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 have been direct. For journeys that include stopovers, the median number of stopovers observed is one. This indicates that while direct options are available, a significant portion of flights on this route will involve at least one connection. Travelers should consider this when planning their itinerary.

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

The typical direct flight from Chicago to San Diego has a duration of approximately 4 hours and 28 minutes. For flights that include one stop, the median travel time increases to about 8 hours and 4 minutes. This route covers an approximate distance of 2768 kilometers. Travelers should account for these differences in duration when choosing between direct and connecting flights.

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

Historically, cheap flights from Chicago to San Diego come up frequently. This route is consistently identified as one with regular opportunities for favorable pricing. Travelers planning this journey can typically expect to find good deals with some regularity. This consistent availability makes it easier to secure a well-priced ticket for this destination.

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 2 days ago

405 airlines compared

80%+ AI score for best value

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

Today’s best flight deals from Chicago to San Diego

Explore current cheapest deals departing from Chicago to San Diego

2026-09-16 – 2026-09-22
CHI - San Diego
72% AI deal score
$234
$190
Round trip
2026-10-28 – 2026-11-10
CHI - San Diego
69% AI deal score
$217
$194
Round trip
2026-10-07 – 2026-10-15
CHI - San Diego
69% AI deal score
$221
$197
Round trip
2026-11-03 – 2026-11-10
CHI - San Diego
77% AI deal score
$259
$197
Round trip
2026-10-26 – 2026-11-10
CHI - San Diego
67% AI deal score
$212
$200
Round trip
2026-08-26 – 2026-08-30
CHI - San Diego
76% AI deal score
$265
$203
Round trip
2026-10-04 – 2026-10-15
CHI - San Diego
80% AI deal score
$298
$205
Round trip
2026-09-27 – 2026-10-15
CHI - San Diego
79% AI deal score
$278
$206
Round trip
2026-10-28 – 2026-11-12
CHI - San Diego
66% AI deal score
$212
$210
Round trip
2026-10-28 – 2026-10-29
CHI - San Diego
70% AI deal score
$247
$210
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 non-stop. For those flights that do include connections, the typical number of stopovers is one. This means you'll frequently encounter itineraries that involve a layover rather than a direct route.

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 favorable option, with a median fare of $287. These months typically provide more budget-friendly travel opportunities compared to other times of the year.

A typical journey from Chicago to San Diego takes about 4h 28m, including connections. This duration reflects the overall travel time for most itineraries, given that a significant portion of flights include at least one stopover. If you fly a connecting route, the median travel time is 8h 58m.

Fares from Chicago to San Diego typically range from $272–$710, with a median of $365. Right now, current fares are above the typical level for this route. Only about 5% of recent fares were classified as a good price, indicating that finding exceptionally low prices might require some flexibility. New deals appear almost daily, suggesting frequent opportunities to find better prices.

How much is a round trip from Chicago to San Diego

Regular price: $196 - $376

Prices are currently below the regular range.

The regular price range for flights from Chicago to San Diego is between $196 and $376. The current lowest deal is $181 with Frontier Airlines for travel from Sep 16-Sep 22.

now $181

Low $196

High $376

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

Sat, Jul 25

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Frontier Airlines

$414

$278

One-way

Sat, Jul 25

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Frontier Airlines

$418

$295

One-way

Sat, Aug 1

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Frontier Airlines

$417

$295

One-way

Fri, Aug 7

⌛ Last-Minute

RFD - San Diego

Chicago (RFD) - San Diego (SAN)

Allegiant Air

$403

$231

One-way

Sat, Aug 8

⌛ Last-Minute

MDW - San Diego

Chicago (MDW) - San Diego (SAN)

Southwest Airlines

$384

$332

One-way

Mon, Aug 17

⌛ Last-Minute

RFD - San Diego

Chicago (RFD) - San Diego (SAN)

Allegiant Air

$336

$210

One-way

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

4 nights

Aug 7 - Aug 11

$403 → $231

43%

4 nights

Aug 17 - Aug 21

$358 → $219

39%

3 nights

Jul 25 - Jul 28

$414 → $278

33%

3 nights

Aug 17 - Aug 20

$358 → $228

36%

Popular Airports to fly from Chicago to San Diego

Chicago - San Diego route insights

💸 Price insights

Current fares are above the typical level

Recent fares for Chicago to San Diego are $181, which is above the typical level.

📅 Best time to fly

Fly in May for the best prices

Historically, May is the cheapest month to fly from Chicago to San Diego, with a median price of $247.

⏱️ Flight duration

Direct flights take 4h 28m

The typical direct flight from Chicago to San Diego takes 4 hours and 28 minutes.

✈️ Airlines & availability

Connecting flights are dominant

Approximately 34.9% of recent flights from Chicago to San Diego are direct.

🏆 Airline highlight

Alaska Airlines offers direct flights

Alaska Airlines, Inc. is one airline that historically offers direct flights on this route.

🎯 Booking tip

Deals appear frequently

Deals for flights from Chicago to San Diego appear frequently, typically every 30 days.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International offers the cheapest flights to San Diego, making it a great value departure option.

📍 ~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 to San Diego, located closer to the city center.

📍 ~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 your journey 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 arrival option 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 for Mexico-bound travelers, with direct access via CBX.

📍 ~29 km from San Diego (reachable by car, requires valid passport and CBX fee)

💸 Flights from ~$272

Business & First Class Flight Deals to San Diego

87% AI deal score

$1,216

$707

Save $509

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. Flights booked within this period have shown an average price of $241. In contrast, booking 14 to 27 days out sees prices rise to an average of $297. For travelers booking very close to departure, within 0-6 days, the average price can be as high as $1139, indicating a significant increase for last-minute arrangements.

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 has been observed at $365. Prices tend to increase significantly beyond this, with 75% of observed prices being $710 or less. Therefore, aiming for a price under $272 is advisable for securing a favorable fare.

Historically, the cheapest months to fly from Chicago to San Diego are April and May, with median prices of $234 and $237, respectively. September also offers relatively lower prices, with a median of $287. These months typically present better value compared to the annual median price of $365 for this route. Travelers looking for more economical options should consider these periods.

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: $196 - $376

Prices are currently below the regular range.

The regular price range for flights from Chicago to San Diego is between $196 and $376. The current lowest deal is $181 with Frontier Airlines for travel from Sep 16-Sep 22.

now $181

Low $196

High $376

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