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

Should you visit Chicago or Portland?

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

Chicago

Chicago is a multicultural, edgey, and cosmopolitan city. It's an amazing and huge city with tons of activities and things to do. Chicago is a gorgeous place to visit. Other reasons to visit include nightlife, live music, and food. See Chicago travel costs.

Portland

Portland is a laid-back, progressive, and quirky city. Don't miss this spot, as it's a charming small town with plenty of activities. Portland offers plenty of beauty for visitors. Other popular activities here include hiking, shopping, and nightlife. See Portland travel costs.

Chicago and Portland: Pros and Cons

Is there more to do in Chicago or Portland?

You'll generally find more things to do in Chicago than Portland. Chicago is bigger than Portland, and it also has more attractions and activities for travelers. Chicago is better known for its museums and attractions, theatre productions, food, nightlife, music, beaches, shopping, christmas markets, and big city activities, while Portland is more popular for its hiking and small town charm. Chicago is well known for its thriving sports scene, its iconic local cuisine, and its world class shopping at the Magnificent Mile. Also, Chicago is famous for The Willis Tower (previously the Sears Tower). Portland is well known for its independent and vintage shops, thriving art scene, lush parks and gardens, progressive and quirky personality, and easy access to amazing natural beauty.

How is Chicago different from Portland?

Which is Better for a Holiday?

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

Chicago is very popular for its museums and history. However, Portland is lacking in good options for its museums and landmarks.

Travelers visit Chicago from around the world to see its many world-famous attractions. 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).

Portland offers a handful of options for museums and historical sights. Visitors usually come for the city's outdoor recreation and eclectic personality more than the landmarks and museums. There are a few places to visit on a rainy day though including Pittock Mansion, the Portland Art Museum, and the Oregon Museum of Science and Industry.

Is Chicago or Portland Better for Theater?

Chicago is very popular for theatre. However, Portland 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.

Portland is not a theatre destination.

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

Chicago is very popular for its restaurants. However, Portland is lacking in good options for its restaurant scene.

Many restaurants in Chicago have been singled out for their culinary prowess. 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.

You'll find the standard options when it comes to food in Portland. The town is more famous for it's craft beer than it's food, but there are still a number of local restaurants that offer unique Oregon dishes. You'll find no shortage of vegetarian and vegan options on most menus. There is also a big farm-to-table scene with many farmers markets around town as well.

Is Chicago or Portland Better for Nightlife?

Chicago is very popular for nightlife. Also, Portland is not quite as popular, but is fairly good for nightlife and partying.

Chicago is a party destination, and you'll find plenty of activity all night long. 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.

Portland has an active nightlife scene for those who seek it out. Famously, this town's nightlife is all about the craft beer and local breweries. Make sure you check out Bailey's Taproom, The Big Legrowlski, and The Commons Brewery.

Is Chicago or Portland Better for Music?

Chicago is very popular for live music. Also, Portland is not quite as popular, but is fairly good for its live music scene.

Chicago is known as a music capital around the world. The city is the birthplace of such interesting styles as modern gospel and the Chicago style blues.

You don't have to look far to find a unique music venue in Portland. The town has a thriving live music and international folk dancing scene.

Is Chicago or Portland Better for Beaches?

Chicago is a city with good options for its beaches. However, Portland 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.

Portland is not a beach destination.

Is Chicago or Portland Better for Hiking?

Portland 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 Portland. Just outside of town you'll find amazing hikes and stunning natural beauty. In town there are many urban hikes through parks and gardens, but in just a short drive you also have access to Mount Hood and many of the region's most beautiful hikes around the Columbia River Gorge.

Chicago is not a hiking destination.

Is the Shopping Better in Chicago or Portland?

Chicago is very popular for shopping. Also, Portland is not quite as popular, but is fairly good for its shopping opportunities.

People travel from around the world to go shopping in Chicago. 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.

Portland offers some nice shopping areas. To fully experience shopping in town, head to the local vendors and thrift shops. There are many vintage clothing shops, book stores, and independent sellers around town. The city is also full of farmers markets. For some of the most interesting shopping, check out the Pearl District, Pioneer Place, Union Way, and Downtown neighborhoods.

Is Chicago or Portland More Beautiful?

