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

Should you visit Chicago or Vail?

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

Chicago

Chicago is a cosmopolitan, diverse, and vibrant city. With plenty of activities and things to do, it's a huge city that draws plenty of visitors. It's a beautiful place to visit, too. Visitors also love the beaches, shopping, and museums.

Vail

Vail is a scenic, vibrant, and upscale ski town. Because it offers so much small town charm with a variety of activities, it attracts plenty of visitors for a good reason. With stunning beauty, it attracts visitors from all around. As it offers a special and quaint atmosphere, visitors come from all over to experience this destination. Other popular activities here include live music, food, and hiking.

Chicago and Vail: Pros and Cons

Pros
  • Popular museums and historical sights
  • Numerous theater shows
  • Popular for food and cuisine
  • Active nightlife
  • Good music scene
  • Popular beach
  • Family-friendly
  • Good for backpackers and budget travelers
  • Good for students
  • Good public transit
  • Big city activities
  • Home to the Willis Tower (previously the Sears Tower)
Things to Consider
  • Less popular with couples
Pros
  • Popular for skiing
  • Active nightlife
  • Nice resorts
  • Good for hiking
  • Family-friendly
  • Good for couples and romance
  • Good for backpackers and budget travelers
  • Small town charm
  • Impressive beauty
  • Quaint atmosphere
  • Home to the Vail Ski Resort
Things to Consider
  • Less popular for food
  • Less active music scene
  • Public transit not as usable


Is there more to do in Chicago or Vail?

Tourists will generally find more to do in Chicago. Although Chicago and Vail are both popular with visitors, Chicago has more sights, activities, and attractions for travelers. Chicago is more popular for its museums, theatre productions, food, nightlife, music, beaches, shopping, and big city activities, while Vail is known for its skiing, resorts, hiking, christmas markets, small town charm, impressive beauty, and quaint atmosphere. Vail is more touristy than Chicago and is popular for its world-class skiing, charming mountain town atmosphere, and adventurous outdoor activities. Chicago is popular for its thriving sports scene, its iconic local cuisine, and its world class shopping at the Magnificent Mile. It is also home to The Willis Tower (previously the Sears Tower).

How is Chicago different from Vail?

Which is Better for a Holiday?

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

Is Chicago or Vail Better for Skiing?

Chicago
Vail

Vail is renowned for winter skiing. However, Chicago is not a skiing destination.

Vail is among the world's best ski destinations. This ski town has produced its share of Olympians. Vail is the third largest ski resort in the US and it has 31 lifts and 195 runs. There are five different bowls that offer beautiful views.

Chicago is not a skiing destination.


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

Chicago
Vail

Chicago is a must-visit destination for its historical sights. However, Vail does not have museums and landmarks.

The museums and tourist attractions in Chicago are world-renowned. 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).

Vail does not have museums and landmarks.

Is Chicago or Vail Better for Theater?

Chicago
Vail

Chicago is a must-visit destination for its theatre productions. However, Vail is not a theatre destination.

The theater and performance venues in Chicago draw crowds from around the world. 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.

Vail is not a theatre destination.

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

Chicago
Vail

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

For foodies, Chicago is an obvious choice, as it is one of the food capitals of the world. 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.

There are many up and coming restaurants in the Vail area. The town has a diverse sampling of restaurants that include different ethnic options as well as taverns with comfort food. It's easy to find mountain-friendly restaurants where you can refuel during your ski vacation.


Is Chicago or Vail Better for Nightlife?

Chicago
Vail

Chicago is a must-visit destination for nightlife and partying. Also, Vail is not as popular, but is still a nice ski town for its evening party scene.

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.

Vail offers plenty to do in the evening. Happy Hours start early, and then the partying can go late into the night. There are bars, lounges, breweries and live music that keep the atmosphere light and offer entertainment after your long day on the slopes. Do keep in mind that many places close or dramatically reduce their hours during the off-peak fall and spring months.

Is Chicago or Vail Better for Music?

Chicago
Vail

Chicago is a must-visit destination for its live music scene. Also, Vail is not as popular, but is still a nice ski town for its music scene.

With so many music venues, you're guaranteed a show any night of the week in Chicago. The city is the birthplace of such interesting styles as modern gospel and the Chicago style blues.

Music lovers will find a few good venues in Vail. You can often find live music at Shakedown Bar, Bridge Street Bar, and the Red Lion.

Is Chicago or Vail Better for Resorts?

Chicago
Vail

Vail is a great destination for its resorts. However, Chicago is not a resort destination.

Vacationers can choose from a number of terrific resorts in Vail. Designed as a resort town, Vail offers great accommodation. Nice resorts include Four Seasons Resort and Residences, the Ritz Carlton Club, and the Grand Hyatt.

Chicago is not a resort destination.


Is Chicago or Vail Better for Beaches?

Chicago
Vail

Chicago is a popular place for the beache. However, Vail is not a beach destination.

Chicago is a good option for a beach vacation. 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.

Vail is not a beach destination.

Is Chicago or Vail Better for Hiking?

Chicago
Vail

Vail is a great destination for its hiking experiences. However, Chicago is not a hiking destination.

