SFO - MDW

$130 Find Cheap Flights from San Francisco to Chicago Midway Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$297
Typical prices: $330-$511
Southwest
Sat 1/20Tue 1/23
SFO - MDW • Non-stop
Cheapest one-way
$130
Typical prices: $176-$309
Frontier
Sat 12/1
SFO - MDW • 1 stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 4h 15m
Direct flights
+1
Direct flights
+1
When to book
11 weeks
in advance
Our data shows that travelers who book at least 11 weeks in advance save around 43% compared to booking last minute.
Insights
Insights
When to travel
February
Cheapest • 14% price drop
June
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Denver Intl (DEN)
Cheapest • Avg $266 (round-trip)
Minneapolis St Paul (MSP)
Shortest trip • 6h 44m (one-way)
Insights
Insights
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We hope you love your trip to Chicago Midway Airport!
Flight Deals
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Flight Deals

Cheap Flights from San Francisco to Midway (SFO-MDW)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from San Francisco to Midway

Sat, Dec 5 - Mon, Dec 7
Southwest Logo
11:35 pm - 6:00 amSFO  San Francisco-MDW Chicago Midway
4h 25mnonstop
Southwest Logo
9:05 pm - 11:55 pmMDW  Chicago Midway-SFO San Francisco
4h 50mnonstop
$297Southwest
Wed, Jan 20 - Sat, Jan 23
Southwest Logo
11:55 pm - 6:05 amSFO  San Francisco-MDW Chicago Midway
4h 10mnonstop
Southwest Logo
10:00 am - 12:50 pmMDW  Chicago Midway-SFO San Francisco
4h 50mnonstop
$297Southwest
Wed, Nov 18 - Wed, Nov 18
Southwest Logo
6:00 am - 12:15 pmSFO  San Francisco-MDW Chicago Midway
4h 15mnonstop
Southwest Logo
9:05 pm - 11:55 pmMDW  Chicago Midway-SFO San Francisco
4h 50mnonstop
$297Southwest
Mon, Nov 16 - Wed, Nov 18
Frontier Logo
11:47 pm - 11:22 amSFO  San Francisco-MDW Chicago Midway
9h 35m1 stop Dallas/Fort Worth
Frontier Logo
6:08 am - 6:10 pmMDW  Chicago Midway-SFO San Francisco
14h 02m1 stop Atlanta Hartsfield-Jackson
$299Frontier
Sun, Nov 15 - Wed, Nov 18
Frontier Logo
11:47 pm - 11:25 amSFO  San Francisco-MDW Chicago Midway
9h 38m1 stop Dallas/Fort Worth
Frontier Logo
12:27 pm - 10:29 pmMDW  Chicago Midway-SFO San Francisco
12h 02m1 stop Dallas/Fort Worth
$299Frontier
Sun, Nov 22 - Thu, Nov 26
Frontier Logo
11:26 pm - 12:21 pmSFO  San Francisco-MDW Chicago Midway
10h 55m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
9:09 am - 4:38 pmMDW  Chicago Midway-SFO San Francisco
9h 29m1 stop Atlanta Hartsfield-Jackson
$302Frontier
Thu, Nov 19 - Wed, Nov 25
Delta Logo
6:00 am - 4:39 pmSFO  San Francisco-MDW Chicago Midway
8h 39m1 stop Minneapolis St Paul
Delta Logo
5:29 pm - 12:01 amMDW  Chicago Midway-SFO San Francisco
8h 32m1 stop Minneapolis St Paul
$303Delta
Fri, Dec 4 - Mon, Dec 7
Delta Logo
10:59 pm - 10:28 amSFO  San Francisco-MDW Chicago Midway
9h 29m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:12 pm - 11:59 pmMDW  Chicago Midway-SFO San Francisco
8h 47m1 stop Atlanta Hartsfield-Jackson
$303Delta
Wed, Nov 11 - Mon, Nov 16
Multiple Airlines Logo
11:47 pm - 11:25 amSFO  San Francisco-MDW Chicago Midway
9h 38m1 stop Dallas/Fort Worth
Multiple Airlines Logo
4:31 pm - 8:19 amMDW  Chicago Midway-SFO San Francisco
17h 48m2 stops Knoxville McGhee Tyson Las Vegas Harry Reid Intl
$396Multiple Airlines
Mon, Nov 9 - Mon, Nov 16
Multiple Airlines Logo
11:47 pm - 11:22 amSFO  San Francisco-MDW Chicago Midway
9h 35m1 stop Dallas/Fort Worth
Multiple Airlines Logo
4:31 pm - 8:19 amMDW  Chicago Midway-SFO San Francisco
17h 48m2 stops Knoxville McGhee Tyson Las Vegas Harry Reid Intl
$399Multiple Airlines
Booking Insights

Price, demand and travel trends for San Francisco to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from San Francisco to Chicago Midway Airport?

Round-trip flights from San Francisco to Chicago Midway Airport typically range from $330 to $511. The lowest price found in the past 5 days was $297, on Southwest.

What's the cheapest day of the week to fly from San Francisco to Chicago Midway Airport?

Based on deals KAYAK users found in the last 12 months, Monday is the cheapest day of the week to fly from San Francisco to Chicago Midway Airport. It’s 13% cheaper than the average day, while Sunday is the most expensive, with prices 29% higher.

What’s the cheapest month to fly from San Francisco to Chicago Midway Airport?

