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

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. It's a gorgeous place to visit. Other reasons to visit include nightlife, live music, and food.

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. It offers plenty of beauty for visitors. Other popular activities here include hiking, shopping, and nightlife.

Chicago and Portland: Pros and Cons

Pros
  • Popular for food and cuisine
  • Good nightlife
  • Good music scene
  • Good for shopping
  • Family-friendly
  • Good for couples and romance
  • Good for backpackers and budget travelers
  • Good public transit
  • Big city activities
Pros
  • Family-friendly
  • Good for couples and romance
  • Good for backpackers and budget travelers
Cons
  • Less popular for food
  • Less popular for nightlife
  • Less active music scene
  • Less popular for shopping
  • Public transit not as usable


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.

Is Chicago or Portland Better for Food?

Chicago
Portland

Chicago has a longer list of notable local restaurants than Portland.

Chicago has long been recognized as a culinary destination with great restaurants. While you're in town you have to try the famous deep dish pizza, Chicago style hot dogs, and Italian beef.

Portland offers some easy restaurants to choose from. 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.


Is Chicago or Portland Better for Nightlife?

Chicago
Portland

Chicago has the better options when it comes to nightlife.

Chicago is a destination that you simply have to visit at least once for nightlife. Popular bars and clubs include the Smart Bar, Beauty Bar, and Le Nocturne.

If you're looking for night time activities Portland has a few options to choose from. 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
Portland

Chicago generally offers more live music options than Portland.

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.

The music scene helps keep Portland active and fun. The town has a thriving live music and international folk dancing scene.

Is Chicago or Portland Better for Shopping?

Chicago
Portland

Most people pick Chicago for the shopping over Portland.

Chicago is a world class destination for shoppers. The most famous shopping area is Michigan Avenue and the famous Magnificent Mile.

Plenty of visitors enjoy shopping while in Portland. To fully experience shopping in town, head to the local vendors and thrift shops.

Is Chicago or Portland Better for Families?

Chicago
Portland

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

Chicago is known to be a very family-friendly place to visit. 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.

Portland offers lots of family activities. Kid-friendly activities in town include the zoo, the aerial tram, and several great museums.


Is Chicago or Portland Better for Couples?

Chicago
Portland

Both Chicago and Portland are good 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.

Portland is a nice destination for couples. 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?

Chicago
Portland

Chicago and Portland are comparable 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.

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

Is Chicago or Portland Better for Public Transit?

Chicago
Portland

Chicago provides more public transit options than Portland.

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 Portland offers some public transit options, it might not be your first choice. The town has a bus and light rail system as well the Aerial tram.

Is Chicago or Portland a more walkable city?

Chicago
Portland

Chicago and Portland both are comparable 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.


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 Portland.

The ideal length of time for a trip to Chicago is 3-5 days, and the ideal length of time for a trip to Portland is 2-3 days.


  • How many days in Chicago or Portland? Ideal Length of Stay
    Chicago 3-5 
    Portland 2-3

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.

Which city is cheaper, Portland or Chicago?

These are the overall average travel costs for the two destinations.

The average daily cost (per person) in Chicago is $221, while the average daily cost in Portland is $143. These costs include accommodation (assuming double occupancy, so the traveler is sharing the room), food, transportation, and entertainment. While every person is different, these costs are an average of past travelers in each city. What follows is a categorical breakdown of travel costs for Chicago and Portland in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Chicago $152
    Portland $76
  • Accommodation Typical double-occupancy room
    Chicago $304
    Portland $152
Compare Hotels in Chicago and Portland

Looking for a hotel in Chicago or Portland? Prices vary by location, date, season, and the level of luxury. See below for options and compare which is best for your budget and travel style.

Hotels in Chicago


Hotels in Portland


Kayak helps you find the best prices for hotels, flights, and rental cars for destinations around the world. Compare prices for multiple destinations when planning your next trip.


Our Analysis
We've analyzed the average and typical hotel prices based on guest reviews, star ratings, and hotel amenities here: Chicago Hotel Prices and Portland Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Chicago $29
    Portland $23
Typical Local Transportation prices in Chicago

Here are some examples of typical transportation prices from actual travelers in Chicago:


  • Parking
    $19
  • Taxi Ride
    $10
  • Taxi from Airport
    $45

Hired Cars and Shuttles in Chicago

Some specific examples of transportation prices in Chicago:

  • Transfers in Chicago: $107
  • Transfer to Chicago Premium Outlets: $288
  • Transfer from O'Hare International Airport to Chicago: $93
  • Private transfer: Chicago to Chicago International Airport (MDW): $105
  • Private transfer: Chicago International Airport (MDW) to Chicago: $105
  • Private Transfer: O'Hare International Airport (ORD) to Chicago: $133
  • Private Transfer: Chicago to O'Hare International Airport (ORD): $133
  • Private Transfer from Chicago City to Chicago (ORD) Airport: $113
  • Private Transfer from Chicago City to Chicago (MDW) Airport: $113
  • Private Transfer from Chicago (ORD) Airport to Chicago City: $113
  • Private Transfer from Chicago (MDW) Airport to Chicago City: $113
  • Private Sedan Transfer from Chicago Downtown to O`Hare airport: $100