You'll find a nice variety of hiking trails around Vail. During the warmer months, this resort town is surrounded by world-class hiking trails. You can enjoy the wildflowers, search for wildlife, or take in the sweeping mountain views. Popular hikes near Vail include Booth Falls, Davos Trail, and Shrine Ridge.

Chicago is not a hiking destination.

Is the Shopping Better in Chicago or Vail?

Chicago
Vail

Chicago is a must-visit destination for its shopping opportunities. Also, Vail is not as popular, but is still a nice ski town for its shopping areas.

Known for shopping, Chicago draws large crowds to its stores. 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.

Browsing through shops is a popular activity in Vail. The cobblestone streets are lined with boutiques and ski shops that sell everything from evening dresses to outdoor gear. It's easy to pop into the many shops around downtown Vail and find anything you might need.


Is Chicago or Vail Better for Christmas?

Chicago
Vail

Vail is renowned for its Christmas activities. Also, Chicago is still popular, but not quite as popular for its Christmas holiday experiences.

Vail is a world class destination for shoppers. The town is a winter wonderland during the holidays. Check out the iconic Christmas tree lighting and wander through the fairytale streets.

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

Is Chicago or Vail Better for Christmas Markets?

Chicago
Vail

Vail is a great destination for its Christmas markets. Also, Chicago is still popular, but not quite as popular for visiting Christmas markets.

Vail has a lively atmosphere around its Christmas markets. The town's Christmas Market is picturesque, and the perfect place to pick up some unique gifts.

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

Is Chicago or Vail Better for Families?

Chicago
Vail

You'll find world-class kid-friendly activities in either Chicago or Vail.

Chicago is one of the most popular family destinations. 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.

Vail is an amazing family-friendly city to visit. With its world class skiing, rock climbing, ice skating, and ice cream, kids love this ski resort. The resort town has two terrain parks - Golden Peak and Avanti. Avanti is perfect for kids. It has small jumps, wide rails, and kid-friendly amenities. Golden Peak is designed for more advanced athletes. Vail also has nice beginner slopes that are great for kids.


Is Chicago or Vail Better for Couples?

Chicago
Vail

Vail is renowned for couples. Also, Chicago is still popular, but not quite as popular for romance.

For those traveling as a couple, Vail has plenty to offer. Couples who enjoy skiing and outdoor adventure will appreciate everything that this ski town has to offer. There are nice restaurants, beautiful gardens, and plenty of romantic activities to choose from.

Chicago is a nice destination for couples. 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.

Is Chicago or Vail Better for Backpackers and Budget Travelers?

Chicago
Vail

Chicago and Vail are good 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.

It's common for backpackers to visit Vail. This ski town isn't completely closed off to budget travelers as there are a couple of hostels around town.

Is Chicago or Vail Better for Students?

Chicago
Vail

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

Many students frequent Chicago. 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.

Vail is not popular with students.


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

Chicago
Vail

Chicago is a must-visit destination for times when you don't have a car. Also, Vail is not as popular, but is still a nice ski town 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.

Vail has a few public transit options. There is a free bus service through the area.

Is Chicago or Vail a more walkable city?

Chicago
Vail

Vail is renowned for its ease of walking around. Also, Chicago is still popular, but not quite as popular for its walkability.

Getting around Vail on foot is easy. The main downtown is pedestrian-only and perfect for popping in shops and restaurants.

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

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

Should I spend more time in Vail or Chicago?

How long in Chicago or Vail?

Both Chicago and Vail have a number of activities to choose from. With generally more activities and things to do, visitors tend to spend more time in Vail than in Chicago. Usually, 3-5 days is a good amount of time for Chicago, and 3-7 days is enough time in Vail.

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

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

Backpackers and budget travelers should spend more time in Chicago than Vail 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 Vail? Ideal Length of Stay
    Chicago 3-5 
    Vail 3-7

One day in Chicago or Vail?

Chicago is a big city destination where you can fill many days. Take your pick from the many activities offered here. With so much to do, one day is probably not enough time to see everything.

Vail is a small town with plenty to do. Travelers enjoy the resorts in the area as well. One reason most visitors come is for the skiing. This ski town 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 Vail?

Chicago is a fun place to experience. But since there are so many activities, you'll likely want to spend more than a weekend exploring. The entire region has so many activities, and you'll want time to do everything.

Vail might be a small town, but there's plenty to do in the area. The length of your trip often depends on your style of travel. Hiking can easily take up a good amount of your time here, too. One reason most visitors come is for the skiing. 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 Vail?

Chicago is a vibrant big city where you can fill many days. This city offers something for everyone. Plenty of people spend five days in the area when traveling. Five days is often enough time to do most activities.

Vail is a great place to explore. It is common to spend five days here. You can also relax and pamper yourself at one of the resorts. Five days is a great amount of time to relax and see the many things that Vail has to offer. Anyone can find something fun to do here.

A week in Chicago or Vail?

The edgey city of Chicago offers food and shopping. The length of your trip often depends on your style of travel. One week is usually plenty of time to spend here with extra days to spare. With this much time, visitors often visit nearby destinations or take day trips.

