A Travel Price Comparison for United States of America Chicago vs. San Diego for Attractions, Food, Nightlife, and Music

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Should you visit Chicago or San Diego?

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 San Diego can help you decide which place is right for you.

Chicago

Chicago is a edgey, cosmopolitan, and diverse 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 museums, theater, and nightlife.

San Diego

San Diego is a fun-filled, hip, and dynamic coastal city. Because this is such a big city, visitors will find many sights and attractions around town. It offers plenty of beauty for visitors. As this is a very quaint destination, you'll find it has a special atmosphere. Other popular activities here include shopping, museums, and nightlife.

How is Chicago different from San Diego?

Which is Better for a Holiday?

Is Chicago or San Diego better for Museums and Historical Sights?

For an educational experience, head to a museum or a notable sight in either Chicago or San Diego.

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

Visitors can fill many days exploring the museums and attractions around San Diego. While the city is famous for it's beaches, zoos, and aquariums, don't overlook the museums and other landmarks. Popular options include the Midway Aircraft Carrier Museum, the Old Town State Historic Park, and Point Loma and Cabrillo Monument.


Is Chicago or San Diego better for Food?

Chicago has a longer list of notable local restaurants than San Diego.

Chicago has long been recognized as a culinary destination. While you're in town you have to try the famous deep dish pizza, Chicago style hot dogs, and Italian beef.

San Diego has a delicious food scene that relies on local flavors. The city has great seafood and a diversity of cuisines. Popular local dishes include fish tacos and California burritos.

Is Chicago or San Diego better for Nightlife?

It's hard to distinguish whether Chicago or San Diego has a better nightlife scene.

Chicago is a destination that you simply have to visit at least once for nightlife. Popular bars and clubs include the Smart Bar, Beauty Bar, and Le Nocturne.

Many people head to San Diego for the nightlife scene. The heart of the city's nightlife scene is in the Gaslamp District, which is filled with bars, clubs, and music venues.

Is Chicago or San Diego better for Music?

Live music enthusiatsts will find something to enjoy in either Chicago or San Diego.

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.

The music scene in San Diego draws a good crowd. Popular venues include the House of Blues, The Belly Up, and The Shout House.

Is Chicago or San Diego better for Beaches?

San Diego is considered to be a more popular beach destination.

With world-famous beaches, San Diego is a very popular vacation destination. The city has great beaches with tidal pools and interesting sea life at low tide. Popular beaches include La Jolla Cove Beach, Coronado Beach, and Pacific Beach.

Chicago offers a nice beach destination. While you don't immediately think of beaches when you think of Chicago, there are some nice beaches by the lake.


Is Chicago or San Diego better for Shopping?

Most people pick Chicago for the shopping over San Diego.

Chicago is a world class destination for shoppers. The most famous shopping area is Michigan Avenue and the famous Magnificent Mile.

Shopping is a popular activity when visiting San Diego. Head to Fashion Valley or Westfield UTC for some fun shopping.

Is Chicago or San Diego better for Families?

You'll find kid-friendly activities in either Chicago or San Diego.

Chicago is known to be a very family-friendly place to visit. 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.

With a huge array of activities for kids, San Diego is very family-friendly. It has a number of kid-friendly activities that everyone can enjoy. There's the world class zoo, several amusement parks, the beaches, aquariums, and more.

Is Chicago or San Diego better for Couples?

Both Chicago and San Diego are good 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.

San Diego makes for a fun place to visit for a couple. For adventurous couples, there are many outdoor activities that you can enjoy together. There are also restaurants and a great nightlife in San Diego.

Is Chicago or San Diego better for Backpackers and Budget Travelers?

Chicago and San Diego are comparable 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 San Diego. Backpackers will enjoy the young vibe of the city. There are a few great hostels near the beach or in town.


Is Chicago or San Diego better for Students?

Chicago and San Diego are comparable places to visit for students.

Students come from all over the world to visit Chicago. The city has a large number of universities that bring in students from around the country and around the globe.

San Diego is a very popular place to visit for students. With its young population and many universities, international students will feel right at home in San Diego.

Is Chicago or San Diego better for Public Transit?

Chicago provides more public transit options than San Diego.

Chicago has a great public transit system. There's a subway (the "L"), a commuter well, as well as buses and countless taxis available.

Public transit is mostly limited in San Diego. The city has a trolley (light rail system) as well as a bus system. Most people depend on cars to get around.

Is Chicago or San Diego a more walkable city?

Chicago and San Diego both are comparable when exploring on foot.

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

San Diego is a somewhat walkable place. The downtown area is walkable, but if you want to travel further, you'll need to find a different form of transportation.

