Which place is cheaper, Kailua-Kona or Chicago?
These are the overall average travel costs for the two destinations. These travel costs come from the actual spending of real travelers.
Jump to 
Should you visit Chicago or Kailua-Kona?
Which is cheaper to visit? Which is more expensive for vacation?
Which city is more affordable and which is best for your travel style? If you're trying to figure out where to go next, comparing the travel costs between Chicago and Kailua-Kona can help you decide which place is right for you.
Where Should I go: Chicago or Kailua-Kona?
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.
Kailua-Kona
Kailua-Kona, often simply called Kona, is a vibrant seaside town located on the west coast of Hawaii’s Big Island. Known for its sunny weather, beautiful beaches, and laid-back atmosphere, Kona offers travelers an appealing mix of natural beauty and Hawaiian culture. The town is famous for its historic waterfront, local coffee farms, and as the gateway to many of the island’s unique adventures. Despite its popularity, Kailua-Kona remains more relaxed and less crowded than some of Hawaii’s other tourist hubs. Beach lovers, water sports enthusiasts, history buffs, and foodies will all find plenty to enjoy here. With a mix of affordable accommodations, local eateries, and free or inexpensive attractions, it’s a great destination for budget travelers. The nearby volcanic landscapes, snorkeling spots, and lively marketplaces make it an excellent base for exploring the west side of the Big Island.
For some great organized tour ideas, see The Best 2-Week Tours from San Francisco, The Best 2-Week Tours from Los Angeles, The Best Family-Friendly Tours to United States of America, and The Best Wildlife Tours to United States of America.
-
Chicago Prices
USA PricesKailua-Kona Prices
USA Prices -
Average Daily Cost Per person, per dayChicago $323Kailua-Kona $274
The average daily cost (per person) in Chicago is $323, while the average daily cost in Kailua-Kona is $274. 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 Chicago and Kailua-Kona in more detail.
Accommodation
-
Accommodation Hotel or hostel for one personChicago $198Kailua-Kona $141
-
Accommodation Typical double-occupancy roomChicago $396Kailua-Kona $282
Compare Hotels in Chicago and Kailua-Kona
Looking for a hotel in Chicago or Kailua-Kona? 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: Chicago Hotel Prices and Kailua-Kona Hotel Prices.
Local Transportation
-
Local Transportation Taxis, local buses, subway, etc.Chicago $37Kailua-Kona $45
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: $44
- Private Transfer ORD Airport to Chicago / Milwaukee / Oak Brook: $46
- 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 Chicago To O'Hare Airport: $95
- Chicago O'Hare Airport (ORD) to Arrival Private Transfer: $103
- Chicago to Chicago O'Hare Airport (ORD): Departure Transfer: $103
- MDW Airport Private Transfer to/from Chicago: $106
Typical Local Transportation Prices in Kailua-Kona
Some typical examples of transportation costs in Kailua-Kona are as follows:
-
Rental Car for One Day$35
Is it cheaper to fly into Chicago or Kailua-Kona?
Prices for flights to both Kailua-Kona and Chicago 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 dayChicago $85Kailua-Kona $100
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.
- City Cruises Lake Michigan Lunch or Dinner Cruise: $67
- Pizza Walking or Bus Tour: $69
- 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 in Chicago: $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
- Taste of Chicago's Chinatown Food Tours: $85
- Downtown Classics Food Tour: Deep Dish, Beef Sandwich & More: $89
- Secret Food Tour: $95
Typical Food Prices in Kailua-Kona
Some typical examples of dining costs in Kailua-Kona are as follows:
-
Buffet Breakfast for Two$53
Entertainment
-
Entertainment Entrance tickets, shows, etc.Chicago $47Kailua-Kona $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:
- Eastside Chicago The Heist Exploration Game and Tour: $7.20
- 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 Haunted Ghost Tour GPS Self-Guided Walking Tour: $9.75
- Chicago’s Millennium Park Self Guided Audio GPS Walking Tour: $9.75
- Illinois Holocaust Museum presents Experience360 Ticket: $12
- The Loop, River North and Chicago’s Theater District: A Self-Guided Audio Tour: $15
- Chicago Scavenger Hunt Adventure Tour Private: $15
- Michigan Avenue Rendezvous GPS App Walking Tour Mobile Game: $17
- Michigan Avenue Rendezvous Walking Tour with Smartphone App: $18
Typical Entertainment Prices in Kailua-Kona
Some typical examples of activities, tours, and entrance ticket prices in Kailua-Kona are as follows:
-
Diving with Manta Rays for Two$162
-
Body Board Rental (1 Day)$12
-
1 Day Kayak Rental$47
-
2 Tank Morning Scuba Dive$115
Tours and Activities in Kailua-Kona
Some specific costs of activities, tours, and entrance tickets for Kailua-Kona are as follows:
- From Kona: Volcano & Waterfall Tour, Small Group: $295
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 dayChicago $25Kailua-Kona $15
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 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 Chicago and Kailua-Kona, we can see that Chicago is more expensive. And not only is Kailua-Kona much less expensive, but it is actually a significantly cheaper destination. So, traveling to Kailua-Kona would let you spend less money overall. Or, you could decide to spend more money in Kailua-Kona 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 Kailua-Kona.
If you're trying to decide if either of these two destinations are within your price range, also see Is Chicago Expensive? and Is Kailua-Kona Expensive?.
Which is Bigger, Chicago or Kailua-Kona?
Chicago has a larger population, and is about 290 times larger than the population of Kailua-Kona. When comparing the sizes of Chicago and Kailua-Kona, 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 Chicago or Kailua-Kona?
Both destinations experience a temperate climate with four distinct seasons. And since both cities are in the northern hemisphere, summer is in July and winter is in January.
