A Travel Price Comparison for United States of America Chicago vs. Portland for Vacations, Tours, and Honeymoons

Should you visit Chicago or Portland?

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

Located in the Midwest, Chicago is the third largest city in the United States. It has a population of almost 3 million and a metropolitan area that covers more than 10,000 square kilometers. It is also a hub for music, comedy and theater. It's skyline is beautiful with modern skyscrapers and Lake Michigan as a backdrop. It is easy to stay entertained in Chicago for weeks. There are world class museums, upscale or eclectic shopping opportunities, and impressive architecture.

Portland

Referred to as "The City of Roses", Portland is the largest city in Oregon. It sits on the banks of the Columbia River and offers breathtaking views of Mount Hood when the weather allows. Portland is famous for its alternative vibe, live music scene, and popular microbreweries. It's also a mecca for environmentally conscious urban planning. The downtown area is quite compact and walkable. While the city itself may be smaller than you expect, it is still the largest metropolitan area between San Francisco and Seattle.

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 $136. 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. Below is a breakdown of travel costs for Chicago and Portland in more detail.



Accommodation

Chicago's average price for two people sharing a typical double-occupancy hotel room is $304. A typical place to stay for one person, per day is $152.

Travelers usually pay around $152 for a double occupancy room in Portland If you want to be in a premiere location or have high end amenities, you can expect to pay a bit more.


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

Food

The price of a meal in Chicago can vary widely. However, the average price for food per day is $37 per person, and a typical meal will cost around $15 based on the spending of previous visitors. Less expensive dining options can be found by eating street food or at fast food restaurants.

While meal prices in Portland can vary, the average travelers spends about $34 per day on food. Based on the spending habits of previous travelers, when dining out, an average meal in Portland should cost around $14 per person. Breakfast prices are usually a little cheaper than lunch or dinner. The price of food in sit-down restaurants in Portland is often higher than fast food prices or street food prices.


  • Food Meals for one day
    Chicago $37
    Portland $34
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
  • Factories to Calories Fulton Market Food Tour: $46
  • Learn to Make Chicago Deep-Dish Pizza with a Local: $49
  • Chicago Crime & Pizza Walk: $50
  • Lonely Planet Experiences: Chicago History and Food Tour: $59
  • Lonely Planet Experiences: River North Historical Food Tour: $61
  • Signature Food Tour at Chicago's Navy Pier: $64
  • Best in Chow: Chicago River North Food Tour: $64
  • Private Fusion Cooking Class in Downtown Chicago: $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

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

Local Transportation

While taxis and private drivers typically cost much more than public transportation, people usually spend around $29 per day to get around in Chicago.

To get around in Portland, the average visitor spends $20 per day, per person. This includes the costs of taxi rides and private drivers as well as public transportation, which tends to be much more affordable.


  • Local Transportation Taxis, local buses, subway, etc.
    Chicago $29
    Portland $20
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.





Entertainment

Activities, things to do, and other forms of entertainment usually cost around $34 per person, per day in Chicago. This cost includes the price of admission tickets to attractions and museums as well as daily tours.

In Portland, the costs for things to do, activities, admission tickets, and other sightseeing expenses are on average $19 per person, per day.


  • 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 Hour Chicago Art and Architecture Segway Tour: $71
  • 2 Hour Pier Fireworks and Evening Segway Tour in Chicago: $65
  • 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
  • 3-Hour Segway Tour of Chicago: $76
  • 360 Chicago Observation Deck Admission: Skip the Ticket Desk: $25
  • 4 Hours Chicago Sightseeing Tour - Luxury Private SUV, ALL Inclusive: $220

Tours and Activities in Portland

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

  • Downtown Portland's Outdoor Sculptures Walking Audio Tour by VoiceMap: $5.20
  • The Eastern Promenade: Explore the sounds and vistas on an audio walking tour: $5.20
  • Portland Scavenger Hunt Adventure: $21
  • Portland Old Town Ghost Tour: $22
  • Downtown Ghost Tour: $23
  • Intro to Portland Small Group Walking Tour: $29
  • Pink Trolley City Tour of Portland - 10am: $29
  • Pink Trolley City Tour of Portland - 2pm: $29
  • Underground Donut Tour: Portland's Only Donut Tour: $30
  • Underground Donut Tour: $30
  • Portland's Only Underground Donut Tour: $31
  • Portland, Maine: 2.5-Hour History Tour with Sweet Treat: $35

Alcohol

While the amount that someone spends on alcohol while visiting Chicago may vary from person to person, on average a person spends $20 per day on alcoholic beverages.

Typically, people visiting Portland spend on average $14 on alcoholic beverages per person, per day.


  • 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
  • Portland's 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.

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Chicago vs. Portland Travel Comparison

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