•February is the cheapest month to fly from San Francisco to Chicago Midway Airport at $339 round-trip.
•January ($666) and November ($454) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 96% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from San Francisco to Chicago Midway Airport the cheapest?

Flights from San Francisco to Chicago Midway Airport are cheapest 11 weeks before departure. Booking in this window typically costs about 43% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Find deals

Key details for San Francisco to Chicago Midway Airport flights

Low season

January

Cheapest flight

$130
Beat the crowds with an average 69% drop in travelers.
The most popular month to fly with an average 67% increase in travelers.
One-way flight from San Francisco to Chicago Midway Airport

When to book flights from San Francisco to Midway

Are your dates flexible? Find out the best times to travel from San Francisco to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your San Francisco to Chicago Midway Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from San Francisco to Chicago Midway Airport?

    These are the earliest and latest flight times available from San Francisco to Chicago Midway Airport:

    • Earliest: departs at 5:20 am and lands at 9:35 am
    • Latest: departs at 11:50 pm and lands at 4:05 am.

    The flight takes about 4h 15m.

  • What cabin classes can I book on flights from San Francisco to Chicago Midway Airport?

    Only Economy Class is available on flights from San Francisco to Chicago Midway Airport.

  • How long is a flight from San Francisco to Chicago Midway Airport?

    A nonstop flight from San Francisco to Chicago Midway Airport takes 4h 15m, covering 1,849 miles.

  • Do I need a passport to fly from San Francisco to Chicago Midway Airport?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a San Francisco to Chicago Midway Airport flight?

    Round-trip flights from San Francisco to Chicago Midway Airport range from $330 to $511, with an average of $394 over the past 12 months. Anything below $330 counts as a good deal.

  • How expensive are last-minute San Francisco to Chicago Midway Airport flights?

    Last-minute fares on this route (booked within two weeks of departure) run 39% above the $394 route average. Book 11 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from San Francisco to Chicago Midway Airport?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $266 round-trip via Denver Intl (DEN), compared to $401 for nonstop.

  • What is the standard checked-bag allowance on flights from San Francisco to Chicago Midway Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from San Francisco to Chicago Midway Airport?

    The Boeing 737 MAX 8 family is used most often on this route, operated mainly by Southwest and United Airlines. Other aircraft seen on the route include Airbus A321-100/200 variants.

  • How are flight departures from San Francisco to Chicago Midway Airport spread across the day?

    Morning is the busiest departure period on San Francisco to Chicago Midway Airport flights, with 50% of flights leaving in that window. Night departures account for 50%, afternoon flights for 0%, and evening flights for 0%.

  • Have flight prices from San Francisco to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $297 to $2,419. That means the highest observed fare was about 8x higher than the lowest one.

  • How are flight prices from San Francisco to Chicago Midway Airport looking right now?

    One-way fares from San Francisco to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $169, which is 31% below the typical average for this route.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates averaging $84 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • Which airports can I use when flying from San Francisco to Chicago Midway Airport?

    Flights from San Francisco to Chicago Midway Airport usually depart from San Francisco (SFO) and arrive at Chicago Midway (MDW).

  • Which airports do connecting flights from San Francisco to Chicago Midway Airport pass through?

    One-stop flights from San Francisco to Chicago Midway Airport most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 69% of one-stop connections
    • Minneapolis St Paul (MSP) - 11% of one-stop connections
    • Phoenix Sky Harbor Intl (PHX) - 7% of one-stop connections
    • Dallas/Fort Worth (DFW) - 4% of one-stop connections

  • Can I save money by using flexible dates for flights from San Francisco to Chicago Midway Airport?

    Yes. Flexible dates can save you up to 33% on flights from San Francisco to Chicago Midway Airport. Monday is the cheapest departure day at $344 round-trip on average, while Sunday is the most expensive at $511, a difference of $167.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from San Francisco to Chicago Midway Airport?

    Only Southwest operates flights between San Francisco and Chicago Midway Airport.

  • How much time can I save by choosing a different layover airport from San Francisco to Chicago Midway Airport?

    Flying via Denver Intl (DEN) gives the shortest average 1-stop total travel time at 6h 14m, compared with 6h 44m via Minneapolis St Paul (MSP) and 6h 54m via Kansas City (MCI).

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

    Chicago Midway Airport is 2 hours ahead of San Francisco (Central Time vs Pacific Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

  • Which airlines offer extra legroom and free seat selection on San Francisco to Chicago Midway Airport flights?

    Among airlines operating San Francisco to Chicago Midway Airport flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on San Francisco to Chicago Midway Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag in Economy Class class
    • JetBlue: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking San Francisco to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Monday departure and avoid flying on Sunday. On this route, Monday flights average $344, about $167 less than Sunday fares (33% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 11 weeks before you fly. On this route, that window historically saves about 43% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your San Francisco to Chicago Midway Airport trip for February. Fares historically average $339 round-trip in that month - typically $327 less than the most expensive month, which is January (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Denver Intl Airport (DEN) can be cheaper than flying direct. The cheapest layover option averages $266 round-trip on this route - about $135 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel Chicago Midway Airport

Prefer to fly direct from San Francisco to Chicago Midway Airport?

 
Find which airlines fly direct from San Francisco Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

San Francisco to Chicago Midway

Monday

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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See more direct flights

Direct returns

Chicago Midway to San Francisco

Monday

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

Southwest

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Sunday

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See more direct flights

More options for your flight from San Francisco to Midway

Complete your trip to Chicago with a hotel stay or car rental

Car rentals in Chicago
Hotels in Chicago
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