A Travel Price Comparison for Families, Couples, and Backpackers San Jose vs. Chicago for Vacations, Tours, and Honeymoons

Should you visit San Jose or Chicago?

Which is cheaper to visit? Which is more expensive for vacation?

If you're trying to decide where to visit between San Jose or Chicago, this travel comparison, which includes costs, can help. The overall cost of travel is usually a consideration when deciding where to go next, and the cost comparison down below can help you decide based on the average prices from other travelers along with your own travel budget.

Where Should I go: San Jose or Chicago?

San Jose

San Jose is the capital city of Costa Rica and is likely to be your first and last stop in a visit to the country. The city is situated in the Central Valley and is surrounded by beautiful mountains and valleys, making for a beautiful flight in. The city has an elevation of 1200 meters and sits on a plateau with a beautiful backdrop of lush green forest. Half of the people in Costa Rica reside in the country's capital city. You are likely to stay only a day or two, but there are a handful of things to do and see including museums and markets. You will also find many embassies, as well as the University of Costa Rica in San Jose.

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 Budget Tours to Costa Rica, The Best Tours for Seniors to Costa Rica, The Best Family-Friendly Tours to United States of America, and The Best Wildlife Tours to United States of America.


Which place is cheaper, Chicago or San Jose?

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

The average daily cost (per person) in San Jose is $89, while the average daily cost in Chicago is $288. 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 Jose and Chicago in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    San Jose $48
    Chicago $198
  • Accommodation Typical double-occupancy room
    San Jose $96
    Chicago $396
Compare Hotels in San Jose and Chicago

Looking for a hotel in San Jose 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.

Hotels in San Jose


Hotels in Chicago


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 Jose Hotel Prices and Chicago Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    San Jose $19
    Chicago $37
Typical Local Transportation Prices in San Jose

Some typical examples of transportation costs in San Jose are as follows:


  • Taxi from SJO
    $25
  • Local Bus
    $2.71

Hired Cars and Shuttles in San Jose

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

  • Private Transfer San José Airport - La Fortuna: $180
  • Airport transfer from SJO Airport to Los Sueños Marriott: $170
  • Arrival Transfer San Jose Airport SJO to Arenal by Minivan: $177
  • Arrival Transfer San Jose Airport to Manuel Antonio by Minivan: $158
  • Direct Transfer From San Jose to Monteverde, English Speaking Driver: $181
  • Juan Santamaria International Airport (SJO) to Jaco - Arrival Private Transfer: $68
  • Juan Santamaria International Airport (SJO) to Jaco - Roundtrip Private Transfer: $136
  • Juan Santamaria Intl Airport(SJO) to Puntarenas city-Round-Trip Private Transfer: $167
  • Juan Santamaria Intl. Airport (SJO) to Puntarenas city- Arrival Private Transfer: $83
  • Juan Santamaria Intl. Airport (SJO) to San Jose – Arrival Private Transfer: $32
  • Juan Santamaria Intl. Airport (SJO) to San Jose – Round-Trip Private Transfer: $64
  • One way Transfer from SJO airport or San José to Playa Dominical max 5 passenger: $240

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:

  • Try find your better than us ! Airport transfer in Chicago APT-HTL (ORD) , (MDW): $128
  • Try find your better than us ! Airport transfer in Chicago APT-HTL (ORD) , (MDW): $126
  • Transfer in private vehicle from Chicago City - Chicago Airport (ORD): $138
  • Transfer in private vehicle from Chicago Airport (ORD) -Chicago City: $138
  • RoundTrip transfer in private car from-to Chicago Airport (ORD)- Chicago City: $276
  • Private one-way airport transfer O'Hare Airport to/from Chicago : $86
  • Private Transfer: Midway Airport MDW to Chicago by Luxury SUV: $163
  • Private Transfer from Chicago City to Chicago (MDW) Airport: $144
  • Private Transfer from Chicago (MDW) Airport to Chicago City: $144
  • Private Transfer Chicago to Chicago Airport by Luxury Car or SUV: $87
  • Private Sedan Transfer from Chicago Downtown to O'Hare airport: $220
  • Private SUV Transfer from Chicago Downtown to O'Hare airport: $240

Is it cheaper to fly into San Jose or Chicago?

