What percentage of Chicago to San Diego flights are direct?

In the trailing 90 days, approximately 34.9% of flights from Chicago to San Diego were direct. For travelers opting for connecting flights, the median number of stopovers was one. This indicates that while direct options are available, a significant portion of flights on this route will include at least one stop. Travelers should consider this when planning their journey.

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

A direct flight from Chicago to San Diego typically takes about 4 hours and 28 minutes. For flights that include one stop, the median travel time extends to approximately 8 hours and 4 minutes. The total distance covered on this route is 2768 kilometers. Travelers should account for these durations when making their travel plans, especially if choosing a connecting flight.

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

Historically, cheap flights from Chicago to San Diego are a frequent occurrence. This route is known for its regular availability of competitively priced fares. Travelers looking for good deals can often find them without extensive searching. This consistent availability makes it easier to plan a trip to San Diego from Chicago without waiting for rare price drops.

Flights From Chicago

To San Diego

Cheap Flights from Chicago to San Diego

Browse current best options from Chicago. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Chicago

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

Prices updated 2 days ago

451 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Aug 17, 2026.)

Today’s best flight deals from Chicago to San Diego

Explore current cheapest deals departing from Chicago to San Diego

2026-09-12 – 2026-09-19
CHI - San Diego
79% AI deal score
$235
$165
Round trip
2026-09-18 – 2026-09-22
CHI - San Diego
84% AI deal score
$294
$165
Round trip
2026-09-18 – 2026-09-24
CHI - San Diego
79% AI deal score
$235
$165
Round trip
2026-09-16 – 2026-09-21
CHI - San Diego
80% AI deal score
$243
$166
Round trip
2026-09-10 – 2026-09-28
CHI - San Diego
80% AI deal score
$237
$166
Round trip
2026-09-16 – 2026-09-18
CHI - San Diego
80% AI deal score
$250
$166
Round trip
2026-10-17 – 2026-10-22
CHI - San Diego
79% AI deal score
$235
$166
Round trip
2026-10-19 – 2026-10-20
CHI - San Diego
80% AI deal score
$239
$166
Round trip
2026-09-12 – 2026-09-15
CHI - San Diego
80% AI deal score
$249
$167
Round trip
2026-09-21 – 2026-09-26
CHI - San Diego
79% AI deal score
$240
$167
Round trip

Chicago to San Diego: Overview

Insights for flights from Chicago to San Diego

Most itineraries for cheap flights from Chicago to San Diego connect at least once, with only 34.9% of recent fares being direct flights. When a connection is involved, the typical number of stopovers is 1. This means you will frequently find options that include a layover on your journey.

Right now, fares from Chicago to San Diego typically range from $272–$710, with a median price of $365. Current fares are above the typical level for this route. Only 5% of recent fares have been classified as a good price, indicating that finding significantly cheaper options may require flexibility.

When considering the cheapest time to fly from Chicago to San Diego, you'll find that April and May offer the lowest median fares, at $234 and $237 respectively. September also presents a more affordable option, with a median fare of $287. These months tend to be more economical compared to the overall median.

A typical journey from Chicago to San Diego takes approximately 4h 28m, including connections. This duration accounts for the fact that most itineraries on this route involve at least one stopover. The distance covered on this route is 2768 km, classifying it as a medium-haul flight.

How much is a round trip from Chicago to San Diego

Regular price: $196 - $393

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 typically between $196 and $393. The current lowest deal is $165 with Frontier Airlines for travel from Sep 12-Sep 19.

now $165

Low $196

High $393

The cheapest time to fly from Chicago to San Diego

The cheapest month to fly from Chicago to San Diego is May, with a median price of $247. The most expensive month is November, with a median price of $563. Prices are generally lower from February to October.

May

Cheapest

Flights from $247

November

Most Expensive

Flights from $563

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

Mon, Aug 17

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Frontier Airlines

$513

$266

One-way

Mon, Aug 17

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Frontier Airlines

$497

$277

One-way

Mon, Aug 17

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Frontier Airlines

$494

$306

One-way

Mon, Aug 17

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Frontier Airlines

$437

$321

One-way

Tue, Aug 18

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Frontier Airlines

$509

$266

One-way

Tue, Aug 18

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Frontier Airlines

$437

$266

One-way

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

1 night

Aug 17 - Aug 18

$513 → $266

48%

2 nights

Aug 18 - Aug 20

$509 → $266

48%

3 nights

Aug 18 - Aug 21

$497 → $266

47%

3 nights

Aug 17 - Aug 20

$497 → $277

44%

Popular Airports to fly from Chicago to San Diego

Chicago - San Diego route insights

💸 Price insights

Recent fares are above the typical level

Recent fares from Chicago to San Diego are above the typical level of $365.