Should I visit Chicago or Kailua-Kona in the Summer?
The summer attracts plenty of travelers to both Chicago and Kailua-Kona. The beaches, the city activities, the music scene, and the family-friendly experiences are the main draw to Chicago this time of year.
In the summer, Chicago is around the same temperature as Kailua-Kona. Typically, the summer temperatures in Chicago in July average around 77°F (25°C), and Kailua-Kona averages at about 78°F (25°C).
In Chicago, it's very sunny this time of the year. Chicago usually receives more sunshine than Kailua-Kona during summer. Chicago gets 326 hours of sunny skies, while Kailua-Kona receives 169 hours of full sun in the summer.
Chicago gets a good bit of rain this time of year. In July, Chicago usually receives more rain than Kailua-Kona. Chicago gets 3.9 inches (100 mm) of rain, while Kailua-Kona receives 2.3 inches (58 mm) of rain each month for the summer.
-
Summer Average Temperatures JulyChicago 77°F (25°C)Kailua-Kona 78°F (25°C)
Should I visit Chicago or Kailua-Kona in the Autumn?
The autumn brings many poeple to Chicago as well as Kailua-Kona. Many travelers come to Chicago for the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area.
In October, Chicago is generally much colder than Kailua-Kona. Daily temperatures in Chicago average around 56°F (14°C), and Kailua-Kona fluctuates around 78°F (26°C).
In the autumn, Chicago often gets more sunshine than Kailua-Kona. Chicago gets 195 hours of sunny skies this time of year, while Kailua-Kona receives 138 hours of full sun.
Chicago usually gets more rain in October than Kailua-Kona. Chicago gets 2.2 inches (56 mm) of rain, while Kailua-Kona receives 1.6 inches (41 mm) of rain this time of the year.
-
Autumn Average Temperatures OctoberChicago 56°F (14°C)Kailua-Kona 78°F (26°C)
Should I visit Chicago or Kailua-Kona in the Winter?
Both Kailua-Kona and Chicago are popular destinations to visit in the winter with plenty of activities. Many visitors come to Chicago in the winter for the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine.
Chicago can get quite cold in the winter. Chicago is much colder than Kailua-Kona in the winter. The daily temperature in Chicago averages around 25°F (-4°C) in January, and Kailua-Kona fluctuates around 74°F (23°C).
Chicago usually receives less sunshine than Kailua-Kona during winter. Chicago gets 134 hours of sunny skies, while Kailua-Kona receives 158 hours of full sun in the winter.
It rains a lot this time of the year in Kailua-Kona. In January, Chicago usually receives less rain than Kailua-Kona. Chicago gets 1.9 inches (47 mm) of rain, while Kailua-Kona receives 3.9 inches (100 mm) of rain each month for the winter.
-
Winter Average Temperatures JanuaryChicago 25°F (-4°C)Kailua-Kona 74°F (23°C)
Should I visit Chicago or Kailua-Kona in the Spring?
Both Kailua-Kona and Chicago during the spring are popular places to visit. Most visitors come to Chicago for the beaches, the activities around the city, and the natural beauty during these months.
In the spring, Chicago is much colder than Kailua-Kona. Typically, the spring temperatures in Chicago in April average around 52°F (11°C), and Kailua-Kona averages at about 74°F (24°C).
It's quite sunny in Chicago. In the spring, Chicago often gets more sunshine than Kailua-Kona. Chicago gets 218 hours of sunny skies this time of year, while Kailua-Kona receives 134 hours of full sun.
It rains a lot this time of the year in Chicago. Chicago usually gets more rain in April than Kailua-Kona. Chicago gets 4.3 inches (108 mm) of rain, while Kailua-Kona receives 3 inches (76 mm) of rain this time of the year.
-
Spring Average Temperatures AprilChicago 52°F (11°C)Kailua-Kona 74°F (24°C)
Typical Weather for Kailua-Kona and Chicago
| Chicago | Kailua-Kona | |||
|---|---|---|---|---|
| Temp (°C) | Rain (mm) | Temp (°C) | Rain (mm) | |
| Jan | 25°F (-4°C) | 1.9 inches (47 mm) | 74°F (23°C) | 3.9 inches (100 mm) |
| Feb | 29°F (-2°C) | 1.4 inches (35 mm) | 73°F (23°C) | 3.2 inches (82 mm) |
| Mar | 41°F (5°C) | 3.7 inches (93 mm) | 74°F (23°C) | 4.4 inches (111 mm) |
| Apr | 52°F (11°C) | 4.3 inches (108 mm) | 74°F (24°C) | 3 inches (76 mm) |
| May | 63°F (17°C) | 3 inches (75 mm) | 76°F (24°C) | 1.6 inches (40 mm) |
| Jun | 73°F (23°C) | 3.9 inches (100 mm) | 77°F (25°C) | 1.8 inches (47 mm) |
| Jul | 77°F (25°C) | 3.9 inches (100 mm) | 78°F (25°C) | 2.3 inches (58 mm) |
| Aug | 76°F (24°C) | 3.5 inches (90 mm) | 78°F (26°C) | 1.9 inches (49 mm) |
| Sep | 68°F (20°C) | 3.8 inches (96 mm) | 79°F (26°C) | 1.1 inches (29 mm) |
| Oct | 56°F (14°C) | 2.2 inches (56 mm) | 78°F (26°C) | 1.6 inches (41 mm) |
| Nov | 44°F (7°C) | 2.2 inches (56 mm) | 76°F (25°C) | 3.3 inches (85 mm) |
| Dec | 31°F (-1°C) | 2.8 inches (71 mm) | 74°F (24°C) | 3.4 inches (87 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.