Which place is cheaper, Berkshires or Chicago?
These are the overall average travel costs for the two destinations.
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Should you visit Chicago or Berkshires?
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 Berkshires can help you decide which place is right for you.
Where Should I go: Chicago or Berkshires?
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.
Berkshires
The Berkshires are a popular highland destination in the western part of Massachusetts and northwest Connecticut. The region has scenic landscape, hiking, lakes, recreational opportunities and other outdoor experiences. The Berkshires also has an impressive cultural scene with music, arts, museums, and live theaters.
The Berkshires can be a bit expensive to visit if you stay at a luxury resort and take advantage of the award winning restaurants in the area. Alternatively, the experience can be equally rewarding by camping, picnicking, and spending your time hiking and enjoying the beautiful natural setting.
For some great organized tour ideas, see The Best Family-Friendly Tours to United States of America, The Best Wildlife Tours to United States of America, The Best Hiking & Trekking Tours in United States of America, and The Best Historical Tours in United States of America.
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Average Daily Cost Per person, per dayChicago $288Berkshires $244
The average daily cost (per person) in Chicago is $288, while the average daily cost in Berkshires is $244. 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 Berkshires in more detail.
Accommodation
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Accommodation Hotel or hostel for one personChicago $198Berkshires $141
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Accommodation Typical double-occupancy roomChicago $396Berkshires $282
Compare Hotels in Chicago and Berkshires
Looking for a hotel in Chicago or Berkshires? 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 Berkshires Hotel Prices.
Local Transportation
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Local Transportation Taxis, local buses, subway, etc.Chicago $37Berkshires $47
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:
- Airport transfer between Chicago O'Hare and Milwaukee: $38
- Arrival Private Transfer: O'Hare Airport ORD to Chicago in Business Car: $152
- Arrival Private Transfer: O'Hare Airport ORD to Chicago in Luxury Car: $233
- Chicago Airport (MDW) to Chicago - Round-Trip Private Transfer: $116
- Chicago Airport Transfer: Chicago to O'Hare Airport ORD in Luxury SUV: $202
- Chicago Airport Transfer: Chicago to O'Hare Airport in Luxury SUV: $150
- Chicago Airport Transfer: O'Hare Airport ORD to Chicago in Business Car: $152
- Chicago Airport Transfer: O'Hare Airport ORD to Chicago in Luxury SUV: $202
- Chicago Midway Airport (MDW) to Chicago -Arrival Private Transfer: $58
- Chicago Midway Airport (MDW) to Chicago City - Round-Trip Private Transfer: $105
- Chicago Midway Airport (MDW) to Chicago hotel/address - Arrival Private Transfer: $52
- Chicago O'Hare Airport (ORD) to Chicago - Round-Trip Private Transfer: $126
Is it cheaper to fly into Chicago or Berkshires?
Prices for flights to both Berkshires 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
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Food Meals for one dayChicago $49Berkshires $73
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.
- Traveling Spoon Chicago-Style Deep Dish Pizza Private Online Cooking Class : $40
- Chicago : Hands-on Cooking Classes With Local Chef: $55
- Downtown Pizza Guided Walking Tour with Tastings: $58
- Fulton Market Delicious Donut Adventure & Walking Food Tour: $63
- Chicago's Delicious Donut Adventure and Walking Food Tour: $63
- Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise: $72
- Chicago Deep Dish Pizza Self-Guided Tour: $75
- Chicago Pizza Tour: $75
- Chicago West Loop Pizza Crawl: $79
- Chicago Bucktown-Wicker Park Pizza Crawl: $79
- Downtown Family Food Tour by Bike with Sightseeing: $80
- Nitti's Supper Club Dinner and Show: $85
Entertainment
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Entertainment Entrance tickets, shows, etc.Chicago $47Berkshires $25
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:
- Discovering Chicago with Walking In App Audio Tour: $6.00
- Haunted Sites Self-Guided Audio Walking Tour: $6.50
- Vice, Crime and Gangsters Self-Guided Audio Tour: $6.99
- Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour: $6.99
- Vice, Crime and Gangsters in A Self-Guided Audio Tour: $6.99
- Must-Sees & Hidden Gems In-App Audio Tour (ENG): $9.00
- App Chicago self-guided tours with multilingual audioguides: $9.63
- Millennium Park Self-Guided Walking Tour: $9.99
- Riverwalk Self-Guided Walking Tour: $9.99
- Scavenger Hunt Adventure Self-Guided City Game: $10
- Self-Guided Audio Tour: $11
- Chicago White Sox Baseball Game Ticket: $12
Tours and Activities in Berkshires
Here are a few actual costs in Berkshires for available activities, ticket prices, and tours:
- 2-Hour Guided Private Forest Bathing Experience Lenox: $40
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 dayChicago $25Berkshires $31
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 Chicago and Berkshires, we can see that Chicago is more expensive. And not only is Berkshires much less expensive, but it is actually a significantly cheaper destination. So, traveling to Berkshires would let you spend less money overall. Or, you could decide to spend more money in Berkshires 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 Berkshires.
If you're trying to decide if either of these two destinations are within your price range, also see Is Chicago Expensive? and Is Berkshires Expensive?.
When is the best time to visit Chicago or Berkshires?
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 Berkshires in the Summer?
