Can I fly direct from San Diego to Chicago?

Yes, direct flights from San Diego to Chicago are available. Approximately 33.2% of flights on this route historically have been direct. For journeys that include stopovers, travelers typically experience a median of 2 stopovers. This indicates that while direct options exist, connecting flights are also a common occurrence for this route.

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

The direct flight from San Diego to Chicago typically takes around 4 hours and 13 minutes, covering a distance of 2776 kilometers. For flights with one stop, the median duration is considerably longer, averaging 8 hours and 55 minutes. Travelers should account for these differences in flight time when planning their journey, depending on whether they choose a direct or connecting option.

How often do San Diego to Chicago flight prices drop?

Historically, flight prices for the San Diego to Chicago route drop frequently. This suggests that travelers have regular opportunities to find reduced fares. Monitoring prices over time can be beneficial for securing a good deal on this route, as price fluctuations are a common characteristic of this travel corridor.

Flights From San Diego

To Chicago

Cheap Flights from San Diego to Chicago

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Deals from

San Diego

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Prices updated 6 days ago

454 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated Aug 25, 2026.)

Today’s best flight deals from San Diego to Chicago

Explore current cheapest deals departing from San Diego to Chicago

2026-10-17 – 2026-10-28
SAN - Chicago
69% AI deal score
$210
$190
Round trip
2026-09-15 – 2026-09-23
SAN - Chicago
69% AI deal score
$213
$191
Round trip
2026-09-26 – 2026-09-30
SAN - Chicago
69% AI deal score
$164
$193
Round trip
2026-09-15 – 2026-09-16
SAN - Chicago
69% AI deal score
$174
$193
Round trip
2026-10-03 – 2026-10-06
SAN - Chicago
69% AI deal score
$171
$193
Round trip
2026-11-03 – 2026-11-10
SAN - Chicago
69% AI deal score
$172
$193
Round trip
2026-11-11 – 2026-11-14
SAN - Chicago
69% AI deal score
$178
$193
Round trip
2026-11-11 – 2026-11-17
SAN - Chicago
69% AI deal score
$172
$193
Round trip
2026-09-16 – 2026-09-19
SAN - Chicago
69% AI deal score
$172
$195
Round trip
2026-10-06 – 2026-10-10
SAN - Chicago
69% AI deal score
$171
$195
Round trip

San Diego to Chicago: Overview

Insights for flights from San Diego to Chicago

Most itineraries from San Diego to Chicago connect at least once, with 33.2% of recent fares being non-stop. For those with connections, the typical number of stopovers is 2. This means that while direct flights from San Diego to Chicago are available, you'll frequently encounter options that include at least one stop.

Right now, if you're looking for cheap flights from San Diego to Chicago, fares are below the typical level. Prices for this route typically range from $289–$716, with a median of $439. Currently, 0% of recent fares have been classified as a good price, indicating that while current prices are lower than usual, exceptional deals are not widely available.

When is the cheapest time to fly from San Diego to Chicago? The most affordable months to fly are November, September, and January, all with a median fare of $174. These months offer significantly lower prices compared to the typical median fare for the route, presenting the best opportunities for budget-conscious travelers.

A typical journey from San Diego to Chicago takes about 4h 13m, including connections. For non-stop flights, the median duration is also 4h 13m. However, if your itinerary includes connections, the median journey time extends significantly to 13h 46m, so it's important to consider this difference when planning your trip.

How much is a round trip from San Diego to Chicago

Regular price: $177 - $358

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

The regular price range for flights from San Diego to Chicago is between $177 and $358. The current lowest deal is $190 with Frontier Airlines for travel from Oct 17-Oct 28.

now $190

Low $177

High $358

The cheapest time to fly from San Diego to Chicago

The cheapest month to fly from San Diego to Chicago is November, with a median price of $179. The most expensive month is December, with a median price of $718. Prices are generally lower from January to November.

November

Cheapest

Flights from $179

December

Most Expensive

Flights from $718

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from San Diego to Chicago

Alaska Airlines, Inc.

