A Travel Price Comparison for United States of America Chicago vs. Boston for Attractions, Food, Nightlife, and Music

Should you visit Chicago or Boston?

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

Chicago

Chicago is a edgey, cosmopolitan, and diverse city. It's an amazing and huge city with tons of activities and things to do. It's a gorgeous place to visit. It's also known for food, beaches, and shopping.

Boston

Boston is a classic, historic, and traditional classic. As it's a big city, visitors will find plenty to do, too. It offers plenty of beauty for visitors. As this is a very quaint destination, you'll find it has a special atmosphere. Other popular activities here include food, shopping, and museums.

How is Chicago different from Boston?

Which is Better for a Holiday?

Is Chicago or Boston better for Museums and Historical Sights?

For an educational experience, head to a museum or a notable sight in either Chicago or Boston.

You'll find many recognizable landmarks that put Chicago on the map. Some of the most famous are the Art Institute of Chicago, Adler Planetarium, and the Museum of Science and Industry. Notable landmarks include the famous Willis Tower - formerly the Sears Tower, Buckingham Fountain, and the iconic Cloud Gate (the bean).

Visitors will find world class museums and historical sights in Boston that are not to be missed. The city itself feels like a living museum. It is famous for Faneuil Hall, the Museum of Fine Arts, the Isabelle Stewart Gardner Museum, the USS Constitution, as well as the many sites along the Freedom Trail. There are also many museums on the campuses of the world renowned universities in the city.


Is Chicago or Boston better for Theater?

With a variety of venues, both Chicago and Boston provide options for theater-goers.

The theater scene in Chicago is world-class. Theater is big here with many of the major Broadway productions visiting the city. There is also an endless list of smaller, local theaters to choose from.

Boston offers many theater and performance venues for visitors. The city has many historic, beautifully restored theaters where you can enjoy a show. Head to the theater district for some of the most famous venues.

Is Chicago or Boston better for Food?

There are opportunities to sample the local cuisine in both Chicago and Boston.

Chicago has long been recognized as a culinary destination. While you're in town you have to try the famous deep dish pizza, Chicago style hot dogs, and Italian beef.

With its innovative style combined with traditional elements, Boston makes for a great culinary experience. Famous local foods include New England Clam Chowder, lobster rolls, and baked beans.

Is Chicago or Boston better for Nightlife?

It's hard to distinguish whether Chicago or Boston has a better nightlife scene.

Chicago is a destination that you simply have to visit at least once for nightlife. Popular bars and clubs include the Smart Bar, Beauty Bar, and Le Nocturne.

Boston has plenty to do after the sun goes down. The city is known for its breweries, craft beer, and vibrant university neighborhoods. It also hosts regular outdoor movies and world class sporting events.

Is Chicago or Boston better for Music?

Chicago generally offers more live music options than Boston.

In Chicago you'll find nightly musicians performing at a variety of venues. The city is the birthplace of such interesting styles as modern gospel and the Chicago style blues.

You don't have to look far to find a unique music venue in Boston. Popular music venues include Lizard Lounge, Blue Hills Bank Pavilion, and The Middle East.


Is Chicago or Boston better for Beaches?

Chicago and Boston are good choices for a beach vacation.

Many people head to Chicago to enjoy the beach. While you don't immediately think of beaches when you think of Chicago, there are some nice beaches by the lake.

Boston is a good spot to see the beach. There are a few urban beaches in the greater Boston area that you can explore on a nice day.

Is Chicago or Boston better for Shopping?

Most people pick Chicago for the shopping over Boston.

Chicago is a world class destination for shoppers. The most famous shopping area is Michigan Avenue and the famous Magnificent Mile.

Boston is a great destination for shopping. Head to Back Bay for some of the best high end shops.

Is Chicago or Boston better for Christmas?

The Christmas season is a nice time to visit both Chicago and Boston.

Visitors come from all around to experience the Christmas activities in Chicago. There's a number of seasonal celebrations, ice skating, and excellent shopping.

Boston is an extremely popular place to visit during the Christmas season. Christmas comes to life in the city with its Christmas Trees, holiday shows, and festivals.

Is Chicago or Boston better for Christmas Markets?

If you're looking for Christmas markets, Chicago and Boston both offer plenty of nice places.

Chicago offers some nice Christmas markets. Shopping is a highlight of a trip to the city, and the Christkindlmarkt is not to be missed.

