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

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.

Where Should I go: Chicago or Pittsburgh?


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.


Pittsburgh is a city in western Pennsylvania at the junction of 3 rivers. Set between the Monongahela and Allegheny Rivers, and a mountain ridge called Mt Washington, Pittsburgh has a unique character that is evident from the moment you arrive. Juxtaposed with the rumbling freight trains and the iconic bridges are the Bladerunner-esque self-driving Uber vehicles, scanning the roads with spinning Lidar scanners. Its Gilded Age sites, including the Carnegie Museum of Natural History, the Carnegie Museum of Art, and the Phipps Conservatory and Botanical Gardens, speak to its history as an early-20th-century industrial capital. In the North Shore neighborhood are the modern Andy Warhol Museum, Heinz Field football stadium, and PNC Park baseball stadium. Experiencing periods of boom and bust since its founding, the city is in a boom now, and it's a fun place to visit, with top-notch museums, great gardens and parks, and amazing food.

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 $279, 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 Hotel or hostel for one person
    Chicago $194
    Pittsburgh $106
  • Accommodation Typical double-occupancy room
    Chicago $388
    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
  • Taxi Ride
  • Taxi from Airport

Hired Cars and Shuttles in Chicago

Some specific examples of transportation prices in Chicago:

  • From Chicago to O'Hare Airport Private Sedan Transfer: $200
  • Chicago O'Hare Airport (ORD): Private Transfer to Chicago: $188
  • Executive Airport transfer Sedan: $141
  • Transfer in private vehicle from Chicago Airport (ORD) -Chicago City: $138
  • Private Transfer in Chicago (ORD/MDW): $130
  • Private Departure Transfer to Chicago Airports (ORD)(MDW): $90
  • Private Arrival Transfer from Chicago Airports (ORD) (MDW): $90
  • Private one-way airport transfer O'Hare Airport to/from Chicago : $80
  • From/to Chicago O´Hare International Airport: Private Round Trip Transfer: $69
  • Airport transfer between Chicago O'Hare and Milwaukee: $36
  • Chicago O´Hare International Airport Private Transfer One-Way: $27

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 Meals for one day
    Chicago $46
    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
  • Dinner for 3

Food Tours and Cooking Classes in Chicago

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

  • Downtown Chicago Walking Pizza Tour: $55
  • Downtown Pizza Guided Walking Tour with Tastings: $58
  • Chicago West Loop Pizza Crawl: $69
  • Chicago Food Tour: Deep Roots to Deep Dish: $69
  • Chicago Small Group Food Tour: $71
  • Chicago Pizza Tour: $75
  • Secret Food Tour: $75
  • Lake Michigan Buffet Brunch, Lunch or Dinner Cruise: $80
  • Downtown Family Food Tour by Bike with Sightseeing: $80
  • Private Indian-Mexican Fusion Cooking Class with a Modern Cook in Chicago: $84
  • Chicago Walking Food Tour With Secret Food Tours: $88
  • Gourmet Brunch, Lunch, or Dinner River Cruise: $88

  • Entertainment Entrance tickets, shows, etc.
    Chicago $43
    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)
  • Aquarium for 4
  • Water Taxi (family of 4)
  • IMAX Movie for Two
  • Shakespeare Play (2)
  • Art Institute (2)
  • U-Boat Tour (2)

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 : $68
  • Windy City Ghosts: Hauntings of Chicago By US Ghost Adventures: $30
  • 2-Hour Chicago Lakefront and Museum Campus Segway Tour: $69
  • 2-Hour Chicago Wine and Cheese Cruise : $65
  • 2-Hour Guided Segway Tour of Chicago: $65
  • 2-Hour Haunted Segway Tour of Chicago: $76
  • 3 Hours Chicago Architecture Tour - Skyscrapers and Photo Ops: $135
  • 360 Chicago Observation Deck Sip and View Ticket: $43
  • 45-Minute Chicago River Architecture Tour from Magnificent Mile: $27
  • 6-Hour Chicago City Tour by SUV: $1,200
  • 90-Minute Chicago River Architecture Tour: $42
  • African American Heritage Tour of Chicago : $125

Tours and Activities in Pittsburgh

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

  • Pittsburgh to Logstown Settler's History: A Self-Guided Driving Tour: $6.32
  • Downtown History and Architecture Tour: $28
  • Evening Ghost Tour: $28
  • Pittsburgh Pirates Baseball Game Ticket: $28
  • Public Art Walking Tour: $29
  • Downtown Whiskey Walking Tour: $29
  • Best of the Burgh Walking Tour: $30
  • Black & Ghost Tour: $30
  • Pittsburg 101 Tour: $30
  • Pittsburgh 101 Walking History Tour: $32
  • Whiskey Walking Tour: $33
  • Pittsburgh Penguins NHL Game Ticket at PPG Paints Arena: $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 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:

  • Haunted Chicago Ghost and Pub Walking Tour: $36
  • Chicago Local Brewery Expedition with Homemade Guacamole: $54
  • 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:

  • Wigle Whiskey Rebellion Distillery Tour: $22
  • Bike and Brewery Tour: $69
  • New! Pittsburgh Bike & Brewery Tour: $79
  • 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.

Which is Bigger, Chicago or Pittsburgh?

Chicago is bigger, and its population is about 8.9 times larger than the population of Pittsburgh. When comparing the population of Chicago vs. 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 and the activities that interest you.

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.
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Chicago vs. Pittsburgh Travel Comparison

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