Which place is cheaper, Chicago or Port-of-Spain?
These are the overall average travel costs for the two destinations. These travel costs come from the actual spending of real travelers.
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Should you visit Port-of-Spain or Chicago?
Which is cheaper to visit? Which is more expensive for vacation?
Trying to figure out where to travel next? This travel comparison between Port-of-Spain and Chicago can help. It includes a travel cost comparison in addition to other factors. For many travelers, the cost of a destination is a primary consideration when choosing where to go.
Where Should I go: Port-of-Spain or Chicago?
Port-of-Spain
Located on the northwest coast of Trinidad island, Port of Spain is the capital of the Caribbean island nation Trinidad & Tobago. It is a hub of activity, especially during the celebration of Carnival for which the island nation is famous.
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.
For some great organized tour ideas, see The Best 2-Week Tours from San Francisco, and The Best 2-Week Tours from Los Angeles.
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Port-of-Spain Prices
Trinidad and Tobago PricesChicago Prices
USA Prices -
Average Daily Cost Per person, per dayPort-of-Spain $213Chicago $323
The average daily cost (per person) in Port-of-Spain is $213, while the average daily cost in Chicago is $323. 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 destination. What follows is a categorical breakdown of travel costs for Port-of-Spain and Chicago in more detail.
Accommodation
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Accommodation Hotel or hostel for one personPort-of-Spain $80Chicago $198
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Accommodation Typical double-occupancy roomPort-of-Spain $160Chicago $396
Compare Hotels in Port-of-Spain and Chicago
Looking for a hotel in Port-of-Spain or Chicago? 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.
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: Port-of-Spain Hotel Prices and Chicago Hotel Prices.
Local Transportation
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Local Transportation Taxis, local buses, subway, etc.Port-of-Spain $49Chicago $37
Typical Local Transportation Prices in Chicago
Here are some examples of typical transportation prices from actual travelers in Chicago:
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Parking$19
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Taxi Ride$10
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Taxi from Airport$45
Hired Cars and Shuttles in Chicago
Some specific examples of transportation prices in Chicago:
- Chicago Private Airport Transfer (ORD) to City: $99
- Chicago to Chicago O'Hare Airport (ORD): Departure Transfer: $103
- Airport Transfer: O'Hare Airport ORD to Chicago by Luxury SUV: $222
- Airport transfer between Chicago O'Hare and Milwaukee: $38
- Arrival Private Transfer: O'Hare Airport ORD to Chicago in Business Car: $165
- Arrival Private Transfer: O'Hare Airport ORD to Chicago in Luxury Car: $255
- Arrival Transfer: O'Hare Airport ORD to Chicago by Luxury SUV: $177
- Chicago ↔ Midway Airport, Top Rated Private Sedan Transfer: $133
- Chicago Airport (MDW) to Chicago - Round-Trip Private Transfer: $150
- Chicago Airport Transfer: Chicago to O'Hare Airport ORD in Business Car: $167
- Chicago Airport Transfer: Chicago to O'Hare Airport ORD in Luxury SUV: $222
- Chicago Airport Transfer: Chicago to O'Hare Airport in Luxury SUV: $150
Is it cheaper to fly into Port-of-Spain or Chicago?
Prices for flights to both Chicago and Port-of-Spain 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
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Food Meals for one dayPort-of-Spain $94Chicago $85
Typical Food Prices in Chicago
Below are a few samples from actual travelers for food and meal costs in Chicago:
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Dinner for 1$24
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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 : $59
- Downtown Pizza Guided Walking Tour with Tastings: $73
- Sushi Making Cooking Class at a Local Distillery in Chicago: $75
- Pasta Making Cooking Class at a Local Distillery: $75
- Sushi Making Cooking Class at a Local Distillery: $75
- Pasta Making Cooking Class at a Local Distillery in Chicago: $75
- Downtown Family Food Tour by Bike with Sightseeing: $80
- Chicago Food Tour & Solve a Murder: Interactive True Crime Tour: $82
- Taste of Chicago's Chinatown Food Tours: $85
- Vito's Vault Chicago finest dinner theatre speakeasy: $85
- Downtown Classics Food Tour: Deep Dish, Beef Sandwich & More: $89
- City Cruises Lake Michigan Lunch or Dinner Cruise: $93
Entertainment
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Entertainment Entrance tickets, shows, etc.Port-of-Spain $59Chicago $47
Typical Entertainment Prices in Chicago
Here are a few typical costs in Chicago for activities, ticket prices, and tours that come from previous visitors:
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Sears Tower (family of 4)$102
