Can I fly direct from San Diego to Chicago?

Yes, direct flights from San Diego to Chicago are available. Historically, approximately 33.2% of all flight options on this route in the trailing 90 days were direct. For travelers opting for connecting flights, the median number of stopovers was 2. This indicates that while direct options exist, a significant portion of flights include at least one stop.

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

The typical direct flight from San Diego to Chicago has a duration of approximately 4 hours and 13 minutes, covering a distance of 2776 kilometers. For flights with one stop, the median duration extends to about 8 hours and 55 minutes. This difference highlights the time savings associated with choosing a direct route.

How often do San Diego to Chicago flight prices drop?

Historically, flight prices for the San Diego to Chicago route have shown frequent drops. This indicates that travelers have regular opportunities to find reduced fares. Monitoring prices consistently over the trailing 30 days can be beneficial for securing a more favorable price for this route.

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 5 days ago

402 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 12, 2026.)

Today’s best flight deals from San Diego to Chicago

Explore current cheapest deals departing from San Diego to Chicago

Round trip

Sort by: Cheapest

September 11 - September 16

Cheapest

SAN - Chicago

$227

$154

Round trip

September 8 - September 14

Earliest

SAN - Chicago

$221

$155

Round trip

September 17 - September 21

Best

SAN - Chicago

$282

$159

Round trip

September 17 - September 23

Best

SAN - Chicago

$273

$160

Round trip

October 19 - November 17

SAN - Chicago

$225

$161

Round trip

October 19 - November 10

SAN - Chicago

$225

$161

Round trip

October 19 - November 14

SAN - Chicago

$225

$161

Round trip

October 19 - November 18

SAN - Chicago

$225

$161

Round trip

September 15 - September 28

SAN - Chicago

$198

$163

Round trip

September 22 - September 28

SAN - Chicago

$222

$163

Round trip

Unlock all 500+ flight deals to Chicago and get alerts when great deals appear

San Diego to Chicago: Overview

Insights for flights from San Diego to Chicago

Most itineraries for flights from San Diego to Chicago connect at least once, with only 33.2% of recent fares being non-stop. When connecting, the typical number of stopovers is 2. This means that while direct flights from San Diego to Chicago are available, you will likely encounter options with layovers.

Right now, if you are looking for cheap flights from San Diego to Chicago, fares are typically $289–$716, with a median of $439. Current fares are below the typical level, indicating a potentially favorable time to book. However, the share of recent fares classified as a good price is 0%, suggesting that while prices are lower than usual, deeply discounted deals are not currently prevalent.

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 overall median, making them ideal 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, connecting itineraries can extend the travel time significantly, with a median duration of 13h 46m.

How much is a round trip from San Diego to Chicago

Regular price: $186 - $288

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

The regular price range for flights from San Diego to Chicago is $186 to $288. The current lowest deal is $155 with Frontier Airlines, for travel from Sep 8-Sep 14.

now $155

Low $186

High $288

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

Sun, Jul 12

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (MDW)

Frontier Airlines

$443

$313

One-way

Wed, Jul 15

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (ORD)

Alaska Airlines, Inc.

$300

$266

One-way

Wed, Jul 15

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (MDW)

Frontier Airlines

$380

$284

One-way

Mon, Jul 27

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (MDW)

Frontier Airlines

$325

$266

One-way

Tue, Jul 28

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (MDW)

Frontier Airlines

$316

$248

One-way

Tue, Aug 4

⌛ Last-Minute

SAN - Chicago

San Diego (SAN) - Chicago (ORD)

Frontier Airlines

$220

$193

One-way

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

3 nights

Jul 8 - Jul 11

$443 → $278

37%

4 nights

Aug 13 - Aug 17

$310 → $211

32%

4 nights

Aug 18 - Aug 22

$309 → $213

31%

5 nights

Aug 12 - Aug 17

$301 → $208

31%

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 $155.

📅 Best time to fly

Fly in November for the best prices

Historically, November is the cheapest month to fly, with a median price of $179.

⏱️ Flight duration

Direct flights take 4h 13m

The typical direct flight from San Diego to Chicago takes 4h 13m.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights make up 66.8% of available routes from San Diego to Chicago.

🏆 Airline highlight

Alaska Airlines offers direct flights

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

🎯 Booking tip

Deals appear frequently

Deals on flights from San Diego to Chicago appear frequently, typically within 30 days.

