors come to Oahu in the autumn for the hiking trails, the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area.

Chicago is much colder than Oahu in the autumn. The daily temperature in Chicago averages around 56°F (14°C) in October, and Oahu fluctuates around 80°F (26°C).

It's quite sunny in Oahu. Chicago usually receives less sunshine than Oahu during autumn. Chicago gets 195 hours of sunny skies, while Oahu receives 246 hours of full sun in the autumn.

In October, Chicago usually receives around the same amount of rain as Oahu. Chicago gets 2.2 inches (56 mm) of rain, while Oahu receives 2.1 inches (54 mm) of rain each month for the autumn.

Should I visit Chicago or Oahu in the Winter?

Both Oahu and Chicago during the winter are popular places to visit. Many visitors come to Chicago in the winter for the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine. Furthermore, most visitors come to Oahu for the museums, the shopping scene, and the cuisine during these months.

Chicago can get quite cold in the winter. In the winter, Chicago is much colder than Oahu. Typically, the winter temperatures in Chicago in January average around 25°F (-4°C), and Oahu averages at about 73°F (23°C).

In Oahu, it's very sunny this time of the year. In the winter, Chicago often gets less sunshine than Oahu. Chicago gets 134 hours of sunny skies this time of year, while Oahu receives 212 hours of full sun.

Chicago usually gets less rain in January than Oahu. Chicago gets 1.9 inches (47 mm) of rain, while Oahu receives 3.9 inches (99 mm) of rain this time of the year.

Should I visit Chicago or Oahu in the Spring?

The spring attracts plenty of travelers to both Chicago and Oahu. Most visitors come to Chicago for the beaches, the activities around the city, and the natural beauty during these months. Furthermore, the spring months attract visitors to Oahu because of the beaches, the activities around the city, and the natural beauty.

In April, Chicago is generally much colder than Oahu. Daily temperatures in Chicago average around 52°F (11°C), and Oahu fluctuates around 76°F (24°C).

People are often attracted to the plentiful sunshine in Oahu this time of the year. In Chicago, it's very sunny this time of the year. Chicago usually receives less sunshine than Oahu during spring. Chicago gets 218 hours of sunny skies, while Oahu receives 253 hours of full sun in the spring.

Chicago gets a good bit of rain this time of year. In April, Chicago usually receives more rain than Oahu. Chicago gets 4.3 inches (108 mm) of rain, while Oahu receives 1.7 inches (42 mm) of rain each month for the spring.

Typical Weather for Oahu and Chicago