Chicago and San Diego: Pros and Cons

Chicago
Pros
  • Popular museums and historical sights
  • Popular for food and cuisine
  • Good music scene
  • Good for shopping
  • Family-friendly
  • Good for couples and romance
  • Good for backpackers and budget travelers
  • Good public transit
  • Big city activities
Cons
  • Less attractive beach
San Diego
Pros
  • Popular museums and historical sights
  • Good music scene
  • Popular beach
  • Family-friendly
  • Good for couples and romance
  • Good for backpackers and budget travelers
Cons
  • Less popular for food
  • Less popular for shopping
  • Public transit not as usable


Should I spend more time in San Diego or Chicago?

How long in Chicago or San Diego?

In either Chicago or San Diego, you'll find plenty of activities to fill your time. You can fill a similar amount of time in either place.

The ideal length of time for a trip to Chicago is 3-5 days, and the ideal length of time for a trip to San Diego is 3-5 days.


  • How many days in Chicago or San Diego? Ideal Length of Stay
    Chicago 3-5 
    San Diego 3-5

One day in Chicago or San Diego?

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 San Diego, you'll find food and scuba diving and snorkeling. You'll find plenty of activities on the beach. One reason most visitors come is for the beaches. This coastal 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 San Diego?

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 San Diego, you'll find scuba diving and snorkeling and shopping. 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 beaches. 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 San Diego?

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.

San Diego is a great place to explore. It is common to spend five days here. Many visitors spend time at the beach while visiting the area. Five days is a great amount of time to relax and see the many things that San Diego has to offer. Anyone can find something fun to do here.

A week in Chicago or San Diego?

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 San Diego. One reason most visitors come is for the beaches. People usually spend lots of time at the beach. One week may feel like too much time here unless you plan to do a lot of relaxing.

Which city is cheaper, San Diego or Chicago?

These are the overall average travel costs for the two destinations.

The average daily cost (per person) in Chicago is $221, while the average daily cost in San Diego is $161. 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 city. What follows is a categorical breakdown of travel costs for Chicago and San Diego in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Chicago $152
    San Diego $91
  • Accommodation Typical double-occupancy room
    Chicago $304
    San Diego $182

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Chicago $29
    San Diego $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:

  • Private Sedan Transfer between ORD and Indianapolis IN: $587
  • Private SUV Transfer Between O'Hare airport & Downtown Madison WI: $427
  • Private Sedan Transfer Between O'Hare airport & Downtown Madison WI: $426
  • Departure Private Transfer Chicago to O'Hare Airport ORD in a Minibus: $333
  • Arrival Private Transfer Chicago O'Hare Airport to Chicago City by Minibus: $333
  • Private SUV Transfer Between O'Hare airport & Downtown Milwaukee WI: $298
  • Transfer to Chicago Premium Outlets: $288
  • Private Sedan Transfer Between O'Hare airport & Downtown Milwaukee WI: $266
  • Chicago O'Hare Private Ground Airport/Hotel Transfer - Round-Trip: $256
  • Chicago Midway Airport/Hotel Round Trip Private Ground Transfer: $256
  • Chicago Midway Airport (MDW) to Chicago City - Round-Trip Private Transfer: $184
  • Chicago Airport Transfer by Private Sedan: $170

Hired Cars and Shuttles in San Diego

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

  • Arrival Private Transfer San Diego Airport SAN to San Diego City by Business Car: $71
  • Arrival Private Transfer San Diego Airport SAN to San Diego by Executive SUV: $85
  • Arrival and Departure Transfer: Hotel to and from San Diego International Airport: $70
  • Departure Private Transfer San Diego to San Diego Airport SAN in Business Car: $63
  • Private Airport Transfer San Deigo Arrival And Departure: $67
  • Private Airport Transfer: Hotel to and from San Diego International Airport: $70
  • Private Airport Transfer: San Diego International Airport (SAN) to San Diego: $46
  • Private Airport Transfer: from San Diego to San Diego Int. Airport (SAN): $35
  • Private Arrival Transfer from SAN San Diego Airport to San Diego City: $49
  • Private Arrival Transfer from San Diego Airport SAN: $48
  • Private Departure Transfer from San Diego to SAN San Diego Airport: $46
  • Private Departure Transfer to San Diego Airport SAN: $48

Is it cheaper to fly into Chicago or San Diego?

