Cheap flights from San Francisco to Chicago from $177
This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
22 Oct — 29 Oct1
Return
1 adult
Economy
Return
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from San Francisco to Chicago are usually found in February or September, booked 65 days in advance, depart on a Monday or Tuesday and return on a Monday
Cheap flight deals from San Francisco to Chicago
Enter your travel dates to find the best prices.
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Cheapest flights from San Francisco to Chicago
Explore the most affordable flight options available from San Francisco to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 22 September 2026.
Wed 4/1122:17 -
1 stop8h 39m
Wed 11/1106:30 -
1 stop6h 47m
Deal found 20/9$363
Tue 3/1123:52 -
1 stop9h 30m
Tue 10/1112:27 -
1 stop12h 02m
Deal found 19/9$365
Thu 22/1014:17 -
1 stop12h 59m
Thu 29/1010:40 -
1 stop13h 49m
Deal found 21/9$365
Mon 12/1023:40 -
Nonstop4h 10m
Thu 15/1021:25 -
Nonstop4h 45m
Deal found 17/9$369
Mon 12/1018:38 -
Nonstop4h 17m
Thu 15/1021:40 -
Nonstop4h 50m
Deal found 17/9$369
Sat 17/1007:20 -
1 stop10h 15m
Sat 24/1006:35 -
2 stops11h 55m
Deal found 17/9$375
Sat 17/1017:45 -
1 stop9h 55m
Thu 22/1007:20 -
1 stop7h 21m
Deal found 17/9$375
Tue 6/1015:00 -
Nonstop4h 37m
Fri 9/1021:40 -
Nonstop4h 50m
Deal found 17/9$380
Thu 22/1014:40 -
1 stop8h 00m
Tue 27/1015:35 -
2 stops8h 05m
Deal found 18/9$382
Wed 4/1108:00 -
2 stops9h 40m
Mon 9/1112:45 -
2 stops9h 25m
Deal found 18/9$389
Wed 4/1110:15 -
1 stop6h 15m
Fri 13/1111:00 -
Nonstop4h 50m
Deal found 17/9$394
Sat 17/1019:11 -
1 stop8h 29m
Fri 23/1015:49 -
1 stop9h 00m
Deal found 17/9$394
Best flights from San Francisco to Chicago
Discover carefully curated flight deals from San Francisco to Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 22 September 2026.
Wed 14/1015:00 -
Nonstop4h 37m
Sat 17/1014:32 -
Nonstop4h 48m
Deal found 17/9$464
Tue 27/1018:38 -
2 stops12h 15m
Mon 2/1108:29 -
2 stops14h 03m
Deal found 21/9$467
Thu 5/1123:35 -
Nonstop4h 25m
Thu 12/1111:00 -
Nonstop4h 50m
Deal found 21/9$473
Fri 16/1016:51 -
2 stops10h 49m
Fri 23/1007:20 -
1 stop7h 21m
Deal found 17/9$560
Tue 3/1123:35 -
Nonstop4h 25m
Tue 10/1121:05 -
Nonstop4h 50m
Deal found 19/9$473
Thu 15/1005:00 -
Nonstop4h 25m
Mon 19/1006:07 -
Nonstop4h 38m
Deal found 22/9$473
Mon 12/1023:40 -
Nonstop4h 10m
Mon 19/1016:30 -
1 stop7h 55m
Deal found 20/9$487
Thu 15/1000:10 -
1 stop6h 43m
Fri 16/1017:30 -
1 stop8h 26m
Deal found 18/9$537
Fri 4/1214:17 -
Nonstop4h 23m
Mon 7/1216:00 -
Nonstop4h 54m
Deal found 20/9$491
Sat 24/1015:50 -
1 stop6h 25m
Mon 26/1021:25 -
Nonstop4h 45m
Deal found 19/9$487
Thu 26/1105:00 -
Nonstop4h 24m
Sun 3/106:00 -
Nonstop5h 01m
Deal found 17/9$491
Thu 15/1018:15 -
1 stop8h 15m
Mon 19/1021:25 -
Nonstop4h 45m
Deal found 22/9$487
Wed 4/1123:35 -
Nonstop4h 25m
Wed 11/1106:00 -
1 stop9h 50m
Deal found 20/9$487
Fri 6/1118:42 -
Nonstop4h 17m
Fri 27/1106:00 -
Nonstop4h 44m
Deal found 21/9$542
Sat 5/1209:35 -
2 stops10h 45m
Sat 12/1210:15 -
Nonstop4h 50m
Deal found 20/9$494
Thu 8/1005:00 -
Nonstop4h 25m
Sun 11/1006:07 -
Nonstop4h 38m
Deal found 17/9$571
Tue 6/1000:35 -
Nonstop4h 21m
Sun 11/1006:07 -
Nonstop4h 38m
Deal found 17/9$575
Tue 1/1214:17 -
Nonstop4h 23m
Fri 11/1205:59 -
Nonstop4h 41m
Deal found 18/9$582
Tue 17/1105:00 -
Nonstop4h 24m
Mon 23/1113:30 -
Nonstop4h 50m
Deal found 21/9$582
Direct flights from San Francisco to Chicago
Explore direct flight options from San Francisco to Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 22 September 2026.
