Cheap Flights from San Francisco to Chicago from S$ 92

Frequently Asked Questions

• Which airlines offer the cheapest flights from San Francisco to Chicago?

  Based on Trip.com data, Frontier Airlines offers Cheapest nonstop one-way flights from S$ 92 (for example, SFO–ORD on Tue, Dec 8). For a Cheapest nonstop return flight, Frontier Airlines offers fares from S$ 226, departing on Wed, Nov 4 and returning on Fri, Nov 6.

• Which airlines offer direct flights from San Francisco to Chicago?

  At the moment, you can catch a direct flight from San Francisco to Chicago with the following airlines, including: American Airlines United Airlines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.

• How long is a flight from San Francisco (SFO) to Chicago (CHI)?

  It takes about 4 hours 28 minutes to fly from San Francisco (SFO) to Chicago (CHI).

• When is the best time to book flights from San Francisco to Chicago?

  By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from San Francisco to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.

• How many flights are there from San Francisco to Chicago each week?

  On average, 142 direct flights operate each week between San Francisco and Chicago. See below the schedules of the main airlines serving this route:
  United Airlines: S/M/T/W/T/F/S – UA2091 (departure at 06:15)

• How can I find the best deals on flights from San Francisco to Chicago?

  Here are some tips for finding the best flight deals from San Francisco to Chicago on Trip.com:
  · Be flexible with your travel dates. The cheapest flight is currently on Tue, Dec 8, with one-way fares from just S$ 92.
  · Compare airlines. American Airlines currently offers the lowest fares on this route.
  · Set up a price alert to track fare changes without searching every day.
  · Check Trip.com regularly for flight deals and available promo codes.
  · Avoid peak season or book early. July is generally the busiest month for travel to Chicago.
  · Get exclusive promo codes on the Trip.com app.

• When is the best time to book a flight from San Francisco to Chicago to get the best price?

  The cheapest month to book a flight from San Francisco to Chicago is usually November, when demand is lower.

• Which upcoming date is the cheapest for flights from San Francisco to Chicago?

  After crunching the numbers on our October flight calendar, it's currently cheapest to fly from San Francisco to Chicago on October 27, 2026 with Frontier Airlines, with prices starting at S$ 76.

• Which airports should you choose for flights from San Francisco to Chicago?

  Flights to Chicago can arrive at: O'Hare International Airport (ORD), Chicago Midway International Airport (MDW) and Chicago Rockford International Airport (RFD). The most common route connects San Francisco International Airport and O'Hare International Airport (SFO–ORD).

• What is the time difference between San Francisco and Chicago?

  The time difference between Chicago and San Francisco is 2h.

• How can I change or cancel my flight ticket from San Francisco to Chicago?

  Tickets can only be changed or cancelled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.

• What is the average cost of a one-way flight from San Francisco to Chicago?

  Based on Trip.com data for flights departing in the next 30 days, the average one-way fare from San Francisco to Chicago is S$ 273. Fares vary by travel date, airline and availability.

• What is the average cost of a round-trip flight from San Francisco to Chicago?

  Based on Trip.com data for travel in the next 30 days, the average round-trip fare from San Francisco to Chicago is S$ 520. The final price depends on the outbound and return dates, airline and fare conditions.

• How do I book flights from San Francisco to Chicago on Trip.com?

  Enter San Francisco and Chicago, choose your travel dates and passengers, then compare flights by price, duration and baggage. Select a fare, review the change and cancellation rules, enter traveller details and complete payment to receive your confirmation.

• Are there budget airlines on the San Francisco to Chicago route?

  Frontier Airlinesare the most popular budget airlines flying from San Francisco to Chicago. Check baggage, seat and payment fees before comparing the final price.