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

Should you visit Chicago or Aspen?

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

Chicago

Chicago is a multicultural, edgey, and cosmopolitan city. Visitors will also find so much to do here because it's a large city with many sights and attractions. It offers plenty of beauty for visitors. Other popular activities here include museums, theater, and nightlife.

Aspen

Aspen is a quaint, vibrant, and artsy ski town. As this is a charming small town, visitors also come to explore the sights and local activities. With stunning beauty, it attracts visitors from all around. As this is a very quaint destination, you'll find it has a special atmosphere. Other popular activities here include live music, food, and hiking.

Chicago and Aspen: Pros and Cons

Is there more to do in Chicago or Aspen?

Travelers will usually find more to do in Chicago. Although Chicago and Aspen are popular destinations, Chicago has more sights and attractions for tourists. Chicago is very popular for its museums, theatre productions, nightlife, music, beaches, shopping, and big city activities, while Aspen attracts visitors for its skiing, resorts, hiking, christmas markets, small town charm, impressive beauty, and quaint atmosphere. Chicago is famous for its thriving sports scene, its iconic local cuisine, and its world class shopping at the Magnificent Mile. It is also well known for The Willis Tower (previously the Sears Tower). Aspen is famous for its world-class skiing, many food, film, and music festivals, and its stunning mountain hikes.

How is Chicago different from Aspen?

Which is Better for a Holiday?

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

Is Chicago or Aspen Better for Skiing?

Aspen is renowned for winter skiing. However, Chicago is not a skiing destination.

Aspen is among the world's best ski destinations. Near the town, there are 4 separate ski resorts. In town you'll find Aspen Mountain, which is known for it's black-diamond runs. Aspen Highlands, a couple miles away, has a mix of slopes and is less crowded. Buttermilk attracts many freestyle skiers and Aspen Snowmass is considered one of the best family-friendly ski areas.

Chicago is not a skiing destination.

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

Chicago is renowned for its museums and landmarks. However, Aspen does not have museums and landmarks.

You'll find many recognizable landmarks that put Chicago on the map. 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).

Aspen does not have museums and landmarks.

Is Chicago or Aspen Better for Theater?

Chicago is renowned for its shows and theatre. However, Aspen is not a theatre destination.

Visitors will find world class theater shows, plays, and musicals in Chicago that are not to be missed. 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.

Aspen is not a theatre destination.

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

There are opportunities to sample the local cuisine at amazing restaurants in both Chicago and Aspen.

Chicago has long been recognized as a culinary destination with great restaurants. 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.

Known for it's food and restaurant scene, Aspen is always at the top of any foodie's travel list. The town hosts many food festivals and there is a growing selection of diverse restaurants. In town you'll find cafes and restaurants that cater to both the local crowd and the travelers who flock to the area during peak seasons.

Is Chicago or Aspen Better for Nightlife?

Chicago is renowned for its evening party scene. Also, Aspen is still popular, but not quite as popular for nightlife.

Chicago is a destination that you simply have to visit at least once for nightlife. 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 in Aspen has something for everybody. The people in Aspen know how to have a good time. The nightlife scene includes craft beer, live music, and dancing. There's a local vibe, particularly during the off-season times when the tourist crowds are less.

Is Chicago or Aspen Better for Music?

Chicago is renowned for its music scene. Also, Aspen is still popular, but not quite as popular for live music.

In Chicago you'll find nightly musicians performing at a variety of venues. The city is the birthplace of such interesting styles as modern gospel and the Chicago style blues.

Aspen has a thriving music scene. Popular music venues in town include Silver City Mountain Saloon and Belly Up Aspen.

Is Chicago or Aspen Better for Resorts?

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

Vacationers can choose from a number of terrific resorts in Aspen. Popular resorts in the area include The Little Nell, Hotel Jerome, and St. Regis Aspen.

Chicago is not a resort destination.

Is Chicago or Aspen Better for Beaches?

Chicago is a city with good options for the beach. However, Aspen is not a beach destination.

Plenty of visitors enjoy relaxing on the beach in Chicago. 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.

Aspen is not a beach destination.

Is Chicago or Aspen Better for Hiking?

Aspen is a great destination for its hiking experiences. However, Chicago is not a hiking destination.

You'll find a nice variety of hiking trails around Aspen. During the summer and fall seasons, hiking is a great way to explore Aspen's nearby beauty. Popular trails include the Ute Trail, the Lost Man Trail, and the famous Maroon Bells Scenic Trail.

Chicago is not a hiking destination.

Is the Shopping Better in Chicago or Aspen?

Chicago is renowned for its shopping areas. Also, Aspen is still popular, but not quite as popular for shopping.

Chicago is a world class destination for shoppers. 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.

Shopping is a popular activity when visiting Aspen. There are many great local shops and art galleries where you can pick interesting items or fine art.