Boston has a large number of Christmas markets. There are a number of European style Christmas markets that pop up during the holiday season around town.


Is Chicago or Boston better for Families?

You'll find kid-friendly activities in either Chicago or Boston.

Chicago is known to be a very family-friendly place to visit. The city has a large number of activities for kids, including zoos, Shedd Aquarium, impressive children's museums, and large and elaborate playgrounds in Millennium Park.

Boston is a very family-friendly place to visit. Popular activities for all ages include the Museum of Science, the New England Aquarium, and exploring the history, gardens, and parks around town.

Is Chicago or Boston better for Couples?

Both Chicago and Boston are good destinations to visit as a couple.

Chicago is a good city for couples to visit. Couples will enjoy exploring the city's vibrant theater scene and diverse neighborhoods.

Boston is a nice destination for couples. Couples who enjoy history will enjoy exploring the city. Take a swan boat ride in the Public Garden and wander the unique route along the Freedom Trail.

Is Chicago or Boston better for Backpackers and Budget Travelers?

Chicago and Boston are comparable places to visit for backpackers and budget travelers.

Chicago is popular with backpackers and budget travelers. The city doesn't have a huge backpacker vibe, but it does have a number of hostels that help keep costs in check.

Boston is a good city to visit for backpackers. Like most larger American cities, the city has a handful of hostels to choose from.

Is Chicago or Boston better for Students?

Chicago and Boston are comparable places to visit for students.

Students come from all over the world to visit Chicago. The city has a large number of universities that bring in students from around the country and around the globe.

Boston is a very popular place to visit for students. It is a city of students, with a number of world renowned universities located here including Harvard University, Boston College, and MIT.


Is Chicago or Boston better for Public Transit?

You'll find somewhat comparable public transit options in both Chicago and Boston.

Chicago has a great public transit system. There's a subway (the "L"), a commuter well, as well as buses and countless taxis available.

Visitors in Boston can get around quickly with the extensive public transit system. There's the T, which is the subway, as well as a trolley, bus, and water transportation system.

Is Chicago or Boston a more walkable city?

Chicago and Boston both are comparable when exploring on foot.

Chicago is a very walkable destination. The city has many restaurants, sights, and hotels that are easily accessible on foot.

It is easy to get around Boston on foot. The many parks and compact neighborhoods are best explored on foot.

Chicago and Boston: Pros and Cons

Pros
  • Popular museums and historical sights
  • Good music scene
  • Popular beach
  • Good for shopping
  • Family-friendly
  • Good for couples and romance
  • Good for backpackers and budget travelers
  • Big city activities
Pros
  • Popular museums and historical sights
  • Family-friendly
  • Good for couples and romance
  • Good for backpackers and budget travelers
  • Big city activities
Cons
  • Less active music scene
  • Less attractive beach
  • Less popular for shopping


Should I spend more time in Boston or Chicago?

How long in Chicago or Boston?

In either Chicago or Boston, you'll find plenty of activities to fill your time. You can fill a similar amount of time in either place.

The ideal length of time for a trip to Chicago is 3-5 days, and the ideal length of time for a trip to Boston is 3-5 days.


  • How many days in Chicago or Boston? Ideal Length of Stay
    Chicago 3-5 
    Boston 3-5

One day in Chicago or Boston?

Chicago is a bustling city that offers something for everyone. But since there are so many activities, you'll likely want to spend more than one day exploring.

In Boston, you'll find food and shopping. Most visitors spend time around the old town while in the area. One reason most visitors come is for the museums. This classic offers something for everyone. One day is usually not enough time for a trip here as there is plenty to do.

A weekend in Chicago or Boston?

Chicago is a great place to explore. With so much to do, a weekend is probably not enough time to see everything. Your budget might influence how long you stay.

In Boston, you'll find shopping and museums. The length of your trip often depends on your style of travel. Visiting the old town is also a must. One reason most visitors come is for the museums. Since there is so much to do in the area, a weekend is probably not enough for all of it.


Five days in Chicago or Boston?

It's hard to know how much time to spend in Chicago. For many, it makes a great getaway for five days. With all of its activities, you can easily fill five days here. It has many unique tourist attractions and fascinating things to do.

Boston is a great place to explore. It is common to spend five days here. The old town is one of the main draws for visitors. Five days is a great amount of time to relax and see the many things that Boston has to offer. Anyone can find something fun to do here.

A week in Chicago or Boston?

