What percentage of Chicago to San Diego flights are direct?

Across the trailing 90 days, approximately 13.8% of flights from Chicago to San Diego were direct. For flights that included stopovers, the median number of stopovers was 2. This indicates that a significant majority of travelers on this route can expect at least one connection. Direct flights are less common, representing a smaller portion of available options.

How many hours is the flight from Chicago to San Diego?

The typical direct flight from Chicago to San Diego has a median duration of 4 hours and 30 minutes. For flights with one stop, the median duration is considerably longer, averaging 9 hours and 55 minutes. The distance covered on this route is 2768 kilometers. Travelers should account for these differences in flight time when planning their journey.

How often do cheap flights from Chicago to San Diego come up?

Based on historical data from the trailing 30 days, cheap flights from Chicago to San Diego are classified as frequent. This suggests that travelers have regular opportunities to find good deals on this route. The consistent availability of affordable options makes it a favorable route for price-conscious travelers. It is one of the more frequently discounted routes.

Flights From Chicago

To San Diego

Cheap Flights from Chicago to San Diego

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Deals from

Chicago

RatePunk searches hundreds of travel sites at once for deals on flights to San Diego

Prices updated 7 days ago

483 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Oct 26, 2026.)

Today’s best flight deals from Chicago to San Diego

Explore current cheapest deals departing from Chicago to San Diego

2027-01-06 – 2027-01-19
CHI - San Diego
77% AI deal score
$165
$132
Round trip
2027-01-18 – 2027-01-19
CHI - San Diego
79% AI deal score
$190
$139
Round trip
2027-01-12 – 2027-01-19
CHI - San Diego
78% AI deal score
$181
$139
Round trip
2027-01-06 – 2027-01-07
CHI - San Diego
77% AI deal score
$185
$143
Round trip
2027-01-06 – 2027-01-20
CHI - San Diego
70% AI deal score
$165
$145
Round trip
2027-01-16 – 2027-01-19
CHI - San Diego
76% AI deal score
$190
$151
Round trip
2027-01-18 – 2027-01-20
CHI - San Diego
76% AI deal score
$190
$152
Round trip
2027-01-12 – 2027-01-20
CHI - San Diego
70% AI deal score
$175
$152
Round trip
2027-01-18 – 2027-02-16
CHI - San Diego
67% AI deal score
$162
$156
Round trip
2027-01-06 – 2027-01-12
CHI - San Diego
70% AI deal score
$181
$160
Round trip

Chicago to San Diego: Overview

Insights for flights from Chicago to San Diego

A small share of recent fares from Chicago to San Diego, specifically 13.8%, are for direct flights. For the majority of itineraries that involve connections, travelers typically encounter 2 stopovers. This indicates that most itineraries connect at least once when flying between these two cities.

For travelers looking for cheap flights from Chicago to San Diego, the fares right now are typically between $329–$802, with a median of $473. Current fares are below the typical level, and only 1% of recent fares were classified as a good price. New deals appear almost daily, suggesting frequent opportunities to find better prices.

When is the cheapest time to fly from Chicago to San Diego? The data indicates that March is the most affordable month, with a median fare of $139. Following closely is May, where the median fare is $182. April also offers competitive pricing, with a median fare of $389.

How long is the flight from Chicago to San Diego? A typical journey, including connections, takes about 4h 30m. This median duration accounts for both direct and connecting itineraries, with non-stop flights also averaging 4h 30m, while connecting flights have a significantly longer median duration of 14h 50m.

The distance between Chicago and San Diego is approximately 2768 kilometers. This route is classified as a medium-haul journey, indicating a moderate travel distance that typically involves several hours in the air.

How much is a round trip from Chicago to San Diego

Regular price: $233 - $544

Prices for flights from Chicago to San Diego are currently below the regular range.

The regular price range for flights from Chicago to San Diego is between $233 and $544. The current lowest deal is $157 with Frontier Airlines for travel from Dec 7-Dec 14.

now $157

Low $233

High $544

The cheapest time to fly from Chicago to San Diego

The cheapest month to fly from Chicago to San Diego is March, with a median price of $139. The most expensive month is January, with a median price of $1269. Prices are generally lower from February to December.

March

Cheapest

Flights from $139

January

Most Expensive

Flights from $1,269

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to San Diego

Alaska Airlines, Inc.

Last-minute flights going from Chicago to San Diego

Tue, Oct 27

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Alaska Airlines, Inc.

