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

Should you visit Chicago or Pittsburgh?

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

Chicago

Chicago is a vibrant, multicultural, and edgey city. Visitors will also find so much to do here because it's a large city with many sights and attractions. It offers plenty of beauty for visitors. It's also popular because of the beaches, shopping, and museums.

Pittsburgh

Pittsburgh is a under-rated, industrial, and authentic city. Because this is such a big city, visitors will find many sights and attractions around town. Other popular activities here include shopping, museums, and nightlife.

Chicago and Pittsburgh: Pros and Cons

Pros
  • Popular museums and historical sights
  • Numerous theater shows
  • Popular for food and cuisine
  • Active nightlife
  • Good music scene
  • Popular beach
  • Fun shopping
  • Popular at Christmas
  • Known for Christmas markets
  • Family-friendly
  • Good for couples and romance
  • Good for backpackers and budget travelers
  • Good for students
  • Good public transit
  • Big city activities
  • Home to the Willis Tower (previously the Sears Tower)
Pros
  • Popular museums and historical sights
  • Active nightlife
Things to Consider
  • Less popular for food
  • Less popular for shopping
  • Less family-friendly
  • Less popular with couples
  • Less popular with backpackers
  • Public transit not as usable


Is there more to do in Chicago or Pittsburgh?

Tourists will generally find more to do in Chicago than Pittsburgh. It is bigger and it has more sights, attractions, and activities for travelers. Chicago is more touristy than Pittsburgh and is popular for its thriving sports scene, its iconic local cuisine, and its world class shopping at the Magnificent Mile. It is also well known for The Willis Tower (previously the Sears Tower). Pittsburgh is famous for its many bridges, its steel industry, and being the home of "Mr. Roger's Neighborhood".

How is Chicago different from Pittsburgh?

Which is Better for a Holiday?

Let's take a look at the differences and similarities between Pittsburgh and Chicago. Then, you can decide for yourself which place is better for your next trip.

Are the Museums and Historical Sights Better in Chicago or Pittsburgh?

Chicago
Pittsburgh

Chicago is a must-visit destination for its historical sights. Also, Pittsburgh is not as popular, but is still a nice city for its sights and museums.

With plenty of landmarks, attractions, and museums, Chicago has many famous sights for visitors. There are countless landmarks, museums, and iconic sights in the area. 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).

You'll find a good number of museums and monuments packed into Pittsburgh. The museums range from science and nature focused, like the Phipps Conservatory and Botanical Garden, to quirky and artsy, like the Mattress Factory. The Warhol Museum is dedicated to the works of Andy Warhol and it's not to be missed. Also worth a visit is the Heinz History Center, Randyland, and the Carnegie Museums of Art and Natural History.


Is Chicago or Pittsburgh Better for Theater?

Chicago
Pittsburgh

Chicago is a must-visit destination for its shows and theatre. However, Pittsburgh is not a theatre destination.

Famous for its theaters and plays, you'll find world-renowned shows in Chicago. 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.

Pittsburgh is not a theatre destination.

Is the Food Better in Chicago or Pittsburgh? Which Destination has the Best Restaurants?

Chicago
Pittsburgh

Chicago is a must-visit destination for its local flavors and cuisine. Also, Pittsburgh is not as popular, but is still a nice city for its local cuisine and restaurants.

Known for it's food and restaurant scene, Chicago is always at the top of any foodie's travel list. With everything from award-winning luxury restaurants to local dives, this city has something for everyone. It also has very distinct local flavors and dishes that create an identity and bring great pride to the locals. While you're in town you have to try the famous deep dish pizza, Chicago style hot dogs, and Italian beef.

Pittsburgh offers number of good local restaurants to choose from. The city is known for its working class roots, and the food is hearty and filling, which is great for those on a budget. Popular local dishes include pierogis, deli sandwiches, Pittsburgh salads (complete with French fries), and hotcakes.

Is Chicago or Pittsburgh Better for Nightlife?

Chicago
Pittsburgh

Chicago is a must-visit destination for its evening party scene. Also, Pittsburgh is not as popular, but is still a nice city for nightlife.

Chicago is a world class party destination. It has a wide range of activities at night, with everything from theater and comedy clubs to dance venues, sporting events, and local bars. It's easy to fill many evenings with whatever activity appeals to you. Popular bars and clubs include the Smart Bar, Beauty Bar, and Le Nocturne.

Pittsburgh has plenty to do after the sun goes down. There's an active music and dance scene in town. For the best bars and clubs, head to the Strip and South Side and for live entertainment and casinos check out the North Shore.


Is Chicago or Pittsburgh Better for Music?

Chicago
Pittsburgh

Chicago is a must-visit destination for its music scene. However, Pittsburgh is not a live music destination.

