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

Should you visit Chicago or Flagstaff?

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

Chicago

Chicago is a multicultural, edgey, and cosmopolitan 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. Other popular activities here include beaches, shopping, and museums.

Flagstaff

Flagstaff is a adventurous , picturesque, and active city. It offers plenty of beauty for visitors. Other popular activities here include shopping, museums, and nightlife.

Chicago and Flagstaff: Pros and Cons

Pros
  • Popular museums and historical sights
  • Numerous theater shows
  • 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
  • Good for hiking
  • Family-friendly
  • Good for couples and romance
  • Good for backpackers and budget travelers
Things to Consider
  • Less museums and historical sights
  • Less popular for nightlife
  • Less popular for shopping
  • Public transit not as usable


Is there more to do in Chicago or Flagstaff?

Tourists will generally find more to do in Chicago than Flagstaff. It is bigger and it has more sights, attractions, and activities for travelers. Chicago is very popular for its museums, theatre productions, food, nightlife, music, beaches, shopping, christmas markets, and big city activities, while Flagstaff attracts visitors for its hiking. Chicago is famous 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). Flagstaff is famous for its nearby craters and volcanic caves as well as its location along the historic Route 66.

How is Chicago different from Flagstaff?

Which is Better for a Holiday?

Let's take a look at the differences and similarities between Flagstaff 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 Flagstaff?

Chicago
Flagstaff

Chicago is a must-visit destination for its museums and landmarks. Also, Flagstaff is still popular, but not quite as popular for its historical sights.

You'll find many recognizable landmarks that put Chicago on the map. 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).

Flagstaff is a good place to visit if you're interested in museums or other recognizable sights. Lowell Observatory is a highlight for many visitors, especially those who are fascinated by space. There's also the Museum of Northern Arizona, the Pioneer Museum, and Fort Tuthill Military History Museum.


Is Chicago or Flagstaff Better for Theater?

Chicago
Flagstaff

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

Visitors will find world class theater shows, plays, and musicals in Chicago that are not to be missed. 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.

Flagstaff is not a theatre destination.

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

Chicago
Flagstaff

Chicago is a must-visit destination for its restaurant scene. Also, Flagstaff is still popular, but not quite as popular for its local flavors and cuisine.

Many restaurants in Chicago have been singled out for their culinary prowess. 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.

The food selection at local restaurants is excellent in Flagstaff. The food scene is diverse and growing. There's a focus on local recipes and ingredients. You'll also find many casual and family-friendly restaurants. American cuisine is common, but you'll also find burritos, Indian curries, and frittatas.

Is Chicago or Flagstaff Better for Nightlife?

Chicago
Flagstaff

Chicago is a must-visit destination for its evening party scene. Also, Flagstaff is still popular, but not quite as popular 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.

If you're looking for night time activities Flagstaff has a few options to choose from. You'll find a range of bars and cocktail lounges around town that come to life in the evening hours.


Is Chicago or Flagstaff Better for Music?

Chicago
Flagstaff

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

In Chicago you'll find nightly musicians performing at a variety of venues. The city is the birthplace of such interesting styles as modern gospel and the Chicago style blues.

Flagstaff is not a live music destination.

Is Chicago or Flagstaff Better for Beaches?

Chicago
Flagstaff

Chicago is a city with good options for the beach. However, Flagstaff is not a beach destination.

Plenty of visitors enjoy relaxing on the beach in Chicago. 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.

Flagstaff is not a beach destination.

Is Chicago or Flagstaff Better for Hiking?

Chicago
Flagstaff

Flagstaff is renowned for its hiking experiences. However, Chicago is not a hiking destination.

Many people visit Flagstaff specifically for its hiking. Nearby you'll find world class hikes through surreal landscapes and diverse environments. The area is filled with desert landscapes and varied rock formations that are best explored on foot. Trails range in length and skill level, but whatever your ability, the hiking in the area is among the best.

Chicago is not a hiking destination.


Is the Shopping Better in Chicago or Flagstaff?

Chicago
Flagstaff

Chicago is a must-visit destination for its shopping areas. Also, Flagstaff is still popular, but not quite as popular for shopping.

Chicago is a world class destination for shoppers. 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.

Plenty of visitors enjoy shopping while in Flagstaff. Located along historic Route 66, you'll find many shops that capture the city's history, particularly in the Southside Historic District. The town also has farmer's markets as well as shopping centers and large malls.

Is Chicago or Flagstaff Better for Christmas?

Chicago
Flagstaff

Chicago is well known for its Christmas activities. However, Flagstaff does not offer Christmas activities.

