Which place is cheaper, Chicago or San Juan?
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 San Juan or Chicago?
Which is cheaper to visit? Which is more expensive for vacation?
Should I visit San Juan or Chicago? This is a common question asked by many travelers. By figuring out which city has activities that align with your interests along with knowing which is more affordable, you'll understand where you can get more bang for your buck. So, let's dive into the details and the data, which all comes from actual travelers.
Where Should I go: San Juan or Chicago?
San Juan
If you've ever set foot on a Caribbean cruise, you've probably spent a bit of time in San Juan, Puerto Rico. However, maybe you should consider spending more than just a port day in this beautiful and historically rich city.
As the capital and largest city in all of Puerto Rico, San Juan is home to approximately 400,000 people. Established in 1521, it is also the second oldest European-founded settlement in the Americas.
As this city fuses a historic paradise with modern day energy, it has absolutely everything to offer. Intellectual wanderers, beach bums, rainforest adventurers and radical surfers will all find plenty to do in San Juan.
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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San Juan Prices
Puerto Rico PricesChicago Prices
USA Prices -
Average Daily Cost Per person, per daySan Juan $218Chicago $323
The average daily cost (per person) in San Juan is $218, 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 San Juan and Chicago in more detail.
Accommodation
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Accommodation Hotel or hostel for one personSan Juan $124Chicago $198
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Accommodation Typical double-occupancy roomSan Juan $248Chicago $396
Compare Hotels in San Juan and Chicago
Looking for a hotel in San Juan 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: San Juan Hotel Prices and Chicago Hotel Prices.
Local Transportation
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Local Transportation Taxis, local buses, subway, etc.San Juan $14Chicago $37
Hired Cars and Shuttles in San Juan
Also for San Juan, here are a few examples of actual transportation services:
- Airport Transfer to Cruise Ships, Hotels, Airbnb in San Juan: $76
- Arrival Private Transfer SJU Airport to Old San Juan by Sedan: $120
- Carabali Rain Forest Round Trip Private Taxi Transfer: $200
- Departure Transfer from Old San Juan to to SJU Airport by Car: $86
- Premium Transfer in Airport, Hotel, Airbnb, Cruise: $25
- Private Airport Transfers to Ceiba Ferry Terminal and Airport: $155
- Private Departure Transfer - Hotel / Accommodation to San Juan Airport: $22
- Private Transfer Puerto Rico:To or From Airports, Hotels &Cruises: $33
- Private Transfer from SJU Airport to Cruise Port Roundtrip Servic: $109
- Private Transfer from SJU Airport to San Juan / Rio Grande: $115
- Private Transfer from or to San Juan and Ceiba Ferry: $93
- Puerto Rico Island Wide Private Transfers, 11Pax Lux Sprinter Van: $93
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:
- Group Van Transfers from Chicago O'Hare and Midway Airports: $300
- Meet and Greet Private SUV Transfer from ORD to Downtown Chicago: $300
- Meet and Greet Private SUV Transfer from MDW to Downtown Chicago: $300
- Departure Private Transfer: Chicago to O'Hare Airport ORD in Luxury Car: $257
- Arrival Private Transfer: O'Hare Airport ORD to Chicago in Luxury Car: $255
- Private SUV Transfer from Chicago Downtown to O'Hare airport: $240
- Meet and Greet Private Sedan Transfer from ORD to Downtown Chicago: $240
- Curbside SUV Transfer from O'Hare/Midway to Downtown Chicago: $240
- Curbside SUV Transfer from ORD to Downtown Chicago: $240
- SUV transfer from downtown Chicago to O'hare Midway Airport: $240
- Meet and Greet Private Sedan Transfer from MDW to Downtown Chicago: $240
- Private SUV Transfer from Chicago Downtown to Midway airport: $240
Is it cheaper to fly into San Juan or Chicago?
Prices for flights to both Chicago and San Juan 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 daySan Juan $62Chicago $85
Food Tours and Cooking Classes in San Juan
For San Juan, here are some samples of tours and activities related to meals and dining experiences:
- Authentic Flavors of San Juan Food Tour: $165
- FlyDining: Sunset & City Lights Dinner Over Old San Juan: $165
- Morning Old San Juan Food Tour: $169
- Cooking and Connecting with a Local in Puerto Rico: $173
- Savor the Sunset: Old San Juan Walking Food Tour: $179
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.San Juan $49Chicago $47
Typical Entertainment Prices in San Juan
For San Juan, here are some examples of average entertainment and activity prices from previous travelers:
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Horseback Riding Tour$40
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Full Day Snorkeling Trip$100
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1 Hr Windsurfing Lesson$75
Tours and Activities in San Juan
Also, here are some specific examples of entertainment, tickets, and activities for San Juan.