Chicago has become a mecca for musicians from around the world. The city is the birthplace of such interesting styles as modern gospel and the Chicago style blues.

Pittsburgh is not a live music destination.

Is Chicago or Pittsburgh Better for Beaches?

Chicago
Pittsburgh

Chicago is a nice place to visit for the beach. However, Pittsburgh is not a beach destination.

Chicago has a beach worth visiting. While you don't immediately think of beaches when you think of Chicago, there are some nice beaches by the lake. If the weather is nice, it's a great area to spend some time.

Pittsburgh is not a beach destination.

Is the Shopping Better in Chicago or Pittsburgh?

Chicago
Pittsburgh

Chicago is a must-visit destination for its shopping areas. Also, Pittsburgh is not as popular, but is still a nice city for shopping.

Many people travel to Chicago specifically to go shopping. There are countless neighborhoods that are filled with boutiques, local vendors, and art galleries. The city has some of the country's best shopping opportunities, and the most notable area is the famous Michigan Avenue and the Magnificent Mile.

Pittsburgh is a great destination for shopping. You'll find local fashion boutiques and shopping centers in the city's downtown. Other great shopping neighborhoods include Shadyside, Station Square, and Fifth Avenue Place.


Is Chicago or Pittsburgh Better for Christmas?

Chicago
Pittsburgh

Chicago is great for its Christmas holiday experiences. However, Pittsburgh does not offer Christmas activities.

Chicago is a very popular destination during Christmas. There's a number of seasonal celebrations, ice skating, and excellent shopping.

Pittsburgh does not offer Christmas activities.

Is Chicago or Pittsburgh Better for Christmas Markets?

Chicago
Pittsburgh

Chicago is a nice place to visit for visiting Christmas markets. However, Pittsburgh does not offer Christmas markets.

Chicago has Christmas markets worth visiting. Shopping is a highlight of a trip to the city, and the Christkindlmarkt is not to be missed.

Pittsburgh does not offer Christmas markets.

Is Chicago or Pittsburgh Better for Families?

Chicago
Pittsburgh

Chicago is a must-visit destination for its kid-friendly activities. Also, Pittsburgh is not as popular, but is still a nice city for its family-friendly activities.

Chicago is an amazing family-friendly city 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. It's easy to keep kids entertained in this very kid-focused city.

Pittsburgh is a family-friendly place to visit. There's a surprising number of kid-friendly activities packed into this city. Check out the National Aviary or visit the popular Pittsburgh Zoo and Aquarium. There are also kid-focused museums and science centers as well as parks and playgrounds. Also make sure you take the cable car up Duquesne Incline or enjoy a boat ride on one of the rivers as well.


Is Chicago or Pittsburgh Better for Couples?

Chicago
Pittsburgh

Chicago is a nice place to visit for couples. However, Pittsburgh is not a good destination for romance.

Chicago is a good city for couples to visit. Couples will enjoy exploring the city's vibrant theater scene and diverse neighborhoods. There are many varied restaurants and entertainment options that make for a great date night. There are also sporting events, parks, and gardens where couples can explore.

Pittsburgh is not the best destination for a couple to visit. There are a few good date night activities like taking river cruises, enjoying dinner and show, or going to a Pirate's game.

Is Chicago or Pittsburgh Better for Backpackers and Budget Travelers?

Chicago
Pittsburgh

Chicago is a nice place to visit for backpackers and budget travelers. However, Pittsburgh is not a good destination for backpackers.

It's common for backpackers to visit Chicago. The city doesn't have a huge backpacker vibe, but it does have a number of hostels that help keep costs in check.

Pittsburgh is a challenging destination for budget travelers and backpackers due to the higher prices. It's usually overlooked by backpackers, but there is some cheap accommodation in town.

Is Chicago or Pittsburgh Better for Students?

Chicago
Pittsburgh

Chicago is a must-visit destination for its student-friendly activities. However, Pittsburgh is not popular with students.

Chicago is a great destination for students. The city has a large number of universities that bring in students from around the country and around the globe. It's a huge international city with economic ties and many opportunities connected to the universities.

Pittsburgh is not popular with students.


Is Chicago or Pittsburgh Better for Public Transit? Which Is Easier to Get Around Without a Car?

Chicago
Pittsburgh

Chicago is a must-visit destination for times when you don't have a car. Also, Pittsburgh is not as popular, but is still a nice city for its public transit.

Chicago has a world-class public transit network to take passengers everywhere in the city. There's a subway (the "L"), a commuter well, as well as buses and countless taxis available.

Pittsburgh has a few public transit options. There are bus and lightrail options through the city's downtown. There's also the unique incline, which is an experience worth doing.

Is Chicago or Pittsburgh a more walkable city?

Chicago
Pittsburgh

Chicago is great for its ease of walking around. Also, Pittsburgh is not as popular, but is still a nice city for its walkability.