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Aquarium for 4$118
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Water Taxi (family of 4)$22
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IMAX Movie for Two$35
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Shakespeare Play (2)$116
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Art Institute (2)$36
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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:
- Eastside Chicago The Heist Exploration Game and Tour: $7.13
- Dragon Kings Quest Experience in Chinatown Chicago: $7.13
- Haunted Chicago Exploration Game and Tour: $7.13
- Chicago Scavenger Hunt and Highlights Self-Guided Tour: $7.82
- Chicago Chocolate Tour: $8.00
- Lincoln Park Zoo Adventure: $8.00
- Chicago Self-Guided Audio Tour: $9.00
- Chicago’s Millennium Park Self Guided Audio GPS Walking Tour: $9.75
- Chicago Haunted Ghost Tour GPS Self-Guided Walking Tour: $9.75
- Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour: $9.99
- Illinois Holocaust Museum presents Experience360 Ticket: $12
- Chicago Millennium Park Self-Guided Walking Tour: $13
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
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Alcohol Drinks for one dayPort-of-Spain $22Chicago $25
Sample the Local Flavors in Chicago
Here are a few nightlife and alcohol tours and activities from local tour providers in Chicago:
- Chicago Bar Crawl: Chi-Town Showdown: $15
- Chicago Local Brewery Expedition with Homemade Guacamole: $63
- Chicago Craft Brewery Barrel Bus Tour: $100
- Craft Brewery Tour by Barrel Bus: $100
- Chicago:Milwaukee City Highlights Day Trip with Brewery Tour: $106
When we compare the travel costs of actual travelers between Port-of-Spain and Chicago, we can see that Chicago is more expensive. And not only is Port-of-Spain much less expensive, but it is actually a significantly cheaper destination. Since Port-of-Spain is in Caribbean Islands and Chicago is in North America, this is one of the main reasons why the costs are so different, as different regions of the world tend to have overall different travel costs. So, traveling to Port-of-Spain would let you spend less money overall. Or, you could decide to spend more money in Port-of-Spain 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 Port-of-Spain.
If you're trying to decide if either of these two destinations are within your price range, also see Is Port-of-Spain Expensive? and Is Chicago Expensive?.
Which is Bigger, Port-of-Spain or Chicago?
Chicago has a larger population, and is about 60 times larger than the population of Port-of-Spain. When comparing the sizes of Port-of-Spain and Chicago, 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 Port-of-Spain or Chicago?
Chicago has a temperate climate with four distinct seasons, but Port-of-Spain experiences a warm climate with fairly sunny weather most of the year.
Should I visit Port-of-Spain or Chicago in the Summer?
Both Chicago and Port-of-Spain are popular destinations to visit in the summer with plenty of activities. The warm climate attracts visitors to Port-of-Spain throughout the year. Also, most visitors come to Chicago for the beaches, the city activities, the music scene, and the family-friendly experiences during these months.
Port-of-Spain is around the same temperature as Chicago in the summer. The daily temperature in Port-of-Spain averages around 27°C (81°F) in July, and Chicago fluctuates around 77°F (25°C).
It's quite sunny in Chicago. The sun comes out a lot this time of the year in Port-of-Spain. Port-of-Spain usually receives less sunshine than Chicago during summer. Port-of-Spain gets 206 hours of sunny skies, while Chicago receives 326 hours of full sun in the summer.
It rains a lot this time of the year in Chicago. It's quite rainy in Port-of-Spain. In July, Port-of-Spain usually receives more rain than Chicago. Port-of-Spain gets 266 mm (10.5 in) of rain, while Chicago receives 3.9 inches (100 mm) of rain each month for the summer.
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Summer Average Temperatures JulyPort-of-Spain 27°C (81°F)Chicago 77°F (25°C)
Should I visit Port-of-Spain or Chicago in the Autumn?
Both Chicago and Port-of-Spain during the autumn are popular places to visit. Plenty of visitors come to Port-of-Spain because of the warm climate and sunshine that lasts throughout the year. Furthermore, 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.
In the autumn, Port-of-Spain is much warmer than Chicago. Typically, the autumn temperatures in Port-of-Spain in October average around 27°C (81°F), and Chicago averages at about 56°F (14°C).
It's quite sunny in Port-of-Spain. In the autumn, Port-of-Spain often gets around the same amount of sunshine as Chicago. Port-of-Spain gets 207 hours of sunny skies this time of year, while Chicago receives 195 hours of full sun.
It rains a lot this time of the year in Port-of-Spain. Port-of-Spain usually gets more rain in October than Chicago. Port-of-Spain gets 199 mm (7.8 in) of rain, while Chicago receives 2.2 inches (56 mm) of rain this time of the year.