Both Berkshires and Chicago are popular destinations to visit in the summer with plenty of activities. Many travelers come to Chicago for the beaches, the city activities, the music scene, and the family-friendly experiences.
In July, Chicago is generally a little warmer than Berkshires. Daily temperatures in Chicago average around 77°F (25°C), and Berkshires fluctuates around 72°F (22°C).
It's quite sunny in Berkshires. The sun comes out a lot this time of the year in Chicago. Chicago usually receives more sunshine than Berkshires during summer. Chicago gets 326 hours of sunny skies, while Berkshires receives 289 hours of full sun in the summer.
It's quite rainy in Chicago. In July, Chicago usually receives more rain than Berkshires. Chicago gets 3.9 inches (100 mm) of rain, while Berkshires receives 2.7 inches (69 mm) of rain each month for the summer.
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Summer Average Temperatures JulyChicago 77°F (25°C)Berkshires 72°F (22°C)
Should I visit Chicago or Berkshires in the Autumn?
Both Berkshires and Chicago during the autumn are popular places to visit. 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.
Chicago is a little warmer than Berkshires in the autumn. The daily temperature in Chicago averages around 56°F (14°C) in October, and Berkshires fluctuates around 51°F (11°C).
In the autumn, Chicago often gets more sunshine than Berkshires. Chicago gets 195 hours of sunny skies this time of year, while Berkshires receives 162 hours of full sun.
Chicago usually gets less rain in October than Berkshires. Chicago gets 2.2 inches (56 mm) of rain, while Berkshires receives 2.6 inches (67 mm) of rain this time of the year.
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Autumn Average Temperatures OctoberChicago 56°F (14°C)Berkshires 51°F (11°C)
Should I visit Chicago or Berkshires in the Winter?
The winter attracts plenty of travelers to both Chicago and Berkshires. Most visitors come to Chicago for the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine during these months.
The weather in Berkshires can be very cold. Chicago can be very cold during winter. In the winter, Chicago is a little warmer than Berkshires. Typically, the winter temperatures in Chicago in January average around 25°F (-4°C), and Berkshires averages at about 22°F (-6°C).
Chicago usually receives around the same amount of sunshine as Berkshires during winter. Chicago gets 134 hours of sunny skies, while Berkshires receives 138 hours of full sun in the winter.
In January, Chicago usually receives around the same amount of rain as Berkshires. Chicago gets 1.9 inches (47 mm) of rain, while Berkshires receives 1.9 inches (49 mm) of rain each month for the winter.
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Winter Average Temperatures JanuaryChicago 25°F (-4°C)Berkshires 22°F (-6°C)
Should I visit Chicago or Berkshires in the Spring?
The spring brings many poeple to Chicago as well as Berkshires. The spring months attract visitors to Chicago because of the beaches, the activities around the city, and the natural beauty.
In April, Chicago is generally a little warmer than Berkshires. Daily temperatures in Chicago average around 52°F (11°C), and Berkshires fluctuates around 47°F (9°C).
The sun comes out a lot this time of the year in Berkshires. People are often attracted to the plentiful sunshine in Chicago this time of the year. In the spring, Chicago often gets around the same amount of sunshine as Berkshires. Chicago gets 218 hours of sunny skies this time of year, while Berkshires receives 223 hours of full sun.
Chicago receives a lot of rain in the spring. Chicago usually gets more rain in April than Berkshires. Chicago gets 4.3 inches (108 mm) of rain, while Berkshires receives 2.6 inches (66 mm) of rain this time of the year.
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Spring Average Temperatures AprilChicago 52°F (11°C)Berkshires 47°F (9°C)
Typical Weather for Berkshires and Chicago
| Chicago | Berkshires | |||
|---|---|---|---|---|
| Temp (°C) | Rain (mm) | Temp (°C) | Rain (mm) | |
| Jan | 25°F (-4°C) | 1.9 inches (47 mm) | 22°F (-6°C) | 1.9 inches (49 mm) |
| Feb | 29°F (-2°C) | 1.4 inches (35 mm) | 24°F (-4°C) | 2 inches (51 mm) |
| Mar | 41°F (5°C) | 3.7 inches (93 mm) | 35°F (2°C) | 2.5 inches (63 mm) |
| Apr | 52°F (11°C) | 4.3 inches (108 mm) | 47°F (9°C) | 2.6 inches (66 mm) |
| May | 63°F (17°C) | 3 inches (75 mm) | 59°F (15°C) | 3 inches (75 mm) |
| Jun | 73°F (23°C) | 3.9 inches (100 mm) | 67°F (20°C) | 3.3 inches (83 mm) |
| Jul | 77°F (25°C) | 3.9 inches (100 mm) | 72°F (22°C) | 2.7 inches (69 mm) |
| Aug | 76°F (24°C) | 3.5 inches (90 mm) | 70°F (21°C) | 3 inches (76 mm) |
| Sep | 68°F (20°C) | 3.8 inches (96 mm) | 62°F (17°C) | 2.8 inches (71 mm) |
| Oct | 56°F (14°C) | 2.2 inches (56 mm) | 51°F (11°C) | 2.6 inches (67 mm) |
| Nov | 44°F (7°C) | 2.2 inches (56 mm) | 41°F (5°C) | 2.9 inches (73 mm) |
| Dec | 31°F (-1°C) | 2.8 inches (71 mm) | 28°F (-2°C) | 2.7 inches (69 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.