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

Across the trailing 90 days, approximately 34.2% of flights from San Francisco to Chicago were non-stop. For flights that included stopovers, travelers typically encountered a median of 2 stopovers. 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 median direct flight time from San Francisco to Chicago is 4 hours and 25 minutes, covering a distance of 2979 kilometers. Flights with one stop typically have a median duration of 10 hours and 31 minutes. This shows a considerable difference in travel time between direct and connecting flights.

Should I set a price alert for San Francisco to Chicago flights?

Historically, deals for flights from San Francisco to Chicago have been frequent. This suggests that setting a price alert could be beneficial for travelers seeking optimal fares. Given the consistent availability of deals, monitoring price changes can help in securing a more favorable booking.

Flights From 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 1 day ago

462 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Sep 15, 2026.)

Today’s best flight deals from San Francisco to Chicago

Explore current cheapest deals departing from San Francisco to Chicago

2026-10-13 – 2026-10-14
SFO - Chicago
82% AI deal score
$273
$163
Round trip
2026-10-19 – 2026-10-21
SFO - Chicago
81% AI deal score
$273
$174
Round trip
2026-10-19 – 2026-10-23
SFO - Chicago
79% AI deal score
$273
$184
Round trip
2026-10-14 – 2026-10-21
SFO - Chicago
78% AI deal score
$258
$189
Round trip
2026-10-17 – 2026-10-19
SFO - Chicago
77% AI deal score
$273
$202
Round trip
2026-10-17 – 2026-10-24
SFO - Chicago
72% AI deal score
$258
$202
Round trip
2026-10-06 – 2026-10-13
SFO - Chicago
72% AI deal score
$258
$203
Round trip
2026-10-13 – 2026-10-15
SFO - Chicago
77% AI deal score
$274
$203
Round trip
2026-10-16 – 2026-10-21
SFO - Chicago
72% AI deal score
$268
$204
Round trip
2026-10-15 – 2026-10-22
SFO - Chicago
71% AI deal score
$258
$208
Round trip

San Francisco to Chicago: Overview

Insights for flights from San Francisco to Chicago

Most itineraries for cheap flights from San Francisco to Chicago connect at least once, with only 34.2% of recent fares being non-stop. For connecting flights, the typical number of stopovers is 2. This means you'll often find yourself with at least one layover when flying this route, impacting overall travel time.

A typical journey from San Francisco to Chicago takes about 4h 25m, including connections. While non-stop flights also average 4h 25m, connecting itineraries can extend significantly, with a median connecting flight time of 14h 34m. This difference highlights the impact of stopovers on your total travel duration.

When is the cheapest time to fly from San Francisco to Chicago? The most affordable months to fly are typically April, with a median fare of $232, followed closely by December at $233, and January at $244. These months offer significantly lower prices compared to the overall median for the route.

Fares for flights from San Francisco to Chicago typically range from $313–$601, with a median of $422. Right now, fares are near the typical level for this route. Only 2% of recent fares were classified as a good price, indicating that finding exceptionally low prices can be challenging. New deals appear almost daily, so setting up a price alert could be beneficial.

How much is a round trip from San Francisco to Chicago

Regular price: $205 - $575

Prices are currently below the regular range.

The regular price range for flights from San Francisco to Chicago is $205 to $575. The current lowest deal is $163 with Frontier Airlines for travel from Oct 14-Oct 20.

now $163

Low $205

High $575

The cheapest time to fly from San Francisco to Chicago

The cheapest month to fly from SFO to CHI is December, with a median price of $168. The most expensive month is November, with a median price of $889. Prices are generally lower from January to December.