Mon 12/1023:40 -
Nonstop4h 10m
Thu 15/1021:25 -
Nonstop4h 45m
Deal found 17/9$369
Mon 12/1018:38 -
Nonstop4h 17m
Thu 15/1021:40 -
Nonstop4h 50m
Deal found 17/9$369
Tue 6/1015:00 -
Nonstop4h 37m
Fri 9/1021:40 -
Nonstop4h 50m
Deal found 17/9$380
Tue 6/1023:40 -
Nonstop4h 10m
Thu 8/1021:25 -
Nonstop4h 45m
Deal found 17/9$399
Fri 16/1018:38 -
Nonstop4h 17m
Mon 19/1021:40 -
Nonstop4h 50m
Deal found 17/9$403
Tue 6/1015:00 -
Nonstop4h 37m
Thu 8/1006:07 -
Nonstop4h 38m
Deal found 17/9$418
Thu 15/1005:35 -
Nonstop4h 10m
Thu 22/1021:25 -
Nonstop4h 45m
Deal found 17/9$421
Wed 18/1105:00 -
Nonstop4h 24m
Fri 27/1106:00 -
Nonstop4h 44m
Deal found 17/9$421
Tue 15/1223:10 -
Nonstop4h 15m
Fri 18/1221:51 -
Nonstop5h 08m
Deal found 17/9$431
Mon 4/123:35 -
Nonstop4h 25m
Mon 11/119:50 -
Nonstop4h 50m
Deal found 17/9$441
Thu 17/1223:30 -
Nonstop4h 26m
Mon 21/1221:51 -
Nonstop5h 08m
Deal found 17/9$441
Fri 16/1023:40 -
Nonstop4h 10m
Mon 19/1021:25 -
Nonstop4h 45m
Deal found 17/9$455
Last-minute flights from San Francisco to Chicago
Discover last-minute flight deals from San Francisco to Chicago. Data last updated 22 September 2026 and is based on user searches.
Tue 29/908:25 -
1 stop8h 56m
Tue 6/1014:21 -
1 stop7h 10m
Deal found 17/9$508
Wed 30/910:10 -
Nonstop4h 31m
Mon 5/1021:40 -
Nonstop4h 50m
Deal found 17/9$558
Wed 30/900:35 -
Nonstop4h 21m
Mon 5/1021:40 -
Nonstop4h 50m
Deal found 17/9$606
Thu 1/1010:44 -
2 stops11h 15m
Wed 7/1007:20 -
1 stop9h 31m
Deal found 17/9$613
Tue 6/1023:40 -
Nonstop4h 10m
Thu 8/1021:25 -
Nonstop4h 45m
Deal found 17/9$399
Wed 7/1014:30 -
1 stop7h 20m
Fri 9/1021:25 -
Nonstop4h 45m
Deal found 17/9$417
Sat 10/1015:50 -
1 stop6h 25m
Sat 17/1005:10 -
1 stop9h 05m
Deal found 17/9$427
Mon 12/1023:40 -
Nonstop4h 10m
Thu 15/1021:25 -
Nonstop4h 45m
Deal found 17/9$369
Thu 15/1018:15 -
1 stop8h 15m
Tue 20/1020:55 -
Nonstop4h 45m
Deal found 17/9$413
Sat 17/1007:20 -
1 stop10h 15m
Sat 24/1006:35 -
2 stops11h 55m
Deal found 17/9$375
Thu 22/1014:40 -
1 stop8h 00m
Tue 27/1015:35 -
2 stops8h 05m
Deal found 18/9$382
Thu 29/1022:55 -
1 stop8h 37m
Sat 31/1013:27 -
1 stop6h 54m
Deal found 18/9$408
One-way flights from San Francisco to Chicago
Search for one-way flight options from San Francisco to Chicago. Find affordable one-way fares based on user searches. Data last updated 22 September 2026.
