Cheap flights from San Francisco to Chicago from $90
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San Francisco to Chicago departing on 8/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Frontier flights from San Francisco to Chicago Midway Airport
Our best Frontier deals on San Francisco to Chicago Midway Airport flight tickets
Delta flights from San Francisco to Chicago Midway Airport
Our best Delta deals on San Francisco to Chicago Midway Airport flight tickets
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How to get the cheapest flight ticket from San Francisco to Chicago Midway Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Chicago Midway Airport?
The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from San Francisco, with most prices found around $184. If you are unable to visit Chicago Midway Airport during the month of September, then departing from San Francisco during the month January is also very affordable. Most momondo users find prices during this month for around $207.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from San Francisco. The lowest ticket price found for a Saturday departure recently was $316. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from San Francisco because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $492.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from San Francisco in the evening is the least expensive time of day to depart. momondo users have found prices as low as $284 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $535. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest San Francisco to Chicago Midway flight route?
Fly from San Francisco to Chicago Midway for the best San Francisco - Chicago Midway flight prices
How far in advance should I book a flight to Chicago Midway Airport?
You are more likely to see cheaper flights to Chicago Midway Airport from San Francisco when booking 13 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $313 when searching 13 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from San Francisco for as low as $134 on momondo.
What cabin class options are available on San Francisco to Chicago Midway flights?
There are 1 cabin classes available to choose from on San Francisco to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from San Francisco to Chicago Midway?
Southwest, Delta, and Frontier are the most popular carriers operating from San Francisco to Chicago Midway
What airlines fly to Chicago Midway Airport?
Southwest, Frontier and United Airlines are the top three most popular airlines that fly to Chicago Midway Airport from San Francisco according to our data. Southwest is the first choice among our users, with 62% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 6 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from San Francisco to Chicago Midway Airport on average per day?
1 flights are operational daily from San Francisco to Chicago Midway Airport as of June 2025. The most popular departure time for this route is 6:00AM, with 55% of flights per day taking off at noon.
How many flights depart from San Francisco to Chicago Midway Airport on average per week?
As of June 2025, 8 flights take off from San Francisco and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 25% of weekly flights taking off on this day.
When to book flights from San Francisco to Chicago Midway Airport
Cheap San Francisco to Chicago Midway Airport (SFO to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from San Francisco to Chicago Midway Airport
How far is San Francisco to Chicago Midway by plane?
A flight from San Francisco to Chicago Midway will travel around 1847.1 mi. In terms of flight time, this usually takes a little over 4h 05m.
When did momondo last update prices for flights from San Francisco Airport to Chicago Midway Airport?
Prices for flights from San Francisco Airport to Chicago Midway Airport are refreshed on a daily basis.
How many operators does momondo search for flights from San Francisco Airport to Chicago Midway Airport?
As of June 2025, there are 6 operators available to choose from for flights from San Francisco Airport to Chicago Midway Airport.
How old do you have to be to fly from San Francisco Airport to Chicago Midway Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from San Francisco Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from San Francisco to Chicago Midway Airport?
Based on momondo bookings for flights between San Francisco and Chicago Midway Airport, the leading plane model is Airbus A321neo, making up 12.95% of the total bookings. Other popular models include Boeing 737-800 with 11.95%, Boeing 777 with 10.34%, and Boeing 737 MAX 9 with 9.94%.
What is the most popular airline from San Francisco to Chicago Midway Airport?
momondo data reveals that the most frequently booked airline on the route from San Francisco to Chicago Midway Airport is Southwest, representing 44% of all bookings. The subsequent popular airlines are Frontier at 39%, Delta at 7%, and United Airlines at 6%.
Best airlines flying from San Francisco to Chicago Midway Airport
Compare and see reviews for airlines that fly from San Francisco to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $48 | Free Cancellation | Rating 5.9 3,295 reviews | |||
| PriceFrom $133 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom $197 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $197 | Free Cancellation | Rating 8.0 10,000 reviews | |||
| PriceFrom $209 | Free Cancellation | Rating 8.0 4,287 reviews | |||
| PriceFrom $236 | Free Cancellation | Rating 8.0 7,946 reviews |
Southwest Flights From San Francisco to Chicago Midway Airport
Southwest flight deals from San Francisco to Chicago Midway Airport start from $209 round-trip. Over the 8 Southwest flights for this route in a normal week, average airfare is usually $397 round-trip - but some users have found much cheaper deals with momondo.
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Why should I use momondo to find a flight deal from San Francisco to Chicago?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from San Francisco.
Can I find flights from San Francisco to Chicago with flexible booking policies on momondo?
Flights from San Francisco to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from San Francisco to Chicago?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from San Francisco to Chicago.
I’m not ready to book a flight from San Francisco to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from San Francisco are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.