December

Cheapest

Flights from $168

November

Most Expensive

Flights from $889

Jan

Feb

Mar

Apr

May

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

Tue, Sep 15

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Frontier Airlines

$530

$316

One-way

Tue, Sep 15

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Frontier Airlines

$521

$333

One-way

Tue, Sep 15

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Frontier Airlines

$518

$357

One-way

Tue, Sep 15

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Frontier Airlines

$528

$362

One-way

Wed, Sep 16

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (RFD)

Frontier Airlines

$558

$347

One-way

Wed, Sep 16

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Frontier Airlines

$521

$357

One-way

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

1 night

Sep 15 - Sep 16

$530 → $316

40%

4 nights

Sep 16 - Sep 20

$558 → $347

38%

3 nights

Sep 15 - Sep 18

$521 → $333

36%

1 night

Sep 19 - Sep 20

$550 → $381

31%

Popular Airports to fly from San Francisco to Chicago

San Francisco - Chicago route insights

💸 Price insights

Recent fares are near the typical level

Recent fares from SFO to CHI are near the typical level of $422.

📅 Best time to fly

Fly in April for the best prices

Historically, April is the cheapest month to fly, with a median price of $232.

⏱️ Flight duration

Direct flights average 4h 25m

Nonstop flights from SFO to CHI typically take 4h 25m. Connecting flights average 14h 34m.

✈️ Airlines & availability

Connecting flights are more common

About 34.2% of recent flights are direct. Connecting flights typically have 2 stopovers.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines has direct flights available for the SFO to CHI route.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from SFO to CHI are frequent, appearing within a 30-day window.

San Francisco main airports to depart from

San Francisco International (SFO)

Cheapest

San Francisco International is a convenient departure airport for flights from San Francisco to Chicago.

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

💸 Flights from ~$190

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 Francisco.

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

💸 Flights from ~$159

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 rail or car)

💸 Flights from ~$366

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 18

Chicago, United States

91% AI deal score

$1,446

$744

Save $702

Alaska Airlines, Inc.

Business Class

From SFO

Elite

Nov 14

Chicago, United States

91% AI deal score

$1,440

$744

Save $696

Alaska Airlines, Inc.

Business Class

From SFO

Elite

Nov 18

Chicago, United States

91% AI deal score

$1,422

$744

Save $678

Alaska Airlines, Inc.

Business Class

From SFO

Elite

Nov 16

Chicago, United States

91% AI deal score

$1,445

$750

Save $695

Alaska Airlines, Inc.

Business Class

From SFO

Elite

Nov 16

Chicago, United States

91% AI deal score

$1,417

$750

Save $667

Alaska Airlines, Inc.

Business Class

From SFO

Elite

Dec 14

Chicago, United States

91% AI deal score

$1,481

$750

Save $731

Alaska Airlines, Inc.

Business Class

From SFO

Elite

Nov 14

Chicago, United States

91% AI deal score

$1,423

$750

Save $673

Alaska Airlines, Inc.

Business Class

From SFO

Elite

Nov 18

Chicago, United States

91% AI deal score

$1,422

$750

Save $672

Alaska Airlines, Inc.

Business Class

From SFO

Elite

Nov 16

Chicago, United States

91% AI deal score

$1,422

$756

Save $666

Alaska Airlines, Inc.

Business Class

From SFO

Elite

Dec 14

Chicago, United States

91% AI deal score

$1,679

$804

Save $875

Alaska Airlines, Inc.

Business Class

From SFO

Elite

Nov 18

Chicago, United States

91% AI deal score

$1,610

$810

Save $800

Alaska Airlines, Inc.

Business Class

From SFO

Elite

Dec 14

Chicago, United States

91% AI deal score

$1,583

$808

Save $775

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 0-6 days window before departure. Flights booked within this timeframe had an average price of $336 across the trailing quarter. In contrast, booking 7-13 days out saw average prices rise to $756. Prices for flights booked 28-59 days in advance averaged $416, while those booked 60+ days out averaged $486.

Across the trailing 90 days, a good price for a flight from San Francisco to Chicago was considered to be $313 or less. The median price for this route was $422 during the same period. Prices around $601 or higher were observed for the more expensive fares.

Historically, the cheapest months to fly from San Francisco to Chicago include April, with a median price of $232, and December, with a median price of $233. January also offered competitive prices, with a median of $244. The annual median price for this route was $422, indicating that certain months offer significant savings compared to the yearly average.

Related routes

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Flights to Chicago from other cities

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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: $205 - $575

Prices are currently below the regular range.