San Diego main airports to depart from

San Diego International (SAN)

Cheapest

San Diego International Airport is a convenient and often most affordable option for flights to Chicago.

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

💸 Flights from ~$155

McClellan–Palomar (CLD)

McClellan–Palomar Airport offers an alternative departure point for travelers heading to Chicago.

📍 ~47 km from San Diego (reachable by car)

💸 Flights from ~$347

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub for flights to Chicago, offering many connections from San Diego.

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

💸 Flights from ~$185

Chicago Midway International (MDW)

Chicago Midway International Airport is a convenient option for reaching Chicago from San Diego.

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

💸 Flights from ~$227

Chicago Rockford International (RFD)

Chicago Rockford International Airport is an alternative for travelers flying from San Diego to the Chicago area.

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

💸 Flights from ~$258

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and is easily accessible from Chicago.

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

💸 Flights from ~$233

Gerald R. Ford International (GRR)

Cheapest

Gerald R. Ford International is Michigan's second largest airport with a robust domestic network.

📍 ~250 km from Chicago (reachable by car)

💸 Flights from ~$223

Dane County Regional (MSN)

Dane County Regional is a reliable regional hub with efficient operations and good amenities.

📍 ~200 km from Chicago (reachable by car)

💸 Flights from ~$278

South Bend International (SBN)

South Bend International is geographically the closest alternative airport to the Chicago metro area.

📍 ~130 km from Chicago (reachable by rail)

💸 Flights from ~$251

Fort Wayne International (FWA)

Fort Wayne International offers multiple cabin classes and solid connectivity for eastern domestic destinations.

📍 ~240 km from Chicago (reachable by car)

💸 Flights from ~$231

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

Aug 20

Chicago, United States

90% AI deal score

$1,306

$727

Save $579

From SAN

Elite

Sep 03

Chicago, United States

90% AI deal score

$1,263

$727

Save $536

From SAN

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Aug 20

Chicago, United States

90% AI deal score

$1,315

$727

Save $588

From SAN

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Aug 20

Chicago, United States

90% AI deal score

$1,287

$727

Save $560

From SAN

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Aug 20

Chicago, United States

90% AI deal score

$1,270

$727

Save $543

From SAN

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Aug 20

Chicago, United States

90% AI deal score

$1,253

$727

Save $526

From SAN

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Aug 20

Chicago, United States

90% AI deal score

$1,282

$727

Save $555

From SAN

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Aug 21

Chicago, United States

90% AI deal score

$1,279

$727

Save $552

From SAN

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Aug 21

Chicago, United States

90% AI deal score

$1,308

$727

Save $581

From SAN

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Aug 21

Chicago, United States

90% AI deal score

$1,247

$727

Save $520

From SAN

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Sep 05

Chicago, United States

90% AI deal score

$1,262

$727

Save $535

From SAN

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Aug 25

Chicago, United States

90% AI deal score

$1,286

$727

Save $559

From SAN

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Aug 25

Chicago, United States

90% AI deal score

$1,315

$727

Save $588

From SAN

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Aug 21

Chicago, United States

90% AI deal score

$1,283

$727

Save $556

From SAN

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Aug 25

Chicago, United States

90% AI deal score

$1,315

$727

Save $588

From SAN

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Aug 21

Chicago, United States

90% AI deal score

$1,283

$727

Save $556

From SAN

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Aug 21

Chicago, United States

90% AI deal score

$1,298

$727

Save $571

From SAN

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Aug 25

Chicago, United States

90% AI deal score

$1,305

$727

Save $578

From SAN

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Aug 21

Chicago, United States

90% AI deal score

$1,294

$727

Save $567

From SAN

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Aug 29

Chicago, United States

90% AI deal score

$1,305

$727

Save $578

From SAN

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Aug 29

Chicago, United States

90% AI deal score

$1,288

$727

Save $561

From SAN

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Oct 22

Chicago, United States

90% AI deal score

$1,235

$727

Save $508

From SAN

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Oct 20

Chicago, United States

90% AI deal score

$1,317

$727

Save $590

From SAN

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Oct 24

Chicago, United States

90% AI deal score

$1,324

$727

Save $597

From SAN

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Oct 22

Chicago, United States

90% AI deal score

$1,319

$727

Save $592

From SAN

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Oct 21

Chicago, United States

90% AI deal score

$1,342

$727

Save $615

From SAN

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Oct 25

Chicago, United States

90% AI deal score

$1,359

$727

Save $632

From SAN

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Aug 24

Chicago, United States

90% AI deal score

$1,305

$747

Save $558

From SAN

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Aug 20

Chicago, United States

90% AI deal score

$1,306

$747

Save $559

From SAN

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Aug 24

Chicago, United States

90% AI deal score

$1,301

$767

Save $534

From SAN

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Aug 24

Chicago, United States

89% AI deal score

$1,358

$727

Save $631

From SAN

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Aug 30

Chicago, United States

89% AI deal score

$1,355

$727

Save $628

From SAN

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Aug 25

Chicago, United States

89% AI deal score

$1,374

$727

Save $647

From SAN

Elite

Oct 16

Chicago, United States

89% AI deal score

$1,361

$727

Save $634

From SAN

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Sep 06

Chicago, United States

89% AI deal score

$1,258

$727

Save $531

From SAN

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Sep 03

Chicago, United States

89% AI deal score

$1,241

$727

Save $514

From SAN

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Aug 20

Chicago, United States

89% AI deal score

$1,246

$727

Save $519

From SAN

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Aug 20

Chicago, United States

88% AI deal score

$1,257

$727

Save $530

From SAN

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Aug 20

Chicago, United States

88% AI deal score

$1,242

$727

Save $515

From SAN

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Aug 24

Chicago, United States

88% AI deal score

$1,250

$727

Save $523

From SAN

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Aug 25

Chicago, United States

88% AI deal score

$1,260

$727

Save $533

From SAN

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Aug 24

Chicago, United States

88% AI deal score

$1,200

$727

Save $473

From SAN

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Aug 20

Chicago, United States

88% AI deal score

$1,202

$727

Save $475

From SAN

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Aug 20

Chicago, United States

88% AI deal score

$1,251

$727

Save $524

From SAN

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Aug 30

Chicago, United States

88% AI deal score

$1,219

$727

Save $492

From SAN

Elite

Aug 24

Chicago, United States

88% AI deal score

$1,267

$727

Save $540

From SAN

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Oct 16

Chicago, United States

88% AI deal score

$1,262

$727

Save $535

From SAN

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Oct 16

Chicago, United States

88% AI deal score

$1,337

$727

Save $610

From SAN

Elite

Aug 29

Chicago, United States

88% AI deal score

$1,222

$727

Save $495

From SAN

Elite

Sep 05

Chicago, United States

88% AI deal score

$1,349

$727

Save $622

From SAN

Elite

Oct 16

Chicago, United States

88% AI deal score

$1,261

$727

Save $534

From SAN

Elite

Oct 22

Chicago, United States

88% AI deal score

$1,349

$727

Save $622

From SAN

Elite

Aug 20

Chicago, United States

88% AI deal score

$1,252

$747

Save $505

From SAN

Elite

Aug 24

Chicago, United States

88% AI deal score

$1,297

$747

Save $550

From SAN

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Sep 06

Chicago, United States

88% AI deal score

$1,142

$727

Save $415

From SAN

Elite

Oct 22

Chicago, United States

87% AI deal score

$1,268

$727

Save $541

From SAN

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Oct 16

Chicago, United States

87% AI deal score

$1,264

$727

Save $537

From SAN

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Sep 09

Chicago, United States

87% AI deal score

$1,244

$727

Save $517

From SAN

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Sep 06

Chicago, United States

87% AI deal score

$1,101

$727

Save $374

From SAN

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Sep 03

Chicago, United States

87% AI deal score

$1,098

$727

Save $371

From SAN

Elite

Oct 01

Chicago, United States

87% AI deal score

$1,156

$742

Save $414

From SAN

Elite

Oct 01

Chicago, United States

87% AI deal score

$1,155

$742

Save $413

From SAN

Elite

Aug 21

Chicago, United States

87% AI deal score

$1,298

$857

Save $441

From SAN

Elite

Jun 23

Chicago, United States

87% AI deal score

$1,483

$945

Save $538

From SAN

Elite

Dec 10

Chicago, United States

86% AI deal score

$1,244

$785

Save $459

From SAN

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Dec 10

Chicago, United States

86% AI deal score

$1,232

$785

Save $447

From SAN

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Aug 20

Chicago, United States

86% AI deal score

$1,456

$727

Save $729

From SAN

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Aug 20

Chicago, United States

86% AI deal score

$1,439

$727

Save $712

From SAN

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Aug 20

Chicago, United States

86% AI deal score

$1,472

$727

Save $745

From SAN

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Aug 20

Chicago, United States

86% AI deal score

$1,390

$727

Save $663

From SAN

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Aug 21

Chicago, United States

86% AI deal score

$1,382

$727

Save $655

From SAN

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Aug 25

Chicago, United States

86% AI deal score

$1,451

$727

Save $724

From SAN

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Aug 21

Chicago, United States

86% AI deal score

$1,461

$727

Save $734

From SAN

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Aug 21

Chicago, United States

86% AI deal score

$1,431

$727

Save $704

From SAN

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Aug 21

Chicago, United States

86% AI deal score

$1,464

$727

Save $737

From SAN

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Aug 25

Chicago, United States

86% AI deal score

$1,386

$727

Save $659

From SAN

Elite

Aug 21

Chicago, United States

86% AI deal score

$1,448

$727

Save $721

From SAN

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Aug 29

Chicago, United States

86% AI deal score

$1,372

$727

Save $645

From SAN

Elite

Aug 29

Chicago, United States

86% AI deal score

$1,448

$727

Save $721

From SAN

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Aug 29

Chicago, United States

86% AI deal score

$1,437

$727

Save $710

From SAN

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Aug 20

Chicago, United States

86% AI deal score

$1,469

$727

Save $742

From SAN

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Aug 26

Chicago, United States

86% AI deal score

$1,435

$731

Save $704

From SAN

Elite

Jun 19

Chicago, United States

86% AI deal score

$2,291

$1,096

Save $1,195

From SAN

Elite

Nov 22

Chicago, United States

85% AI deal score

$1,193

$799

Save $394

From SAN

Elite

Dec 10

Chicago, United States

85% AI deal score

$1,234

$801

Save $433

From SAN

Elite

Jun 23

Chicago, United States

85% AI deal score

$1,579

$943

Save $636

From SAN

Elite

Jun 22

Chicago, United States

85% AI deal score

$1,581

$947

Save $634

From SAN

Elite

Jul 20

Chicago, United States

85% AI deal score

$1,322

$785

Save $537

From SAN

Elite

Aug 24

Chicago, United States

84% AI deal score

$1,171

$729

Save $442

From SAN

Elite

Dec 01

Chicago, United States

83% AI deal score

$1,211

$864

Save $347

From SAN

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Dec 01

Chicago, United States

83% AI deal score

$1,205

$864

Save $341

From SAN

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Dec 01

Chicago, United States

83% AI deal score

$1,205

$864

Save $341

From SAN

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Dec 01

Chicago, United States

83% AI deal score

$1,197

$864

Save $333

From SAN

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Aug 22

Chicago, United States

83% AI deal score

$1,097

$729

Save $368

From SAN

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Aug 22

Chicago, United States

83% AI deal score

$1,104

$739

Save $365

From SAN

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Dec 01

Chicago, United States

82% AI deal score

$1,197

$880

Save $317

From SAN

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Jul 22

Chicago, United States

82% AI deal score

$1,263

$864

Save $399

From SAN

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Jun 19

Chicago, United States

82% AI deal score

$2,341

$1,041

Save $1,300

From SAN

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Jul 09

Chicago, United States

82% AI deal score

$1,883

$1,107

Save $776

From SAN

Elite

Aug 28

Chicago, United States

82% AI deal score

$1,459

$1,117

Save $342

Frequently Asked Questions About Flights to Chicago

Historically, booking flights from San Diego to Chicago at least 60 days in advance typically yields the lowest prices. Across the trailing quarter, the average price for flights booked within 0-6 days of departure was $866. In contrast, flights booked 60+ days out had an average price of $445. This suggests that planning significantly ahead can result in substantial savings.

In the trailing 90 days, 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 during that period was $439. Prices around $716 or higher were observed in the upper quartile of fares. Therefore, aiming for prices under $289 is advisable for travelers seeking value.

Historically, the cheapest months to fly from San Diego to Chicago include November, September, and January, all with a median price of $174. The annual median price for this route across the trailing 270 days was $439. While November also appeared as the most expensive month in some observations, the overall trend indicates significant savings during these specific months.

Related routes

Consider alternative routes from San Diego

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