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Autumn Average Temperatures OctoberPort-of-Spain 27°C (81°F)Chicago 56°F (14°C)
Should I visit Port-of-Spain or Chicago in the Winter?
The winter attracts plenty of travelers to both Port-of-Spain and Chicago. Warm weather and sunshine bring visitors to Port-of-Spain year-round. Furthermore, the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine are the main draw to Chicago this time of year.
It's quite cold in Chicago in the winter. In January, Port-of-Spain is generally much warmer than Chicago. Daily temperatures in Port-of-Spain average around 26°C (78°F), and Chicago fluctuates around 25°F (-4°C).
In Port-of-Spain, it's very sunny this time of the year. Port-of-Spain usually receives more sunshine than Chicago during winter. Port-of-Spain gets 241 hours of sunny skies, while Chicago receives 134 hours of full sun in the winter.
In January, Port-of-Spain usually receives more rain than Chicago. Port-of-Spain gets 71 mm (2.8 in) of rain, while Chicago receives 1.9 inches (47 mm) of rain each month for the winter.
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Winter Average Temperatures JanuaryPort-of-Spain 26°C (78°F)Chicago 25°F (-4°C)
Should I visit Port-of-Spain or Chicago in the Spring?
The spring brings many poeple to Port-of-Spain as well as Chicago. Port-of-Spain attracts visitors year-round for its warm weather and sunny climate. Additionally, many travelers come to Chicago for the beaches, the activities around the city, and the natural beauty.
Port-of-Spain is much warmer than Chicago in the spring. The daily temperature in Port-of-Spain averages around 27°C (81°F) in April, and Chicago fluctuates around 52°F (11°C).
The sun comes out a lot this time of the year in Chicago. People are often attracted to the plentiful sunshine in Port-of-Spain this time of the year. In the spring, Port-of-Spain often gets more sunshine than Chicago. Port-of-Spain gets 238 hours of sunny skies this time of year, while Chicago receives 218 hours of full sun.
It's quite rainy in Chicago. Port-of-Spain usually gets less rain in April than Chicago. Port-of-Spain gets 51 mm (2 in) of rain, while Chicago receives 4.3 inches (108 mm) of rain this time of the year.
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Spring Average Temperatures AprilPort-of-Spain 27°C (81°F)Chicago 52°F (11°C)
Typical Weather for Chicago and Port-of-Spain
| Port-of-Spain | Chicago | |||
|---|---|---|---|---|
| Temp (°C) | Rain (mm) | Temp (°C) | Rain (mm) | |
| Jan | 26°C (78°F) | 71 mm (2.8 in) | 25°F (-4°C) | 1.9 inches (47 mm) |
| Feb | 26°C (79°F) | 43 mm (1.7 in) | 29°F (-2°C) | 1.4 inches (35 mm) |
| Mar | 26°C (80°F) | 34 mm (1.3 in) | 41°F (5°C) | 3.7 inches (93 mm) |
| Apr | 27°C (81°F) | 51 mm (2 in) | 52°F (11°C) | 4.3 inches (108 mm) |
| May | 28°C (82°F) | 117 mm (4.6 in) | 63°F (17°C) | 3 inches (75 mm) |
| Jun | 27°C (81°F) | 252 mm (9.9 in) | 73°F (23°C) | 3.9 inches (100 mm) |
| Jul | 27°C (81°F) | 266 mm (10.5 in) | 77°F (25°C) | 3.9 inches (100 mm) |
| Aug | 27°C (81°F) | 225 mm (8.9 in) | 76°F (24°C) | 3.5 inches (90 mm) |
| Sep | 27°C (81°F) | 203 mm (8 in) | 68°F (20°C) | 3.8 inches (96 mm) |
| Oct | 27°C (81°F) | 199 mm (7.8 in) | 56°F (14°C) | 2.2 inches (56 mm) |
| Nov | 27°C (80°F) | 228 mm (9 in) | 44°F (7°C) | 2.2 inches (56 mm) |
| Dec | 26°C (79°F) | 155 mm (6.1 in) | 31°F (-1°C) | 2.8 inches (71 mm) |
Budget Your Trip is all about finding out how much everything costs so that you can travel cheaper and longer. Created by avid travelers Laurie and Bryan, our goal is to help you plan your next trip on the right budget. With average daily travel costs that are calculated from the budgets of real travelers, plus an analysis of hotel and tour prices, you can find out how much money you need to plan your next adventure. We also have plenty of travel advice, accommodation reviews, and activity suggestions.