The regular price range for flights from San Francisco to Chicago is $205 to $575. The current lowest deal is $163 with Frontier Airlines for travel from Oct 14-Oct 20.

now $163

Low $205

High $575

The cheapest time to fly from San Francisco to Chicago

December

Cheapest

Flights from $168

November

Most Expensive

Flights from $889

Jan

Feb

Mar

Apr

May

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

Tue, Sep 15

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Frontier Airlines

$530

$316

One-way

Tue, Sep 15

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Frontier Airlines

$521

$333

One-way

Tue, Sep 15

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Frontier Airlines

$518

$357

One-way

Tue, Sep 15

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Frontier Airlines

$528

$362

One-way

Wed, Sep 16

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (RFD)

Frontier Airlines

$558

$347

One-way

Wed, Sep 16

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Frontier Airlines

$521

$357

One-way

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

1 night

Sep 15 - Sep 16

$530 → $316

40%

4 nights

Sep 16 - Sep 20

$558 → $347

38%

3 nights

Sep 15 - Sep 18

$521 → $333

36%

1 night

Sep 19 - Sep 20

$550 → $381

31%

Popular Airports to fly from San Francisco to Chicago

San Francisco - Chicago route insights

💸 Price insights

Recent fares are near the typical level

Recent fares from SFO to CHI are near the typical level of $422.

📅 Best time to fly

Fly in April for the best prices

Historically, April is the cheapest month to fly, with a median price of $232.

⏱️ Flight duration

Direct flights average 4h 25m

Nonstop flights from SFO to CHI typically take 4h 25m. Connecting flights average 14h 34m.

✈️ Airlines & availability

Connecting flights are more common

About 34.2% of recent flights are direct. Connecting flights typically have 2 stopovers.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines has direct flights available for the SFO to CHI route.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from SFO to CHI are frequent, appearing within a 30-day window.

San Francisco main airports to depart from

San Francisco International (SFO)

Cheapest

San Francisco International is a convenient departure airport for flights from San Francisco to Chicago.

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

💸 Flights from ~$190

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 Francisco.

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

💸 Flights from ~$159

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.

Chicago, United States

91% AI deal score

$1,583

$808

Save $775

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Chicago

Cheap Flights from San Francisco to Chicago

Today’s best flight deals from San Francisco to Chicago

San Francisco to Chicago: Overview

Insights for flights from San Francisco to Chicago

How much is a round trip from San Francisco to Chicago

The cheapest time to fly from San Francisco to Chicago

Direct flights from San Francisco to Chicago

Last-minute flights going from San Francisco to Chicago

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

Popular Airports to fly from San Francisco to Chicago

San Francisco - Chicago route insights

Recent fares are near the typical level

Fly in April for the best prices

Direct flights average 4h 25m

Connecting flights are more common

United Airlines offers direct flights

Deals are frequent on this route

San Francisco 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 18

Nov 14

Nov 18

Nov 16

Nov 16

Dec 14

Nov 14

Nov 18

Nov 16

Dec 14

Nov 18

Dec 14

Frequently Asked Questions About Flights to Chicago

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

What is a good price for a flight from San Francisco to Chicago?

Which months have the cheapest flights from San Francisco to Chicago?

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

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

Should I set a price alert for San Francisco to Chicago flights?

Related routes

More routes from San Francisco

Flights to Chicago from other cities

San Francisco to Chicago: Overview

Insights for flights from San Francisco to Chicago

How much is a round trip from San Francisco to Chicago

The cheapest time to fly from San Francisco to Chicago

Direct flights from San Francisco to Chicago

Last-minute flights going from San Francisco to Chicago

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

Popular Airports to fly from San Francisco to Chicago

San Francisco - Chicago route insights

Recent fares are near the typical level

Fly in April for the best prices

Direct flights average 4h 25m

Connecting flights are more common

United Airlines offers direct flights

Deals are frequent on this route

San Francisco 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 18

Nov 14

Nov 18

Nov 16

Nov 16

Dec 14

Nov 14

Nov 18

Nov 16

Dec 14

Nov 18

Dec 14

Frequently Asked Questions About Flights to Chicago

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

What is a good price for a flight from San Francisco to Chicago?

Which months have the cheapest flights from San Francisco to Chicago?