Cheap flights from SFO to MDW (San Francisco Intl. to Midway Intl.)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Cheap Flights from SFO to MDW starting at $102 One Way, $191 Round Trip

Prices starting at $191 for return flights and $102 for one-way flights to Midway Intl. were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, May 24 - Sat, May 31
SFO
San Francisco
MDW
Chicago
$191 Roundtrip, found 6 days ago
$191
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, May 24 from San Francisco to Chicago, returning Sat, May 31, priced at $191 found 6 days ago
Tue, May 6 - Wed, May 7
SFO
San Francisco
MDW
Chicago
$206 Roundtrip, found 5 hours ago
$206
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, May 6 from San Francisco to Chicago, returning Wed, May 7, priced at $206 found 5 hours ago
Wed, Jun 25 - Wed, Jul 2
SFO
San Francisco
MDW
Chicago
$207 Roundtrip, found 5 days ago
$207
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Jun 25 from San Francisco to Chicago, returning Wed, Jul 2, priced at $207 found 5 days ago
Sat, May 31 - Sat, Jun 7
SFO
San Francisco
MDW
Chicago
$208 Roundtrip, found 1 day ago
$208
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, May 31 from San Francisco to Chicago, returning Sat, Jun 7, priced at $208 found 1 day ago
Tue, May 13 - Tue, May 20
SFO
San Francisco
MDW
Chicago
$210 Roundtrip, found 22 hours ago
$210
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Tue, May 13 from San Francisco to Chicago, returning Tue, May 20, priced at $210 found 22 hours ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
The price is $129 per night from May 26 to May 27
$129
includes taxes & fees
$110 per night
May 26 - May 27
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,019 reviews)
"Nice location"

Reviewed on Apr 28, 2025

Crowne Plaza Chicago West Loop by IHG
Sonder South Wabash
Sonder South Wabash
3.5 out of 5
1419 South Wabash Avenue, Chicago, IL
The price is $132 per night from May 26 to May 27
$132
includes taxes & fees
$112 per night
May 26 - May 27
Stay at this 3.5-star aparthotel in Chicago. Enjoy a fitness center, concierge services, and in-room washers/dryers. Popular attractions Soldier Field and Grant ...
8.8/10 Excellent! (484 reviews)
Enjoyable stay
"Decent studio apartment with a well stocked kitchen. Secure building, easy access with codes. Walkable to train and soldier field. Comfy bed, decent sized bathroom. Some noise in hall (doors, people talking) as expected but otherwise fairly quite building. We could hear the train but it didn’t disrupt ..."

Reviewed on Apr 24, 2025

Sonder South Wabash
Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHG
3 out of 5
506 West Harrison Street, Chicago, IL
The price is $154 per night from May 4 to May 5
$154
includes taxes & fees
$131 per night
May 4 - May 5
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8/10 Very Good! (1,000 reviews)
"The floors were dirty as if they don't even mop....not really close to anything....construction is going on"

Reviewed on Apr 29, 2025

Holiday Inn & Suites Chicago - Downtown by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels In Chicago

Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
The price is $189 per night from May 11 to May 12
$189
includes taxes & fees
$161 per night
May 11 - May 12
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.2/10 Very Good! (3,962 reviews)
"Housemaid cleaned only twice during my 4 overnight stays"

Reviewed on Apr 30, 2025

Embassy Suites by Hilton Chicago Downtown River North
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $168 per night from May 12 to May 13
$168
includes taxes & fees
$143 per night
May 12 - May 13
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,733 reviews)
"Really nice hotel next to millennium park."

Reviewed on Apr 28, 2025

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is $188 per night from May 11 to May 12
$188
includes taxes & fees
$160 per night
May 11 - May 12
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,163 reviews)
"Nice place to stay ! Walkable to the Michigan AVE where everything is. Quiet stay was lovely."

Reviewed on Apr 29, 2025

Hilton Chicago/Magnificent Mile Suites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Chicago Hotels With Airport Transportation

Motel 6 Elk Grove Village, IL - O'Hare
Motel 6 Elk Grove Village, IL - O'Hare
2 out of 5
2881 Touhy Ave, Elk Grove Village, IL
The price is $62 per night from May 1 to May 2
$62
includes taxes & fees
$55 per night
May 1 - May 2
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,426 reviews)
"Easy check in and staff was friendly !"

Reviewed on Apr 30, 2025

Motel 6 Elk Grove Village, IL - O'Hare
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
3 out of 5
777 E Grand Avenue, Bensenville, IL
The price is $102 per night from May 4 to May 5
$102
includes taxes & fees
$92 per night
May 4 - May 5
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
6.8/10 (1,002 reviews)
"Very well kept hotel"

Reviewed on Apr 28, 2025

Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Comfort Suites Chicago O'Hare Airport
Comfort Suites Chicago O'Hare Airport
3 out of 5
4200 North River Road, Schiller Park, IL
The price is $101 per night from May 14 to May 15
$101
includes taxes & fees
$88 per night
May 14 - May 15
Stay at this 3-star business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
8/10 Very Good! (2,461 reviews)
"Very easy to navigate! And the bed was so comfortable! Clean room and there were stores conveniently within walking distance. Next door."

