What percentage of Chicago to San Diego flights are direct?

Across the trailing quarter, approximately 34.9% of flights from Chicago to San Diego have been direct. For travelers who prefer non-stop journeys, this percentage indicates a notable availability. When a direct flight is not an option, connecting flights typically involve one stopover. This information can help in planning travel preferences.

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 28 minutes. This covers an approximate distance of 2768 kilometers. For flights that include one stop, the median travel time increases to 8 hours and 4 minutes. Travelers should account for these differences when planning their journey.

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 classified as offering frequent opportunities for good deals. Travelers can often find favorable prices when planning their trips. This consistent availability suggests that with some flexibility, securing a well-priced flight is achievable.

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 1 day ago

461 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Sep 14, 2026.)

Today’s best flight deals from Chicago to San Diego

Explore current cheapest deals departing from Chicago to San Diego

2026-11-11 – 2026-11-17
CHI - San Diego
78% AI deal score
$241
$174
Round trip
2026-11-04 – 2026-11-10
CHI - San Diego
78% AI deal score
$238
$177
Round trip
2026-12-07 – 2026-12-12
CHI - San Diego
81% AI deal score
$322
$193
Round trip
2026-10-13 – 2026-10-21
CHI - San Diego
69% AI deal score
$216
$194
Round trip
2026-11-07 – 2026-11-10
CHI - San Diego
72% AI deal score
$252
$198
Round trip
2026-11-10 – 2026-11-15
CHI - San Diego
71% AI deal score
$247
$200
Round trip
2026-10-05 – 2026-10-10
CHI - San Diego
70% AI deal score
$234
$201
Round trip
2026-10-24 – 2026-10-28
CHI - San Diego
70% AI deal score
$237
$201
Round trip
2026-10-20 – 2026-10-27
CHI - San Diego
69% AI deal score
$225
$201
Round trip
2026-11-04 – 2026-11-08
CHI - San Diego
71% AI deal score
$251
$201
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. When connecting, the typical itinerary includes 1 stopover. This means you will frequently find options that involve a layover rather than a direct route.

Right now, fares from Chicago to San Diego are typically $272–$710, with a median of $365. Current fares are above the typical level, and only 5% of recent fares were classified as a good price. New deals appear almost daily, so monitoring prices can be beneficial.

When is the cheapest time to fly from Chicago to San Diego? The data indicates that April is the most affordable month, with a median fare of $234. Following closely is May, with a median fare of $237, and September also offers competitive pricing at a median of $287. These months present the best opportunities for lower-priced travel.

How long is the flight from Chicago to San Diego? A typical journey from Chicago to San Diego takes about 4h 28m, including connections. For itineraries that involve a stop, the median connecting flight time is 8h 58m, while direct flights from Chicago to San Diego have a median duration of 4h 28m. This route covers a distance of 2768 km, classifying it as a medium-haul flight.

How much is a round trip from Chicago to San Diego

Regular price: $200 - $366

Prices are currently below the regular range.

Regular prices for flights from Chicago to San Diego typically range from $200 to $366. The current lowest deal is $174 with Frontier Airlines, for travel from Nov 11-Nov 17.

now $174

Low $200

High $366

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

Tue, Sep 15

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Alaska Airlines, Inc.

$448

$359

One-way

Tue, Sep 15

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Alaska Airlines, Inc.

$437

$361

One-way

Tue, Sep 15

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Alaska Airlines, Inc.

$440

$389

One-way

Wed, Sep 16

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Frontier Airlines

$440

$314

One-way

Thu, Sep 17

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Frontier Airlines

$422

$354

One-way

Fri, Sep 18

⌛ Last-Minute

ORD - San Diego

Chicago (ORD) - San Diego (SAN)

Frontier Airlines

$422

$334

One-way

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

1 night

Sep 15 - Sep 16

$448 → $278

38%

3 nights

Sep 15 - Sep 18

$440 → $294

33%

5 nights

Dec 7 - Dec 12

$322 → $193

40%

3 nights

Sep 16 - Sep 19

$424 → $314

26%

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 for Chicago to San Diego are above the typical level, with a median 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 median flight duration for a direct flight is 4h 28m, while connecting flights average 8h 58m.

✈️ Airlines & availability

Connecting flights are more common

Connecting flights make up 65.1% of routes, with a median of 1 stopover.

🏆 Airline highlight

Frontier Airlines offers a deal at $174

Frontier Airlines has a recent deal for $174 from November 11-17, 2026.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Chicago to San Diego are frequent, appearing within a 30-day window.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International is a major hub offering many flight options from Chicago to San Diego.

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

💸 Flights from ~$183

Chicago Midway International (MDW)

Chicago Midway International provides a convenient alternative for flights from Chicago to San Diego.

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

💸 Flights from ~$216

Chicago Rockford International (RFD)

Chicago Rockford International offers another departure point for travelers flying from Chicago to San Diego.

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

💸 Flights from ~$196

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 city center (reachable by car)

💸 Flights from ~$179

Airports nearby San Diego used as alternative

Tijuana International (TIJ)

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

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

💸 Flights from ~$275

Business & First Class Flight Deals to San Diego

$737

Save $454

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 for a flight has been observed at approximately $241. Booking within 7-13 days of departure sees the average price rise to around $780, while waiting until 0-6 days before can result in an average price of $1139. Planning ahead by more than 60 days also tends to be more expensive, with an average price of $486.

Based on historical data for the trailing 90 days, a flight from Chicago to San Diego is considered a good deal if it is priced at or below $272. The median price for this route has been $365. Prices tend to increase significantly beyond this threshold, with 75% of prices observed at $710 or higher. Therefore, aiming for fares under $272 can help secure a favorable price.

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 competitive prices, with a median of $287. These months tend to be more affordable compared to the annual median price of $365 for this route. Travelers looking for the best value 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: $200 - $366

Prices are currently below the regular range.

Regular prices for flights from Chicago to San Diego typically range from $200 to $366. The current lowest deal is $174 with Frontier Airlines, for travel from Nov 11-Nov 17.

now $174

Low $200

High $366

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