Hired Cars and Shuttles in Portland

Also for Portland, here are a few examples of actual transportation services:

  • Arrival Business Class Private Transfer Portland Airport PDX to Portland City: $75
  • Arrival Private Transfer from Portland Airport PDX to Oregon, West Linn or Tigar: $82
  • Departure Business Class Private Transfer from Portland Airport PDX to Portland: $75
  • PDX - Portland Airport Transfer - Chauffeured Round Trip in a Luxury Sedan/SUV: $267
  • PDX - Portland One Way Airport Transfer in a Chauffeured Sedan/SUV: $133
  • Portland Airport (PDX) to Beaverton hotel - Round-Trip Private Transfer: $281
  • Portland Airport (PDX) to Beaverton hotel or address - Arrival Private Transfer: $141
  • Portland Airport (PDX) to Lake Oswego - Arrival Private Transfer: $141
  • Portland Airport (PDX) to Lake Oswego - Round-Trip Private Transfer: $281
  • Portland Airport (PDX) to Portland downtown - Arrival Private Transfer: $102
  • Portland Airport (PDX) to Portland downtown - Round-Trip Private Transfer: $204
  • Portland Airport (PDX) to Tigard hotel or address - Arrival Private Transfer: $141

Is it cheaper to fly into Chicago or Portland?

Prices for flights to both Portland and Chicago change regularly based on dates and travel demand. We suggest you find the best prices for your next trip on Kayak, because you can compare the cost of flights across multiple airlines for your prefered dates.





Food
  • Food Meals for one day
    Chicago $37
    Portland $35
Typical Food prices in Chicago

Below are a few samples from actual travelers for food and meal costs in Chicago:


  • Dinner for 1
    $24
  • Dinner for 3
    $118

Food Tours and Cooking Classes in Chicago

Also, here are some specific examples of food and dining related activities in Chicago.

  • Traveling Spoon Chicago-Style Deep Dish Pizza Private Online Cooking Class: $27
  • Learn to Make Chicago Deep-Dish Pizza with a Local: $49
  • Lonely Planet Experiences: River North Historical Food Tour: $61
  • Private Fusion Cooking Class in Downtown Chicago: $64
  • Best in Chow: Chicago River North Food Tour: $64
  • Signature Food Tour at Chicago's Navy Pier: $64
  • Skip the Line: Tommy Gun's Garage Dinner and Show Ticket: $67
  • Small-Group Chicago Food Tour: Gold Coast and Old Town: $75
  • Best of Chicago Tour Including a Deep-Dish Pizza: $75
  • River North Walking Food Tour: $75
  • Chicago's Wicker Park Food Tour: $75
  • Private Indian-Mexican Fusion Cooking Class with a Modern Cook: $78

Typical Food prices in Portland

For Portland, here are some examples of average food and meal prices for travelers:


  • Afternoon Drinks (for 2)
    $9.50

Food Tours and Cooking Classes in Portland

For Portland, here are some samples of tours and activities related to meals and dining experiences:

  • Arts District Food Tour: $84
  • Portland's Art District Food Tour: $84
  • Walking Food Tour in Downtown Portland with Brunch: $86
  • Downtown Deluxe Food Tour: $89
  • Tastes of Downtown Portland Walking Food Tour: $89
  • 2.5-Hour Dinner Cruise Through Downtown Portland: $108

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Chicago $34
    Portland $19
Typical Entertainment prices in Chicago

Here are a few typical costs in Chicago for activities, ticket prices, and tours that come from previous visitors:


  • Sears Tower (family of 4)
    $102
  • Aquarium for 4
    $118
  • Water Taxi (family of 4)
    $22
  • IMAX Movie for Two
    $35
  • Shakespeare Play (2)
    $116
  • Art Institute (2)
    $36
  • U-Boat Tour (2)
    $8.00

Tours and Activities in Chicago

Here are a few actual costs in Chicago for available activities, ticket prices, and tours:

  • 2 Hours Chicago Sightseeing Tour - Luxury Private Stretch Limo / 8 Passengers: $250
  • 2-Hour Chicago City Lights and Skyline Segway Tour: $76
  • 2-Hour Chicago Fireworks Segway Tour: $76
  • 2-Hour Chicago Lakefront and Museum Campus Segway Tour: $73
  • 2-Hour Haunted Segway Tour of Chicago: $76
  • 2-Hour History of Chicago Architecture and Art Segway Tour: $75
  • 3 Hours Chicago Sightseeing Tour - Luxury Private SUV, ALL Inclusive: $392
  • 4 Hours Chicago Sightseeing Tour - Luxury Private SUV, ALL Inclusive: $220
  • 4 Hours Chicago Sightseeing Tour - Luxury Private Sedan: $215
  • 4 Hours Chicago Sightseeing Tour - Luxury Private Stretch Limousine/8 passengers: $728
  • A Most Magnificent Mile Shopping and Sightseeing Tour: $40
  • A Storied Neighborhood: Dance the dialectic with Bill Ayers on an audio tour: $5.00