Last-minute flights going from San Diego to Chicago

Tue, Sep 1

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (MDW)

$325

$306

One-way

Tue, Sep 1

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (ORD)

Frontier Airlines

$421

$313

One-way

Tue, Sep 1

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (MDW)

$480

$395

One-way

Tue, Sep 1

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (MDW)

$483

$405

One-way

Wed, Sep 2

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (MDW)

$467

$375

One-way

Wed, Sep 2

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (MDW)

$464

$392

One-way

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

1 night

Sep 1 - Sep 2

$421 → $313

26%

3 nights

Sep 2 - Sep 5

$467 → $375

20%

4 nights

Sep 1 - Sep 5

$480 → $395

18%

3 nights

Nov 5 - Nov 8

$294 → $216

27%

Popular Airports to fly from San Diego to Chicago

San Diego - Chicago route insights

💸 Price insights

Recent fares are below the typical level.

Recent fares from San Diego to Chicago are below the typical level at $190.

📅 Best time to fly

Fly in November, September, or January for the best prices.

Historically, the cheapest months to fly are November, September, and January, with median prices around $174.

⏱️ Flight duration

Direct flights take 4h 13m.

Direct flights to Chicago typically take 4h 13m, while connecting flights average 13h 46m.

✈️ Airlines & availability

Connecting flights are dominant on this route.

Only 33.2% of recent flights from San Diego to Chicago are direct.

🏆 Airline highlight

Alaska Airlines, Inc. offers direct flights.

Alaska Airlines, Inc. has offered direct flights on this route recently.

🎯 Booking tip

Deals are frequent on this route.

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

San Diego main airports to depart from

San Diego International (SAN)

Cheapest

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

📍 ~3 km from city center (reachable by car)

💸 Flights from ~$155

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

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

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

💸 Flights from ~$185

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

Cheapest

General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.

📍 ~135 km from Chicago (reachable by rail or car, but requires travel across state lines into Wisconsin)

💸 Flights from ~$194

Business & First Class Flight Deals to Chicago

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

Elite

Best Elite deals to Chicago

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

From SAN

Elite

Nov 14

Chicago, United States

91% AI deal score

$1,316

$687

Save $629

Alaska Airlines, Inc.

Business Class

From SAN

Elite

Nov 03

Chicago, United States

91% AI deal score

$1,340

$697

Save $643

Alaska Airlines, Inc.

Business Class

From SAN

Elite

Nov 04

Chicago, United States

90% AI deal score

$1,216

$687

Save $529

Alaska Airlines, Inc.

Business Class

From SAN

Elite

Nov 10

Chicago, United States

90% AI deal score

$1,191

$687

Save $504

Alaska Airlines, Inc.

Business Class

From SAN

Elite

Nov 10

Chicago, United States

90% AI deal score

$1,222

$687

Save $535

Alaska Airlines, Inc.

Business Class

From SAN

Elite

Nov 11

Chicago, United States

90% AI deal score

$1,224

$687

Save $537

Alaska Airlines, Inc.

Business Class

From SAN

Elite

Nov 11

Chicago, United States

90% AI deal score

$1,224

$687

Save $537

Alaska Airlines, Inc.

Business Class

From SAN

Elite

Nov 04

Chicago, United States

90% AI deal score

$1,216

$687

Save $529

Alaska Airlines, Inc.

Business Class

From SAN

Elite

Oct 27

Chicago, United States

90% AI deal score

$1,192

$687

Save $505

Alaska Airlines, Inc.

Business Class

From SAN

Elite

Oct 27

Chicago, United States

90% AI deal score

$1,331

$695

Save $636

Alaska Airlines, Inc.

Business Class

From SAN

Elite

Nov 03

Chicago, United States

90% AI deal score

$1,203

$697

Save $506

Alaska Airlines, Inc.

Business Class

From SAN

Elite

Dec 12

Chicago, United States

90% AI deal score

$1,332

$727

Save $605

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, booking flights from San Diego to Chicago 60+ days in advance typically yields the lowest prices, with an average of $445. Prices tend to increase as the departure date approaches. For example, flights booked 28-59 days out average $509, while those booked 0-6 days before departure can average as high as $866. Planning ahead by at least 60 days is advisable to secure more favorable rates.

Across the trailing quarter, a flight from San Diego to Chicago is considered a good deal if it is priced at or below $289. The median price for this route historically stands at $439. Prices can go up to $716 or more for higher-cost options. Therefore, aiming for prices around $289 or less indicates a particularly advantageous fare.

Historically, the cheapest months to fly from San Diego to Chicago are November, September, and January, all with a median price of $174. This is significantly lower than the annual median price for the route, which is $439. Travelers looking for the most economical options should consider planning their trips during these months to take advantage of the lower fares.