Visitors come from all around to experience the Christmas activities in Chicago. There's a number of seasonal celebrations, ice skating, and excellent shopping.

Flagstaff does not offer Christmas activities.

Is Chicago or Flagstaff Better for Christmas Markets?

Chicago
Flagstaff

Chicago is a city with good options for its Christmas markets. However, Flagstaff does not offer Christmas markets.

Chicago is a nice place to see Christmas markets. Shopping is a highlight of a trip to the city, and the Christkindlmarkt is not to be missed.

Flagstaff does not offer Christmas markets.


Is Chicago or Flagstaff Better for Families?

Chicago
Flagstaff

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

Chicago is an extremely popular city to visit for families. 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.

Flagstaff is a very family-friendly destination. The city is filled with outdoor activities for kids like ropes courses and adventure parks. Kids will also enjoy climbing around the Lava River Cave, visiting Sunset Crater Volcano National Monument, or hiking through the many diverse landscapes in the area. There are also museums that educate visitors on the city's history as well as Lowell Observatory, which will intrigue all the space enthusiasts among us.

Is Chicago or Flagstaff Better for Couples?

Chicago
Flagstaff

Both Chicago and Flagstaff are nice destinations to visit as a couple.

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.

Flagstaff is a nice destination for couples. Hiking and outdoor adventure sports make this city a good destination for couples who enjoy active living. There are many parks that you can visit as well as hiking trails and unique natural settings.

Is Chicago or Flagstaff Better for Backpackers and Budget Travelers?

Chicago
Flagstaff

Flagstaff is a great destination for backpackers. Also, Chicago is still popular, but not quite as popular for backpackers and budget travelers.

Flagstaff is a very popular city for backpackers and budget travelers. There are campgrounds nearby as well as tons of nature parks and countless hiking trails in the area.

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.


Is Chicago or Flagstaff Better for Students?

Chicago
Flagstaff

Chicago is a must-visit destination for students. However, Flagstaff is not popular with students.

Chicago is a very popular city 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.

Flagstaff is not popular with students.

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

Chicago
Flagstaff

Chicago is a must-visit destination for its public transit. However, Flagstaff is not particularly known for times when you don't have a car.

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.

Public transit is mostly limited in Flagstaff. The Mountain Line offers eight routes through town.

Is Chicago or Flagstaff a more walkable city?

Chicago
Flagstaff

Chicago is well known for its ease of walking around. Also, Flagstaff is still popular, but not quite as popular for its walkability.

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

Flagstaff is somewhat walkable. The downtown is compact and walkable, but you'll really want to have a car to explore the nearby hiking trails and natural areas.


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

Should I spend more time in Flagstaff or Chicago?

How long in Chicago or Flagstaff?

It's fun to spend time in either Chicago or Flagstaff. Generally, people tend to spend more time in Chicago due to the larger number of activities and things to do. Usually, 3-5 days is a good amount of time for Chicago, and 2-4 days is enough time in Flagstaff.

Families should spend more time in Chicago than Flagstaff. 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 Flagstaff. 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 Flagstaff 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 Flagstaff? Ideal Length of Stay
    Chicago 3-5 
    Flagstaff 2-4

One day in Chicago or Flagstaff?

People visit Chicago because there is so much to do. Since there is so much to do in the area, one day is probably not enough for all of it. It has many unique tourist attractions and fascinating things to do.

In Flagstaff, you'll find nightlife and food. Many travelers plan to spend time hiking while in the area. One reason most visitors come is for the hiking. 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 Flagstaff?

People visit Chicago because there is so much to do. A weekend is usually not enough time for a trip here as there is plenty to do. This city offers a variety of activities to choose from.

In Flagstaff, you'll find food and shopping. The length of your trip often depends on your style of travel. A weekend here is typical. Hiking can easily take up a good amount of your time here, too. One reason most visitors come is for the hiking. A weekend is a great amount of time to relax and see the many things that Flagstaff has to offer.

Five days in Chicago or Flagstaff?

People visit Chicago because there is so much to do. The length of your ideal trip is an individual decision. If you have five days, this city makes for a great vacation. Five days should give you a good understanding of everything this city has to offer.

Flagstaff is a great place to explore. Hikers are also drawn to this area. 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 Flagstaff?

Chicago is a popular choice for travelers. 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 will give you the chance to have new experiences.

It's hard to know how much time to spend in Flagstaff. Many people enjoy the museums and nightlife when visiting Flagstaff. One reason most visitors come is for the hiking. Many visitors also spend a good bit of time hiking. 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 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, Flagstaff 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 Flagstaff is $166. 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 Flagstaff in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Chicago $198
    Flagstaff $86
  • Accommodation Typical double-occupancy room
    Chicago $396
    Flagstaff $172
Compare Hotels in Chicago and Flagstaff

Looking for a hotel in Chicago or Flagstaff? 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 Flagstaff


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 Flagstaff Hotel Prices.