Travelers enjoy the museums and theater when visiting the edgey big city of Chicago. This city offers a variety of activities to choose from. Most people find that one week is more than enough time to see everything.

It's hard to know how much time to spend in Boston. One reason most visitors come is for the museums. Exploring the old town is a popular activity. One week may feel like too much time here unless you plan to do a lot of relaxing.

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. What follows is a categorical breakdown of travel costs for Chicago and Boston in more detail.



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

Local Transportation
  • 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:

  • Private Airport Transfer: O’Hare International Airport (ORD) to Chicago: $43
  • Private Airport Transfer: from Chicago to O’Hare International Airport (ORD): $43
  • Private Airport Transfer: Midway International Airport (MDW) to Chicago: $55
  • Private Airport Transfer: from Chicago to Midway International Airport (MDW): $55
  • Private Arrival Transfer from Chicago Midway Airport to Chicago City: $66
  • Private Departure Transfer from Chicago City to Midway International Airport: $66
  • Private Arrival Transfer from Chicago O'Hare Airport to Chicago City: $78
  • Private Departure Transfer from Chicago City to O'Hare International Airport: $78
  • Arrival Private Transfer Chicago O'Hare Airport ORD to Chicago by Sedan Car: $79
  • Departure Private Transfer Chicago City to O'Hare Airport ORD by Sedan Car: $79
  • Private Departure Transfer to Chicago Airports (ORD)(MDW): $80
  • Private Arrival Transfer from Chicago Airports (ORD) (MDW): $80

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 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 to Boston Logan Airport (BOS) - Departure Private Transfer: $71
  • Boston Logan International Airport Private Transfer: $68
  • Private Boston International Airport (BOS) Transfer: $112
  • 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.





Food
  • 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
  • Learn to Make Chicago Deep-Dish Pizza with a Local: $49
  • Lonely Planet Experiences: River North Historical Food Tour: $61
  • Private Fusion Cooking Class in Downtown Chicago: $64
  • Best in Chow: Chicago River North Food Tour: $64
  • Signature Food Tour at Chicago's Navy Pier: $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
  • River North Walking Food Tour: $75
  • Chicago's Wicker Park Food Tour: $75
  • Private Indian-Mexican Fusion Cooking Class with a Modern Cook: $78

Food Tours and Cooking Classes in Boston

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

  • 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
  • Buffet Lunch or Dinner Cruise on Boston Harbor: $81
  • Private Tour: Secret Food Tours Boston North End: $103
  • Spirit of Boston Sunset Dinner Cruise with Buffet: $105
  • Boston Odyssey Dinner Cruise: $118
  • Lunch or Dinner Cruise on the Odyssey: $122
  • North End Neighborhood Food Tour: $150

Entertainment
  • 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
  • Riverwalk Self-Guided Walking Tour: $6.00
  • Millennium Park Self-Guided Walking Tour: $6.00
  • Chicago Riverwalk Self-Guided Walking Tour: $6.00
  • Skip the Line: American Writers Museum Admission Ticket: $14
  • Pilsen Walking Tour of Local Publicly Displayed Art: $15
  • Behind-the-Scenes Tour of Historic Chicago Theatre: $18
  • Chicago Scavenger Hunt Adventure: $21
  • Windy City Ghost Tour: $24
  • Street Art & Mural Tours By Native 312- Wabash Arts Corridor: $25
  • In the Streets: Milwaukee Ave Guided Bike Tour: $25

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
  • The Great Cannoli Tour: $5.00
  • Boston Harborwalk & Tea Party Self-Guided Audio Tour: $5.00
  • Boston's Freedom Trail - Smart Phone guided (GPS) walking tour - go anytime: $5.00
  • The Ghosts of Boston's Past Haunted Self-guided Tour: $5.00
  • Boston's Freedom Trail, 3 tours in 1, Smart Phone Guided Tour (GPS) - go anytime: $7.99
  • Freedom Trail Best Tour (Boston Common to Faneuil Hall): $15
  • Boston Self-Guided Audio Tour: $15
  • Freedom Trail Walking Tours: $16
  • Tour of The Freedom Trail: $16
  • Downtown Freedom Trail Walking Tour in Boston: $20

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, The Best Museums in Chicago, Free Things to Do in Boston, Must-See Monuments and Memorials In Boston, and The Best Things To Do in Boston with Kids.


Alcohol
  • 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: $56
  • Sip of Boston Guided Brewery Tour: $90


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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