S$183 Cheap Flights from San Francisco to Chicago

View S$183 flight on Wed, 19 Nov, 2025Opens in a new window

Popular airlines from San Francisco Intl. Airport (SFO) to Chicago

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Cheap Flights from San Francisco to Chicago (SFO-CHI)

Prices were available within the past 7 days and start at S$183 for one-way flights and S$369 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, 12 Nov - Sat, 15 Nov
SFO
San Francisco
ORD
Chicago
S$369 Return, found 5 days ago
S$369
Return
found 5 days ago
Select Delta flight, departing Wed, 12 Nov from San Francisco to Chicago, returning Sat, 15 Nov, priced at S$369 found 5 days ago
Delta
Wed, 12 Nov - Sat, 15 Nov
SFO
San Francisco
ORD
Chicago
S$391 Return, found 5 days ago
S$391
Return
found 5 days ago
Select Delta flight, departing Wed, 12 Nov from San Francisco to Chicago, returning Sat, 15 Nov, priced at S$391 found 5 days ago
Delta
Sun, 2 Nov - Thu, 6 Nov
SFO
San Francisco
ORD
Chicago
S$406 Return, found 4 days ago
S$406
Return
found 4 days ago
Select Delta flight, departing Sun, 2 Nov from San Francisco to Chicago, returning Thu, 6 Nov, priced at S$406 found 4 days ago
Delta
Fri, 14 Nov - Mon, 17 Nov
SFO
San Francisco
ORD
Chicago
S$407 Return, found 3 days ago
S$407
Return
found 3 days ago
Select Delta flight, departing Fri, 14 Nov from San Francisco to Chicago, returning Mon, 17 Nov, priced at S$407 found 3 days ago
Delta
Tue, 16 Dec - Wed, 24 Dec
SFO
San Francisco
ORD
Chicago
S$414 Return, found 6 days ago
S$414
Return
found 6 days ago
Select Delta flight, departing Tue, 16 Dec from San Francisco to Chicago, returning Wed, 24 Dec, priced at S$414 found 6 days ago
United
Wed, 12 Nov - Sat, 15 Nov
SFO
San Francisco
ORD
Chicago
S$415 Return, found 5 days ago
S$415
Return
found 5 days ago
Select United flight, departing Wed, 12 Nov from San Francisco to Chicago, returning Sat, 15 Nov, priced at S$415 found 5 days ago
American Airlines
Wed, 12 Nov - Sat, 15 Nov
SFO
San Francisco
ORD
Chicago
S$422 Return, found 5 days ago
S$422
Return
found 5 days ago
Select American Airlines flight, departing Wed, 12 Nov from San Francisco to Chicago, returning Sat, 15 Nov, priced at S$422 found 5 days ago
Delta
Fri, 14 Nov - Mon, 17 Nov
SFO
San Francisco
ORD
Chicago
S$432 Return, found 3 days ago
S$432
Return
found 3 days ago
Select Delta flight, departing Fri, 14 Nov from San Francisco to Chicago, returning Mon, 17 Nov, priced at S$432 found 3 days ago
Delta
Wed, 12 Nov - Sat, 15 Nov
SFO
San Francisco
ORD
Chicago
S$436 Return, found 5 days ago
S$436
Return
found 5 days ago
Select Delta flight, departing Wed, 12 Nov from San Francisco to Chicago, returning Sat, 15 Nov, priced at S$436 found 5 days ago
Delta
Wed, 12 Nov - Sat, 15 Nov
SFO
San Francisco
ORD
Chicago
S$438 Return, found 5 days ago
S$438
Return
found 5 days ago
Select Delta flight, departing Wed, 12 Nov from San Francisco to Chicago, returning Sat, 15 Nov, priced at S$438 found 5 days ago

Find the cheapest month to fly from San Francisco (SFO) to Chicago (CHI)

September is typically the cheapest month to fly

From S$166 - S$303 per traveller.
San Francisco to Chicago route information
Origin airport
San Francisco Intl.
Destination airport
O'Hare Intl.
Return price
S$369
Distance
2947 km

Perfect flights from San Francisco to Chicago

Your Journey from San Francisco to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from San Francisco to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta, American Airlines, United. Our selection of flights from San Francisco Intl. to CHI-All Airports caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with San Francisco to Chicago Flights

Experience the joy of finding cheap flights from San Francisco Intl. to CHI-All Airports that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$183 and roundtrip prices from S$369*.
 

Pre-Flight Essentials

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Experience the Vibrant Chicago

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Added Convenience on Your San Francisco to Chicago Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from San Francisco to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from San Francisco to Chicago with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from San Francisco to Chicago with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Explore a world of travel with Expedia

San Francisco Airports

Oakland

Oakland Intl. to Chicago
S$1,091.30

San Jose

*Available to Expedia members.