Which city is cheaper, San Diego or Chicago?
These are the overall average travel costs for the two destinations.
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.
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
- 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
- Less popular for food
- Less popular for shopping
- Public transit not as usable
How is Chicago different from San Diego?
Which is Better for a Holiday?
Let's take a look at the differences and similarities between San Diego and Chicago. Then, you can decide for yourself which place is better for your next trip.
Is Chicago or San Diego Better for Museums and Historical Sights?
Chicago
San Diego
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).
With a variety of museums, monuments, and historical sights, a trip to San Diego can be an interesting and educational experience. 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
San Diego
Chicago has a longer list of notable local restaurants than San Diego.
Chicago has long been recognized as a culinary destination with great restaurants. While you're in town you have to try the famous deep dish pizza, Chicago style hot dogs, and Italian beef.
There are plenty of up and coming restaurants around San Diego. 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?
Chicago
San Diego
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.
The nightlife in San Diego has something for everybody. 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?
Chicago
San Diego
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.
San Diego has a thriving music scene. Popular venues include the House of Blues, The Belly Up, and The Shout House.
Is Chicago or San Diego Better for Beaches?
Chicago
San Diego
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 has a beach worth visiting. 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?
Chicago
San Diego
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.
Plenty of visitors enjoy shopping while in San Diego. Head to Fashion Valley or Westfield UTC for some fun shopping.
Is Chicago or San Diego Better for Families?
Chicago
San Diego
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.
San Diego is an amazing family-friendly city to visit. 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?
Chicago
San Diego
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 is a nice destination for couples. 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
San Diego
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
San Diego
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 great destination 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
San Diego
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
San Diego
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 somewhat walkable. The downtown area is walkable, but if you want to travel further, you'll need to find a different form of transportation.
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.
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How many days in Chicago or San Diego? Ideal Length of StayChicago 3-5San 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. Many people enjoy the museums and nightlife when visiting 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 unless you plan to do a lot of relaxing.
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Average Daily Cost Per person, per dayChicago $221San Diego $161
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
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Accommodation Hotel or hostel for one personChicago $152San Diego $91
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Accommodation Typical double-occupancy roomChicago $304San Diego $182
Compare Hotels in Chicago and San Diego
Looking for a hotel in Chicago or San Diego? 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.
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 San Diego Hotel Prices.
Local Transportation
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Local Transportation Taxis, local buses, subway, etc.Chicago $29San Diego $19
Typical Local Transportation prices in Chicago
Here are some examples of typical transportation prices from actual travelers in Chicago:
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Parking$19
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Taxi Ride$10
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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
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Food Meals for one dayChicago $37San Diego $36
Typical Food prices in Chicago
Below are a few samples from actual travelers for food and meal costs in Chicago:
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Dinner for 1$24
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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:
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Mexican Lunch for Two$27
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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
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Entertainment Entrance tickets, shows, etc.Chicago $34San 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:
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Sears Tower (family of 4)$102
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Aquarium for 4$118
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Water Taxi (family of 4)$22
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IMAX Movie for Two$35
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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:
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San Diego Zoo$15
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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
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Alcohol Drinks for one dayChicago $20San 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
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.
When is the best time to visit Chicago or San Diego?
Both places have a temperate climate with four distinct seasons. As both cities are in the northern hemisphere, summer is in July and winter is in January.
Should I visit Chicago or San Diego in the Summer?
Both San Diego and Chicago during the summer are popular places to visit. Many visitors come to Chicago in the summer for the beaches, the city activities, the music scene, and the family-friendly experiences. Furthermore, most visitors come to San Diego for the beaches, snorkeling, the hiking, the city activities, the music scene, and the family-friendly experiences during these months.
In July, Chicago is generally a little warmer than San Diego. Temperatures in Chicago average around 77°F (25°C), and San Diego stays around 71°F (22°C).
In San Diego, it's very sunny this time of the year. It's quite sunny in Chicago. In the summer, Chicago often gets around the same amount of sunshine as San Diego. Chicago gets 326 hours of sunny skies this time of year, while San Diego receives 306 hours of full sun.
It rains a lot this time of the year in Chicago. Chicago usually gets more rain in July than San Diego. Chicago gets 3.9 inches (100 mm) of rain, while San Diego receives 0 inches (1 mm) of rain this time of the year.
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Summer Average Temperatures JulyChicago 77°F (25°C)San Diego 71°F (22°C)
Should I visit Chicago or San Diego in the Autumn?
The autumn attracts plenty of travelers to both Chicago and San Diego. Most visitors come to Chicago for the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area during these months. Furthermore, the autumn months attract visitors to San Diego because of the hiking trails, the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area.
