How many flights from San Francisco to Chicago are non-stop?

Across the trailing quarter, approximately 25% of flights from San Francisco to Chicago are non-stop. For flights that do include stopovers, the median number of stopovers observed in the trailing 90 days is 2. This indicates that while direct options are available, a significant portion of routes involve connections.

What's the flight time from San Francisco to Chicago?

The typical direct flight from San Francisco to Chicago has a median duration of 4 hours and 31 minutes. For flights with one stop, the median flight time increases significantly to 12 hours and 3 minutes. The distance between the two cities is approximately 2979 kilometers. Travelers should account for these differences when planning their journey.

How much more do direct flights from San Francisco to Chicago cost?

Historically, direct flights from San Francisco to Chicago typically cost about 1% more than connecting flights. Across the trailing quarter, the median price for a direct flight was $448, while connecting flights had a median price of $444. Direct flights constituted approximately 24.4% of the available options in the trailing 90 days. This indicates a relatively small price difference for the convenience of a non-stop journey.

Flights From San Francisco

To Chicago

Cheap Flights from San Francisco to Chicago

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Deals from

San Francisco

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

Prices updated 7 days ago

483 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Oct 26, 2026.)

Today’s best flight deals from San Francisco to Chicago

Explore current cheapest deals departing from San Francisco to Chicago

2026-12-07 – 2026-12-09
SFO - Chicago
86% AI deal score
$363
$170
Round trip
2026-12-01 – 2026-12-02
SFO - Chicago
86% AI deal score
$364
$173
Round trip
2026-12-10 – 2026-12-16
SFO - Chicago
85% AI deal score
$341
$173
Round trip
2026-12-07 – 2026-12-16
SFO - Chicago
83% AI deal score
$321
$174
Round trip
2026-12-11 – 2026-12-14
SFO - Chicago
85% AI deal score
$362
$178
Round trip
2027-02-01 – 2027-02-22
SFO - Chicago
71% AI deal score
$227
$189
Round trip
2027-01-06 – 2027-02-02
SFO - Chicago
71% AI deal score
$221
$190
Round trip
2027-02-16 – 2027-02-22
SFO - Chicago
77% AI deal score
$251
$192
Round trip
2026-12-09 – 2026-12-13
SFO - Chicago
83% AI deal score
$361
$194
Round trip
2027-02-16 – 2027-02-23
SFO - Chicago
73% AI deal score
$251
$194
Round trip

San Francisco to Chicago: Overview

Insights for flights from San Francisco to Chicago

Most itineraries for flights from San Francisco to Chicago connect at least once, with only 25% of recent fares being non-stop. For connecting itineraries, the typical number of stopovers is 2. This means that while direct flights from San Francisco to Chicago are available, you'll often find yourself with at least one stop on your journey.

A typical journey from San Francisco to Chicago takes about 4h 31m, including connections. For those looking for cheap flights from San Francisco to Chicago, this median duration reflects the overall travel time you can expect. Non-stop flights also typically take 4h 31m, while connecting flights have a significantly longer median duration of 16h 7m.

When is the cheapest time to fly from San Francisco to Chicago? The most affordable month to fly is often March, with a median fare of $129. Other budget-friendly options include April, with a median fare of $325, and February, where the median fare is $363. Planning your trip during these months could lead to more significant savings.

Fares for flights from San Francisco to Chicago typically range from $325–$656, with a median of $445. Right now, fares are above the typical level. Only 5% of recent fares were classified as a good price, indicating that finding a deeply discounted fare can be challenging. However, new deals appear almost daily, suggesting that consistent monitoring could yield better prices.

How much is a round trip from San Francisco to Chicago

Regular price: $190 - $285

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

The typical price range for this route is between $190 and $285. The current lowest deal is $184 with Frontier Airlines, for travel from Feb 8 to Feb 23.

now $184

Low $190

High $285

The cheapest time to fly from San Francisco to Chicago

The cheapest month to fly from SFO to CHI is March, with a median price of $129. The most expensive month is June, with a median price of $2798. Prices are generally lower from February to December.

March

Cheapest

Flights from $129

June

Most Expensive

Flights from $2,798

Jan

Feb

Mar

Apr

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from San Francisco to Chicago

United Airlines

Last-minute flights going from San Francisco to Chicago

Mon, Nov 23

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Alaska Airlines, Inc.