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

Pittsburgh is somewhat walkable. Some of the attractions are spread out, but if you're willing to do a bit of walking, it's possible to get around on foot.

For even more information, also check out Is Chicago Worth Visiting? and Is Pittsburgh Worth Visiting?.

Should I spend more time in Pittsburgh or Chicago?

How long in Chicago or Pittsburgh?

Visitors can find plenty of fun things to do in both Chicago and Pittsburgh. With generally more activities and things to do, visitors tend to spend more time in Chicago than in Pittsburgh. Usually, 3-5 days is a good amount of time for Chicago, and 2-3 days is enough time in Pittsburgh.

Families should spend more time in Chicago than Pittsburgh. Because of the many family-friendly attractions and fun things to do for kids in Chicago, it's a great place to visit with the whole family.

Couples should spend more time in Chicago than Pittsburgh. You'll find plenty of romantic sights and fun activities in Chicago that are great for a weekend getaway or a longer couple's trip.

Backpackers and budget travelers should spend more time in Chicago than Pittsburgh if your budget allows for it. With a larger number of budget-friendly sights, good nightlife, and active things to do, anyone traveling on a budget would have a good time in Chicago.


  • How many days in Chicago or Pittsburgh? Ideal Length of Stay
    Chicago 3-5 
    Pittsburgh 2-3

One day in Chicago or Pittsburgh?

When visiting Chicago, people usually allow for lots of time. Anyone can find something fun to do here. But since there are so many activities, you'll likely want to spend more than one day exploring.

In Pittsburgh, you'll find nightlife and food. This city 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 Pittsburgh?

When visiting Chicago, people usually allow for lots of time. It offers something for everyone. With so much to do, a weekend is probably not enough time to see everything.

In Pittsburgh, you'll find food and shopping. The length of your trip often depends on your style of travel. A weekend here is typical. A weekend is a great amount of time to relax and see the many things that Pittsburgh has to offer.

Five days in Chicago or Pittsburgh?

Chicago, a popular city, is full of activities for travelers. This is a popular place to visit for five days. In five days, you should have a good grasp of this city. Your budget might influence how long you stay.

Pittsburgh is a great place to explore. Five days is more than enough time to enjoy everything. Take some day trips to nearby places to fill the extra days. Anyone can find something fun to do here.

A week in Chicago or Pittsburgh?

Chicago is a popular place that is full of things to see and experience. One week is plenty of time to see everything, even with extra days to spare. It has many unique tourist attractions and fascinating things to do.

It's hard to know how much time to spend in Pittsburgh. Many people enjoy the museums and nightlife when visiting Pittsburgh. One week may feel like too much time unless you plan to do a lot of relaxing.


For some great organized tour ideas, see The Best 2-Week Tours in United States of America, The Best 3-Week Tours in United States of America, Tours for Outdoor and Nature Lovers in United States of America, and The Best Coach Bus Tours in United States of America.


Which place is cheaper, Pittsburgh or Chicago?

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

The average daily cost (per person) in Chicago is $288, while the average daily cost in Pittsburgh is $181. 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 Pittsburgh in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Chicago $198
    Pittsburgh $106
  • Accommodation Typical double-occupancy room
    Chicago $396
    Pittsburgh $212
Compare Hotels in Chicago and Pittsburgh

Looking for a hotel in Chicago or Pittsburgh? 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.

Hotels in Chicago


Hotels in Pittsburgh


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 Pittsburgh Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Chicago $37
    Pittsburgh $22
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:

  • Meet and Greet Private SUV Transfer from MDW to Downtown Chicago: $300
  • Meet and Greet Private Sedan Transfer from MDW to Downtown Chicago: $240
  • Private SUV Transfer from Chicago Downtown to Midway airport: $240
  • Meet and Greet Private Sedan Transfer from ORD to Downtown Chicago: $240
  • Departure Private Transfer: Chicago to O'Hare Airport ORD in Luxury Car: $233
  • Private Chicagoland One-Way Transfer by Mercedes Sprinter : $229
  • Private Sedan Transfer from Chicago Downtown to Midway airport: $220
  • Chicago Airport Transfer: O'Hare Airport ORD to Chicago in Luxury SUV: $202
  • Departure Private Transfer: Chicago to O'Hare Airport ORD in Luxury SUV: $202
  • Curbside Sedan Transfer from O'Hare Airport to Downtown Chicago: $190
  • Private Round trip Transfer - Chicago O'Hare Airport (ORD): $189
  • Chicago O'Hare Airport (ORD): Private Transfer to Chicago: $188

Hired Cars and Shuttles in Pittsburgh

Also for Pittsburgh, here are a few examples of actual transportation services:

  • Pittsburgh Airport (PIT) to Pittsburgh City - Round-Trip Private Transfer: $96
  • Pittsburgh Airport (PIT) to Pittsburgh hotel/address - Arrival Private Transfer: $48
  • Pittsburgh City to Pittsburgh Airport (PIT) - Departure Private Transfer: $48

Is it cheaper to fly into Chicago or Pittsburgh?