Chicago is cooler than San Diego in the autumn. The temperature in Chicago is usually 56°F (14°C) in October, and San Diego stays around 68°F (20°C).
People are often attracted to the plentiful sunshine in San Diego this time of the year. Chicago usually receives less sunshine than San Diego during autumn. Chicago gets 195 hours of sunny skies, while San Diego receives 244 hours of full sun in the autumn.
In October, Chicago usually receives more rain than San Diego. Chicago gets 2.2 inches (56 mm) of rain, while San Diego receives 0.4 inches (9 mm) of rain each month for the autumn.
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Autumn Average Temperatures OctoberChicago 56°F (14°C)San Diego 68°F (20°C)
Should I visit Chicago or San Diego in the Winter?
The winter brings many poeple to Chicago as well as San Diego. The winter months attract visitors to Chicago because of the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine. Additionally, the museums, the shopping scene, and the cuisine are the main draw to San Diego this time of year.
The weather in Chicago can be very cold. In the winter, Chicago is much colder than San Diego. Typically, the winter temperatures in Chicago in January are around 25°F (-4°C), and San Diego is about 57°F (14°C).
The sun comes out a lot this time of the year in San Diego. In the winter, Chicago often gets less sunshine than San Diego. Chicago gets 134 hours of sunny skies this time of year, while San Diego receives 239 hours of full sun.
Chicago usually gets around the same amount of rain in January as San Diego. Chicago gets 1.9 inches (47 mm) of rain, while San Diego receives 1.8 inches (46 mm) of rain this time of the year.
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Winter Average Temperatures JanuaryChicago 25°F (-4°C)San Diego 57°F (14°C)
Should I visit Chicago or San Diego in the Spring?
Both San Diego and Chicago are popular destinations to visit in the spring with plenty of activities. The beaches, the activities around the city, and the natural beauty are the main draw to Chicago this time of year. Also, many travelers come to San Diego for the beaches, the activities around the city, and the natural beauty.
In April, Chicago is generally cooler than San Diego. Temperatures in Chicago average around 52°F (11°C), and San Diego stays around 62°F (17°C).
It's quite sunny in San Diego. The sun comes out a lot this time of the year in Chicago. Chicago usually receives less sunshine than San Diego during spring. Chicago gets 218 hours of sunny skies, while San Diego receives 277 hours of full sun in the spring.
It's quite rainy in Chicago. In April, Chicago usually receives more rain than San Diego. Chicago gets 4.3 inches (108 mm) of rain, while San Diego receives 0.8 inches (20 mm) of rain each month for the spring.
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Spring Average Temperatures AprilChicago 52°F (11°C)San Diego 62°F (17°C)
Typical Weather for San Diego and Chicago
| Chicago | San Diego | |||
|---|---|---|---|---|
| Temp (°C) | Rain (mm) | Temp (°C) | Rain (mm) | |
| Jan | 25°F (-4°C) | 1.9 inches (47 mm) | 57°F (14°C) | 1.8 inches (46 mm) |
| Feb | 29°F (-2°C) | 1.4 inches (35 mm) | 59°F (15°C) | 1.5 inches (39 mm) |
| Mar | 41°F (5°C) | 3.7 inches (93 mm) | 59°F (15°C) | 1.8 inches (45 mm) |
| Apr | 52°F (11°C) | 4.3 inches (108 mm) | 62°F (17°C) | 0.8 inches (20 mm) |
| May | 63°F (17°C) | 3 inches (75 mm) | 64°F (18°C) | 0.2 inches (5 mm) |
| Jun | 73°F (23°C) | 3.9 inches (100 mm) | 67°F (19°C) | 0.1 inches (2 mm) |
| Jul | 77°F (25°C) | 3.9 inches (100 mm) | 71°F (22°C) | 0 inches (1 mm) |
| Aug | 76°F (24°C) | 3.5 inches (90 mm) | 73°F (23°C) | 0.1 inches (3 mm) |
| Sep | 68°F (20°C) | 3.8 inches (96 mm) | 71°F (22°C) | 0.2 inches (6 mm) |
| Oct | 56°F (14°C) | 2.2 inches (56 mm) | 68°F (20°C) | 0.4 inches (9 mm) |
| Nov | 44°F (7°C) | 2.2 inches (56 mm) | 62°F (17°C) | 1.5 inches (37 mm) |
| Dec | 31°F (-1°C) | 2.8 inches (71 mm) | 57°F (14°C) | 1.6 inches (40 mm) |
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