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

Should you visit Saint Croix or Chicago?

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

Should I visit Saint Croix 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: Saint Croix or Chicago?

Saint Croix

Sometimes all you want out of a vacation is the warmth of the sun, the sound of the waves and the taste of a cold drink. No more. No less. That's exactly what you can expect in St. Croix.

The largest of the U.S. Virgin Islands, St. Croix is a place of our leisure and relaxation. It's a bit of an expensive lifestyle for its 50,000 residents and daily visitors, but when you're living on island time, money is never a worry. There are no worries on island time.

This once volcanic island is covered in incredible beaches, stunning mountains, palm tress in the wind and historic colonial towns. While they may be a bit old and rundown, the Danish architecture still stands as a unique part of this island's legacy. Don't expect much window-shopping, though. That was not a feature incorporated in this style of architecture. If you want to know if a store is open, just step on in, but remember, shop hours are also running on island time.

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.


Which place is cheaper, Chicago or Saint Croix?

These are the overall average travel costs for the two destinations. These travel costs come from the actual spending of real travelers.

  • Saint Croix Prices
    USVI Prices
    Chicago Prices
    USA Prices
  • Average Daily Cost Per person, per day
    Saint Croix $277
    Chicago $323

The average daily cost (per person) in Saint Croix is $277, 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 Saint Croix and Chicago in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Saint Croix $149
    Chicago $198
  • Accommodation Typical double-occupancy room
    Saint Croix $298
    Chicago $396
Compare Hotels in Saint Croix and Chicago

Looking for a hotel in Saint Croix 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 Saint Croix


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: Saint Croix Hotel Prices and Chicago Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Saint Croix $35
    Chicago $37

Hired Cars and Shuttles in Saint Croix

Some specific examples of transportation prices in Saint Croix:

  • Henry E. Rohlsen Airport (STX) to St.Croix - Round-Trip Transfer: $167
  • Private Transfer from St. Croix Airport to St. Croix Cruise Port : $87
  • Private Transfer from St. Croix Henry E. Rohlsen Airport (STX) to St. Croix : $180
  • Private Transfer from St. Croix Port to St. Croix Airport (STX): $87
  • Private Transfer from St.Croix Cruise Port to St.Croix hotels: $175
  • Private Transfer from St.Croix hotels to St. Croix Cruise Port : $175
  • St. Croix to Henry E. Rohlsen Airport (STX) - Departure Transfer: $84
  • St. Croix to St. Croix Airport (STX) - Departure Private Transfer: $91
  • St.Croix Airport (STX) to St.Croix - Arrival Private Transfer: $91

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:

  • Airport transfer between Chicago O'Hare and Milwaukee: $38
  • Private Airport Transfer to/from ORD Airport: $43
  • Private Transfer ORD Airport to Chicago / Milwaukee / Oak Brook: $46
  • Chicago Midway Airport (MDW) to Chicago -Arrival Private Transfer: $75
  • Chicago O'Hare Airport (ORD) to Chicago hotel/address - Arrival Private Transfer: $76
  • Chicago City to Chicago Midway Airport (MDW) - Departure Private Transfer: $78
  • Chicago O'Hare International Airport private transfer, pick up: $80
  • Private Departure Transfer to Chicago Airports (ORD)(MDW): $90
  • Round Trip Private Transfer ORD Airport to Chicago City Oak Brook: $92
  • Private One-Way Airport Transfer from O'Hare Airport to Chicago: $94
  • Private One-Way Airport Transfer From Chicago To O'Hare Airport: $94
  • Chicago Private Transfer from City To Airport (ORD): $99

Is it cheaper to fly into Saint Croix or Chicago?

Prices for flights to both Chicago and Saint Croix 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
    Saint Croix $97
    Chicago $85

Food Tours and Cooking Classes in Saint Croix

Also, here are some specific examples of food and dining related activities in Saint Croix.

  • A Evening Cultural Experience Through Food Cooking Class St. Croix: $90
  • A Morning Cultural Experience Through Food Cooking Class St. Croix: $90
  • C'sted Sip & Savor Mixology Class with VI Food Tours: $131
  • Taste of Twin City Food Tour with VI Food Tours: $145

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 : $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
  • Entertainment Entrance tickets, shows, etc.
    Saint Croix $58
    Chicago $47

Tours and Activities in Saint Croix

Some specific costs of activities, tours, and entrance tickets for Saint Croix are as follows:

  • Christiansted's Artisan Shopping Tour: $33
  • St. Croix Ghost Tour of Historic Christiansted: $45
  • Frederiksted Moke Tour: $75
  • The Frederiksted St. Croix Sea Turtles Snorkeling Tour: $89
  • Guided Kayak Tour of Salt River Bay Ecology and History: $115
  • St Croix Island Tour: $118
  • Parasail Experience in St Croix: $132
  • Horseback Riding Experience: $160
  • Private Sailing Tour of Pirate Waters and Shipwrecks: $175

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:

  • 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
  • Alcohol Drinks for one day
    Saint Croix $27
    Chicago $25

Sample the Local Flavors in Saint Croix

Also in Saint Croix, these are the prices for nightlife and alcohol related activities from various tour providers:

  • Farm to Bottle Tour at Prosperity Farm Distillery: $35

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

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



When is the best time to visit Saint Croix or Chicago?