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Flights to Chicago from other cities

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San Diego to Chicago: Overview

Insights for flights from San Diego to Chicago

How much is a round trip from San Diego to Chicago

Regular price: $177 - $358

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

The regular price range for flights from San Diego to Chicago is between $177 and $358. The current lowest deal is $190 with Frontier Airlines for travel from Oct 17-Oct 28.

now $190

Low $177

High $358

The cheapest time to fly from San Diego to Chicago

November

Cheapest

Flights from $179

December

Most Expensive

Flights from $718

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from San Diego to Chicago

Alaska Airlines, Inc.

Last-minute flights going from San Diego to Chicago

Tue, Sep 1

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (MDW)

$325

$306

One-way

Tue, Sep 1

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (ORD)

Frontier Airlines

$421

$313

One-way

Tue, Sep 1

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (MDW)

$480

$395

One-way

Tue, Sep 1

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (MDW)

$483

$405

One-way

Wed, Sep 2

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (MDW)

$467

$375

One-way

Wed, Sep 2

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (MDW)

$464

$392

One-way

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

1 night

Sep 1 - Sep 2

$421 → $313

26%

3 nights

Sep 2 - Sep 5

$467 → $375

20%

4 nights

Sep 1 - Sep 5

$480 → $395

18%

3 nights

Nov 5 - Nov 8

$294 → $216

27%

Popular Airports to fly from San Diego to Chicago

San Diego - Chicago route insights

💸 Price insights

Recent fares are below the typical level.

Recent fares from San Diego to Chicago are below the typical level at $190.

📅 Best time to fly

Fly in November, September, or January for the best prices.

Historically, the cheapest months to fly are November, September, and January, with median prices around $174.

⏱️ Flight duration

Direct flights take 4h 13m.

Direct flights to Chicago typically take 4h 13m, while connecting flights average 13h 46m.

✈️ Airlines & availability

Connecting flights are dominant on this route.

Only 33.2% of recent flights from San Diego to Chicago are direct.

🏆 Airline highlight

Alaska Airlines, Inc. offers direct flights.

Alaska Airlines, Inc. has offered direct flights on this route recently.

🎯 Booking tip

Deals are frequent on this route.

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

San Diego main airports to depart from

San Diego International (SAN)

Cheapest

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

📍 ~3 km from city center (reachable by car)

💸 Flights from ~$155

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

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

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

💸 Flights from ~$185

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

Cheapest

General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.

Chicago, United States

90% AI deal score

$1,332

$727

Save $605

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Chicago

Cheap Flights from San Diego to Chicago

Today’s best flight deals from San Diego to Chicago

San Diego to Chicago: Overview

Insights for flights from San Diego to Chicago

How much is a round trip from San Diego to Chicago

The cheapest time to fly from San Diego to Chicago

Direct flights from San Diego to Chicago

Last-minute flights going from San Diego to Chicago

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

Popular Airports to fly from San Diego to Chicago

San Diego - Chicago route insights

Recent fares are below the typical level.

Fly in November, September, or January for the best prices.

Direct flights take 4h 13m.

Connecting flights are dominant on this route.

Alaska Airlines, Inc. offers direct flights.

Deals are frequent on this route.

San Diego main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Nov 14

Nov 03

Nov 04

Nov 10

Nov 10

Nov 11

Nov 11

Nov 04

Oct 27

Oct 27

Nov 03

Dec 12

Frequently Asked Questions About Flights to Chicago

How early should I book San Diego to Chicago flights to get the cheapest price?

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

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

Can I fly direct from San Diego to Chicago?

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

How often do San Diego to Chicago flight prices drop?

Related routes

More routes from San Diego

Flights to Chicago from other cities

San Diego to Chicago: Overview

Insights for flights from San Diego to Chicago

How much is a round trip from San Diego to Chicago

The cheapest time to fly from San Diego to Chicago

Direct flights from San Diego to Chicago

Last-minute flights going from San Diego to Chicago

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

Popular Airports to fly from San Diego to Chicago

San Diego - Chicago route insights

Recent fares are below the typical level.

Fly in November, September, or January for the best prices.

Direct flights take 4h 13m.

Connecting flights are dominant on this route.

Alaska Airlines, Inc. offers direct flights.

Deals are frequent on this route.

San Diego main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Nov 14

Nov 03

Nov 04

Nov 10

Nov 10

Nov 11

Nov 11

Nov 04

Oct 27

Oct 27

Nov 03

Dec 12

Frequently Asked Questions About Flights to Chicago

How early should I book San Diego to Chicago flights to get the cheapest price?

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

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