A Travel Price Comparison for United States of America Chicago vs. Maui for Attractions, Food, Beaches, and Families

Should you visit Chicago or Maui?

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 Maui can help you decide which place is right for you.

Chicago

Chicago is a cosmopolitan, diverse, and vibrant 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. And you can't forget about the beaches, shopping, and museums.

Maui

Maui is a breathtaking, stunning, and idyllic island. The famous beauty of this place is one of the main draws. Other popular activities here include hiking, shopping, and scuba diving and snorkeling.

Chicago and Maui: Pros and Cons

Is there more to do in Chicago or Maui?

Tourists will generally find more to do in Chicago. Although Chicago and Maui are both popular with visitors, Chicago has more sights, activities, and attractions for travelers. Chicago is more popular for its museums, theatre productions, food, nightlife, music, shopping, christmas markets, and big city activities, while Maui is known for its resorts, scuba diving & snorkeling, beaches, hiking, and impressive beauty. Maui is more touristy than Chicago and is known for its beach-filled coastline, world-class snorkeling and scuba diving, dramatic landscapes, and paradise environment. Chicago is popular for its thriving sports scene, its iconic local cuisine, and its world class shopping at the Magnificent Mile. It is also home to The Willis Tower (previously the Sears Tower).

How is Chicago different from Maui?

Which is Better for a Holiday?

Let's take a look at the differences and similarities between Maui 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 Maui?

Chicago is a must-visit destination for its museums and landmarks. However, Maui is a island with minimal options for its historical sights.

The museums, monuments, and landmarks in Chicago are among the most recognizable in the world. 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).

While most people don't head to Maui specifically for the museums and attractions, it does offer a few options. Most people prefer not to spend their time inside or at a museum, but for a rainy day you can check out the Maui Ocean Center.

Is Chicago or Maui Better for Theater?

Chicago is a must-visit destination for its theatre productions. However, Maui is not a theatre destination.

The theater and performance venues in Chicago draw crowds from around the world. 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.

Maui is not a theatre destination.

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

Chicago is a must-visit destination for its restaurant scene. However, Maui is a island with minimal options for its local flavors and cuisine.

For foodies, Chicago is an obvious choice, as it is one of the food capitals of the world. 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.

Maui may not make the list for most foodies, but you'll find what you need while you're in town. Like the other Hawaiian islands, food is expensive and of varying quality here, but the food scene continues to grow and improve. There are eclectic food trucks where you can try local flavors. There's also plenty of fresh tropical produce like mangos, avocadoes, and coconuts. Seafood is common on many menus as well.

Is Chicago or Maui Better for Nightlife?

Chicago is a must-visit destination for nightlife and partying. However, Maui is a island with minimal options for its evening party scene.

Chicago is a world class party destination. 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.

The nightlife scene is quiet in Maui The island is not known for its nightlife, but the limited activities that do exist you'll find in Kaanapali and Lahaina.

Is Chicago or Maui Better for Music?

Chicago is a must-visit destination for its live music scene. However, Maui is not a live music destination.

Live music, and music in many other forms, is everyone in Chicago The city is the birthplace of such interesting styles as modern gospel and the Chicago style blues.

Maui is not a live music destination.

Is Chicago or Maui Better for Resorts?

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

Vacationers can choose from a number of terrific resorts in Maui. There are a number of nice resorts, but there are also VRBOs, condos, and local hotels where you can stay. High-end luxury resorts on the island include The Ritz-Carlton Maui, Kapalua and Grand Wailea, A Waldorf Astoria Resort. There are also more reasonable priced resorts without all of the glitz and glam.

Chicago is not a resort destination.

Is Chicago or Maui Better for Scuba Diving and Snorkeling?

Maui 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 Maui. The island has excellent snorkeling and scuba diving. You can really find it anywhere on the island, but some places are more crowded than others. Some of the best beaches for snorkeling include Honolua Bay, Slaughterhouse (Mokuleia Bay), DT Fleming Beach, and Kapalua Bay.

Chicago is not a scuba or snorkeling destination.

Is Chicago or Maui Better for Beaches?

