A Travel Price Comparison for United States of America Chicago vs. Boston for Vacations, Tours, and Honeymoons

Should you visit Chicago or Boston?

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 Boston can help you decide which place is right for you.

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 $221, while the average daily cost in Boston is $203. 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

Chicago's average price for two people sharing a typical double-occupancy hotel room is $304. A typical place to stay for one person, per day is $152.

Accommodation prices vary by location and style, but travelers pay on average about $264 for a double occupancy room in Boston.


  • Accommodation Hotel or hostel for one person
    Chicago $152
    Boston $132
  • Accommodation Typical double-occupancy room
    Chicago $304
    Boston $264

Food

The price of a meal in Chicago can vary widely. However, the average price for food per day is $37 per person, and a typical meal will cost around $15 based on the spending of previous visitors. Less expensive dining options can be found by eating street food or at fast food restaurants.

In Boston travelers spend around $40 a day on food. You can save money by choosing casual restaurants or food stalls, or you can spend plenty more by dining in nicer restaurants at every meal.


  • Food Meals for one day
    Chicago $37
    Boston $40
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: $27
  • Factories to Calories Fulton Market Food Tour: $46
  • Learn to Make Chicago Deep-Dish Pizza with a Local: $49
  • Chicago Crime & Pizza Walk: $50
  • Lonely Planet Experiences: Chicago History and Food Tour: $59
  • Lonely Planet Experiences: River North Historical Food Tour: $61
  • Signature Food Tour at Chicago's Navy Pier: $64
  • Best in Chow: Chicago River North Food Tour: $64
  • Private Fusion Cooking Class in Downtown Chicago: $64
  • Skip the Line: Tommy Gun's Garage Dinner and Show Ticket: $67
  • Small-Group Chicago Food Tour: Gold Coast and Old Town: $75
  • Best of Chicago Tour Including a Deep-Dish Pizza: $75

Food Tours and Cooking Classes in Boston

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

  • Boston North End Pizza Tour: $49
  • Historic Taverns and Pizza Tour: $49
  • Boston's North End "Little Italy" Pizza, Cannoli, and Freedom Trail Walking Tour: $49
  • Haunted Pizza Tour: $66
  • Italian Food Tour with Pizza, Meats, Cheese, & Bread: $69
  • Boston's North End Small-Group Walking Food Tour: $71
  • Fenway Neighborhood Food Tour (Boston): $79
  • Boston Buffet Dinner Cruise: $99
  • Private Tour: Secret Food Tours Boston North End: $103
  • Spirit of Boston Sunset Dinner Cruise with Buffet: $105
  • Boston Dinner Cruise On The Odyssey: $111
  • Boston Odyssey Dinner Cruise: $118

Local Transportation

While taxis and private drivers typically cost much more than public transportation, people usually spend around $29 per day to get around in Chicago.

The cost of a taxi ride in Boston is significantly more than public transportation. On average, past travelers have spent $28 per person, per day, on local transportation in Boston.


  • Local Transportation Taxis, local buses, subway, etc.
    Chicago $29
    Boston $28
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:

  • Midway Airport Shared Transfers: $36
  • Private Airport Transfer: O’Hare International Airport (ORD) to Chicago: $43
  • Private Airport Transfer: from Chicago to O’Hare International Airport (ORD): $43
  • Chicago O'Hare International Airport Shared Transfer: $44
  • Private Airport Transfer: from Chicago to Midway International Airport (MDW): $55
  • Private Airport Transfer: Midway International Airport (MDW) to Chicago: $55
  • Private Departure Transfer from Chicago City to Midway International Airport: $66
  • Private Arrival Transfer from Chicago Midway Airport to Chicago City: $66
  • Private Departure Transfer from Chicago City to O'Hare International Airport: $78
  • Private Arrival Transfer from Chicago O'Hare Airport to Chicago City: $78
  • Departure Private Transfer Chicago City to O'Hare Airport ORD by Sedan Car: $79
  • Arrival Private Transfer Chicago O'Hare Airport ORD to Chicago by Sedan Car: $79

