Which place is cheaper, Chicago or Grand Cayman?
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 Grand Cayman or Chicago?
Which is cheaper to visit? Which is more expensive for vacation?
Which city should you visit? Read on to compare the activities as well as the prices of travel for Grand Cayman and Chicago. We'll break down costs for accommodation, food, transportation and more to help you learn more about these two destinations. Then, you can figure out if either of these two places are accessible based on your travel budget, schedule, and interests. So, let's dig into it.
Where Should I go: Grand Cayman or Chicago?
Grand Cayman
When people think of the Cayman Islands, they typically think of offshore bank accounts and sunny, cruise ship ports. Grand Cayman has more to offer travelers than a playground for the wealthy or a short stopover for cruise passengers. This tropical island is the largest of the three Cayman Islands, it is a shopper's heaven, a center for global finance and an ideal vacation spot.
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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Grand Cayman Prices
Cayman Islands PricesChicago Prices
USA Prices -
Average Daily Cost Per person, per dayGrand Cayman $242Chicago $323
The average daily cost (per person) in Grand Cayman is $242, 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 Grand Cayman and Chicago in more detail.
Accommodation
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Accommodation Hotel or hostel for one personGrand Cayman $149Chicago $198
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Accommodation Typical double-occupancy roomGrand Cayman $298Chicago $396
Compare Hotels in Grand Cayman and Chicago
Looking for a hotel in Grand Cayman 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: Grand Cayman Hotel Prices and Chicago Hotel Prices.
Local Transportation
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Local Transportation Taxis, local buses, subway, etc.Grand Cayman $31Chicago $37
Hired Cars and Shuttles in Grand Cayman
Also for Grand Cayman, here are a few examples of actual transportation services:
- Privat Transfer from Owen Roberts Airport GCM to George Town Port: $103
- Private Transfer from Airport to morritts: $180
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:
- Wheelchair Accessible Airport Transfer Chicago to O’Hare, Midway : $149
- 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
- Round Trip Private Transfer ORD Airport to Chicago City Oak Brook: $92
- Private Transfer: Midway Airport MDW to Chicago by Luxury SUV: $190
- Private Transfer in Chicago (ORD/MDW): $130
- Private Transfer ORD Airport to Chicago / Milwaukee / Oak Brook: $46
- Private Transfer Chicago Airport MDW to Chicago Downtown: $50
- Private Sedan Transfer from O'Hare and Midway Airport to Chicago: $120
- Private Sedan Transfer from Chicago Downtown to O'Hare airport: $220
- Private Sedan Transfer from Chicago Downtown to Midway airport: $220
- Private SUV Transfer from Chicago Downtown to O'Hare airport: $240
Is it cheaper to fly into Grand Cayman or Chicago?
Prices for flights to both Chicago and Grand Cayman 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 dayGrand Cayman $67Chicago $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.
- Tamales and Tacos with Margarita Cooking Class at Su Casa: $59
- Downtown Pizza Guided Walking Tour with Tastings: $73
- Sushi Making Cooking Class at a Local Distillery: $75
- Pasta Making Cooking Class at a Local Distillery: $75
- Sushi Making Cooking Class at a Local Distillery in Chicago: $75
- Downtown Family Food Tour by Bike with Sightseeing: $80
- Vito's Vault Chicago finest dinner theatre speakeasy: $85
- Chicago Loop District Food Tour with Deep Dish & Beef Sandwich: $89
- City Cruises Lake Michigan Lunch or Dinner Cruise: $93
- Secret Food Tour: $93
- City Cruises Premier Lunch or Dinner Cruise: $94
- River North Walking Food Tour: $99
Entertainment
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Entertainment Entrance tickets, shows, etc.Grand Cayman $41Chicago $47
Tours and Activities in Grand Cayman
For Grand Cayman, here are a few prices for actual activities, tours, and tickets provided by various companies:
- CaymanVisitor Hide & Seek GeoTour Self-Drive Tour: $13
- Diamonds and Cocktails a Shopping Experience in Grand Cayman: $25
- 2 Stop Reef Snorkel and Glass Bottom Boat Adventure: $35
- Grand Cayman Hop On Hop Off Island Adventure: $40
- Stingray City and Snorkeling Tour Starfish Point Adventure: $53
- Stingray City, Snorkeling, & StarFish Adventure: $55
- Stingray City and Starfish Experience with Coral Reef Snorkeling: $55
- Stingray City Catamaran Sunset Tour: $59
- West Bay Sightseeing Tour Plus Seven Mile Beach Visit: $65
- 3 Stop Boat Tour Stingray City Coral Gardens and Starfish Point: $65
- Stingray City Sandbar Experience: $65
- StingrayCity ,Coral Garden & Starfish 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:
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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
- 2-Hour Guided Segway Tour of Chicago: $65
- 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
- A Storied Neighborhood: A Self-Guided Audio Tour with Bill Ayers: $5.40
- African American Heritage Tour of Chicago : $125
- Amazing Lakefront Segway Tour of Chicago: $52
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 dayGrand Cayman $13Chicago $25
Typical Alcohol Prices in Grand Cayman
Below are a few samples from actual travelers for alcohol and nightlife costs in Grand Cayman:
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Beer$4.95
Sample the Local Flavors in Grand Cayman
Here are a few nightlife and alcohol tours and activities from local tour providers in Grand Cayman:
- Cayman Spirits Co. Distillery Tour Pass Ticket Only: $24
- Cayman Art and Wine Tour: $150
Sample the Local Flavors in Chicago
Here are a few nightlife and alcohol tours and activities from local tour providers in Chicago:
- 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 Grand Cayman and Chicago, we can see that Chicago is more expensive. And not only is Grand Cayman much less expensive, but it is actually a significantly cheaper destination. Since Grand Cayman 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 Grand Cayman would let you spend less money overall. Or, you could decide to spend more money in Grand Cayman 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 Grand Cayman.
