A Travel Price Comparison for Vacations, Tours, and Honeymoons Chicago vs. Boston

Should you visit Chicago or Boston?

Should I visit Chicago or Boston? This is a common question asked by many travelers. By figuring out which city is more affordable, you'll understand where you can get more bang for your buck. So, let's dive into the data, which all comes from actual travelers.

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.

Boston

Boston is one of the oldest and most historic cities in New England. It is also the capital of the state of Massachusetts and the largest city in the region. The city proper covers 48 square miles and has a population of more than 600,000. The Greater Boston area has 4.5 million people and is the tenth largest metropolitan area in the country.

Which city is cheaper, Boston or Chicago?

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

The average daily cost (per person) in Chicago is $180, while the average daily cost in Boston is $212. 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 city. Below is a breakdown of travel costs for Chicago and Boston in more detail.


Accommodation

Accommodation prices vary by location and style, but travelers pay on average about $226 for a double occupancy room in Chicago.

A hotel room in Boston is about $302 This assumes double occupancy and modest accommodations.


  • Accommodation Hotel or hostel for one person
    Chicago $113
    Boston $151
  • Accommodation Typical double-occupancy room
    Chicago $225
    Boston $302


Food

Chicago food costs typically run travelers around $34 per day. Eating every meal in a nicer restaurant will drive the cost up, and grabbing fast food or casual meals will help you save money.

The average traveler spends about $32 per day in Boston for food, but obviously this is dependent on the type of restaurant and the amount of food ordered. To save money you can grab a lighter lunch or dinner, or you can try fast food or street food.


  • Food Meals for one day
    Chicago $34
    Boston $32
Typical Food prices in Chicago

Some typical examples of dining costs in Chicago are as follows:


  • 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.

  • Lonely Planet Experiences: Chicago History and Food Tour: $59
  • Chicago Fireworks Buffet Dinner Cruise: $136
  • Secret Food Tour: $240
  • Chicago Dinner Cruise on The Odyssey: $149
  • 3-Hour 3-Course Buffet Dinner Cruise: $109
  • Chicago Fireworks Dinner Cruise On The Odyssey: $160
  • Factories to Calories Fulton Market Food Tour: $46
  • Chicago Crime & Pizza Walk: $50
  • Traveling Spoon Chicago-Style Deep Dish Pizza Private Online Cooking Class: $27
  • Learn to Make Chicago Deep-Dish Pizza with a Local: $49

Food Tours and Cooking Classes in Boston

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

  • Italian Food Tour with Pizza, Meats, Cheese, & Bread: $69
  • Boston's North End: Secret Food Tour: $258
  • Boston North End Pizza Tour: $49
  • Boston Buffet Dinner Cruise: $99
  • Boston Dinner Cruise On The Odyssey: $111
  • Historic Taverns and Pizza Tour: $49
  • Haunted Pizza Tour: $66
  • Boston's North End "Little Italy" Pizza, Cannoli, and Freedom Trail Walking Tour: $49
  • Boston's North End Small-Group Walking Food Tour: $71
  • Fenway Neighborhood Food Tour (Boston): $79


Local Transportation

The cost of a taxi ride in Chicago is significantly more than public transportation. On average, past travelers have spent $34 per person, per day, on local transportation in Chicago.

The cost of a taxi ride in Boston is significantly more than public transportation. On average, past travelers have spent $27 per person, per day, on local transportation in Boston.


  • Local Transportation Taxis, local buses, subway, etc.
    Chicago $34
    Boston $27
Typical Local Transportation prices in Chicago

Some typical examples of transportation costs in Chicago are as follows:


  • Parking
    $19
  • Taxi Ride
    $10
  • Taxi from Airport
    $45

Hired Cars and Shuttles in Chicago

Some specific examples of transportation prices in Chicago:

  • Chicago Airport Transfer by Private Sedan: $119
  • ORD to Chicago City Hotels: 1-Way Private Transfer: $122
  • O'Hare Airport Transfer by Private SUV: $134
  • Midway Airport Shared Transfers: $36
  • Chicago O'Hare International Airport Shared Transfer: $44
  • Chicago Private Transfer to O’Hare Airport (ORD): $90
  • Chicago Private Transfer to Midway Airport (MDW): $90
  • From Chicago to O'Hare Airport Private Sedan Transfer: $99
  • MDW to Chicago City Hotels: 1-Way Private Transfer: $122
  • Chicago Airport: Private Transfer: $149

Typical Local Transportation prices in Boston

Some typical examples of transportation costs in Boston are as follows:


