Can I fly direct from San Diego to Chicago?

Direct flights from San Diego to Chicago are available, making up 17% of all flights on this route across the trailing quarter. For flights with one or more stops, the median number of stopovers was 2. This suggests that while direct options exist, connecting flights are more common.

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

The median flight time for a direct flight from San Diego to Chicago is 4 hours and 18 minutes. For flights with one stop, the median duration increases to 9 hours and 55 minutes. The air distance between San Diego and Chicago is approximately 2776 kilometers.

How often do San Diego to Chicago flight prices drop?

Prices for flights from San Diego to Chicago are classified as dropping frequently. This indicates that travelers may often find opportunities for price reductions. Historically, this route has shown consistent price fluctuations over a 30-day period.

Flights From San Diego

To Chicago

Cheap Flights from San Diego to Chicago

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

Deals from

San Diego

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

Prices updated 4 days ago

476 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated Oct 12, 2026.)

Today’s best flight deals from San Diego to Chicago

Explore current cheapest deals departing from San Diego to Chicago

2026-11-12 – 2026-11-16
SAN - Chicago
79% AI deal score
$244
$172
Round trip
2026-11-12 – 2026-11-14
SAN - Chicago
79% AI deal score
$244
$172
Round trip
2026-12-10 – 2026-12-15
SAN - Chicago
78% AI deal score
$242
$172
Round trip
2026-11-05 – 2026-11-09
SAN - Chicago
78% AI deal score
$246
$175
Round trip
2026-12-03 – 2026-12-07
SAN - Chicago
78% AI deal score
$245
$178
Round trip
2026-12-02 – 2026-12-07
SAN - Chicago
77% AI deal score
$239
$178
Round trip
2026-11-03 – 2026-11-10
SAN - Chicago
76% AI deal score
$232
$181
Round trip
2026-11-13 – 2026-11-16
SAN - Chicago
76% AI deal score
$244
$188
Round trip
2026-11-13 – 2026-11-18
SAN - Chicago
72% AI deal score
$239
$188
Round trip
2026-11-06 – 2026-11-11
SAN - Chicago
69% AI deal score
$170
$190
Round trip

San Diego to Chicago: Overview

Insights for flights from San Diego to Chicago

A typical journey from San Diego to Chicago takes about 4h 18m, including connections. This route is classified as medium-haul, covering a distance of 2776 kilometers. While the direct flight time is also 4h 18m, connecting itineraries typically extend the travel time to 15h 8m.

For travelers seeking cheap flights from San Diego to Chicago, prices typically range from $282–$828, with a median of $458. Right now, current fares are above the typical level for this route. Only 1% of recent fares were classified as a good price, indicating that finding deals can be challenging. New deals appear almost daily, so setting up a price alert can be beneficial.

When is the cheapest time to fly from San Diego to Chicago? The most affordable month to fly is typically January, with a median fare of $257. Other cost-effective months include October, where the median fare is $326, and March, with a median fare of $327. Planning your trip during these months could result in lower travel costs.

Most itineraries for flights from San Diego to Chicago connect at least once, with only 17% of recent fares being non-stop. For connecting flights, the typical number of stopovers is two. This means that if you fly this route, you are likely to have at least one connection, and often two, extending the overall travel time.

How much is a round trip from San Diego to Chicago

Regular price: $191 - $318

Prices are currently below the regular range.

The regular price range for flights from San Diego to Chicago is typically between $191 and $318. The current lowest deal is $124 with Frontier Airlines for travel from Nov 3-Nov 10.

now $124

Low $191

High $318

The cheapest time to fly from San Diego to Chicago

The cheapest month to fly from San Diego to Chicago is January, with a median price of $257. The most expensive month is July, with a median price of $973. Prices are generally lower from January to October.

January

Cheapest

Flights from $257

July

Most Expensive

Flights from $973

Jan

Feb

Mar

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, Oct 6

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (ORD)

Frontier Airlines

$360

$312

One-way

Wed, Oct 7

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (ORD)

Frontier Airlines

$445

$360

One-way

Thu, Oct 8

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (ORD)

Frontier Airlines

$385

$382

One-way

Thu, Oct 8

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (ORD)

Frontier Airlines

$433

$407

One-way

Tue, Oct 13

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (ORD)

Frontier Airlines

$288

$317

One-way

Wed, Oct 14

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (ORD)

Frontier Airlines

$240

$241

One-way

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

4 nights

Jan 21 - Jan 25

$252 → $176

30%

5 nights

Jan 20 - Jan 25

$254 → $181

29%

3 nights

Dec 3 - Dec 6

$301 → $234

22%

13 nights

Dec 2 - Dec 15

$255 → $190

25%

Popular Airports to fly from San Diego to Chicago

San Diego - Chicago route insights

💸 Price insights

Recent fares are above the typical level.

Recent fares from San Diego to Chicago are above the typical level for this route.

📅 Best time to fly

January offers the lowest median price at $257.

Historically, January, October, and March offer the lowest median prices for this route.

⏱️ Flight duration

Direct flights average 4h 18m.

Direct flights typically take 4 hours and 18 minutes, while connecting flights average 15 hours and 8 minutes.

✈️ Airlines & availability

Connecting flights are dominant on this route.

Only 17% of recent flights are direct, with connecting flights typically having 2 stopovers.

🏆 Airline highlight

Frontier Airlines offers a deal at $124.

Frontier Airlines has a deal for $124 from November 3 to November 10, 2026.

🎯 Booking tip

Deals are frequent for this route.

Deals for 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 or bus)

💸 Flights from ~$172

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering extensive connections for your trip to Chicago.

📍 ~25 km from Chicago city center (reachable by car, train, and bus).