If you're trying to decide if either of these two destinations are within your price range, also see Is Grand Cayman Expensive? and Is Chicago Expensive?.
Which is Bigger, Grand Cayman or Chicago?
Chicago has a larger population, and is about 100 times larger than the population of Grand Cayman. When comparing the sizes of Grand Cayman 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 Grand Cayman or Chicago?
Chicago has a temperate climate with four distinct seasons, but Grand Cayman experiences a warm climate with fairly sunny weather most of the year.
Should I visit Grand Cayman or Chicago in the Summer?
Both Chicago and Grand Cayman during the summer are popular places to visit. Plenty of visitors come to Grand Cayman because of the warm climate and sunshine that lasts throughout the year. Also, many visitors come to Chicago in the summer for the beaches, the city activities, the music scene, and the family-friendly experiences.
Grand Cayman is a little warmer than Chicago in the summer. The daily temperature in Grand Cayman averages around 28°C (83°F) in July, and Chicago fluctuates around 77°F (25°C).
Chicago gets a good bit of rain this time of year. It rains a lot this time of the year in Grand Cayman. Grand Cayman usually gets more rain in July than Chicago. Grand Cayman gets 179 mm (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 JulyGrand Cayman 28°C (83°F)Chicago 77°F (25°C)
Should I visit Grand Cayman or Chicago in the Autumn?
The autumn attracts plenty of travelers to both Grand Cayman and Chicago. Warm weather and sunshine bring visitors to Grand Cayman year-round. Also, most visitors come to Chicago for the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area during these months.
In the autumn, Grand Cayman is much warmer than Chicago. Typically, the autumn temperatures in Grand Cayman in October average around 27°C (81°F), and Chicago averages at about 56°F (14°C).
Grand Cayman gets a good bit of rain this time of year. In October, Grand Cayman usually receives more rain than Chicago. Grand Cayman gets 238 mm (9.4 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 OctoberGrand Cayman 27°C (81°F)Chicago 56°F (14°C)
Should I visit Grand Cayman or Chicago in the Winter?
The winter brings many poeple to Grand Cayman as well as Chicago. Grand Cayman attracts visitors year-round for its warm weather and sunny climate. Also, the winter months attract visitors to Chicago because of the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine.
The weather in Chicago can be very cold. In January, Grand Cayman is generally much warmer than Chicago. Daily temperatures in Grand Cayman average around 24°C (76°F), and Chicago fluctuates around 25°F (-4°C).
Grand Cayman usually gets more rain in January than Chicago. Grand Cayman 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 JanuaryGrand Cayman 24°C (76°F)Chicago 25°F (-4°C)
Should I visit Grand Cayman or Chicago in the Spring?
Both Chicago and Grand Cayman are popular destinations to visit in the spring with plenty of activities. The warm climate attracts visitors to Grand Cayman throughout the year. Also, the beaches, the activities around the city, and the natural beauty are the main draw to Chicago this time of year.
Grand Cayman is much warmer than Chicago in the spring. The daily temperature in Grand Cayman averages around 26°C (79°F) in April, and Chicago fluctuates around 52°F (11°C).
It rains a lot this time of the year in Chicago. In April, Grand Cayman usually receives less rain than Chicago. Grand Cayman gets 48 mm (1.9 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 AprilGrand Cayman 26°C (79°F)Chicago 52°F (11°C)
Typical Weather for Chicago and Grand Cayman
| Grand Cayman | Chicago | |||
|---|---|---|---|---|
| Temp (°C) | Rain (mm) | Temp (°C) | Rain (mm) | |
| Jan | 24°C (76°F) | 58 mm (2.3 in) | 25°F (-4°C) | 1.9 inches (47 mm) |
| Feb | 24°C (76°F) | 51 mm (2 in) | 29°F (-2°C) | 1.4 inches (35 mm) |
| Mar | 25°C (77°F) | 31 mm (1.2 in) | 41°F (5°C) | 3.7 inches (93 mm) |
| Apr | 26°C (79°F) | 48 mm (1.9 in) | 52°F (11°C) | 4.3 inches (108 mm) |
| May | 27°C (81°F) | 131 mm (5.1 in) | 63°F (17°C) | 3 inches (75 mm) |
| Jun | 28°C (82°F) | 183 mm (7.2 in) | 73°F (23°C) | 3.9 inches (100 mm) |
| Jul | 28°C (83°F) | 179 mm (7 in) | 77°F (25°C) | 3.9 inches (100 mm) |
| Aug | 28°C (82°F) | 172 mm (6.8 in) | 76°F (24°C) | 3.5 inches (90 mm) |
| Sep | 28°C (82°F) | 212 mm (8.3 in) | 68°F (20°C) | 3.8 inches (96 mm) |
| Oct | 27°C (81°F) | 238 mm (9.4 in) | 56°F (14°C) | 2.2 inches (56 mm) |
| Nov | 26°C (79°F) | 141 mm (5.6 in) | 44°F (7°C) | 2.2 inches (56 mm) |
| Dec | 25°C (78°F) | 57 mm (2.3 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.