Prices for flights to both Pittsburgh 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 $49
    Pittsburgh $54
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 : $40
  • Bucktown Pizza Crawl in Chicago: $53
  • Chicago : Hands-on Cooking Classes With Local Chef: $55
  • Fulton Market Delicious Donut Adventure and Walking Food Tour: $63
  • Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise: $72
  • Downtown Pizza Guided Walking Tour with Tastings: $73
  • Chicago Deep Dish Pizza Self-Guided Tour: $75
  • Chicago Bucktown-Wicker Park Pizza Crawl: $79
  • Friday Pizza Walk of Downtown Chicago: $79
  • Downtown Family Food Tour by Bike with Sightseeing: $80
  • Lake Michigan Buffet Brunch, Lunch or Dinner Cruise: $86
  • Secret Food Tour: $88

Food Tours and Cooking Classes in Pittsburgh

For Pittsburgh, here are some samples of tours and activities related to meals and dining experiences:

  • Pittsburgh's Strip District Food Tour: $49
  • Pittsburgh's Strip District Food Tour: $70

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Chicago $47
    Pittsburgh $38
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:

  • Field Museum of Natural History Early Access Ticket : $73
  • Windy City Ghosts: Hauntings of Chicago Walking Tour: $28
  • 1 Hour E-Bike Tour Of The Chicago Lakefront And Nearby Landmarks: $30
  • 2 Hour Chicago Pier Fireworks & Evening Segway Tour: $78
  • 2 Hour Magnificent Chicago Tour with Photos: $75
  • 2-Hour Chicago Wine and Cheese Cruise : $65
  • 2-Hour Guided Segway Tour of Chicago: $65
  • 2-Hour Haunted Segway Tour of Chicago: $78
  • 3 Hours Chicago Architecture Tour - Skyscrapers and Photo Ops: $135
  • A Storied Neighborhood: A Self-Guided Audio Tour with Bill Ayers: $5.40
  • Adults Party Art Experience: $66
  • Amazing Lakefront Segway Tour of Chicago: $79

Tours and Activities in Pittsburgh

Also, here are some specific examples of entertainment, tickets, and activities for Pittsburgh.

  • Eastbound Pennsylvania Turnpike: A Self-Guided Driving Tour: $6.22
  • Pittsburgh to Logstown Settler's History: A Self-Guided Driving Tour: $6.32
  • Entrance Ticket to AT BLAQK House Collections: $7.00
  • Downtown Quest Experience in Pittsburgh: $8.16
  • Scavenger Hunt Adventure in Pittsburgh by Crazy Dash: $10
  • Pittsburg 101 Tour: $24
  • Pittsburgh Ghosts Steel City Haunted Tour: $24
  • Smartphone-Guided Walking Tour of Downtown Pittsburgh: $25
  • Smartphone-Guided Tour of Downtown Pittsburgh Sights & Stories: $28
  • Public Art Walking Tour: $30
  • Pittsburgh 101 Walking History Tour: $32
  • Black & Ghost Tour: $33

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 day
    Chicago $25
    Pittsburgh $33

Sample the Local Flavors in Chicago

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

  • Chicago Walking Brewery Tour in Malt Row: $30
  • Malt Row Walking Brewery Tour: $30
  • Walking tour to Chicago dive bars: $41
  • Milwaukee,Miller Brewery Tour&Tasting 1-Day Tour from Chicago: $93
  • Chicago Craft Brewery Barrel Bus Tour: $100
  • Craft Brewery Tour by Barrel Bus: $100

Sample the Local Flavors in Pittsburgh

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

  • Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl: $13
  • Wigle Whiskey Rebellion Distillery Tour: $22
  • New! Beers in the Burgh: Pittsburgh Brewery Walk: $50
  • Bike and Brewery Tour: $89
  • Pittsburgh Signature Guided Brewery Tour: $105


When we compare the travel costs of actual travelers between Chicago and Pittsburgh, we can see that Chicago is more expensive. And not only is Pittsburgh much less expensive, but it is actually a significantly cheaper destination. So, traveling to Pittsburgh would let you spend less money overall. Or, you could decide to spend more money in Pittsburgh 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 Pittsburgh.

If you're trying to decide if either of these two destinations are within your price range, also see Is Chicago Expensive? and Is Pittsburgh Expensive?.


Which is Bigger, Chicago or Pittsburgh?

Chicago has a larger population, and is about 9 times larger than the population of Pittsburgh. When comparing the sizes of Chicago and Pittsburgh, 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.