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:

  • Airport Transfer by Private Car Service: $55
  • Arrival Private Transfer Boston Airport BOS to Boston Business or Luxury Vehicle: $67
  • Boston Airport Private Sedan Transfer: $143
  • Boston Airport Shared Transfer Service: $29
  • Boston Airport Transfer Arrival And Departure: $340
  • Boston Logan Airport (BOS) to Boston - Arrival Private Transfer: $71
  • Boston Logan Airport (BOS) to Boston - Round-Trip Private Transfer: $142
  • Boston Private Transfer to Logan Airport (BOS): $117
  • Boston to Boston Logan Airport (BOS) - Departure Private Transfer: $71
  • Boston’s Logan International Airport to Providence - Round-Trip Private Transfer: $361
  • Boston’s Logan International Airport to Providence – Arrival Private Transfer: $180
  • Departure Private Transfer Boston to Boston Airport BOS Business-Luxury Vehicle: $67

Is it cheaper to fly into Chicago or Boston?

Prices for flights to both Boston 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.





Entertainment

Activities, things to do, and other forms of entertainment usually cost around $34 per person, per day in Chicago. This cost includes the price of admission tickets to attractions and museums as well as daily tours.

Entertainment and activities in Boston typically cost an average of $26 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 $34
    Boston $26
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:

  • A Storied Neighborhood: Dance the dialectic with Bill Ayers on an audio tour: $5.00
  • Discovering Vintage The Loop Walking Audio Tour by VoiceMap: $5.34
  • Chicago Riverwalk Self-Guided Walking Tour: $6.00
  • Millennium Park Exploration Game & Self-Guided Tour: $12
  • Skip the Line: American Writers Museum Admission Ticket: $14
  • Pilsen Walking Tour of Local Publicly Displayed Art: $15
  • The Chicago Theatre Marquee Tour: $18
  • Behind-the-Scenes Tour of Historic Chicago Theatre: $18
  • Chicago Scavenger Hunt Adventure: $21
  • Chicago Skydeck Experience Ticket: $22
  • Ghosts of Lincoln Park Walking Tour: $22
  • Best Architecture Walking Tour for Design Lovers: $22

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 Smartphone Ghost Walking Tour in Boston: $3.95
  • Self-Guided Boston Christmas Tour: $4.50
  • Boston's Freedom Trail - Smart Phone guided (GPS) walking tour - go anytime: $5.00
  • The Great Cannoli Tour: $5.00
  • Boston Harborwalk & Tea Party Self-Guided Audio Tour: $5.00
  • The Ghosts of Boston's Past Haunted Self-guided Tour: $5.00
  • Freedom Trail Self-Guided Tour: $6.33
  • Boston's Freedom Trail, 3 tours in 1, Smart Phone Guided Tour (GPS) - go anytime: $7.99
  • Harvard: 70-Minute Hahvahd Tour: $12
  • Public Tour of MIT: $12
  • Self-Guided Audio Tour: $14
  • Freedom Trail Lantern Tour: $14

Alcohol

While the amount that someone spends on alcohol while visiting Chicago may vary from person to person, on average a person spends $20 per day on alcoholic beverages.

The average person spends about $22 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 $20
    Boston $22

Sample the Local Flavors in Chicago

Here are a few nightlife and alcohol tours and activities from local tour providers 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:

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


When comparing the travel costs between Chicago and Boston, we can see that Chicago is more expensive. However, the two cities are actually relatively comparable in price, as the difference is somewhat minimal. Generally, this means that you could travel with generally the same travel style and level of luxury in each place. Since both cities are in North America, it's no surprise that their costs are relatively close, as many destinations here have somewhat similar travel prices overall.

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Chicago vs. Boston Travel Comparison

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