You'll find a similar quality of notable scenery and beauty in both Chicago and Portland.

Chicago offers plenty of beauty for visitors. The water makes this city a truly unique place to explore, and the world class architecture is not to be missed.

Portland is a gorgeous place to visit. Surrounded by mountains and filled with parks and greenspace, many people find this town to be quite beautiful.

Is Chicago or Portland Better for Families?

Chicago is very popular for its kid-friendly activities. Also, Portland is not quite as popular, but is fairly good for its family-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.

You'll find plenty of kid-friendly things to do in Portland. This is an outdoor city by nature, so families will appreciate the many parks and outdoor recreational activities around town. It's easy to fill a couple of days exploring and having fun with the kids. Kid-friendly activities include the zoo, the aerial tram, and several great museums.

Is Chicago or Portland Better for Couples?

Both Chicago and Portland are notable destinations to visit as a couple.

Chicago is a good city for couples to visit. 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.

Portland is a nice destination for couples. The laid-back, alternative vibe is fun to explore as a couple. There are independent bookstores, nice parks, and plenty of outdoor activities to choose from. Couples who enjoy an eclectic city, breweries, and nature, will find a lot to do in town.

Is Chicago or Portland Better for Backpackers and Budget Travelers?

Portland is a great destination for backpackers. Also, Chicago is still popular, but not quite as popular for backpackers and budget travelers.

Portland is a very popular city for backpackers and budget travelers. The town has drawn young explorers for years, and backpackers who like to step away from the mainstream will feel right at home here.

It's common for backpackers to 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.

Is Chicago or Portland Better for Students?

Chicago is very popular for its student-friendly activities. Also, Portland is not quite as popular, but is fairly good for 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.

Portland is popular with students. It's a young and relaxed city that attracts independent thinkers. There are many bookstores and breweries around town. The cost of living can be a bit high though.

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

Chicago is very popular for times when you don't have a car. Also, Portland is not quite as popular, but is fairly good for its public transit.

Chicago has an effecient and thorough public transportation system which can take you anywhere in the city. There's a subway (the "L"), a commuter well, as well as buses and countless taxis available.

You'll find some public transit in Portland, but it may not be enough to take you everywhere. The town has a bus and light rail system as well the Aerial tram.

Is Chicago or Portland a more walkable city?

Chicago and Portland 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.

Portland is very walkable. It is quite walkable, particularly in the tourist areas such as Downtown, Pearl, and Old Town Chinatown.

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

Should I spend more time in Portland or Chicago?

How long in Chicago or Portland?

Visitors can find plenty of fun things to do in both Chicago and Portland. With generally more activities and things to do, visitors tend to spend more time in Chicago than in Portland. Usually, 3-5 days is a good amount of time for Chicago, and 2-3 days is enough time in Portland.

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

Chicago is a big city with plenty to do. With so much to do, one day is probably not enough time to see everything. It will give you the chance to have new experiences.

In Portland, you'll find shopping and nightlife. Many travelers plan to spend time hiking while in the area. This city 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 Portland?

Chicago is a popular place that is full of things to see and experience. But since there are so many activities, you'll likely want to spend more than a weekend exploring. Take your pick from the many activities offered here.

In Portland, you'll find nightlife and live music. The length of your trip often depends on your style of travel. A weekend here is typical. Hiking can easily take up a good amount of your time here, too. A weekend is a great amount of time to relax and see the many things that Portland has to offer.

Five days in Chicago or Portland?

Chicago is a popular choice for travelers. Five days here is typical. While some people choose to spend more or less time in Chicago, five days is sufficent for most. The entire region has so many activities, and you'll want time to do everything.

Portland is a great place to explore. Hikers are also drawn to this area. Five days is more than enough time to enjoy everything. Take some day trips to nearby places to fill the extra days. Anyone can find something fun to do here.

A week in Chicago or Portland?

Chicago is a great place to explore. One week is more than enough time to enjoy everything. Take some day trips to nearby places to fill the extra days. This city offers something for everyone.

It's hard to know how much time to spend in Portland. Many people enjoy the shopping and nightlife when visiting Portland. Many visitors also spend a good bit of time hiking. 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 2-Week Tours from San Francisco, The Best 2-Week Tours from Los Angeles, The Best Family-Friendly Tours to United States of America, and The Best Wildlife Tours to United States of America.