Tue 5/112:00 -
1 stop7h 55m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 17/9$177
Tue 15/1212:39 -
1 stop9h 20m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 17/9$177
Sat 17/1007:20 -
1 stop10h 15m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 17/9$184
Mon 12/1023:40 -
Nonstop4h 10m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 18/9$185
Mon 5/1023:10 -
1 stop12h 37m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 18/9$185
Wed 7/1014:30 -
1 stop7h 20m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 17/9$199
Mon 16/1108:20 -
1 stop8h 39m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 17/9$199
Tue 6/1022:55 -
1 stop8h 37m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 17/9$205
Thu 12/1114:12 -
1 stop7h 47m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 17/9$205
Thu 29/1011:45 -
2 stops7h 10m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 17/9$206
Fri 16/1023:40 -
Nonstop4h 10m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 17/9$219
Fri 1/122:34 -
Nonstop4h 23m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 17/9$219
Find flight deals from San Francisco to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from San Francisco (SFO) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 22 September 2026.
Customise your flight search to find flights from San Francisco to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated 22 September 2026.
Use the filters below to find and compare flights from San Francisco to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
Cheapest return flight
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Wed 6/1
06:35-16:30
2 stops7h 55m
Chicago Midway
Wed 31/12
00:00-22:00
Nonstop0h 00m
$184
San FranciscoChicago
SFO San Francisco - ORD Chicago O'Hare Intl
SFOORD
San Francisco
Mon 5/10
23:10-13:47
1 stop12h 37m
Chicago O'Hare Intl
Wed 31/12
00:00-22:00
Nonstop0h 00m
$185
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Wed 7/10
14:30-23:50
1 stop7h 20m
Chicago Midway
Wed 31/12
00:00-22:00
Nonstop0h 00m
$199
San FranciscoChicago
SFO San Francisco - ORD Chicago O'Hare Intl
SFOORD
San Francisco
Fri 1/1
22:34-04:57
Nonstop4h 23m
Chicago O'Hare Intl
Wed 31/12
00:00-22:00
Nonstop0h 00m
$219
San FranciscoChicago
SFO San Francisco - ORD Chicago O'Hare Intl
SFOORD
San Francisco
Fri 16/10
18:38-00:55
Nonstop4h 17m
Chicago O'Hare Intl
Wed 31/12
00:00-22:00
Nonstop0h 00m
$219
San FranciscoChicago
SFO San Francisco - ORD Chicago O'Hare Intl
SFOORD
San Francisco
Tue 6/10
06:10-12:45
Nonstop4h 35m
Chicago O'Hare Intl
Wed 31/12
00:00-22:00
Nonstop0h 00m
$233
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Mon 7/12
23:35-06:00
Nonstop4h 25m
Chicago Midway
Wed 31/12
00:00-22:00
Nonstop0h 00m
$237
San FranciscoChicago
SFO San Francisco - ORD Chicago O'Hare Intl
SFOORD
San Francisco
Fri 15/1
23:10-05:34
Nonstop4h 24m
Chicago O'Hare Intl
Wed 31/12
00:00-22:00
Nonstop0h 00m
$255
San FranciscoChicago
SFO San Francisco - ORD Chicago O'Hare Intl
SFOORD
San Francisco
Sat 26/12
06:34-13:03
Nonstop4h 29m
Chicago O'Hare Intl
Wed 31/12
00:00-22:00
Nonstop0h 00m
$257
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Mon 21/12
23:59-11:01
1 stop9h 02m
Chicago Midway
Wed 31/12
00:00-22:00
Nonstop0h 00m
$271
Flights are sorted by cheapest return flights first.