Prices for flights to both Chicago and San Jose 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
    San Jose $18
    Chicago $49

Food Tours and Cooking Classes in San Jose

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

  • Bites and Sights: Walking Food Tour in San Jose, Costa Rica: $34
  • San Jose By Night Tour: Farm to Table Dinner & Cocktail Class: $57
  • San Jose Bites and Sights Walking Food Tour and visit Gold Museum : $60
  • Half-Day San Jose Evening Bus Tour with Dinner and Pickup: $76
  • Explore San Jose By Night: Food and Culture Tour with Local Dinner: $80
  • Dinner + Typical Show in the best viewpoint of the City: $99
  • Arenal Volcano Full-Day Combo Tour with Lunch and Dinner: $179

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 : $40
  • Downtown Pizza Guided Walking Tour with Tastings: $58
  • Chicago's Delicious Donut Adventure and Walking Food Tour: $63
  • Chicago Small Group Food Tour: $69
  • Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise: $72
  • Chicago Pizza Tour: $75
  • Chicago Deep Dish Pizza Self-Guided Tour: $75
  • Chicago Bucktown-Wicker Park Pizza Crawl: $79
  • Chicago West Loop Pizza Crawl: $79
  • Downtown Family Food Tour by Bike with Sightseeing: $80
  • Nitti's Supper Club Dinner and Show: $80
  • Lake Michigan Buffet Brunch, Lunch or Dinner Cruise: $86

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    San Jose $21
    Chicago $47

Tours and Activities in San Jose

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

  • Entrance Ticket to the Farm of Hacienda Orosi: $11
  • Entrance ticket to the Hacienda Orosi: $21
  • Hiking Experience in El Quetzal Private Reserve: $26
  • Private Roasting and Cupping Coffee Experience: $30
  • Sarapiqui Frog Tour: $30
  • Hacienda Alsacia Starbucks Coffe Tour: $31
  • Poas Volcano National Park - Admission Ticket: $32
  • San Jose Walking Nature Tour: Sloths, Birds and Trees: $33
  • Skip the Line: Rescate Wildlife Rescue Centre General Admission Ticket: $35
  • San Jose Like a Local: Customized Private Tour: $35
  • San Jose ART Walking Tour - small groups, creative experience: $35
  • Corso Lecheria Tour: $40

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:

  • Chicagoland Sightseeing in Style Luxury Private Sedan: $190
  • Field Museum of Natural History Early Access Ticket : $73
  • Windy City Ghosts: Hauntings of Chicago Walking Tour: $28
  • 2 Hour Pier Fireworks and Evening Segway Tour in Chicago: $78
  • 2-Hour Chicago Fireworks Segway Tour: $80
  • 2-Hour Chicago Lakefront and Museum Campus Segway Tour: $72
  • 2-Hour Guided Segway Tour of Chicago: $65
  • 2-Hour Haunted Segway Tour of Chicago: $78
  • 3 Hours Chicago Architecture Tour - Skyscrapers and Photo Ops: $135
  • Adults Party Art Experience: $66
  • Amazing Lakefront Segway Tour of Chicago: $79
  • App Chicago self-guided tours with multilingual audioguides: $9.69

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
    San Jose $16
    Chicago $25

Sample the Local Flavors in San Jose

Some specific costs for nightlife related activities in San Jose:

  • Bar Crawl in Downtown San Jose: $38
  • Wine Tour and Tasting: $85
  • Bar Crawl in San Jose in a Deluxe Party Bus: $100

Sample the Local Flavors in Chicago

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

  • Malt Row Walking Brewery Tour: $30
  • Walking tour to Chicago dive bars: $41
  • Chicago Craft Brewery Barrel Bus Tour: $100
  • Craft Brewery Tour by Barrel Bus: $100


When we compare the travel costs of actual travelers between San Jose and Chicago, we can see that Chicago is more expensive. And not only is San Jose much less expensive, but it is actually a significantly cheaper destination. Since San Jose is in Central America 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 Jose would let you spend less money overall. Or, you could decide to spend more money in San Jose 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 Jose.

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


Which is Bigger, San Jose or Chicago?

Chicago has a larger population, and is about 8 times larger than the population of San Jose. When comparing the sizes of San Jose 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 Jose or Chicago?

Chicago has a temperate climate with four distinct seasons, but San Jose experiences a warm climate with fairly sunny weather most of the year.

Should I visit San Jose or Chicago in the Summer?

Both Chicago and San Jose during the summer are popular places to visit. Plenty of visitors come to San Jose because of the warm climate and sunshine that lasts throughout the year. Furthermore, the summer months attract visitors to Chicago because of the beaches, the city activities, the music scene, and the family-friendly experiences.

In July, San Jose is generally around the same temperature as Chicago. Daily temperatures in San Jose average around 28°C (82°F), and Chicago fluctuates around 77°F (25°C).

In Chicago, it's very sunny this time of the year. In the summer, San Jose often gets less sunshine than Chicago. San Jose gets 164 hours of sunny skies this time of year, while Chicago receives 326 hours of full sun.