📅 Best time to fly

Fly in April for the best prices

Historically, April, May, and September offer the lowest median prices for this route.

⏱️ Flight duration

Direct flights take 4h 28m

The typical direct flight from Chicago to San Diego takes 4h 28m.

✈️ Airlines & availability

Connecting flights are more common

Connecting flights are more common, with 34.9% of recent flights being direct.

🏆 Airline highlight

Frontier Airlines offers a $165 deal

Frontier Airlines has a recent deal for $165 from Chicago to San Diego.

🎯 Booking tip

Deals are frequent for this route

Deals on flights from Chicago to San Diego are frequent, appearing often.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International offers the cheapest flights from Chicago to San Diego, making it a great value choice.

📍 ~25 km from Chicago city center (reachable by car or train).

💸 Flights from ~$153

Chicago Midway International (MDW)

Chicago Midway International is a convenient option for flights from Chicago to San Diego.

📍 ~14 km from Chicago city center (reachable by car or train).

💸 Flights from ~$226

Chicago Rockford International (RFD)

Chicago Rockford International provides an alternative departure point for flights to San Diego.

📍 ~126 km from Chicago city center (reachable by car).

💸 Flights from ~$203

San Diego main airports to arrive at

San Diego International (SAN)

Cheapest

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

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

💸 Flights from ~$153

Airports nearby San Diego used as alternative

Tijuana International (TIJ)

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

📍 ~25 km from San Diego (reachable by car)

💸 Flights from ~$280

Business & First Class Flight Deals to San Diego

Discover luxury on the budget with premium cabin class on flights from Chicago to San Diego.

Elite

Best Elite deals to San Diego

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From ORD

Elite

Dec 02

San Diego, United States

88% AI deal score

$1,332

$727

Save $605

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 14

San Diego, United States

88% AI deal score

$1,304

$727

Save $577

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 14

San Diego, United States

88% AI deal score

$1,326

$727

Save $599

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Oct 28

San Diego, United States

88% AI deal score

$1,338

$727

Save $611

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Oct 29

San Diego, United States

87% AI deal score

$1,261

$727

Save $534

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Oct 15

San Diego, United States

87% AI deal score

$1,278

$727

Save $551

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 09

San Diego, United States

87% AI deal score

$1,277

$728

Save $549

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 05

San Diego, United States

87% AI deal score

$1,284

$728

Save $556

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 10

San Diego, United States

87% AI deal score

$1,166

$727

Save $439

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 12

San Diego, United States

87% AI deal score

$1,194

$727

Save $467

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 15

San Diego, United States

87% AI deal score

$1,193

$727

Save $466

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 05

San Diego, United States

87% AI deal score

$1,186

$727

Save $459

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 between 28 and 59 days prior to departure. During this period, the average price observed was $241. Prices tend to increase significantly for bookings made closer to the travel date, with flights booked 0-6 days out averaging $1139. Conversely, booking more than 60 days in advance also shows a higher average price of $486, indicating that the sweet spot for savings is within the 28-59 day range.

Across the trailing quarter, a flight from Chicago to San Diego is generally considered a good deal if it is priced at or below $272. The median price for this route over the same period was $365. Prices can go significantly higher, with 75% of observed fares being $710 or less. Therefore, aiming for a price under $272 can help secure a favorable fare.

Historically, the cheapest months to fly from Chicago to San Diego are April, May, and September. In April, the median price was $234, while in May it was $237. September also offered competitive fares with a median of $287. These months typically offer prices below the annual median of $365 for this route, making them ideal for budget-conscious travelers.

Related routes

More routes from Chicago

Flights from Chicago to Ho Chi Minh City Flights from Chicago to Salt Lake City Flights from Chicago to San Antonio Flights from Chicago to San Francisco Flights from Chicago to San Juan Flights from Chicago to Sarasota Flights from Chicago to Savannah Flights from Chicago to Savusavu Flights from Chicago to Seattle Flights from Chicago to Singapore Flights from Chicago to Sydney Flights from Chicago to Tirana

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: $196 - $393

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 typically between $196 and $393. The current lowest deal is $165 with Frontier Airlines for travel from Sep 12-Sep 19.