💸 Flights from ~$115

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

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

📍 ~135 km from Chicago (reachable by car or train)

💸 Flights from ~$321

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

Dec 15

Chicago, United States

89% AI deal score

$1,272

$699

Save $573

Alaska Airlines, Inc.

Business Class

From SAN

Elite

Feb 27

Chicago, United States

89% AI deal score

$1,111

$699

Save $412

Alaska Airlines, Inc.

Business Class

From SAN

Elite

Dec 08

Chicago, United States

89% AI deal score

$1,180

$699

Save $481

Alaska Airlines, Inc.

Business Class

From SAN

Elite

Dec 12

Chicago, United States

88% AI deal score

$1,204

$699

Save $505

Alaska Airlines, Inc.

Business Class

From SAN

Elite

Dec 02

Chicago, United States

88% AI deal score

$1,218

$699

Save $519

Alaska Airlines, Inc.

Business Class

From SAN

Elite

Dec 12

Chicago, United States

88% AI deal score

$1,233

$699

Save $534

Alaska Airlines, Inc.

Business Class

From SAN

Elite

Feb 27

Chicago, United States

88% AI deal score

$1,107

$699

Save $408

Alaska Airlines, Inc.

Business Class

From SAN

Elite

Dec 12

Chicago, United States

87% AI deal score

$1,109

$699

Save $410

Alaska Airlines, Inc.

Business Class

From SAN

Elite

Jan 05

Chicago, United States

87% AI deal score

$1,146

$699

Save $447

Alaska Airlines, Inc.

Business Class

From SAN

Elite

Dec 15

Chicago, United States

87% AI deal score

$1,108

$699

Save $409

Alaska Airlines, Inc.

Business Class

From SAN

Elite

Dec 16

Chicago, United States

87% AI deal score

$1,108

$699

Save $409

Alaska Airlines, Inc.

Business Class

From SAN

Elite

Dec 12

Chicago, United States

87% AI deal score

$1,109

$699

Save $410

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the best prices for flights from San Diego to Chicago are found when booking 28-59 days in advance. During this period, the average price was $636. Booking 14-27 days out saw an average price of $687, which is still considerably lower than prices closer to departure. For example, flights booked 0-6 days before departure typically averaged $1114.

Across the trailing quarter, a good deal for a flight from San Diego to Chicago was considered to be $282 or less. The median price for this route was $458 during the same period. Prices above $828 were in the most expensive quartile, indicating less favorable deals.

Historically, the cheapest months to fly from San Diego to Chicago include January, with a median price of $257, and October, with a median price of $326. March also showed a median price of $327. The annual median price for this route was $458, indicating that certain months offer significant savings.

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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: $191 - $318

Prices are currently below the regular range.

The regular price range for flights from San Diego to Chicago is typically between $191 and $318. The current lowest deal is $124 with Frontier Airlines for travel from Nov 3-Nov 10.

now $124

Low $191

High $318

The cheapest time to fly from San Diego to Chicago

January

Cheapest

Flights from $257

July

Most Expensive

Flights from $973

Jan

Feb

Mar

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, Oct 6

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (ORD)

Frontier Airlines

$360

$312

One-way

Wed, Oct 7

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (ORD)

Frontier Airlines

$445

$360

One-way

Thu, Oct 8

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (ORD)

Frontier Airlines

$385

$382

One-way

Thu, Oct 8

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (ORD)

Frontier Airlines

$433

$407

One-way

Tue, Oct 13

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (ORD)

Frontier Airlines

$288

$317

One-way

Wed, Oct 14

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (ORD)

Frontier Airlines

$240

$241

One-way

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

4 nights

Jan 21 - Jan 25

$252 → $176

30%

5 nights

Jan 20 - Jan 25

$254 → $181

29%

3 nights

Dec 3 - Dec 6

$301 → $234

22%

13 nights

Dec 2 - Dec 15

$255 → $190

25%

Popular Airports to fly from San Diego to Chicago

San Diego - Chicago route insights

💸 Price insights

Recent fares are above the typical level.

Recent fares from San Diego to Chicago are above the typical level for this route.

📅 Best time to fly

January offers the lowest median price at $257.

Historically, January, October, and March offer the lowest median prices for this route.

⏱️ Flight duration

Direct flights average 4h 18m.

Direct flights typically take 4 hours and 18 minutes, while connecting flights average 15 hours and 8 minutes.

✈️ Airlines & availability

Connecting flights are dominant on this route.

Only 17% of recent flights are direct, with connecting flights typically having 2 stopovers.

🏆 Airline highlight

Frontier Airlines offers a deal at $124.

Frontier Airlines has a deal for $124 from November 3 to November 10, 2026.

🎯 Booking tip

Deals are frequent for this route.

Deals for 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 or bus)

💸 Flights from ~$172

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering extensive connections for your trip to Chicago.

📍 ~25 km from Chicago city center (reachable by car, train, and bus).

💸 Flights from ~$115

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

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

Chicago, United States

87% AI deal score

$1,109

$699

Save $410

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 above the typical level.

January offers the lowest median price at $257.

Direct flights average 4h 18m.

Connecting flights are dominant on this route.

Frontier Airlines offers a deal at $124.

Deals are frequent for 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

Dec 15

Feb 27

Dec 08

Dec 12

Dec 02

Dec 12

Feb 27

Dec 12

Jan 05

Dec 15

Dec 16

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 above the typical level.

January offers the lowest median price at $257.

Direct flights average 4h 18m.

Connecting flights are dominant on this route.

Frontier Airlines offers a deal at $124.

Deals are frequent for 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

Dec 15

Feb 27

Dec 08

Dec 12

Dec 02

Dec 12

Feb 27

Dec 12

Jan 05

Dec 15

Dec 16

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?