Is Chicago or Aspen Better for Christmas?

Aspen is renowned for its Christmas activities. Also, Chicago is still popular, but not quite as popular for its Christmas holiday experiences.

Aspen is a world class destination for shoppers. There are a number of beautiful activities that will bring the holiday season to life in the town.

Chicago is a very popular destination during Christmas. There's a number of seasonal celebrations, ice skating, and excellent shopping.

Is Chicago or Aspen Better for Christmas Markets?

Aspen is a great destination for its Christmas markets. Also, Chicago is still popular, but not quite as popular for visiting Christmas markets.

Aspen has a lively atmosphere around its Christmas markets. The town has a charming Christmas market that is fun to explore and has around 40 vendors.

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

Is Chicago or Aspen Better for Families?

Chicago is renowned for its family-friendly activities. Also, Aspen is still popular, but not quite as popular for its kid-friendly activities.

Chicago is an extremely popular city to visit for families. 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.

Aspen offers lots of family activities. Families that enjoy skiing together, hiking, rock climbing, and having adventures will enjoy a visit to this town. Aspen Mountain is not a great option for beginning skiers, but further away, Aspen Snowmass offers good beginner slopes.

Is Chicago or Aspen Better for Couples?

Aspen is a great destination for couples. Also, Chicago is still popular, but not quite as popular for romance.

Couples visit Aspen frequently as it offers plenty of romantic activities. Aspen is both a popular ski destination as well as an established town. There are many great restaurants and activities that couples can enjoy and the setting is cute and very scenic, making it a beautiful and romantic destination.

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 Aspen Better for Backpackers and Budget Travelers?

Chicago is a city with good options for backpackers. However, Aspen is a ski town with minimal options for backpackers and budget travelers.

Chicago is a good city to visit for backpackers. The city doesn't have a huge backpacker vibe, but it does have a number of hostels that help keep costs in check.

Aspen is a challenging destination for budget travelers and backpackers due to the higher prices. Because it is both a town and a ski resort, there are a couple of more affordable accommodation options. Even so, this is an expensive destination that isn't always ideal for budget travelers.

Is Chicago or Aspen Better for Students?

Chicago is renowned for students. However, Aspen is not popular with students.

Chicago is a very popular city 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.

Aspen is not popular with students.

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

Chicago is renowned for its public transit. Also, Aspen is still popular, but not quite as popular for times when you don't have a car.

Chicago has a great public transit system. There's a subway (the "L"), a commuter well, as well as buses and countless taxis available.

While Aspen offers some public transit options, it might not be your first choice. There are several shuttle buses around the town.

Is Chicago or Aspen a more walkable city?

Chicago and Aspen both are superb when exploring on foot.

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

Aspen is very walkable. The town is compact enough that it can be explored on foot. If you're planning to head into the mountains to hike, you'll likely need a car.

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

Should I spend more time in Aspen or Chicago?

How long in Chicago or Aspen?

In either Chicago or Aspen, you'll find plenty of activities to fill your time. In our opinion, Chicago has more to see and do, so we recommend that you spend more time in Chicago than Aspen. However, 3-5 days is a good amount of time to spend in either destination.

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

Backpackers and budget travelers should spend more time in Chicago than Aspen 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 Aspen?

Each neighborhood in Chicago has its own distinct appeal, so there are pleny of areas to explore. This city offers a variety of activities to choose from. Since there is so much to do in the area, one day is probably not enough for all of it.

Aspen is a small town with plenty to do. Travelers enjoy the resorts in the area as well. This ski town 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 Aspen?

It's hard to know how much time to spend in Chicago. A weekend is usually not enough time for a trip here as there is plenty to do. The length of your ideal trip is an individual decision.

Aspen might be a small town, but there's plenty to do in the area. 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 Aspen?

Chicago is a fun place to experience. Each neighborhood in Chicago has its own distinct appeal, so there are pleny of areas to explore. This would be the perfect place to spend five days, as it has just the right amount of activities.

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

A week in Chicago or Aspen?

You'll find shopping and museums around the cosmopolitan big city of Chicago. Take your pick from the many activities offered here. One week is plenty of time to see everything, even with extra days to spare.

It's hard to know how much time to spend in Aspen. Since Aspen is a small town, it's easily explored when your time is limited. It's also a relaxing resort destination. One week may feel like too much time unless you plan to do a lot of relaxing.

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 Aspen, we can see that Aspen 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 Aspen Expensive?.

Which is Bigger, Chicago or Aspen?

Chicago has a larger population, and is about 490 times larger than the population of Aspen. When comparing the sizes of Chicago and Aspen, keep in mind that a larger population does not always imply the destination has more attractions or better activities. So, always research the type of place that you want to visit along with the activities and attractions that interest you.