  • Taxi
    $35
  • Subway Daily Pass
    $9.00

Hired Cars and Shuttles in Boston

Some specific examples of transportation prices in Boston:

  • Logan Airport to Boston Hotels Private Transfer: $123
  • Boston Airport Shared Transfer Service: $29
  • Boston Private Transfer to Logan Airport (BOS): $117
  • Boston Airport Private Sedan Transfer: $143
  • Private Arrival Transfer from Boston Airport BOS: $28
  • Private Departure Transfer to Boston Airport BOS: $28
  • Shared Arrival Transfer: Boston Airport to Hotel: $30
  • Shared Departure Transfer: Hotel to Boston Airport: $30
  • Airport Transfer by Private Car Service: $55
  • Private Arrival Transfer Boston Airport to Boston City: $60


Entertainment

Entertainment and activities in Chicago typically cost an average of $32 per person, per day. This includes fees paid for admission tickets to museums and attractions, day tours, and other sightseeing expenses.

Entertainment and activities in Boston typically cost an average of $20 per person, per day. This includes fees paid for admission tickets to museums and attractions, day tours, and other sightseeing expenses.


  • Entertainment Entrance tickets, shows, etc.
    Chicago $32
    Boston $20
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:

  • Chicago River: 45-Minute Family-Friendly Architecture Cruise: $23
  • Haunted Bar Tour: $25
  • Chicago's Modern Skyscrapers Guided Walking Tour: $26
  • Downtown Architectural Interiors Tour: $30
  • Wicker Park Donut Tour: $35
  • Chicago 1893 World Fair Walking Tour with Bars: $42
  • Chicago Lakefront Bike Tour of Lincoln Park: $43
  • Bobby's Fright Hike: Halloween Edition Chicago Bike Tour: $50
  • Chicago Evening Segway Tour: $55
  • 2 Hour Pier Fireworks and Evening Segway Tour in Chicago: $65

Typical Entertainment prices in Boston

Some typical examples of activities, tours, and entrance ticket prices in Boston are as follows:


  • Two Tickets to Celtics Game
    $101
  • Duck Tour
    $32

Tours and Activities in Boston

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

  • Self-Guided Audio Tour: $14
  • Sightseeing Trolley Tour: $47
  • Revolutionary Story Walking Tour: $50
  • Irish Christmas Carol Holiday Cruise Northern Lights: $56
  • Weekend Brunch Cruise aboard Classic "Northern Lights": $74
  • Plimoth Plantation & Plymouth Waterfront Tour from Boston: $85
  • Classic Bites of Boston Tour & Optional Beer Tasting: $86
  • Guided Sightseeing Tour with Harbor Cruise: $145
  • Boston Citywalks: Private Personalized Walking Tour: $450
  • Historic After Dark Ghosts and Spirits Tour: $23


Alcohol

The average person spends about $17 on alcoholic beverages in Chicago per day. The more you spend on alcohol, the more fun you might be having despite your higher budget.

The average person spends about $19 on alcoholic beverages in Boston per day. The more you spend on alcohol, the more fun you might be having despite your higher budget.


  • Alcohol Drinks for one day
    Chicago $17
    Boston $19

Sample the Local Flavors in Chicago

Some specific costs for nightlife related activities in Chicago:

  • Haunted Chicago Ghost and Pub Walking Tour: $25
  • Walking tour to Chicago dive bars: $41
  • Chicago Barrel Bus Craft Distillery Tour: $90
  • Chicago Craft Brewery Barrel Bus Tour: $90
  • Ultimate Girl's Night Out in Sparkling Wine, Photo Shoot, Burlesque: $900

Sample the Local Flavors in Boston

Some specific costs for nightlife related activities in Boston:

  • North End Wine Tasting Tour: $96
  • Back Bay Wine Tasting Tour: $96
  • Historic Pub Crawl Tour along the Freedom Trail: $40
  • Craft Brewery Beer Tour: $82
  • South End Wine Tasting Tour: $96
  • Haunted Boston Ghost and Pub Walking Tour: $27
  • Sip of Boston Guided Brewery Tour: $90



When we compare the travel costs of actual travelers between Chicago and Boston, we can see that Boston is more expensive. And not only is Chicago much less expensive, but it is actually a significantly cheaper destination. So, traveling to Chicago would let you spend less money overall. Or, you could decide to spend more money in Chicago 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 Boston would naturally cost you much more money, so you would probably want to keep your budget a little tighter in Boston than you might in Chicago.

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Chicago vs. Boston Travel Comparison

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