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

Over the trailing 90 days, approximately 34.2% of flights from San Francisco to Chicago were non-stop. For flights that included stopovers, the median number of stopovers was 2. This indicates that a significant portion of travelers on this route typically experience at least one connection.

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

The median flight time for a direct flight from San Francisco to Chicago is 4 hours and 25 minutes. For flights with one stop, the median duration extends to 10 hours and 31 minutes. The distance covered on this route is approximately 2979 kilometers. Travelers should account for these differences when planning their journey.

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

Historically, price fluctuations 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. Over the trailing 30 days, this route has consistently shown price changes that make alerts a useful tool for tracking potential savings.

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 2 days ago

405 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 26, 2026.)

Today’s best flight deals from San Francisco to Chicago

Explore current cheapest deals departing from San Francisco to Chicago

2026-09-09 – 2026-09-12
SFO - Chicago
81% AI deal score
$309
$198
Round trip
2026-09-23 – 2026-09-28
SFO - Chicago
79% AI deal score
$306
$212
Round trip
2026-09-22 – 2026-09-28
SFO - Chicago
71% AI deal score
$223
$213
Round trip
2026-09-21 – 2026-09-28
SFO - Chicago
71% AI deal score
$229
$213
Round trip
2026-10-17 – 2026-10-20
SFO - Chicago
73% AI deal score
$252
$213
Round trip
2026-10-19 – 2026-10-27
SFO - Chicago
72% AI deal score
$237
$213
Round trip
2026-10-07 – 2026-10-10
SFO - Chicago
72% AI deal score
$226
$213
Round trip
2026-10-08 – 2026-10-13
SFO - Chicago
73% AI deal score
$247
$213
Round trip
2026-10-17 – 2026-10-24
SFO - Chicago
72% AI deal score
$230
$213
Round trip
2026-10-20 – 2026-10-22
SFO - Chicago
73% AI deal score
$237
$213
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.

Right now, fares to Chicago from San Francisco are typically $313–$601, with a median of $422. Current fares are near the typical level, and only 2% of recent fares were classified as a good price. New deals appear almost daily, offering frequent opportunities to find competitive prices.

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 by December at $233, and January at $244. These months offer significantly lower median prices compared to the overall typical fare.

A typical journey from San Francisco to Chicago takes about 4h 25m, including connections. For non-stop flights, the median duration is also 4h 25m, while connecting flights have a significantly longer median journey time of 14h 34m.

The distance between San Francisco and Chicago is 2979 kilometers, classifying this as a medium-haul route. This distance typically involves several hours of flight time, often with connections depending on the chosen itinerary.

How much is a round trip from San Francisco to Chicago

Regular price: $243 - $402

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

The regular price range for flights from San Francisco to Chicago is between $243 and $402. The current lowest deal is $220 with Frontier Airlines for travel from Sep 10-Sep 15.

now $220

Low $243

High $402

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

Sat, Aug 1

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (MDW)

Frontier Airlines

$579

$374

One-way

Sat, Aug 1

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (MDW)

Frontier Airlines

$592

$390

One-way

Sun, Aug 9

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (MDW)

Frontier Airlines

$393

$268

One-way

Tue, Aug 11

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Frontier Airlines

$250

$234

One-way

Tue, Aug 11

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (MDW)

Frontier Airlines

$319

$239

One-way

Tue, Aug 11

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (MDW)

Frontier Airlines

$342

$239

One-way

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

3 nights

Aug 1 - Aug 4

$579 → $374

35%

2 nights

Aug 1 - Aug 3

$592 → $390

34%

7 nights

Dec 5 - Dec 12

$416 → $246

41%

3 nights

Dec 11 - Dec 14

$450 → $294

35%

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 San Francisco to Chicago are near the typical level at a median of $422.

📅 Best time to fly

December is historically the cheapest month to fly

Historically, December is the cheapest month to fly from San Francisco to Chicago, with a median price of $168.

⏱️ Flight duration

Direct flights take 4h 25m

A direct flight from San Francisco to Chicago typically takes 4 hours and 25 minutes.

✈️ Airlines & availability

Connecting flights are more common

Connecting flights are more common, making up 65.8% of recent fares from San Francisco to Chicago.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines has offered direct flights from San Francisco International to Chicago Rockford International.

🎯 Booking tip

Deals appear frequently on this route

Deals for flights from San Francisco to Chicago appear frequently, with many deals in the last 30 days.

San Francisco main airports to depart from

San Francisco International (SFO)

Cheapest

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

📍 ~18 km from San Francisco (reachable by car or train)

💸 Flights from ~$172

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

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

Milwaukee offers a major international airport with significant carrier presence and direct flight options.

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

💸 Flights from ~$270

Business & First Class Flight Deals to Chicago

90% AI deal score

$1,598

$835

Save $763

Frequently Asked Questions About Flights to Chicago

Historically, the lowest average prices for flights from San Francisco to Chicago have been found when booking within 0-6 days of departure, with an average price of $336. Booking 7-13 days out typically sees a significantly higher average price of $756. Prices for flights booked 14-27 days in advance averaged $423, while those booked 28-59 days ahead averaged $416. For bookings made 60 or more days out, the average price was around $486.

Across the trailing quarter, 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. Prices typically ranged up to $601, which represented the 75th percentile of prices observed over the 90-day period.

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 pricing, with a median of $244. These prices are notably lower than the annual median price of $422 for the route.

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: $243 - $402

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

The regular price range for flights from San Francisco to Chicago is between $243 and $402. The current lowest deal is $220 with Frontier Airlines for travel from Sep 10-Sep 15.

now $220

Low $243

High $402

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

Sat, Aug 1

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (MDW)

Frontier Airlines

$579

$374

One-way

Sat, Aug 1

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (MDW)

Frontier Airlines

$592

$390

One-way

Sun, Aug 9

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (MDW)

Frontier Airlines

$393

$268

One-way

Tue, Aug 11

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (ORD)

Frontier Airlines

$250

$234

One-way

Tue, Aug 11

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (MDW)

Frontier Airlines

$319

$239

One-way

Tue, Aug 11

⌛ Last-Minute

SFO - Chicago

San Francisco (SFO) - Chicago (MDW)

Frontier Airlines

$342

$239

One-way

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

3 nights

Aug 1 - Aug 4

$579 → $374

35%

2 nights

Aug 1 - Aug 3

$592 → $390

34%

7 nights

Dec 5 - Dec 12

$416 → $246

41%

3 nights

Dec 11 - Dec 14

$450 → $294

35%

Popular Airports to fly from San Francisco to Chicago