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

With world-famous beaches, Maui is a very popular vacation destination. The island has stunning beaches and more miles of swimmable beach than any of the other Hawaiian islands. One of the best swimming beaches is Kapalua Beach, but other favorite beaches include Makena Beach State Park, Ka'anapali Beach, Baldwin Beach Park, and Wai'anapanapa State Park.

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 Maui Better for Hiking?

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

Many people visit Maui specifically for its hiking. There are many diverse hikes on the island that pass through different landscapes and ecosystems. Hikes range from easy to challenging and are of varying length. Some of the favorites include 'Iao Valley State Park, Haleakala's Sliding Sands Trail (in Haleakala National Park), and The Pipiwai Trail.

Chicago is not a hiking destination.

Is the Shopping Better in Chicago or Maui?

Chicago is a must-visit destination for its shopping opportunities. Also, Maui is still popular, but not quite as popular for its shopping areas.

The abundance of shops in Chicago make it a world-class shopping destination. 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.

Maui has a variety of shopping areas worth visiting. There are many shopping centers where you'll find souvenirs, Hawaiian clothing, and even handmade crafts. If you forgot something from home, you'll also find many of the major chains that are common on the mainland.

Is Chicago or Maui Better for Christmas?

Chicago is a great destination for its Christmas activities. However, Maui does not offer Christmas activities.

Visitors come from all around to experience the Christmas activities in Chicago. There's a number of seasonal celebrations, ice skating, and excellent shopping.

Maui does not offer Christmas activities.

Is Chicago or Maui Better for Christmas Markets?

Chicago is a popular place for its Christmas markets. However, Maui does not offer Christmas markets.

Many visitors go to the Christmas markets in Chicago. Shopping is a highlight of a trip to the city, and the Christkindlmarkt is not to be missed.

Maui does not offer Christmas markets.

Is Chicago or Maui Better for Families?

You'll find world-class kid-friendly activities in either Chicago or Maui.

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.

Maui is an amazing family-friendly city to visit. It is one of the best of the Hawaiian islands to explore with kids. There's plenty of snorkeling, outdoor adventure sports, and hiking that are great for kids of all ages. There are some kid-friendly beaches where kids can play in the water. There's also the Maui Ocean Center, Ali'i Kula Lavender Farm, and 'Iao Valley State Park.

Is Chicago or Maui Better for Couples?

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

For those traveling as a couple, Maui has plenty to offer. Couples will enjoy the outdoor sports, excellent snorkeling and diving, and beautiful waterfalls that make for a romantic getaway. There are world-class resorts and breathtaking scenery that attract honeymooning couples from around the globe.

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 Maui Better for Backpackers and Budget Travelers?

Chicago is a popular place for backpackers. However, Maui is a island with minimal options for backpackers and budget travelers.

Plenty of budget travelers visit Chicago. The city doesn't have a huge backpacker vibe, but it does have a number of hostels that help keep costs in check.

Maui is a challenging destination for budget travelers and backpackers due to the higher prices. Like most of the Hawaiian Islands, everything is expensive here and even though there are a couple of hostels, you can still expect to pay high prices for them. Public transportation is also limited so you'll really need to rent a car if you hope to explore the island in depth.

Is Chicago or Maui Better for Students?

Chicago is a must-visit destination for students. However, Maui is not popular with students.

Many students frequent Chicago. 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.

Maui is not popular with students.

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

Chicago is a must-visit destination for its public transit. However, Maui is a island with minimal options for times when you don't have a car.

Chicago has a world-class public transit network to take passengers everywhere in the city. There's a subway (the "L"), a commuter well, as well as buses and countless taxis available.

Public transit is mostly limited in Maui. The island does have a bus system with 14 routes, but most visitors prefer to have their own transportation to get around.

Is Chicago or Maui a more walkable city?

Chicago is a great destination for its high level of walkability. However, Maui is a island with minimal 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.

Maui is not a very walkable city. The island is large enough that you'll want to have access to a car if you hope to explore it in its entirety.

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

Should I spend more time in Maui or Chicago?

How long in Chicago or Maui?

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

Families should spend more time in Chicago than Maui. 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 Maui. 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 Maui 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 Maui?

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 Maui, you'll find scuba diving and snorkeling and shopping. 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 Maui?

