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?

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.

Pueblo

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 San Francisco, The Best 2-Week Tours from Los Angeles, The Best Family-Friendly Tours to United States of America, and The Best Wildlife Tours to 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
  • 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
    $19
  • Taxi Ride
    $10
  • Taxi from Airport
    $45

Hired Cars and Shuttles in Chicago

Some specific examples of transportation prices in Chicago:

  • Chicago O´Hare International Airport Private Transfer One-Way: $27
  • Airport transfer between Chicago O'Hare and Milwaukee: $34
  • Chicago Midway Airport (MDW) to Chicago hotel/address - Arrival Private Transfer: $53
  • Chicago to Chicago O'Hare Airport (ORD): Departure Transfer: $57
  • Chicago O'Hare Airport (ORD) to Arrival Private Transfer: $57
  • From/to Chicago O´Hare International Airport: Private Round Trip Transfer: $69
  • ORD Airport Private Transfer to/from Chicago: $81
  • Private one-way airport transfer O'Hare Airport to/from Chicago : $87
  • Private Departure Transfer to Chicago Airports (ORD)(MDW): $90
  • MDW Airport Private Transfer to/from Chicago: $100
  • Chicago Midway Airport (MDW) to Chicago City - Round-Trip Private Transfer: $106
  • Midway Airport and O'Hare from/to Hotels Private Transfer: $110

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
  • 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
    $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
  • Downtown Chicago Walking Pizza Tour: $55
  • Chicago : Hands-on Cooking Classes With Local Chef: $55
  • Chicago's Delicious Donut Adventure & Walking Food Tour: $55
  • Downtown Pizza Guided Walking Tour with Tastings: $58
  • Fulton Market Delicious Donut Adventure & Walking Food Tour: $65
  • Chicago Bucktown-Wicker Park Pizza Crawl: $69
  • Friday Pizza Walk of Downtown Chicago: $69
  • Chicago Small Group Food Tour: $69
  • Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise: $72
  • Chicago Pizza Tour: $75
  • Chicago Deep Dish Pizza Self-Guided Tour: $75

Entertainment
  • 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)
    $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: A Self-Guided Audio Tour with Bill Ayers: $5.40
  • Discovering Chicago with Walking In App Audio Tour: $6.00
  • Haunted Sites Self-Guided Audio Walking Tour: $6.50
  • Chicago's Dark Side Smartphone (GPS/APP) Audio / Self Guided Walking Tour: $6.95
  • Vice, Crime and Gangsters in A Self-Guided Audio Tour: $6.99
  • Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour: $6.99
  • Vice, Crime and Gangsters Self-Guided Audio Tour: $6.99
  • Must-Sees & Hidden Gems In-App Audio Tour (ENG): $9.00
  • Chicago Self-Guided Audio Tour: $9.00
  • Chicago Cubs Baseball Game Ticket at Wrigley Field: $9.77
  • App Chicago self-guided tours with multilingual audioguides: $9.77
  • Chicago Cubs Baseball Game Ticket at Wrigley Field: $9.96

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
    Pueblo -

Sample the Local Flavors in Chicago

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

  • Malt Row Walking Brewery Tour: $30
  • Walking tour to Chicago dive bars: $41
  • Chicago Local Brewery Expedition with Homemade Guacamole: $54
  • Chicago Walking Brewery Tour in Malt Row: $75
  • Chicago Craft Brewery Barrel Bus Tour: $100
  • Craft Brewery Tour by Barrel Bus: $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.