Deals found on 17/9
Showing 1-10 of 40 resultsSorted by cheapest first
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Best time to book a flight from San Francisco to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from San Francisco with our price prediction graph.
SFO-CHI
SFO-ORD
SFO-MDW
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from San Francisco to Chicago
SFO-CHI
SFO-ORD
SFO-MDW
What is the cheapest month to book a flight from San Francisco to Chicago?
Currently, February is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $518). Flying from San Francisco to Chicago in June is currently the most expensive (average of $679). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from SFO to CHI?
Find hourly flight availability from San Francisco to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 22 September 2026.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 31% on flights from San Francisco to Chicago by exploring options for tickets at midday.
Weekly flight availability from San Francisco to Chicago
Explore weekly flight availability from San Francisco to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 22 September 2026.
The most flights from SFO to CHI are scheduled on a Sunday (101 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (47 on average).
How much does it cost for a return flight from San Francisco to Chicago?
Airfare is below average for this route at the moment.
San Francisco to Chicago flights typically cost between $424 and $721 in November.The cheapest return price found within the last 5 days was $363 on Frontier (4 Nov–11 Nov).
How often are flights from San Francisco to Chicago delayed?
About 10% of weekly flights between San Francisco and Chicago have experienced delays in the past year, with the average delay time being 186 minutes.
What is the most punctual flight time for San Francisco to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on San Francisco to Chicago flights?
Over the past year, United Airlines have had the lowest number of delays on this route, with just 9% of flights being delayed.
How far ahead should I book a flight from San Francisco to Chicago?
The best time to book flights from San Francisco to Chicago is 66 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Related info for your journey
Find useful and relevant information for your journey from San Francisco to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
What airport do you fly from for flights from San Francisco to Chicago?
San Francisco (SFO) is the airport you will fly out of if you book a flight from San Francisco to Chicago. You should not have trouble finding flights to Chicago from San Francisco; the airport handles an average of 76 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the San Francisco airport to Chicago. It is only a 17.7 km journey to San Francisco (SFO) from San Francisco’s city centre.
How long is the flight from San Francisco to Chicago?
Southwest, United Airlines, and Alaska Airlines can get you from San Francisco to Chicago in just under 4h 18m. Your travel time can differ by up to 5h 55m. The distance between San Francisco and Chicago is about 2963 km. This flight may include one or multiple stops.
What are the most reliable airlines from San Francisco to Chicago?
Before booking your flight to Chicago from San Francisco, have a look at the most reliable airlines to get you to your destination on time: ITA Airways (92%), Aer Lingus (79%), Austrian Airlines( 77%).
Can I find deals for flights from San Francisco to Chicago that include hotel bookings?
Yes. In addition to deals on San Francisco to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.
How can I find direct flights from San Francisco to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Francisco to Chicago.
Can I find deals for business class flights from San Francisco to Chicago?
Yes. Cheapflights offers flight deals from San Francisco to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from San Francisco to Chicago?
Currently, February is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $518). Flying from San Francisco to Chicago in June is currently the most expensive (average of $679). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 22 September 2026.
Browse through other flights departing from San Francisco. Flights are based on user searches made on Cheapflights and were last updated on 22 September 2026.
Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.
How does Cheapflights help users find flights from San Francisco to Chicago?
Cheapflights makes it easy to find San Francisco to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.
Why should you use Cheapflights to find cheap flight tickets from San Francisco to Chicago?
Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from San Francisco to Chicago for you. Better yet — we are completely free to use.
Can Cheapflights find flights from San Francisco to Chicago with no change fees?
Users can book flights with no change fees policies with our dedicated filters. Book flights from San Francisco to Chicago flexibly with Cheapflights today.
Can Cheapflights notify me if prices for flights from San Francisco to Chicago become cheaper?
Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!
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