- Transportation in San Juan, Isla verde, Condado, Hotels, Cruises & Airbnb's SJU: $14
- San Juan Self-Guided Walking Audio Tour: $17
- Eco Friendly Farming Tour to Explore Dorado's Most Beautiful Farm: $20
- Discover Superb Self-Guided Audio Tour: $20
- Group Transportation in airport, cruise ships, hotels, bnb's in San Juan, PR: $23
- Old San Juan Walking Tour with a Local Certified Guide: $25
- San Juan Ghost Tour: Shrieks in the Sugarcane: $32
- Historic Old San Juan Sunset Walking Tour: $39
- Old San Juan City Walking Tour: $39
- Old San Juan Walking Tour: $39
- Top Rated El Yunque Rainforest & Waterslide – VIP SmallGroup Tour: $45
- Ron del Barrilito Heritage Skip-the-Line Tour: $46
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:
- Field Museum of Natural History Early Access Ticket : $73
- 2 Hour Chicago Landmarks & Lakefront E-Bike Tour: $69
- 2 Hour Chicago Pier Fireworks & Evening Segway Tour: $78
- 2 Hour Private Chicago Soul House Tour: $65
- 2-Hour Chicago Lakefront & Museum Campus Segway Tour: $67
- 3 Hours Chicago Architecture Tour - Skyscrapers and Photo Ops: $135
- 360 Chicago Observation Deck Sip and View Ticket: $44
- 90 minute Chicago's Chinatown History and Culture Tour: $30
- African American Heritage Tour of Chicago : $125
- Amazing Lakefront Segway Tour of Chicago: $52
- American Writers Museum Admission Ticket: $16
- Architectural and Historical Private Tour in Downtown Chicago: $199
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 daySan Juan $12Chicago $25
Sample the Local Flavors in San Juan
Some specific costs for nightlife related activities in San Juan:
- Old San Juan Bar Crawl: Experience Local Hotspots: $65
- The Pinones Pub crawl Bar crawl : $70
- Local Puerto Rican Rum Distillery Tour - Ron Pepon: $90
- Puerto Rico's First and Only Craft Beer Brewery Tour! : $99
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 San Juan and Chicago, we can see that Chicago is more expensive. And not only is San Juan much less expensive, but it is actually a significantly cheaper destination. Since San Juan 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 San Juan would let you spend less money overall. Or, you could decide to spend more money in San Juan 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 San Juan.
If you're trying to decide if either of these two destinations are within your price range, also see Is San Juan Expensive? and Is Chicago Expensive?.
Which is Bigger, San Juan or Chicago?
Chicago has a larger population, and is about 7 times larger than the population of San Juan. When comparing the sizes of San Juan 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 San Juan or Chicago?
Chicago has a temperate climate with four distinct seasons, but San Juan experiences a warm climate with fairly sunny weather most of the year.
Should I visit San Juan or Chicago in the Summer?
The summer brings many poeple to San Juan as well as Chicago. San Juan attracts visitors year-round for its warm weather and sunny climate. Additionally, many travelers come to Chicago for the beaches, the city activities, the music scene, and the family-friendly experiences.
In July, San Juan is generally a little warmer than Chicago. Daily temperatures in San Juan average around 28°C (83°F), and Chicago fluctuates around 77°F (25°C).
The sun comes out a lot this time of the year in Chicago. People are often attracted to the plentiful sunshine in San Juan this time of the year. In the summer, San Juan often gets less sunshine than Chicago. San Juan gets 287 hours of sunny skies this time of year, while Chicago receives 326 hours of full sun.
It's quite rainy in Chicago. San Juan usually gets around the same amount of rain in July as Chicago. San Juan gets 95 mm (3.7 in) of rain, while Chicago receives 3.9 inches (100 mm) of rain this time of the year.
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Summer Average Temperatures JulySan Juan 28°C (83°F)Chicago 77°F (25°C)
Should I visit San Juan or Chicago in the Autumn?
Both Chicago and San Juan are popular destinations to visit in the autumn with plenty of activities. The warm climate attracts visitors to San Juan throughout the year. Also, 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.