Tours and Activities in Portland

For Portland, here are a few prices for actual activities, tours, and tickets provided by various companies:

  • The Eastern Promenade: Explore the sounds and vistas on an audio walking tour: $5.20
  • Downtown Portland's Outdoor Sculptures Walking Audio Tour by VoiceMap: $5.20
  • Portland Scavenger Hunt Adventure: $21
  • Portland Old Town Ghost Tour: $22
  • Intro to Portland Small Group Walking Tour: $29
  • Pink Trolley City Tour of Portland - 2pm: $29
  • Pink Trolley City Tour of Portland - 10am: $29
  • Underground Donut Tour: Portland's Only Donut Tour: $30
  • Portland's Only Underground Donut Tour: $31
  • Vintage Fire Truck Sightseeing Tour of Portland Maine: $35
  • Private Tour: Downtown Portland and City Highlights: $38
  • Essential Portland Bike Tour: $40

For more ideas for your next trip, check out The Best Free Things to Do in Chicago, Chicago Bucket List: The Best Places to See, and The Best Museums in Chicago.


Alcohol
  • Alcohol Drinks for one day
    Chicago $20
    Portland $14

Sample the Local Flavors in Chicago

Here are a few nightlife and alcohol tours and activities from local tour providers in Chicago:

  • Haunted Chicago Ghost and Pub Walking Tour: $25
  • Walking tour to Chicago dive bars: $41
  • Chicago Barrel Bus Craft Distillery Tour: $90
  • Chicago Craft Brewery Barrel Bus Tour: $90
  • Ultimate Girl's Night Out in Sparkling Wine, Photo Shoot, Burlesque: $900

Sample the Local Flavors in Portland

Some specific costs for nightlife related activities in Portland:

  • Power Through Portland Bar Crawl: $12
  • Oregon Priority Wine Tasting Pass: $40
  • Weird Bar Crawl with Fanatical Local: $49
  • Eastside Craft Brewery Walking Tour: $55
  • Portland Brewery Bike Tour: $71
  • Oregon Famous Wine Country Wine Tasting Adventure: $75
  • Brews & Bites - Food Carts & Brewery Tour: $94
  • Views and Brews, Portland Brewery Bike Tour: $118
  • 5-Hour Willamette Valley Wine Tour with Tastings: $120
  • Oregon Coast Brewery Tour: $130
  • Willamette Valley Wine Tasting from Portland: $139
  • Full-Day City & Oregon Wine Tasting Tour: $140


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.


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 are around 77°F (25°C), and Portland is 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.


  • Summer Average Temperatures July
    Chicago 77°F (25°C) 
    Portland 68°F (20°C)

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. Temperatures in Chicago average around 56°F (14°C), and Portland stays 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.


  • Autumn Average Temperatures October
    Chicago 56°F (14°C) 
    Portland 55°F (13°C)

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 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 temperature in Chicago is usually 25°F (-4°C) in January, and Portland stays 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.


  • Winter Average Temperatures January
    Chicago 25°F (-4°C) 
    Portland 40°F (4°C)

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 are around 52°F (11°C), and Portland is 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.


  • Spring Average Temperatures April
    Chicago 52°F (11°C) 
    Portland 51°F (11°C)

Typical Weather for Portland and Chicago

Chicago Portland
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 25°F (-4°C) 1.9 inches (47 mm) 40°F (4°C) 5.2 inches (132 mm)
Feb 29°F (-2°C) 1.4 inches (35 mm) 44°F (7°C) 3.9 inches (98 mm)
Mar 41°F (5°C) 3.7 inches (93 mm) 47°F (9°C) 3.6 inches (92 mm)
Apr 52°F (11°C) 4.3 inches (108 mm) 51°F (11°C) 2.4 inches (61 mm)
May 63°F (17°C) 3 inches (75 mm) 57°F (14°C) 2 inches (51 mm)
Jun 73°F (23°C) 3.9 inches (100 mm) 64°F (18°C) 1.5 inches (39 mm)
Jul 77°F (25°C) 3.9 inches (100 mm) 68°F (20°C) 0.7 inches (18 mm)
Aug 76°F (24°C) 3.5 inches (90 mm) 69°F (20°C) 1 inches (25 mm)
Sep 68°F (20°C) 3.8 inches (96 mm) 63°F (17°C) 1.7 inches (44 mm)
Oct 56°F (14°C) 2.2 inches (56 mm) 55°F (13°C) 2.6 inches (67 mm)
Nov 44°F (7°C) 2.2 inches (56 mm) 46°F (8°C) 5.4 inches (136 mm)
Dec 31°F (-1°C) 2.8 inches (71 mm) 40°F (5°C) 6.1 inches (156 mm)


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Chicago vs. Portland Travel Comparison

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