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

Should you visit Sao Paulo or Chicago?

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

If you're trying to decide where to visit between Sao Paulo 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: Sao Paulo or Chicago?

Sao Paulo

With a population of around 11 million, and 20 million in the metropolitan area, Sao Paulo is the largest city in Brazil. It's also one of the wealthiest cities in the southern hemisphere, although you don't have to look far to see the income disparities and inequalities that exist. The city is diverse and culturally rich, with excellent food, music, and entertainment.

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 Tours for Outdoor and Nature Lovers in Brazil, The Best Adventure Tours to Brazil, 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 Sao Paulo?

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

The average daily cost (per person) in Sao Paulo is $53, 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 Sao Paulo and Chicago in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Sao Paulo $30
    Chicago $198
  • Accommodation Typical double-occupancy room
    Sao Paulo $60
    Chicago $396
Compare Hotels in Sao Paulo and Chicago

Looking for a hotel in Sao Paulo 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 Sao Paulo


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: Sao Paulo Hotel Prices and Chicago Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Sao Paulo $5.96
    Chicago $37

Hired Cars and Shuttles in Sao Paulo

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

  • Campinas Airport (VCP) to Praia Grande/Santos - Private Transfer: $63
  • Campinas Airport (VCP) to Praia/Santos Hotels Round-Trip Transfer: $125
  • Campinas Airport (VCP) to Praia/Santos hotels - Arrival Transfer: $63
  • Campinas Airport (VCP) to Sao Paulo hotels - Arrival Transfer: $38
  • Campinas Airport (VCP) to Sao Paulo hotels - Round-Trip Transfer: $77
  • Campinas Airport (VCP)to Praia Grande/Santos - RoundTrip Transfer: $125
  • Campinas Viracopos Airport (VCP) to Sao Paulo - Private Transfer: $38
  • Departure Private Transfers: Sao Paulo to Guarulhos Airport GRU in Business Car: $123
  • Departure private transfer from São Paulo city to Guarulhos Airport by minibus: $197
  • Downtown to Sao Paulo Airport (GRU) - Departure Private Transfer: $181
  • Private Arrival Transfer | Congonhas Airport (CGH) x São Paulo City: $95
  • Private Arrival Transfer | Viracopos Airport (VCP) x São Paulo City : $300

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:

  • Meet and Greet Private SUV Transfer from MDW to Downtown Chicago: $300
  • Meet and Greet Private SUV Transfer from ORD to Downtown Chicago: $300
  • RoundTrip transfer in private car from-to Chicago Airport (ORD)- Chicago City: $276
  • Private SUV Transfer from Chicago Downtown to O'Hare airport: $240
  • Meet and Greet Private Sedan Transfer from MDW to Downtown Chicago: $240
  • Private SUV Transfer from Chicago Downtown to Midway airport: $240
  • Meet and Greet Private Sedan Transfer from ORD to Downtown Chicago: $240
  • Arrival Private Transfer: O'Hare Airport ORD to Chicago in Luxury Car: $234
  • Private Sedan Transfer from Chicago Downtown to O'Hare airport: $220
  • Arrival Private Transfer: O'Hare Airport ORD to Chicago in Luxury SUV: $203
  • Chicago Airport Transfer: O'Hare Airport ORD to Chicago in Luxury SUV: $203
  • Chicago Airport Transfer: Chicago to O'Hare Airport ORD in Luxury SUV: $203

Is it cheaper to fly into Sao Paulo or Chicago?

Prices for flights to both Chicago and Sao Paulo 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
    Sao Paulo $15
    Chicago $49

Food Tours and Cooking Classes in Sao Paulo

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

  • Private Traditional Brazilian or Paulistano Cooking Class with a Chef: $130
  • Authentic Brazilian Cooking Experience in SP: Feijoada & Moqueca: $189

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.
    Sao Paulo $4.08
    Chicago $47

Tours and Activities in Sao Paulo

Also, here are some specific examples of entertainment, tickets, and activities for Sao Paulo.

  • Downtown São Paulo's Epic History: A Self-Guided Audio Tour: $5.99
  • São Paulo (Ibirapuera) Scavenger Hunt and Sights Self-Guided Tour: $7.84
  • São Paulo Paulista Avenue City Sights Self-Guided Tour: $7.89
  • Walking Tour Historic Center in São Paulo: $13
  • Discover Sao Paulo History Guided Tour: $27
  • Night Walking Tour through the Bars of São Paulo : $35
  • Night Walking Tour through the Bars of Augusta street: $35
  • Breakfast Tour in Bom Retiro: $43
  • São Paulo: 2 Hours - Liberdade "Street Food" Tour: $54
  • City Tour Meet São Paulo Half-Day: $64
  • Bixiga Walking Tour: $67
  • Sao Paulo Culture Walking Tour: $69

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
    Sao Paulo $3.55
    Chicago $25

Sample the Local Flavors in Sao Paulo

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

  • São Paulo Nightlife: Pub Crawl in the City that Never Sleeps!: $49
  • Half Day Private Wine Tour from São Roque: $54
  • Wine Tour in São Roque by car - tour with local guides: $98
  • 4 Hours Pub Crawl in Vila Madalena: $150

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 Sao Paulo and Chicago, we can see that Chicago is more expensive. And not only is Sao Paulo much less expensive, but it is actually a significantly cheaper destination. Since Sao Paulo is in South 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 Sao Paulo would let you spend less money overall. Or, you could decide to spend more money in Sao Paulo 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 Sao Paulo.