San Juan is much warmer than Chicago in the autumn. The daily temperature in San Juan averages around 28°C (82°F) in October, and Chicago fluctuates around 56°F (14°C).
The sun comes out a lot this time of the year in San Juan. San Juan usually receives more sunshine than Chicago during autumn. San Juan gets 235 hours of sunny skies, while Chicago receives 195 hours of full sun in the autumn.
It's quite rainy in San Juan. In October, San Juan usually receives more rain than Chicago. San Juan gets 135 mm (5.3 in) of rain, while Chicago receives 2.2 inches (56 mm) of rain each month for the autumn.
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Autumn Average Temperatures OctoberSan Juan 28°C (82°F)Chicago 56°F (14°C)
Should I visit San Juan or Chicago in the Winter?
Both Chicago and San Juan during the winter are popular places to visit. Plenty of visitors come to San Juan because of the warm climate and sunshine that lasts throughout the year. Also, most visitors come to Chicago for the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine during these months.
Chicago can be very cold during winter. In the winter, San Juan is much warmer than Chicago. Typically, the winter temperatures in San Juan in January average around 25°C (77°F), and Chicago averages at about 25°F (-4°C).
It's quite sunny in San Juan. In the winter, San Juan often gets more sunshine than Chicago. San Juan gets 240 hours of sunny skies this time of year, while Chicago receives 134 hours of full sun.
San Juan usually gets more rain in January than Chicago. San Juan gets 58 mm (2.3 in) of rain, while Chicago receives 1.9 inches (47 mm) of rain this time of the year.
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Winter Average Temperatures JanuarySan Juan 25°C (77°F)Chicago 25°F (-4°C)
Should I visit San Juan or Chicago in the Spring?
The spring attracts plenty of travelers to both San Juan and Chicago. Warm weather and sunshine bring visitors to San Juan year-round. Also, the spring months attract visitors to Chicago because of the beaches, the activities around the city, and the natural beauty.
In April, San Juan is generally much warmer than Chicago. Daily temperatures in San Juan average around 26°C (79°F), and Chicago fluctuates around 52°F (11°C).
People are often attracted to the plentiful sunshine in Chicago this time of the year. In San Juan, it's very sunny this time of the year. San Juan usually receives more sunshine than Chicago during spring. San Juan gets 272 hours of sunny skies, while Chicago receives 218 hours of full sun in the spring.
Chicago receives a lot of rain in the spring. In April, San Juan usually receives less rain than Chicago. San Juan gets 69 mm (2.7 in) of rain, while Chicago receives 4.3 inches (108 mm) of rain each month for the spring.
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Spring Average Temperatures AprilSan Juan 26°C (79°F)Chicago 52°F (11°C)
Typical Weather for Chicago and San Juan
| San Juan | Chicago | |||
|---|---|---|---|---|
| Temp (°C) | Rain (mm) | Temp (°C) | Rain (mm) | |
| Jan | 25°C (77°F) | 58 mm (2.3 in) | 25°F (-4°C) | 1.9 inches (47 mm) |
| Feb | 25°C (77°F) | 41 mm (1.6 in) | 29°F (-2°C) | 1.4 inches (35 mm) |
| Mar | 26°C (78°F) | 45 mm (1.8 in) | 41°F (5°C) | 3.7 inches (93 mm) |
| Apr | 26°C (79°F) | 69 mm (2.7 in) | 52°F (11°C) | 4.3 inches (108 mm) |
| May | 27°C (81°F) | 120 mm (4.7 in) | 63°F (17°C) | 3 inches (75 mm) |
| Jun | 28°C (82°F) | 82 mm (3.2 in) | 73°F (23°C) | 3.9 inches (100 mm) |
| Jul | 28°C (83°F) | 95 mm (3.7 in) | 77°F (25°C) | 3.9 inches (100 mm) |
| Aug | 28°C (83°F) | 130 mm (5.1 in) | 76°F (24°C) | 3.5 inches (90 mm) |
| Sep | 28°C (83°F) | 130 mm (5.1 in) | 68°F (20°C) | 3.8 inches (96 mm) |
| Oct | 28°C (82°F) | 135 mm (5.3 in) | 56°F (14°C) | 2.2 inches (56 mm) |
| Nov | 27°C (80°F) | 132 mm (5.2 in) | 44°F (7°C) | 2.2 inches (56 mm) |
| Dec | 26°C (78°F) | 92 mm (3.6 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.