When we compare the travel costs of actual travelers between Chicago and Portland, we can see that Chicago is more expensive. And not only is Portland much less expensive, but it is actually a significantly cheaper destination. So, traveling to Portland would let you spend less money overall. Or, you could decide to spend more money in Portland and be able to afford a more luxurious travel style by staying in nicer hotels, eating at more expensive restaurants, taking tours, and experiencing more activities. The same level of travel in Chicago would naturally cost you much more money, so you would probably want to keep your budget a little tighter in Chicago than you might in Portland.

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

Which is Bigger, Chicago or Portland?

Chicago has a larger population, and is about 5 times larger than the population of Portland. When comparing the sizes of Chicago and Portland, 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.

When is the best time to visit Chicago or Portland?

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 Portland in the Summer?

The summer brings many poeple to Chicago as well as Portland. Many travelers come to Chicago for the beaches, the city activities, the music scene, and the family-friendly experiences. Also, many visitors come to Portland in the summer for the hiking, the small town charm, the music scene, and the family-friendly experiences.

In the summer, Chicago is a little warmer than Portland. Typically, the summer temperatures in Chicago in July average around 77°F (25°C), and Portland averages at about 68°F (20°C).

The sun comes out a lot this time of the year in Portland. 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 Portland. Chicago gets 326 hours of sunny skies this time of year, while Portland receives 338 hours of full sun.

Chicago receives a lot of rain in the summer. Chicago usually gets more rain in July than Portland. Chicago gets 3.9 inches (100 mm) of rain, while Portland receives 0.7 inches (18 mm) of rain this time of the year.

Should I visit Chicago or Portland in the Autumn?

Both Portland and Chicago are popular destinations to visit in the autumn with plenty of activities. Many visitors come to Chicago in the autumn for the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area. Also, most visitors come to Portland for the hiking trails, the shopping scene, the music scene, the small town atmosphere, and the natural beauty of the area during these months.

In October, Chicago is generally around the same temperature as Portland. Daily temperatures in Chicago average around 56°F (14°C), and Portland fluctuates around 55°F (13°C).

Chicago usually receives more sunshine than Portland during autumn. Chicago gets 195 hours of sunny skies, while Portland receives 155 hours of full sun in the autumn.

In October, Chicago usually receives less rain than Portland. Chicago gets 2.2 inches (56 mm) of rain, while Portland receives 2.6 inches (67 mm) of rain each month for the autumn.

Should I visit Chicago or Portland in the Winter?

Both Portland and Chicago during the winter are popular places to visit. Most visitors come to Chicago for the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine during these months. Furthermore, the winter months attract visitors to Portland because of the museums, the shopping scene, and the cuisine.

The weather in Portland can be very cold. Chicago can be very cold during winter. Chicago is much colder than Portland in the winter. The daily temperature in Chicago averages around 25°F (-4°C) in January, and Portland fluctuates around 40°F (4°C).

In the winter, Chicago often gets more sunshine than Portland. Chicago gets 134 hours of sunny skies this time of year, while Portland receives 86 hours of full sun.

Portland gets a good bit of rain this time of year. Chicago usually gets less rain in January than Portland. Chicago gets 1.9 inches (47 mm) of rain, while Portland receives 5.2 inches (132 mm) of rain this time of the year.

Should I visit Chicago or Portland in the Spring?

The spring attracts plenty of travelers to both Chicago and Portland. The spring months attract visitors to Chicago because of the beaches, the activities around the city, and the natural beauty. Furthermore, the small town charm and the natural beauty are the main draw to Portland this time of year.

In the spring, Chicago is around the same temperature as Portland. Typically, the spring temperatures in Chicago in April average around 52°F (11°C), and Portland averages at about 51°F (11°C).

People are often attracted to the plentiful sunshine in Portland this time of the year. In Chicago, it's very sunny this time of the year. Chicago usually receives around the same amount of sunshine as Portland during spring. Chicago gets 218 hours of sunny skies, while Portland receives 231 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 Portland. Chicago gets 4.3 inches (108 mm) of rain, while Portland receives 2.4 inches (61 mm) of rain each month for the spring.

Typical Weather for Portland and Chicago