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

Should I visit Saint Croix or Chicago in the Summer?

The summer attracts plenty of travelers to both Saint Croix and Chicago. Warm weather and sunshine bring visitors to Saint Croix year-round. Furthermore, many travelers come to Chicago for the beaches, the city activities, the music scene, and the family-friendly experiences.

In the summer, Saint Croix is a little warmer than Chicago. Typically, the summer temperatures in Saint Croix in July average around 29°C (83°F), and Chicago averages at about 77°F (25°C).

Chicago receives a lot of rain in the summer. In July, Saint Croix usually receives less rain than Chicago. Saint Croix gets 66 mm (2.6 in) of rain, while Chicago receives 3.9 inches (100 mm) of rain each month for the summer.


  • Summer Average Temperatures July
    Saint Croix 29°C (83°F) 
    Chicago 77°F (25°C)

Should I visit Saint Croix or Chicago in the Autumn?

The autumn brings many poeple to Saint Croix as well as Chicago. Saint Croix attracts visitors year-round for its warm weather and sunny climate. Additionally, 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.

In October, Saint Croix is generally much warmer than Chicago. Daily temperatures in Saint Croix average around 28°C (82°F), and Chicago fluctuates around 56°F (14°C).

Saint Croix receives a lot of rain in the autumn. Saint Croix usually gets more rain in October than Chicago. Saint Croix gets 146 mm (5.7 in) of rain, while Chicago receives 2.2 inches (56 mm) of rain this time of the year.


  • Autumn Average Temperatures October
    Saint Croix 28°C (82°F) 
    Chicago 56°F (14°C)

Should I visit Saint Croix or Chicago in the Winter?

Both Chicago and Saint Croix are popular destinations to visit in the winter with plenty of activities. The warm climate attracts visitors to Saint Croix 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. Saint Croix is much warmer than Chicago in the winter. The daily temperature in Saint Croix averages around 26°C (78°F) in January, and Chicago fluctuates around 25°F (-4°C).

In January, Saint Croix usually receives less rain than Chicago. Saint Croix gets 43 mm (1.7 in) of rain, while Chicago receives 1.9 inches (47 mm) of rain each month for the winter.


  • Winter Average Temperatures January
    Saint Croix 26°C (78°F) 
    Chicago 25°F (-4°C)

Should I visit Saint Croix or Chicago in the Spring?

Both Chicago and Saint Croix during the spring are popular places to visit. Plenty of visitors come to Saint Croix because of the warm climate and sunshine that lasts throughout the year. Also, the spring months attract visitors to Chicago because of the beaches, the activities around the city, and the natural beauty.

In the spring, Saint Croix is much warmer than Chicago. Typically, the spring temperatures in Saint Croix in April average around 27°C (80°F), and Chicago averages at about 52°F (11°C).

Chicago gets a good bit of rain this time of year. Saint Croix usually gets less rain in April than Chicago. Saint Croix gets 72 mm (2.8 in) of rain, while Chicago receives 4.3 inches (108 mm) of rain this time of the year.


  • Spring Average Temperatures April
    Saint Croix 27°C (80°F) 
    Chicago 52°F (11°C)

Typical Weather for Chicago and Saint Croix

Saint Croix Chicago
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 26°C (78°F) 43 mm (1.7 in) 25°F (-4°C) 1.9 inches (47 mm)
Feb 26°C (78°F) 39 mm (1.5 in) 29°F (-2°C) 1.4 inches (35 mm)
Mar 26°C (79°F) 49 mm (1.9 in) 41°F (5°C) 3.7 inches (93 mm)
Apr 27°C (80°F) 72 mm (2.8 in) 52°F (11°C) 4.3 inches (108 mm)
May 28°C (82°F) 94 mm (3.7 in) 63°F (17°C) 3 inches (75 mm)
Jun 28°C (83°F) 64 mm (2.5 in) 73°F (23°C) 3.9 inches (100 mm)
Jul 29°C (83°F) 66 mm (2.6 in) 77°F (25°C) 3.9 inches (100 mm)
Aug 29°C (84°F) 101 mm (4 in) 76°F (24°C) 3.5 inches (90 mm)
Sep 28°C (83°F) 127 mm (5 in) 68°F (20°C) 3.8 inches (96 mm)
Oct 28°C (82°F) 146 mm (5.7 in) 56°F (14°C) 2.2 inches (56 mm)
Nov 27°C (81°F) 126 mm (4.9 in) 44°F (7°C) 2.2 inches (56 mm)
Dec 26°C (80°F) 71 mm (2.8 in) 31°F (-1°C) 2.8 inches (71 mm)