Prices for flights to both San Diego 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 $37
    San Diego $36
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: $27
  • Learn to Make Chicago Deep-Dish Pizza with a Local: $49
  • Lonely Planet Experiences: River North Historical Food Tour: $61
  • Private Fusion Cooking Class in Downtown Chicago: $64
  • Best in Chow: Chicago River North Food Tour: $64
  • Signature Food Tour at Chicago's Navy Pier: $64
  • Skip the Line: Tommy Gun's Garage Dinner and Show Ticket: $67
  • Small-Group Chicago Food Tour: Gold Coast and Old Town: $75
  • Best of Chicago Tour Including a Deep-Dish Pizza: $75
  • River North Walking Food Tour: $75
  • Chicago's Wicker Park Food Tour: $75
  • Private Indian-Mexican Fusion Cooking Class with a Modern Cook: $78

Typical Food prices in San Diego

Here are some examples of typical meal expenses from previous travelers to San Diego:


  • Mexican Lunch for Two
    $27
  • Breakfast at Starbucks
    $20

Food Tours and Cooking Classes in San Diego

For San Diego, here are some samples of tours and activities related to meals and dining experiences:

  • San Diego North Park Food Tour: $49
  • Liberty Station Food Tour: $49
  • Market and Guacamole Cooking Class in Tijuana Mexico: $89
  • Private Cooking Demonstration of Indian Fusion Cuisine in San Diego: $96
  • Farmers Market Tour & Social Cooking With A Chef: $100
  • San Diego Harbor Dinner Cruise: $111
  • Private Tour: Secret Food Tours San Diego: $129
  • Secret Food Tours San Diego w/ Private Tour Option: $277

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Chicago $34
    San Diego $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)
    $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:

  • 2 Hours Chicago Sightseeing Tour - Luxury Private Stretch Limo / 8 Passengers: $250
  • 2-Hour Chicago City Lights and Skyline Segway Tour: $76
  • 2-Hour Chicago Fireworks Segway Tour: $76
  • 2-Hour Chicago Lakefront and Museum Campus Segway Tour: $73
  • 2-Hour Haunted Segway Tour of Chicago: $76
  • 2-Hour History of Chicago Architecture and Art Segway Tour: $75
  • 3 Hours Chicago Sightseeing Tour - Luxury Private SUV, ALL Inclusive: $392
  • 4 Hours Chicago Sightseeing Tour - Luxury Private SUV, ALL Inclusive: $220
  • 4 Hours Chicago Sightseeing Tour - Luxury Private Sedan: $215
  • 4 Hours Chicago Sightseeing Tour - Luxury Private Stretch Limousine/8 passengers: $728
  • A Most Magnificent Mile Shopping and Sightseeing Tour: $40
  • A Storied Neighborhood: Dance the dialectic with Bill Ayers on an audio tour: $5.00

Typical Entertainment prices in San Diego

For San Diego, here are some examples of average entertainment and activity prices from previous travelers:


  • San Diego Zoo
    $15
  • Sea World Parking
    $12

Tours and Activities in San Diego

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

  • La Jolla: Explore California's Riviera on a self-guided audio tour: $5.40
  • La Jolla: Ultimate Self-Guided Combo Tour: $12
  • San Diego Zoo Hunt: Roar with Rex Adventure at the San Diego Zoo: $12
  • San Diego's Gaslamp Quarter Historic True Crime Tour: $16
  • San Diego Scavenger Hunt Adventure: $21
  • San Diego Balboa Park Scavenger Hunt Adventure: $21
  • Behind-the-Scenes at Petco Park Tour: $23
  • San Diego Gaslamp District Ghost Tour: $24
  • Ghost-Themed Walking Tour: $25
  • Skip-the-Line: USS Midway Museum Entry Ticket: $26
  • San Diego Harbor Cruise: $28
  • Tijuana Walking Tour from San Diego: $28

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 $20
    San Diego $17

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: $25
  • Walking tour to Chicago dive bars: $41
  • Chicago Barrel Bus Craft Distillery Tour: $90
  • Chicago Craft Brewery Barrel Bus Tour: $90
  • Ultimate Girl's Night Out in Sparkling Wine, Photo Shoot, Burlesque: $900

Sample the Local Flavors in San Diego

Also in San Diego, these are the prices for nightlife and alcohol related activities from various tour providers:

  • San Diego Bar Hunt: Slammin' San Diego Bar Crawl: $12
  • Wine Tasting Or Beer Tasting: $15
  • San Diego Brewery Tour: $85
  • San Diego Micro Brewery Tour: $91
  • The San Diego Downtown Craft Brewery Tour: $95
  • The San Diego Downtown Craft Brewery Tour: $101
  • Private San Diego Brewery Tour: $107
  • All inclusive brewery tour-Fire Truck: $189
  • Luxury Private Wine Tasting Tour to Guadalupe Valley from San Diego.: $249
  • Private Wine Tour of Temecula from San Diego: $475

About these numbers

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

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Chicago vs. San Diego Travel Comparison

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