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

Should you visit Chicago or Pueblo?

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

Where Should I go: Chicago or Pueblo?


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.


Pueblo is a surprisingly large community in the state of Colorado that has a population of more than 100,000. Many travelers pass through this area if they're heading into the mountain area from the southeast. It's sits along Interstate Highway 25 and is only forty five miles from Colorado Springs. There's a regional airport in the area as well. In town there is a bus service run by the City Of Pueblo Transit. Rides cost $1.00, but it is highly recommended that you have your own vehicle when visiting town.

For some great organized tour ideas, see The Best 2-Week Tours from Los Angeles, The Best Family-Friendly Tours to United States of America, The Best Wildlife Tours to United States of America, and The Best Hiking & Trekking Tours in United States of America.

Which place is cheaper, Pueblo 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 Pueblo is $284. 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 Pueblo in more detail.

  • Accommodation Hotel or hostel for one person
    Chicago $198
    Pueblo $276
  • Accommodation Typical double-occupancy room
    Chicago $396
    Pueblo $552
Compare Hotels in Chicago and Pueblo

Looking for a hotel in Chicago or Pueblo? 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 Pueblo

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 Pueblo Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Chicago $37
    Pueblo -
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:

  • Chicago O´Hare International Airport Private Transfer One-Way: $27
  • Private Arrival Transfer from Chicago Airports ORD Or MDW: $50
  • Chicago City to Chicago Midway Airport (MDW) - Departure Private Transfer: $52
  • Chicago Midway Airport (MDW) to Chicago hotel/address - Arrival Private Transfer: $53
  • Chicago to Chicago O'Hare Airport (ORD): Departure Transfer: $57
  • Chicago Midway Airport (MDW) to Chicago -Arrival Private Transfer: $58
  • Chicago to Chicago Airport (MDW) - Departure Private Transfer: $58
  • Private Transfer from Chicago Airport (ORD) - Chicago City: $58
  • Private Transfer from Chicago City to Chicago Airport (ORD): $58
  • Chicago to Chicago O'Hare Airport (ORD) - Departure Private Car Transfer: $63
  • Private Departure Transfer to Chicago Airports (ORD)(MDW): $90
  • Private Arrival Transfer from Chicago Airports (ORD) (MDW): $90

Is it cheaper to fly into Chicago or Pueblo?

Prices for flights to both Pueblo 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 $49
    Pueblo $7.64
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.

  • Traveling Spoon Chicago-Style Deep Dish Pizza Private Online Cooking Class : $40
  • Fulton Market Delicious Donut Adventure and Walking Food Tour: $63
  • Chicago West Loop Pizza Crawl: $79
  • Friday Pizza Walk of Downtown Chicago: $79
  • Chicago Walking Food Tour With Secret Food Tours: $89
  • Chicago Buffet Dinner Cruise on Lake Michigan: $96
  • Saturday Chicago Pizza History and Tastings Bus Tour: $99
  • Chicago Half-Day Walking Food Tour with Free Bike or Kayak Rental: $99
  • Chicago Food Tour in Devon Ave: $125
  • Chicago Fireworks Dinner Cruise with Buffet: $129
  • Mother's Day Signature Dinner Cruise on Lake Michigan: $130
  • Chicago Gourmet Dinner Cruise on Lake Michigan: $132

  • Entertainment Entrance tickets, shows, etc.
    Chicago $47
    Pueblo -
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:

  • A Storied Neighborhood: A Self-Guided Audio Tour with Bill Ayers: $5.40
  • Gangster Story Quest Experience in Chicago: $5.66
  • Chicago Lincoln Square Quest Experience: $5.72
  • Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour: $6.99
  • Vice, Crime and Gangsters in A Self-Guided Audio Tour: $6.99
  • Chicago Self-Guided Audio Tour: $9.00
  • Chicago White Sox Baseball Game Ticket at Guaranteed Rate Field: $9.43
  • The Loop, River North and Chicago’s Theater District: A Self-Guided Audio Tour: $12
  • Chicago Millennium Park Self-Guided Walking Tour: $15
  • Experience the season with a scavenger hunt in Chicago with Holly Jolly Hunt: $20
  • Chicago's Navy Pier Centennial Wheel Ticket: $21
  • The Chicago Theatre Tour Experience: $24

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
    Pueblo -

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
  • 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

When comparing the travel costs between Chicago and Pueblo, 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.

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

Which is Bigger, Chicago or Pueblo?

Chicago has a larger population, and is about 30 times larger than the population of Pueblo. When comparing the sizes of Chicago and Pueblo, 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.