Chicago gets a good bit of rain this time of year. It rains a lot this time of the year in San Jose. San Jose usually gets more rain in July than Chicago. San Jose gets 164 mm (6.5 in) of rain, while Chicago receives 3.9 inches (100 mm) of rain this time of the year.


  • Summer Average Temperatures July
    San Jose 28°C (82°F) 
    Chicago 77°F (25°C)

Should I visit San Jose or Chicago in the Autumn?

The autumn attracts plenty of travelers to both San Jose and Chicago. Warm weather and sunshine bring visitors to San Jose year-round. Furthermore, the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area are the main draw to Chicago this time of year.

San Jose is much warmer than Chicago in the autumn. The daily temperature in San Jose averages around 27°C (81°F) in October, and Chicago fluctuates around 56°F (14°C).

San Jose usually receives less sunshine than Chicago during autumn. San Jose gets 169 hours of sunny skies, while Chicago receives 195 hours of full sun in the autumn.

San Jose gets a good bit of rain this time of year. In October, San Jose usually receives more rain than Chicago. San Jose gets 254 mm (10 in) of rain, while Chicago receives 2.2 inches (56 mm) of rain each month for the autumn.


  • Autumn Average Temperatures October
    San Jose 27°C (81°F) 
    Chicago 56°F (14°C)

Should I visit San Jose or Chicago in the Winter?

The winter brings many poeple to San Jose as well as Chicago. San Jose attracts visitors year-round for its warm weather and sunny climate. Additionally, many travelers come to Chicago for the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine.

Be prepared for some very cold days in Chicago. In the winter, San Jose is much warmer than Chicago. Typically, the winter temperatures in San Jose in January average around 27°C (81°F), and Chicago averages at about 25°F (-4°C).

People are often attracted to the plentiful sunshine in San Jose this time of the year. In the winter, San Jose often gets more sunshine than Chicago. San Jose gets 264 hours of sunny skies this time of year, while Chicago receives 134 hours of full sun.

San Jose usually gets less rain in January than Chicago. San Jose gets 8 mm (0.3 in) of rain, while Chicago receives 1.9 inches (47 mm) of rain this time of the year.


  • Winter Average Temperatures January
    San Jose 27°C (81°F) 
    Chicago 25°F (-4°C)

Should I visit San Jose or Chicago in the Spring?

Both Chicago and San Jose are popular destinations to visit in the spring with plenty of activities. The warm climate attracts visitors to San Jose throughout the year. Also, many visitors come to Chicago in the spring for the beaches, the activities around the city, and the natural beauty.

In April, San Jose is generally much warmer than Chicago. Daily temperatures in San Jose average around 29°C (85°F), and Chicago fluctuates around 52°F (11°C).

It's quite sunny in Chicago. The sun comes out a lot this time of the year in San Jose. San Jose usually receives more sunshine than Chicago during spring. San Jose gets 255 hours of sunny skies, while Chicago receives 218 hours of full sun in the spring.

It rains a lot this time of the year in Chicago. In April, San Jose usually receives less rain than Chicago. San Jose gets 28 mm (1.1 in) of rain, while Chicago receives 4.3 inches (108 mm) of rain each month for the spring.


  • Spring Average Temperatures April
    San Jose 29°C (85°F) 
    Chicago 52°F (11°C)

Typical Weather for Chicago and San Jose

San Jose Chicago
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 27°C (81°F) 8 mm (0.3 in) 25°F (-4°C) 1.9 inches (47 mm)
Feb 28°C (83°F) 2 mm (0.1 in) 29°F (-2°C) 1.4 inches (35 mm)
Mar 29°C (84°F) 4 mm (0.2 in) 41°F (5°C) 3.7 inches (93 mm)
Apr 29°C (85°F) 28 mm (1.1 in) 52°F (11°C) 4.3 inches (108 mm)
May 29°C (83°F) 226 mm (8.9 in) 63°F (17°C) 3 inches (75 mm)
Jun 28°C (82°F) 226 mm (8.9 in) 73°F (23°C) 3.9 inches (100 mm)
Jul 28°C (82°F) 164 mm (6.5 in) 77°F (25°C) 3.9 inches (100 mm)
Aug 26°C (79°F) 289 mm (11.4 in) 76°F (24°C) 3.5 inches (90 mm)
Sep 28°C (82°F) 328 mm (12.9 in) 68°F (20°C) 3.8 inches (96 mm)
Oct 27°C (81°F) 254 mm (10 in) 56°F (14°C) 2.2 inches (56 mm)
Nov 27°C (81°F) 121 mm (4.8 in) 44°F (7°C) 2.2 inches (56 mm)
Dec 27°C (81°F) 33 mm (1.3 in) 31°F (-1°C) 2.8 inches (71 mm)