It's hard to know how much time to spend in Vail. Vail is a small town where visitors enjoy the nightlife and live music. One reason most visitors come is for the skiing. It's also a relaxing resort destination. With all of its activities, you can easily fill one week here.


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


Which place is cheaper, Vail 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 Vail is $291. 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 Vail in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Chicago $198
    Vail $174
  • Accommodation Typical double-occupancy room
    Chicago $396
    Vail $348
Compare Hotels in Chicago and Vail

Looking for a hotel in Chicago or Vail? 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 Vail


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 Vail Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Chicago $37
    Vail $19
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 ORD to Downtown Chicago: $300
  • Meet and Greet Private SUV Transfer from MDW to Downtown Chicago: $300
  • Chicago Private 4-Hour Sightseeing Transfer by Luxury SUV: $250
  • Meet and Greet Private Sedan Transfer from MDW to Downtown Chicago: $240
  • Private SUV Transfer from Chicago Downtown to O'Hare 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: $236
  • Arrival Private Transfer: O'Hare Airport ORD to Chicago in Luxury Car: $236
  • Private Chicagoland One-Way Transfer by Mercedes Sprinter : $229
  • Private Sedan Transfer from Chicago Downtown to Midway airport: $220
  • Chicago Airport Transfer: Chicago to O'Hare Airport ORD in Luxury SUV: $205
  • Departure Private Transfer: Chicago to O'Hare Airport ORD in Luxury SUV: $205

Hired Cars and Shuttles in Vail

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

  • Avon/Vail Valley to Denver Airport (DEN) - Departure Private Transfer : $240
  • EGE Airport Roundtrip Transfer to Vail, Beaver Creek, and Avon: $231
  • Eagle Airport (EGE) to Glenwood Resorts Round-Trip Transfer: $154
  • Eagle Airport (EGE) to Glenwood Springs Resorts Arrival Transfer: $77
  • Eagle County Airport to Breckenridge Keystone: Arrival Transfer: $94
  • Eagle County Airport to Steamboat - Round-Trip Private Transfer: $154
  • Eagle County Airport to Steamboat Springs-Round-Trip Transfer: $121
  • Eagle County Airport to Vail/Beaver Creek/Avon-Arrival Transfer: $116
  • Eagle County Airport(EGE) to Steamboat - Arrival Private Transfer: $77
  • Eagle County Regional (EGE) to Steamboat Springs-Arrival Transfer: $121
  • Private Arrival Transfer from Vail Airport EGE: $156
  • Private Departure Transfer to Vail Airport EGE: $128

Is it cheaper to fly into Chicago or Vail?

Prices for flights to both Vail 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
    Vail $74
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
  • Chicago : Hands-on Cooking Classes With Local Chef: $55
  • Bucktown Pizza Crawl in Chicago: $59
  • Fulton Market Delicious Donut Adventure and Walking Food Tour: $63
  • Downtown Chicago Walking Pizza Tour: $69
  • Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise: $72
  • Downtown Pizza Guided Walking Tour with Tastings: $73
  • Chicago West Loop Pizza Crawl: $79
  • Secret Food Tour: $79
  • Downtown Family Food Tour by Bike with Sightseeing: $80
  • Nitti's Supper Club Dinner and Show: $80
  • Lake Michigan Buffet Brunch, Lunch or Dinner Cruise: $86

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Chicago $47
    Vail $133
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
  • 2 Hour Chicago Pier Fireworks & Evening Segway Tour: $78
  • 2 Hour Magnificent Chicago Tour with Photos: $75
  • 2 Hour Private Chicago Soul House Tour: $65
  • 2-Hour Chicago Fireworks Segway Tour: $68
  • 2-Hour Guided Segway Tour of Chicago: $65
  • 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
  • App Chicago self-guided tours with multilingual audioguides: $9.73

Tours and Activities in Vail

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

  • Smartphone Driving Tour between Denver & Vail / Breckenridge: $9.99
  • Save the Mountain Escape Room Adventure: $45
  • Avon Segway Tour: $89
  • Vail Segway Tour from Vail Village: $89
  • Stand Up Paddle Board Colorado River Adventure: Guided Half Day : $98
  • Inflatable Kayak Adventure Colorado River: Half Day Guided Tour : $109
  • Bike Tour or Mountain Bike down Vail Mountain: $120
  • Dillon Marina & Shopping Tour: $267

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
    Vail $9.79

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: $15
  • Walking tour to Chicago dive bars: $41
  • Milwaukee,Miller Brewery Tour&Tasting 1-Day Tour from Chicago: $93
  • Milwaukee Harley-Davidson Museum & Brewery Day Tour: $98
  • Chicago Craft Brewery Barrel Bus Tour: $100
  • Craft Brewery Tour by Barrel Bus: $100


When comparing the travel costs between Chicago and Vail, we can see that Vail 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 Vail Expensive?.


Which is Bigger, Chicago or Vail?

Chicago has a larger population, and is about 620 times larger than the population of Vail. When comparing the sizes of Chicago and Vail, 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.