Reviewed on Apr 27, 2025

Comfort Suites Chicago O'Hare Airport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Low Priced Chicago Hotels

Freehand Chicago
Freehand Chicago
4 out of 5
19 East Ohio Street, Chicago, IL
The price is $117 per night from May 26 to May 27
$117
includes taxes & fees
$100 per night
May 26 - May 27
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.8/10 Good! (1,753 reviews)
"Perfect Location for the Magnificent mile, reasonable prices, friendly staff. Smaller rooms but couldn’t beat the price. Walking distance from everything the Navy Pier, the river walk, shopping, and authentic Chicago signature dishes…will stay here again"

Reviewed on Apr 29, 2025

Freehand Chicago
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
2 out of 5
65 E Harrison St, Chicago, IL
The price is $110 per night from May 1 to May 2
$110
includes taxes & fees
$94 per night
May 1 - May 2
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
6.8/10 (2,108 reviews)
"Great location for walking"

Reviewed on Apr 29, 2025

Travelodge by Wyndham Downtown Chicago
Motel 6 Elk Grove Village, IL - O'Hare
Motel 6 Elk Grove Village, IL - O'Hare
2 out of 5
2881 Touhy Ave, Elk Grove Village, IL
The price is $62 per night from May 1 to May 2
$62
includes taxes & fees
$55 per night
May 1 - May 2
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,426 reviews)
"Easy check in and staff was friendly !"

Reviewed on Apr 30, 2025

Motel 6 Elk Grove Village, IL - O'Hare
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Chicago

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4 out of 5
511 North Columbus Drive, Chicago, IL
The price is $210 per night from May 11 to May 12
$210
includes taxes & fees
$179 per night
May 11 - May 12
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (2,649 reviews)
"Continental breakfast was amazing.. Friendly staff. Location was walking distance to Riverboat rides."

Reviewed on Apr 29, 2025

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4 out of 5
17 E Monroe St, Chicago, IL
The price is $194 per night from May 26 to May 27
$194
includes taxes & fees
$169 per night
May 26 - May 27
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,704 reviews)
"This is a lovely older hotel"

Reviewed on Apr 30, 2025

Palmer House a Hilton Hotel
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
The price is $189 per night from May 11 to May 12
$189
includes taxes & fees
$161 per night
May 11 - May 12
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.2/10 Very Good! (3,962 reviews)
"Housemaid cleaned only twice during my 4 overnight stays"

Reviewed on Apr 30, 2025

Embassy Suites by Hilton Chicago Downtown River North
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

SFO to MDW Route Info

Origin Airport
San Francisco
Destination Airport
Chicago
Number Of Airlines Serving
1
Distance
1851 mi
Shortest Flight Departure Time
10:10AM CDT
Shortest Flight Departure Date
May 7
SFO Address & GPS
Address:
San Francisco CA, 94128
United States
IATA Code:
SFO
Longitude:
-122.389881
Latitude:
37.615215
Time Zone:
America/Los_Angeles
MDW Address & GPS
Address:
5700 South Cicero
Chicago IL, 60638
United States
IATA Code:
MDW
Longitude:
-87.740871
Latitude:
41.788136
Time Zone:
America/Chicago

Frequently asked questions

Am I able to catch a flight from San Francisco, CA Airport (SFO-San Francisco Intl.) to Chicago, IL Airport (MDW-Midway Intl.) now?
Head to the Covid-19 Travel Advisor for the most useful info on travel restrictions and quarantine requirements when catching a flight from San Francisco, CA Airport (SFO-San Francisco Intl.) to Chicago, IL Airport (MDW-Midway Intl.).
Are there non-stop flights from San Francisco Intl. Airport (SFO) to MDW?
Before you hop on the aircraft at San Francisco, CA Airport (SFO-San Francisco Intl.), be sure to pack loads of delicious treats in your cabin bag. Southwest Airlines flies directly to Midway Intl. Airport (MDW), so you won’t get the opportunity to replenish your supplies en route.
What is the shortest flight from San Francisco Airport to Chicago Airport?
From Tenderloin, the distinctive sights and sounds of West Lawn are 5 hours and 14 minutes away. Secure your favorite seat, or perhaps even upgrade to one with more legroom, and jet to your destination in total comfort.
How many hours flight from San Francisco, CA Airport (SFO-San Francisco Intl.) to Chicago Airport?
From San Francisco, CA Airport (SFO-San Francisco Intl.) to Midway Intl. Airport (MDW), you’ll be in your plane seat for around 5 hours and 22 minutes. Sit back, order a glass of Champagne and put on your noise-canceling headphones. It’s time for a movie marathon.
If I am not able to travel due to COVID-19, can I cancel my flight to Chicago, IL Airport (MDW-Midway Intl.)?
We get that traveling right now has its challenges, so it’s good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago, IL Airport (MDW-Midway Intl.) have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you’ll quickly see what options are available. Our Customer Service Portal is the place to go for more information.
Are there flights to Chicago, IL Airport (MDW-Midway Intl.) with flexible change policies?
In most cases you’ll have the option to reschedule your flight to Chicago, IL Airport (MDW-Midway Intl.) without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the “no change fees” filter and book with confidence.
What airlines have the most flights from San Francisco Airport to Chicago Airport?
Southwest Airlines is your ticket to an amazing vacation. This trusted carrier has 65 flights per month between Tenderloin and West Lawn.

Map To Nearby Hotels

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.