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 Maui, you'll find shopping and scuba diving and snorkeling. 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 Maui?

Chicago is a vibrant 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.

Maui 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 Maui has to offer. Anyone can find something fun to do here.

A week in Chicago or Maui?

The vibrant 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 Maui. In Maui, you'll find shopping 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 Maui, we can see that Chicago 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 Maui Expensive?.

When is the best time to visit Chicago or Maui?

Both destinations experience a temperate climate with four distinct seasons. And since both cities are in the northern hemisphere, summer is in July and winter is in January.

Should I visit Chicago or Maui in the Summer?

Both Maui and Chicago are popular destinations to visit in the summer with plenty of activities. Most visitors come to Chicago for the beaches, the city activities, the music scene, and the family-friendly experiences during these months. Also, the summer months attract visitors to Maui because of the beaches, snorkeling, the hiking, and the family-friendly experiences.

In July, Chicago is generally around the same temperature as Maui. Daily temperatures in Chicago average around 77°F (25°C), and Maui fluctuates around 79°F (26°C).

It's quite sunny in Maui. The sun comes out a lot this time of the year in Chicago. Chicago usually receives more sunshine than Maui during summer. Chicago gets 326 hours of sunny skies, while Maui receives 290 hours of full sun in the summer.

It's quite rainy in Chicago. In July, Chicago usually receives more rain than Maui. Chicago gets 3.9 inches (100 mm) of rain, while Maui receives 0.4 inches (10 mm) of rain each month for the summer.

Should I visit Chicago or Maui in the Autumn?

Both Maui and Chicago during the autumn are popular places to visit. The autumn months attract visitors to Chicago because of the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area. Also, the hiking trails, the shopping scene, and the natural beauty of the area are the main draw to Maui this time of year.

Chicago is much colder than Maui in the autumn. The daily temperature in Chicago averages around 56°F (14°C) in October, and Maui fluctuates around 78°F (26°C).

In Maui, it's very sunny this time of the year. In the autumn, Chicago often gets less sunshine than Maui. Chicago gets 195 hours of sunny skies this time of year, while Maui receives 245 hours of full sun.

Chicago usually gets more rain in October than Maui. Chicago gets 2.2 inches (56 mm) of rain, while Maui receives 1.2 inches (31 mm) of rain this time of the year.

Should I visit Chicago or Maui in the Winter?

The winter attracts plenty of travelers to both Chicago and Maui. The museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine are the main draw to Chicago this time of year. Also, many travelers come to Maui for the museums, the shopping scene, and the cuisine.

It's quite cold in Chicago in the winter. In the winter, Chicago is much colder than Maui. Typically, the winter temperatures in Chicago in January average around 25°F (-4°C), and Maui averages at about 72°F (22°C).

People are often attracted to the plentiful sunshine in Maui this time of the year. Chicago usually receives less sunshine than Maui during winter. Chicago gets 134 hours of sunny skies, while Maui receives 217 hours of full sun in the winter.

Maui receives a lot of rain in the winter. In January, Chicago usually receives less rain than Maui. Chicago gets 1.9 inches (47 mm) of rain, while Maui receives 4.1 inches (105 mm) of rain each month for the winter.

Should I visit Chicago or Maui in the Spring?

The spring brings many poeple to Chicago as well as Maui. Many travelers come to Chicago for the beaches, the activities around the city, and the natural beauty. Also, many visitors come to Maui in the spring for the beaches and the natural beauty.

In April, Chicago is generally much colder than Maui. Daily temperatures in Chicago average around 52°F (11°C), and Maui fluctuates around 74°F (24°C).

The sun comes out a lot this time of the year in Maui. People are often attracted to the plentiful sunshine in Chicago this time of the year. In the spring, Chicago often gets around the same amount of sunshine as Maui. Chicago gets 218 hours of sunny skies this time of year, while Maui receives 231 hours of full sun.

Chicago receives a lot of rain in the spring. Chicago usually gets more rain in April than Maui. Chicago gets 4.3 inches (108 mm) of rain, while Maui receives 1.8 inches (47 mm) of rain this time of the year.

Typical Weather for Maui and Chicago