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

  • Airport transfer between Chicago O'Hare and Milwaukee: $38
  • Arrival Private Transfer: O'Hare Airport ORD to Chicago in Business Car: $152
  • Arrival Private Transfer: O'Hare Airport ORD to Chicago in Luxury Car: $233
  • Chicago Airport (MDW) to Chicago - Round-Trip Private Transfer: $116
  • Chicago Airport Transfer: Chicago to O'Hare Airport ORD in Luxury SUV: $202
  • Chicago Airport Transfer: Chicago to O'Hare Airport in Luxury SUV: $150
  • Chicago Airport Transfer: O'Hare Airport ORD to Chicago in Business Car: $152
  • Chicago Airport Transfer: O'Hare Airport ORD to Chicago in Luxury SUV: $202
  • Chicago Midway Airport (MDW) to Chicago -Arrival Private Transfer: $58
  • Chicago Midway Airport (MDW) to Chicago City - Round-Trip Private Transfer: $105
  • Chicago Midway Airport (MDW) to Chicago hotel/address - Arrival Private Transfer: $52
  • Chicago O'Hare Airport (ORD) to Chicago - Round-Trip Private Transfer: $126

Is it cheaper to fly into Chicago or Flagstaff?

Prices for flights to both Flagstaff 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
    Flagstaff $55
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
  • Downtown Pizza Guided Walking Tour with Tastings: $58
  • Fulton Market Delicious Donut Adventure & Walking Food Tour: $63
  • Chicago's Delicious Donut Adventure and Walking Food Tour: $63
  • Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise: $72
  • Chicago Deep Dish Pizza Self-Guided Tour: $75
  • Chicago Pizza Tour: $75
  • Chicago West Loop Pizza Crawl: $79
  • Chicago Bucktown-Wicker Park Pizza Crawl: $79
  • Downtown Family Food Tour by Bike with Sightseeing: $80
  • Nitti's Supper Club Dinner and Show: $85

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Chicago $47
    Flagstaff $28
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:

  • Discovering Chicago with Walking In App Audio Tour: $6.00
  • Haunted Sites Self-Guided Audio Walking Tour: $6.50
  • Vice, Crime and Gangsters Self-Guided Audio Tour: $6.99
  • Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour: $6.99
  • Vice, Crime and Gangsters in A Self-Guided Audio Tour: $6.99
  • Must-Sees & Hidden Gems In-App Audio Tour (ENG): $9.00
  • App Chicago self-guided tours with multilingual audioguides: $9.63
  • Millennium Park Self-Guided Walking Tour: $9.99
  • Riverwalk Self-Guided Walking Tour: $9.99
  • Scavenger Hunt Adventure Self-Guided City Game: $10
  • Self-Guided Audio Tour: $11
  • Chicago White Sox Baseball Game Ticket: $12

Tours and Activities in Flagstaff

Here are a few actual costs in Flagstaff for available activities, ticket prices, and tours:

  • Grand Canyon South Rim: Self-Guided GPS Audio Tour: $11
  • Full-Day Grand Canyon South Rim Audio Driving Tour: $11
  • Grand Canyon South Rim: Audio Driving Tour: $12
  • Self-Guided Audio Driving Tour of Sedona: $13
  • Flagstaff, AZ: Murder Mystery Detective Experience: $15
  • Murder Mystery Detective Experience Flagstaff, AZ: $15
  • Flagstaff Scavenger Hunt Walking Tour and Game: $25
  • Family Friendly Haunted Walking Tour: $25
  • Downtown Flagstaff Haunted History Tour: $28
  • Downtown Haunted History Walking Tour: $28
  • Flagstaff Ghosts Tour By Us Ghost Adventures: $30
  • Mountain Town Of Madness, Original *Adult Only* Haunted Downtown Flagstaff Tour: $30

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
    Flagstaff $29

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 Craft Brewery Barrel Bus Tour: $100
  • Craft Brewery Tour by Barrel Bus: $100

Sample the Local Flavors in Flagstaff

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

  • Spirits With The Spirits, Haunted Pub Crawl Of Downtown Flagstaff: $50
  • Haunted Pub Crawl with Guide: $50


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

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


Which is Bigger, Chicago or Flagstaff?

Chicago has a larger population, and is about 50 times larger than the population of Flagstaff. When comparing the sizes of Chicago and Flagstaff, 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.