$198

$242

One-way

Mon, Nov 23

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Alaska Airlines, Inc.

$197

$243

One-way

Thu, Nov 26

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Frontier Airlines

$194

$218

One-way

Thu, Nov 26

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Frontier Airlines

$203

$218

One-way

Thu, Nov 26

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Frontier Airlines

$202

$223

One-way

Thu, Nov 26

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Frontier Airlines

$228

$231

One-way

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

2 nights

Dec 7 - Dec 9

$363 → $185

49%

1 night

Dec 1 - Dec 2

$364 → $188

48%

4 nights

Dec 11 - Dec 15

$361 → $198

45%

5 nights

Dec 2 - Dec 7

$352 → $195

45%

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 SFO to CHI are above the typical level for this route.

📅 Best time to fly

March is historically the cheapest month to fly.

Historically, March is the cheapest month to fly from San Francisco to Chicago, with a median price of $129.

⏱️ Flight duration

Direct flights take 4h 31m.

Direct flights from San Francisco to Chicago typically take 4 hours and 31 minutes.

✈️ Airlines & availability

Connecting flights are dominant on this route.

Connecting flights make up 75% of recent deals, with a median of 2 stopovers.

🏆 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 appear frequently on this route.

Deals for flights from San Francisco to Chicago appear frequently, typically every 30 days.

San Francisco main airports to depart from

San Francisco International (SFO)

Cheapest

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

📍 ~18 km from city center (reachable by car or train)

💸 Flights from ~$119

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.

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

💸 Flights from ~$185

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International is a major international airport with significant carrier presence and direct flight options.

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

💸 Flights from ~$310

Business & First Class Flight Deals to Chicago

$885

Save $566

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the cheapest flights from San Francisco to Chicago are typically found when booking in the 28-59 days window prior to departure. Across the trailing quarter, the average price for this booking window was $587. Booking within 0-6 days of departure typically sees prices rise to an average of $796, while booking 7-13 days out averages $813. Even booking 60+ days in advance tends to be slightly more expensive, with an average price of $640.

Across the trailing quarter, a good price for a flight from San Francisco to Chicago is considered to be $325 or less. Historically, the median price for this route has been around $445. Prices can go higher, with 75% of deals observed in the trailing 90 days being $656 or less. Aiming for prices at or below the $325 threshold typically represents a favorable deal.

Historically, March has offered the cheapest flights from San Francisco to Chicago, with a median price of $129. April also presents a good value, with a median price of $325. February, while being the most expensive month in the trailing 270 days with a median of $363, still offers prices below the annual median of $445 for this route. Travelers looking for lower fares might consider these months.

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San Francisco to Chicago: Overview

Insights for flights from San Francisco to Chicago

How much is a round trip from San Francisco to Chicago

Regular price: $190 - $285

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

The typical price range for this route is between $190 and $285. The current lowest deal is $184 with Frontier Airlines, for travel from Feb 8 to Feb 23.

now $184

Low $190

High $285

The cheapest time to fly from San Francisco to Chicago

The cheapest month to fly from SFO to CHI is March, with a median price of $129. The most expensive month is June, with a median price of $2798. Prices are generally lower from February to December.

March

Cheapest

Flights from $129

June

Most Expensive

Flights from $2,798

Jan

Feb

Mar

Apr

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from San Francisco to Chicago

United Airlines

Last-minute flights going from San Francisco to Chicago

Mon, Nov 23

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Alaska Airlines, Inc.

$198

$242

One-way

Mon, Nov 23

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Alaska Airlines, Inc.

$197

$243

One-way

Thu, Nov 26

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Frontier Airlines

$194

$218

One-way

Thu, Nov 26

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Frontier Airlines

$203

$218

One-way

Thu, Nov 26

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Frontier Airlines

$202

$223

One-way

Thu, Nov 26

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Frontier Airlines

$228

$231

One-way

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

2 nights

Dec 7 - Dec 9

$363 → $185

49%

1 night

Dec 1 - Dec 2

$364 → $188

48%

4 nights

Dec 11 - Dec 15

$361 → $198

45%

5 nights

Dec 2 - Dec 7

$352 → $195

45%

Popular Airports to fly from San Francisco to Chicago