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


Which is Bigger, Sao Paulo or Chicago?

Sao Paulo has a larger population, and is about 4 times larger than the population of Chicago. When comparing the sizes of Sao Paulo 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 Sao Paulo or Chicago?

Even though both destinations experience a temperate climate with four distinct seasons, they experience these seasons at different times of the year. Sao Paulo is in the southern hemisphere and summer is in January and winter is in July, but Chicago has summer in [NORTHERNSUMMERMONTH] and winter in [NORTHERNWINTERMONTH].

Should I visit Sao Paulo or Chicago in the Summer?

The summer brings many poeple to Sao Paulo as well as Chicago. Additionally, the summer months attract visitors to Chicago because of the beaches, the city activities, the music scene, and the family-friendly experiences.

Sao Paulo is around the same temperature as Chicago in the summer. The daily temperature in Sao Paulo averages around 25°C (77°F) in January, and Chicago fluctuates around 77°F (25°C)in July.

It's quite rainy in Chicago. Sao Paulo receives a lot of rain in the summer. Sao Paulo usually gets more rain in January than Chicagoin July. Sao Paulo gets 170 mm (6.7 in) of rain, while Chicago receives 3.9 inches (100 mm) of rain this time of the year.


  • Summer Average Temperatures January and July
    Sao Paulo 25°C (77°F) 
    Chicago 77°F (25°C)

Should I visit Sao Paulo or Chicago in the Autumn?

Both Chicago and Sao Paulo are popular destinations to visit in the autumn with plenty of activities. Also, 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.

In the autumn, Sao Paulo is much warmer than Chicago. Typically, the autumn temperatures in Sao Paulo in April average around 22°C (72°F), and Chicago averages at about 56°F (14°C)in October.

In April, Sao Paulo usually receives less rain than Chicagoin October. Sao Paulo gets 50 mm (2 in) of rain, while Chicago receives 2.2 inches (56 mm) of rain each month for the autumn.


  • Autumn Average Temperatures April and October
    Sao Paulo 22°C (72°F) 
    Chicago 56°F (14°C)

Should I visit Sao Paulo or Chicago in the Winter?

Both Chicago and Sao Paulo during the winter are popular places to visit. Also, 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 July, Sao Paulo is generally much warmer than Chicagoin January. Daily temperatures in Sao Paulo average around 19°C (66°F), and Chicago fluctuates around 25°F (-4°C).

Sao Paulo usually gets less rain in July than Chicagoin January. Sao Paulo gets 20 mm (0.8 in) of rain, while Chicago receives 1.9 inches (47 mm) of rain this time of the year.


  • Winter Average Temperatures July and January
    Sao Paulo 19°C (66°F) 
    Chicago 25°F (-4°C)

Should I visit Sao Paulo or Chicago in the Spring?

The spring attracts plenty of travelers to both Sao Paulo and Chicago. Also, many visitors come to Chicago in the spring for the beaches, the activities around the city, and the natural beauty.

Sao Paulo is much warmer than Chicago in the spring. The daily temperature in Sao Paulo averages around 21°C (70°F) in October, and Chicago fluctuates around 52°F (11°C)in April.

Chicago receives a lot of rain in the spring. In October, Sao Paulo usually receives less rain than Chicagoin April. Sao Paulo gets 90 mm (3.5 in) of rain, while Chicago receives 4.3 inches (108 mm) of rain each month for the spring.


  • Spring Average Temperatures October and April
    Sao Paulo 21°C (70°F) 
    Chicago 52°F (11°C)

Typical Weather for Chicago and Sao Paulo

Sao Paulo Chicago
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 25°C (77°F) 170 mm (6.7 in) 25°F (-4°C) 1.9 inches (47 mm)
Feb 25°C (77°F) 170 mm (6.7 in) 29°F (-2°C) 1.4 inches (35 mm)
Mar 24°C (75°F) 120 mm (4.7 in) 41°F (5°C) 3.7 inches (93 mm)
Apr 22°C (72°F) 50 mm (2 in) 52°F (11°C) 4.3 inches (108 mm)
May 21°C (70°F) 30 mm (1.2 in) 63°F (17°C) 3 inches (75 mm)
Jun 19°C (66°F) 20 mm (0.8 in) 73°F (23°C) 3.9 inches (100 mm)
Jul 19°C (66°F) 20 mm (0.8 in) 77°F (25°C) 3.9 inches (100 mm)
Aug 19°C (66°F) 10 mm (0.4 in) 76°F (24°C) 3.5 inches (90 mm)
Sep 21°C (70°F) 60 mm (2.4 in) 68°F (20°C) 3.8 inches (96 mm)
Oct 21°C (70°F) 90 mm (3.5 in) 56°F (14°C) 2.2 inches (56 mm)
Nov 23°C (73°F) 110 mm (4.3 in) 44°F (7°C) 2.2 inches (56 mm)
Dec 24°C (75°F) 150 mm (5.9 in) 31°F (-1°C) 2.8 inches (71 mm)