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Cheap Flights from San Francisco to Chicago starting at S$ 60

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • One way
  • Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Cheapest time to fly from San Francisco to Chicago

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the lowest average weekly prices of the corresponding route on Trip.com.
Cheapest Airlines flying from San Francisco to Chicago

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Frontier Airlines
From S$ 98
Alaska Airlines
From S$ 111
American Airlines
From S$ 119
Southwest Airlines
From S$ 140
Delta Air Lines
From S$ 155
United Airlines
From S$ 174
Sun Country Airlines
From S$ 216
Jetblue Airways
From S$ 384
ANA airlines

Find more flights and airlines

Alternative Routes from San Francisco to Chicago

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from San Francisco to Chicago.

  • Cheapest
    Frontier Airlines
    SFO
    15:58
    4h 11m
    Direct
    MDW
    22:09
    San Francisco International Airport - Midway International Airport
    Sat, May 4Frontier Airlines
    S$ 98
  • Frontier Airlines
    SFO
    16:48
    6h 32m
    Direct
    ORD
    01:20
    San Francisco International Airport - O'Hare International Airport
    Tue, Apr 9Frontier Airlines
    S$ 130
  • Frontier Airlines
    SFO
    21:41
    21h 15m
    1 transfer
    RFD
    20:56
    San Francisco International Airport - Chicago Rockford International Airport
    Wed, Apr 24Frontier Airlines
    S$ 238
  • Frontier Airlines
    SFO
    21:41
    21h 15m
    1 transfer
    RFD
    20:56
    San Francisco International Airport - Chicago Rockford International Airport
    Wed, Apr 24Frontier Airlines
    S$ 238
    Find More Flights

Frequently Asked Questions

  • When to buy flight tickets from San Francisco (SFO) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from San Francisco to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
  • How much is a flight from San Francisco (SFO) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around S$ 407.
  • How long is a flight from San Francisco (SFO) to Chicago (CHI)?

    It takes about 4 hours 45 minutes to fly from San Francisco (SFO) to Chicago (CHI).
  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
  • What time does the earliest flight from San Francisco to Chicago depart?

    The earliest flight departs from San Francisco (SFO) at 05:04 and arrives in Chicago (ORD) at 11:10.
  • What time does the latest flight from San Francisco to Chicago depart?

    The latest flight departs from San Francisco (SFO) at 18:35 and arrives in Chicago (ORD) at 00:56.
  • What are the most popular airlines that fly from San Francisco (SFO) to Chicago (CHI)?

  • What's the most popular airline for direct flights from San Francisco (SFO) to Chicago (CHI)?

    Alaska Airlines operates 10 direct flights from San Francisco (SFO) to Chicago (CHI).
  • How many airports in Chicago?

Find cheapest flight ticket from San Francisco to Chicago

Cheapest direct flight price

S$ 60

Cheapest return ticket price

S$ 118

Cheapest month

December

Peak season for travel

September