$418

$431

One-way

Tue, Oct 27

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Deutsche Luft Hansa

$422

$515

One-way

Sat, Dec 5

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Frontier Airlines

$269

$182

One-way

Tue, Dec 8

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Frontier Airlines

$285

$184

One-way

Sat, Dec 12

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Frontier Airlines

$316

$182

One-way

Mon, Dec 14

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Frontier Airlines

$317

$178

One-way

Biggest price drops on these dates for flights from Chicago to San Diego

2 nights

Dec 14 - Dec 16

$317 → $164

48%

5 nights

Dec 5 - Dec 10

$309 → $163

47%

7 nights

Dec 7 - Dec 14

$299 → $157

47%

7 nights

Dec 9 - Dec 16

$299 → $157

47%

Popular Airports to fly from Chicago to San Diego

Chicago - San Diego route insights

💸 Price insights

Recent fares are below the typical level.

Recent fares from Chicago to San Diego are below the typical level at $473.

📅 Best time to fly

March is historically the cheapest month to fly.

Historically, March is the cheapest month to fly with a median price of $139.

⏱️ Flight duration

Direct flights take 4h 30m.

Direct flights to San Diego typically take 4h 30m, while connecting flights average 14h 50m.

✈️ Airlines & availability

Connecting flights are dominant for this route.

Connecting flights are dominant, with only 13.8% of recent flights being direct.

🏆 Airline highlight

Alaska Airlines, Inc. offers direct flights.

Alaska Airlines, Inc. has direct flights available for this route.

🎯 Booking tip

Deals are frequent for flights to San Diego.

Deals for flights from Chicago to San Diego are frequent, appearing every 30 days.

Chicago main airports to depart from

Chicago Rockford International (RFD)

Cheapest

Chicago Rockford International offers a budget-friendly option for flights from Chicago to San Diego.

📍 ~126 km from Chicago (reachable by car)

💸 Flights from ~$207

Chicago Midway International (MDW)

Chicago Midway International is a convenient choice for travelers flying from Chicago to San Diego.

📍 ~14 km from Chicago (reachable by car)

💸 Flights from ~$257

O Hare International (ORD)

O Hare International provides a major hub for flights from Chicago to San Diego.

📍 ~25 km from Chicago (reachable by car)

💸 Flights from ~$223

San Diego main airports to arrive at

San Diego International (SAN)

Cheapest

San Diego International Airport is a convenient arrival choice for flights from Chicago to San Diego.

📍 ~3 km from San Diego (reachable by car)

💸 Flights from ~$166

Airports nearby San Diego used as alternative

Tijuana International (TIJ)

Tijuana International (TIJ) is a useful alternative for Mexico-bound travelers with direct access via CBX.

📍 ~25 km from San Diego (requires valid passport and CBX fee)

💸 Flights from ~$296

Business & First Class Flight Deals to San Diego

$687

Save $382

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to San Diego

Historically, the optimal booking window for flights from Chicago to San Diego is typically 28-59 days before departure. During this period, the average price across the trailing quarter was $657. Booking within 0-6 days of departure saw average prices rise significantly to $1240. Even booking 60+ days out resulted in a slightly higher average price of $685, indicating that prices tend to increase closer to the departure date.

Across the trailing 90 days, a flight from Chicago to San Diego is considered a good deal if it is priced at or below $329. The median price for this route was $473 in the trailing quarter. Prices above $802 typically indicate a more expensive fare. Travelers aiming for the best value should target prices around the $329 mark.

Historically, the cheapest months to fly from Chicago to San Diego are March and May, with median prices of $139 and $182 respectively. April also offered a median price of $389. The annual median price for this route is $473, making March and May significantly more affordable. Travelers looking for lower fares should consider these months.

Related routes

More routes from Chicago

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Flights to San Diego from other cities

Flights from Colorado Springs to San Diego Flights from Dallas to San Diego Flights from Denver to San Diego Flights from Detroit to San Diego Flights from Dublin to San Diego Flights from El Paso to San Diego Flights from Fresno to San Diego Flights from Hong Kong to San Diego Flights from Honolulu to San Diego Flights from Houston to San Diego Flights from Indianapolis to San Diego Flights from Spokane to San Diego

Chicago to San Diego: Overview

Insights for flights from Chicago to San Diego

How much is a round trip from Chicago to San Diego

Regular price: $233 - $544

Prices for flights from Chicago to San Diego are currently below the regular range.

The regular price range for flights from Chicago to San Diego is between $233 and $544. The current lowest deal is $157 with Frontier Airlines for travel from Dec 7-Dec 14.

now $157

Low $233

High $544

The cheapest time to fly from Chicago to San Diego

March

Cheapest

Flights from $139

January

Most Expensive

Flights from $1,269

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec