FlightsFrom San Francisco

To Chicago

Cheap Flights from San Francisco to Chicago

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

Deals from

San Francisco

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

Prices updated 24 days ago

486,190 searches this week

171 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)

Today’s best flight deals from San Francisco to Chicago

Explore current cheapest deals departing from San Francisco to Chicago

September 15 - September 29

Cheapest

SFO - Chicago

$219

$214

Round trip

September 9 - September 15

Cheapest

SFO - Chicago

$232

$214

Round trip

September 23 - September 30

Cheapest

SFO - Chicago

$249

$214

Round trip

September 1 - September 15

Cheapest

SFO - Chicago

$200

$214

Round trip

August 12 - August 18

Best

SFO - Chicago

$303

$215

Round trip

August 11 - August 12

Earliest

SFO - Chicago

$269

$215

Round trip

September 28 - October 28

SFO - Chicago

$270

$215

Round trip

September 28 - October 21

SFO - Chicago

$271

$215

Round trip

September 29 - October 21

SFO - Chicago

$272

$215

Round trip

September 29 - October 28

SFO - Chicago

$271

$215

Round trip

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

Route Intelligence — 486,190 Searches this Week

Insights for flights from San Francisco to Chicago

For flights from San Francisco to Chicago, a meaningful share of itineraries are non-stop, the rest connect once, with 44.8% of recent fares being direct. For itineraries that include connections, the typical number of stopovers is 2. This means you will find a mix of options when planning your trip.
When considering cheap flights from San Francisco to Chicago, prices are right now above the typical level. Fares typically range from $256–$545, with a median of $391. Currently, only 1% of recent fares are classified as a good price, indicating that finding a low fare may require some flexibility. New deals appear almost daily, so setting up a price alert could be beneficial.
The cheapest time to fly from San Francisco to Chicago is typically during April, with a median fare of $232. Other cost-effective months include December, where the median fare is $233, and January, with a median fare of $244. Planning your travel during these months could lead to significant savings.
A typical journey from San Francisco to Chicago takes approximately 12h 1m, including connections. This duration accounts for both direct and connecting itineraries, reflecting the overall travel time you can expect for this route.
The distance between San Francisco and Chicago is 2979 km, classifying this as a medium-haul route. This distance typically involves a longer flight duration, often with connecting options available.

How much is a round trip from San Francisco to Chicago

Regular price: $215 - $357

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

The regular price range for flights from San Francisco to Chicago is between $215 and $357. The current lowest deal is $215 with Frontier Airlines, for travel from Sep 28-Oct 28.

now $215

Low $215

High $357

The cheapest time to fly from San Francisco to Chicago

The cheapest month to fly from San Francisco to Chicago is April, with a median price of $232. The most expensive month is November, with a median price of $904. Generally, prices are lower from January to December.

April

Cheapest

Flights from $232

November

Most Expensive

Flights from $904

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

Direct flights from San Francisco to Chicago

Airline logo

United Airlines

Last-minute flights going from San Francisco to Chicago

Mon, Jul 6

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

$245

$315

One-way

Mon, Jul 6

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

$242

$315

One-way

Tue, Jul 7

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

$262

$315

One-way

Tue, Jul 7

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

$245

$315

One-way

Wed, Jul 8

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

$249

$315

One-way

Wed, Jul 8

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

$233

$315

One-way

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

8 nights

Dec 16 - Dec 24

$448  →  $365

19%

8 nights

Dec 17 - Dec 25

$448  →  $374

16%

9 nights

Dec 16 - Dec 25

$444  →  $374

16%

3 nights

Dec 2 - Dec 5

$395  →  $335

15%

Popular Airports to fly from San Francisco to Chicago

San Francisco - Chicago route insights

💸 Price insights

Recent fares are above the typical level.

Recent fares from San Francisco to Chicago are above the typical level for the last 90 days.

📅 Best time to fly

April, December, and January are historically cheapest.

Historically, the cheapest months to fly from San Francisco to Chicago are April ($232), December ($233), and January ($244).

⏱️ Flight duration

Flights typically take 12h 1m.

The median flight duration from San Francisco to Chicago is 12h 1m, covering a distance of 2979 km.

✈️ Airlines & availability

Direct flights are available.

Approximately 44.8% of recent deals for this route are for direct flights.

🏆 Airline highlight

United Airlines offers direct flights.

United Airlines is one of the airlines that offers direct flights from San Francisco to Chicago.

🎯 Booking tip

Deals are frequent for this route.

Historically, deals for flights from San Francisco to Chicago are frequent, with over 1 deal per day.

San Francisco main airports to depart from

San Francisco International (SFO)

Cheapest

San Francisco International is a good option for flights from San Francisco to Chicago.

📍 ~20 km from city center (reachable by car or train)

💸 Flights from ~$214

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

Consider Chicago Midway International for flights to Chicago, offering a convenient arrival option.

📍 ~15 km from Chicago city center (reachable by car)

💸 Flights from ~$214

Chicago Rockford International (RFD)

Chicago Rockford International is an alternative arrival airport for flights to the Chicago area.

📍 ~120 km from Chicago city center (reachable by car)

💸 Flights from ~$248

O Hare International (ORD)

O Hare International is a major airport for flights to Chicago, providing extensive connectivity.

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

💸 Flights from ~$214

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

Consider MKE for its excellent proximity to Chicago and high-frequency flight options, despite potential traffic.

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

💸 Flights from ~$338

South Bend International (SBN)

SBN is geographically the closest alternative to the Chicago area, offering easier security and parking.

📍 ~120 km from Chicago (reachable by car or train)

💸 Flights from ~$253

Gerald R. Ford International (GRR)

Cheapest

GRR is a major regional hub, a good alternative for travelers on the eastern side of the Chicago metro area.

📍 ~200 km from Chicago (reachable by car)

💸 Flights from ~$245

Dane County Regional (MSN)

MSN is a reliable regional airport with consistent service, less congested than major Chicago airports.

📍 ~200 km from Chicago (reachable by car)

💸 Flights from ~$262

Fort Wayne International (FWA)

FWA offers stable regional service and is an alternative for travelers in the southeastern Chicago suburbs.

📍 ~240 km from Chicago (reachable by car)

💸 Flights from ~$301

Business & First Class Flight Deals to Chicago

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

Elite

Best Elite deals to Chicago

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

From SFO

Elite

Nov 19

Chicago, United States

91% AI deal score

$1,632

$835

Save $797

From SFO

Elite

Nov 03

Chicago, United States

90% AI deal score

$1,502

$835

Save $667

From SFO

Elite

Nov 18

Chicago, United States

90% AI deal score

$1,519

$835

Save $684

From SFO

Elite

Nov 10

Chicago, United States

90% AI deal score

$1,510

$835

Save $675

From SFO

Elite

Nov 14

Chicago, United States

90% AI deal score

$1,505

$835

Save $670

From SFO

Elite

Nov 04

Chicago, United States

90% AI deal score

$1,502

$835

Save $667

From SFO

Elite

Dec 02

Chicago, United States

90% AI deal score

$1,662

$835

Save $827

From SFO

Elite

Nov 10

Chicago, United States

90% AI deal score

$1,546

$835

Save $711

From SFO

Elite

Nov 07

Chicago, United States

90% AI deal score

$1,547

$835

Save $712

From SFO

Elite

Nov 12

Chicago, United States

90% AI deal score

$1,546

$835

Save $711

From SFO

Elite

Nov 04

Chicago, United States

90% AI deal score

$1,548

$835

Save $713

From SFO

Elite

Sep 30

Chicago, United States

90% AI deal score

$1,598

$835

Save $763

From SFO

Elite

Nov 18

Chicago, United States

90% AI deal score

$1,643

$835

Save $808

From SFO

Elite

Nov 04

Chicago, United States

90% AI deal score

$1,520

$835

Save $685

From SFO

Elite

Nov 14

Chicago, United States

90% AI deal score

$1,539

$835

Save $704

From SFO

Elite

Nov 10

Chicago, United States

90% AI deal score

$1,542

$835

Save $707

From SFO

Elite

Nov 02

Chicago, United States

90% AI deal score

$1,521

$835

Save $686

From SFO

Elite

Nov 03

Chicago, United States

90% AI deal score

$1,520

$835

Save $685

From SFO

Elite

Nov 03

Chicago, United States

90% AI deal score

$1,537

$835

Save $702

From SFO

Elite

Nov 02

Chicago, United States

90% AI deal score

$1,522

$835

Save $687

From SFO

Elite

Nov 03

Chicago, United States

90% AI deal score

$1,544

$835

Save $709

From SFO

Elite

Nov 04

Chicago, United States

90% AI deal score

$1,536

$835

Save $701

From SFO

Elite

Nov 10

Chicago, United States

90% AI deal score

$1,543

$835

Save $708

From SFO

Elite

Nov 10

Chicago, United States

90% AI deal score

$1,644

$835

Save $809

From SFO

Elite

Nov 02

Chicago, United States

90% AI deal score

$1,537

$835

Save $702

From SFO

Elite

Nov 14

Chicago, United States

90% AI deal score

$1,630

$835

Save $795

From SFO

Elite

Nov 16

Chicago, United States

90% AI deal score

$1,542

$835

Save $707

From SFO

Elite

Nov 14

Chicago, United States

90% AI deal score

$1,512

$835

Save $677

From SFO

Elite

Nov 18

Chicago, United States

90% AI deal score

$1,508

$835

Save $673

From SFO

Elite

Oct 27

Chicago, United States

90% AI deal score

$1,534

$835

Save $699

From SFO

Elite

Oct 24

Chicago, United States

90% AI deal score

$1,539

$835

Save $704

From SFO

Elite

Dec 02

Chicago, United States

90% AI deal score

$1,559

$835

Save $724

From SFO

Elite

Oct 05

Chicago, United States

90% AI deal score

$1,551

$836

Save $715

From SFO

Elite

Aug 25

Chicago, United States

90% AI deal score

$1,542

$848

Save $694

From SFO

Elite

Nov 14

Chicago, United States

89% AI deal score

$1,518

$848

Save $670

From SFO

Elite

Nov 02

Chicago, United States

89% AI deal score

$1,501

$848

Save $653

From SFO

Elite

Nov 18

Chicago, United States

89% AI deal score

$1,517

$848

Save $669

From SFO

Elite

Nov 04

Chicago, United States

89% AI deal score

$1,504

$848

Save $656

From SFO

Elite

Nov 03

Chicago, United States

89% AI deal score

$1,501

$848

Save $653

From SFO

Elite

Nov 10

Chicago, United States

89% AI deal score

$1,510

$848

Save $662

From SFO

Elite

Nov 10

Chicago, United States

89% AI deal score

$1,330

$835

Save $495

From SFO

Elite

Nov 11

Chicago, United States

89% AI deal score

$1,329

$835

Save $494

From SFO

Elite

Nov 14

Chicago, United States

89% AI deal score

$1,343

$835

Save $508

From SFO

Elite

Aug 05

Chicago, United States

88% AI deal score

$1,264

$833

Save $431

From SFO

Elite

Aug 05

Chicago, United States

88% AI deal score

$1,271

$833

Save $438

From SFO

Elite

Nov 11

Chicago, United States

88% AI deal score

$1,230

$835

Save $395

From SFO

Elite

Nov 03

Chicago, United States

88% AI deal score

$1,242

$835

Save $407

From SFO

Elite

Nov 19

Chicago, United States

88% AI deal score

$1,241

$835

Save $406

From SFO

Elite

Nov 05

Chicago, United States

88% AI deal score

$1,259

$835

Save $424

From SFO

Elite

Nov 04

Chicago, United States

88% AI deal score

$1,244

$835

Save $409

From SFO

Elite

Nov 07

Chicago, United States

88% AI deal score

$1,295

$835

Save $460

From SFO

Elite

Nov 02

Chicago, United States

88% AI deal score

$1,242

$835

Save $407

From SFO

Elite

Jul 26

Chicago, United States

87% AI deal score

$1,237

$640

Save $597

From SFO

Elite

Jul 27

Chicago, United States

87% AI deal score

$1,254

$640

Save $614

From SFO

Elite

Aug 05

Chicago, United States

87% AI deal score

$1,219

$833

Save $386

From SFO

Elite

Nov 11

Chicago, United States

87% AI deal score

$1,224

$835

Save $389

From SFO

Elite

Nov 11

Chicago, United States

87% AI deal score

$1,224

$835

Save $389

From SFO

Elite

Nov 14

Chicago, United States

87% AI deal score

$1,224

$835

Save $389

From SFO

Elite

Nov 10

Chicago, United States

87% AI deal score

$1,224

$835

Save $389

From SFO

Elite

Nov 10

Chicago, United States

87% AI deal score

$1,224

$835

Save $389

From SFO

Elite

Nov 14

Chicago, United States

87% AI deal score

$1,224

$835

Save $389

From SFO

Elite

Nov 19

Chicago, United States

87% AI deal score

$1,224

$835

Save $389

From SFO

Elite

Nov 07

Chicago, United States

87% AI deal score

$1,224

$835

Save $389

From SFO

Elite

Nov 04

Chicago, United States

86% AI deal score

$1,638

$830

Save $808

From SFO

Elite

Jul 18

Chicago, United States

86% AI deal score

$1,437

$783

Save $654

From SFO

Elite

Jul 18

Chicago, United States

86% AI deal score

$1,426

$783

Save $643

From SFO

Elite

Jul 09

Chicago, United States

86% AI deal score

$2,201

$1,195

Save $1,006

From SFO

Elite

Jul 08

Chicago, United States

86% AI deal score

$2,201

$1,198

Save $1,003

From SFO

Elite

Jul 09

Chicago, United States

86% AI deal score

$2,193

$1,208

Save $985

From SFO

Elite

Jul 10

Chicago, United States

86% AI deal score

$2,207

$1,208

Save $999

From SFO

Elite

Jul 21

Chicago, United States

86% AI deal score

$2,241

$1,208

Save $1,033

From SFO

Elite

Jul 27

Chicago, United States

86% AI deal score

$2,201

$1,208

Save $993

From SFO

Elite

Jun 17

Chicago, United States

85% AI deal score

$1,994

$1,101

Save $893

From SFO

Elite

Jul 22

Chicago, United States

85% AI deal score

$1,427

$865

Save $562

From SFO

Elite

Aug 07

Chicago, United States

85% AI deal score

$1,599

$901

Save $698

From SFO

Elite

Jul 20

Chicago, United States

85% AI deal score

$1,457

$803

Save $654

From SFO

Elite

Jul 20

Chicago, United States

85% AI deal score

$1,453

$803

Save $650

From SFO

Elite

Jul 21

Chicago, United States

85% AI deal score

$1,457

$803

Save $654

From SFO

Elite

Jul 18

Chicago, United States

85% AI deal score

$1,453

$820

Save $633

From SFO

Elite

Jul 18

Chicago, United States

85% AI deal score

$1,427

$820

Save $607

From SFO

Elite

Jul 18

Chicago, United States

85% AI deal score

$1,369

$820

Save $549

From SFO

Elite

Jul 18

Chicago, United States

85% AI deal score

$1,369

$820

Save $549

From SFO

Elite

Jul 19

Chicago, United States

85% AI deal score

$1,369

$820

Save $549

From SFO

Elite

Jul 20

Chicago, United States

85% AI deal score

$1,427

$820

Save $607

From SFO

Elite

Jul 21

Chicago, United States

85% AI deal score

$1,426

$820

Save $606

From SFO

Elite

Jul 24

Chicago, United States

85% AI deal score

$1,457

$820

Save $637

From SFO

Elite

Nov 13

Chicago, United States

85% AI deal score

$2,261

$1,198

Save $1,063

From SFO

Elite

Aug 17

Chicago, United States

84% AI deal score

$1,222

$780

Save $442

From SFO

Elite

Aug 29

Chicago, United States

84% AI deal score

$1,261

$783

Save $478

From SFO

Elite

Aug 28

Chicago, United States

84% AI deal score

$1,273

$783

Save $490

From SFO

Elite

Jul 19

Chicago, United States

84% AI deal score

$1,453

$839

Save $614

From SFO

Elite

Jul 19

Chicago, United States

84% AI deal score

$1,437

$839

Save $598

From SFO

Elite

Jul 20

Chicago, United States

84% AI deal score

$1,437

$839

Save $598

From SFO

Elite

Jul 20

Chicago, United States

84% AI deal score

$1,426

$839

Save $587

From SFO

Elite

Jul 21

Chicago, United States

84% AI deal score

$1,436

$839

Save $597

From SFO

Elite

Jul 22

Chicago, United States

84% AI deal score

$1,436

$857

Save $579

From SFO

Elite

Jul 22

Chicago, United States

84% AI deal score

$1,457

$874

Save $583

From SFO

Elite

Jul 22

Chicago, United States

84% AI deal score

$1,453

$874

Save $579

From SFO

Elite

Jul 19

Chicago, United States

84% AI deal score

$1,457

$875

Save $582

From SFO

Elite

Jun 19

Chicago, United States

84% AI deal score

$1,651

$1,058

Save $593

Frequently Asked Questions About Flights to Chicago

Historically, the cheapest flights from San Francisco to Chicago are typically found when booking in the 0-6 days window before departure, with an average price of $336. Booking 28-59 days out shows an average price of $416, while flights booked 7-13 days in advance average $756. Across the trailing 90 days, the best average prices were observed for last-minute bookings.

In the trailing 90 days, a good price for a flight from San Francisco to Chicago was $256. The median price for this route was $391, and prices typically ranged up to $545. This means that about 25% of all observed prices were at or below $256.

Historically, the cheapest months to fly from San Francisco to Chicago are April and December, with median prices of $232 and $233 respectively. January also offers relatively low prices, with a median of $244. The annual median price for this route is $391, indicating that these months offer significant savings.