now $165

Low $196

High $393

The cheapest time to fly from Chicago to San Diego

May

Cheapest

Flights from $247

November

Most Expensive

Flights from $563

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

Mon, Aug 17

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Frontier Airlines

$513

$266

One-way

Mon, Aug 17

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Frontier Airlines

$497

$277

One-way

Mon, Aug 17

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Frontier Airlines

$494

$306

One-way

Mon, Aug 17

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Frontier Airlines

$437

$321

One-way

Tue, Aug 18

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Frontier Airlines

$509

$266

One-way

Tue, Aug 18

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Frontier Airlines

$437

$266

One-way

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

1 night

Aug 17 - Aug 18

$513 → $266

48%

2 nights

Aug 18 - Aug 20

$509 → $266

48%

3 nights

Aug 18 - Aug 21

$497 → $266

47%

3 nights

Aug 17 - Aug 20

$497 → $277

44%

Popular Airports to fly from Chicago to San Diego

Chicago - San Diego route insights

💸 Price insights

Recent fares are above the typical level

Recent fares from Chicago to San Diego are above the typical level of $365.

📅 Best time to fly

Fly in April for the best prices

Historically, April, May, and September offer the lowest median prices for this route.

⏱️ Flight duration

Direct flights take 4h 28m

The typical direct flight from Chicago to San Diego takes 4h 28m.

✈️ Airlines & availability

Connecting flights are more common

Connecting flights are more common, with 34.9% of recent flights being direct.

🏆 Airline highlight

Frontier Airlines offers a $165 deal

Frontier Airlines has a recent deal for $165 from Chicago to San Diego.

🎯 Booking tip

Deals are frequent for this route

Deals on flights from Chicago to San Diego are frequent, appearing often.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International offers the cheapest flights from Chicago to San Diego, making it a great value choice.

📍 ~25 km from Chicago city center (reachable by car or train).

💸 Flights from ~$153

Chicago Midway International (MDW)

Chicago Midway International is a convenient option for flights from Chicago to San Diego.

📍 ~14 km from Chicago city center (reachable by car or train).

💸 Flights from ~$226

Chicago Rockford International (RFD)

Chicago Rockford International provides an alternative departure point for flights to San Diego.

📍 ~126 km from Chicago city center (reachable by car).

💸 Flights from ~$203

San Diego main airports to arrive at

San Diego International (SAN)

Cheapest

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

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

💸 Flights from ~$153

Airports nearby San Diego used as alternative

Tijuana International (TIJ)

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

San Diego, United States

87% AI deal score

$1,186

$727

Save $459

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to San Diego

Cheap Flights from Chicago to San Diego

Today’s best flight deals from Chicago 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

The cheapest time to fly from Chicago to San Diego

Direct flights from Chicago to San Diego

Last-minute flights going from Chicago to San Diego

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

Popular Airports to fly from Chicago to San Diego

Chicago - San Diego route insights

Recent fares are above the typical level

Fly in April for the best prices

Direct flights take 4h 28m

Connecting flights are more common

Frontier Airlines offers a $165 deal

Deals are frequent for this route

Chicago main airports to depart from

San Diego main airports to arrive at

Airports nearby San Diego used as alternative

Business & First Class Flight Deals to San Diego

Best Elite deals to San Diego

Dec 02

Dec 14

Dec 14

Oct 28

Oct 29

Oct 15

Dec 09

Dec 05

Dec 10

Dec 12

Dec 15

Dec 05

Frequently Asked Questions About Flights to San Diego

When is the best time to book flights from Chicago to San Diego?

How do I know if a Chicago to San Diego flight is a good deal?

When is the cheapest time of year to fly from Chicago to San Diego?

What percentage of Chicago to San Diego flights are direct?

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

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

Related routes

More routes from Chicago

Flights to San Diego from other cities

Chicago to San Diego: Overview

Insights for flights from Chicago to San Diego

How much is a round trip from Chicago to San Diego

The cheapest time to fly from Chicago to San Diego

Direct flights from Chicago to San Diego

Last-minute flights going from Chicago to San Diego

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

Popular Airports to fly from Chicago to San Diego

Chicago - San Diego route insights

Recent fares are above the typical level

Fly in April for the best prices

Direct flights take 4h 28m

Connecting flights are more common

Frontier Airlines offers a $165 deal

Deals are frequent for this route

Chicago main airports to depart from

San Diego main airports to arrive at

Airports nearby San Diego used as alternative

Business & First Class Flight Deals to San Diego

Best Elite deals to San Diego

Dec 02

Dec 14

Dec 14

Oct 28

Oct 29

Oct 15

Dec 09

Dec 05

Dec 10

Dec 12

Dec 15

Dec 05

Frequently Asked Questions About Flights to San Diego

When is the best time to book flights from Chicago to San Diego?

How do I know if a Chicago to San Diego flight is a good deal?

When is the cheapest time of year to fly from Chicago to San Diego?