Cheap flights from SAT to MDW (San Antonio Intl. to Midway Intl.)

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Cheap Flights from SAT to MDW starting at $54 One Way, $108 Round Trip

Prices starting at $108 for return flights and $54 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.

Wed, May 15 - Thu, May 16
SAT
San Antonio
MDW
Chicago
$108 Roundtrip, found 1 day ago
$108
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, May 15 from San Antonio to Chicago, returning Thu, May 16, priced at $108 found 1 day ago
Fri, May 10 - Tue, May 14
SAT
San Antonio
MDW
Chicago
$118 Roundtrip, found 1 day ago
$118
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, May 10 from San Antonio to Chicago, returning Tue, May 14, priced at $118 found 1 day ago
Fri, May 10 - Fri, May 17
SAT
San Antonio
MDW
Chicago
$128 Roundtrip, found 3 days ago
$128
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, May 10 from San Antonio to Chicago, returning Fri, May 17, priced at $128 found 3 days ago
Fri, May 17 - Thu, May 23
SAT
San Antonio
MDW
Chicago
$130 Roundtrip, found 3 days ago
$130
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, May 17 from San Antonio to Chicago, returning Thu, May 23, priced at $130 found 3 days ago
Mon, May 13 - Thu, May 16
SAT
San Antonio
MDW
Chicago
$134 Roundtrip, found 1 day ago
$134
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, May 13 from San Antonio to Chicago, returning Thu, May 16, priced at $134 found 1 day ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Best Western Grant Park Hotel
Best Western Grant Park Hotel
2.5 out of 5
1100 S Michigan Ave, Chicago, IL
The price is $98 per night from May 28 to May 29
$98
per night
May 28 - May 29
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast, and valet parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
7.8/10 Good! (2,538 reviews)
"Good and comfortable"

Reviewed on Apr 25, 2024

Best Western Grant Park Hotel
Hotel Chicago West Loop
Hotel Chicago West Loop
2.5 out of 5
1622 W Jackson Blvd, Chicago, IL
The price is $142 per night from Apr 29 to Apr 30
$142
per night
Apr 29 - Apr 30
Stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and onsite parking. Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (1,001 reviews)
Nice!
"Nice older hotel located close to rush hospital UIC campus plenty of restaurants in bars in the area"

Reviewed on Apr 24, 2024

Hotel Chicago West Loop
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $120 per night from Apr 30 to May 1
$120
per night
Apr 30 - May 1
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 rooms ...
7.6/10 Good! (6,602 reviews)
"Our room was clean and pleasant, seemed to be relatively recently renovated. Convenient location with a lovely view over Grant Park. Surprisingly spacious closet. Polite staff and a good value room, no hidden fees or anything. The hotel as a whole is older but we had but no real complaints, it was ..."

Reviewed on Apr 27, 2024

Congress Plaza Hotel
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

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
The price is $85 per night from Apr 29 to Apr 30
$85
per night
Apr 29 - Apr 30
Stay at this family-friendly hotel in Chicago. Enjoy WiFi, a 24-hour fitness center, and valet parking. Our guests praise the helpful staff and the clean rooms ...
7.6/10 Good! (2,532 reviews)
"My stay was very wonderful and pleasant"

Reviewed on Apr 27, 2024

Warwick Allerton - Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $120 per night from Apr 30 to May 1
$120
per night
Apr 30 - May 1
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 rooms ...
7.6/10 Good! (6,602 reviews)
"Our room was clean and pleasant, seemed to be relatively recently renovated. Convenient location with a lovely view over Grant Park. Surprisingly spacious closet. Polite staff and a good value room, no hidden fees or anything. The hotel as a whole is older but we had but no real complaints, it was ..."

Reviewed on Apr 27, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $149 per night from Apr 29 to Apr 30
$149
per night
Apr 29 - Apr 30
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (2,805 reviews)
"Wonderful stay in the best part of town"

Reviewed on Apr 24, 2024

River Hotel
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 $60 per night from Apr 29 to Apr 30
$60
per night
Apr 29 - Apr 30
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 ...
8/10 Very Good! (1,147 reviews)
"Good safe place and comfortable parking"

Reviewed on Apr 26, 2024

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 East Grand Avenue, Bensenville, IL
The price is $85 per night from Apr 29 to Apr 30
$85
per night
Apr 29 - Apr 30
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions ...
6.4/10 (1,004 reviews)
"Great place to stay at, close to the airport and has shuttles to and from the airport!"

Reviewed on Apr 19, 2024

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 $89 per night from May 12 to May 13
$89
per night
May 12 - May 13
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 ...
8.2/10 Very Good! (1,879 reviews)
"."

Reviewed on Apr 21, 2024

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

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 $60 per night from Apr 29 to Apr 30
$60
per night
Apr 29 - Apr 30
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 ...
8/10 Very Good! (1,147 reviews)
"Good safe place and comfortable parking"

Reviewed on Apr 26, 2024

Motel 6 Elk Grove Village, IL - O'Hare
Freehand Chicago
Freehand Chicago
4 out of 5
19 East Ohio Street, Chicago, IL
The price is $89 per night from Apr 30 to May 1
$89
per night
Apr 30 - May 1
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. ...
7.6/10 Good! (1,003 reviews)
Loved it
"it was really nice, my friend and i chose the private quarter. it was a lot of fun, though small, it definitely exceed expectations this hotel has a cool speak easy vibe to it"

Reviewed on Apr 24, 2024

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 $90 per night from Apr 29 to Apr 30
$90
per night
Apr 29 - Apr 30
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
6.2/10 (1,634 reviews)
Grunion run
"Horrible view but was satisfied with room and sleep"

Reviewed on Apr 24, 2024

Travelodge by Wyndham Downtown Chicago
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 River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
The price is $161 per night from May 12 to May 13
$161
per night
May 12 - May 13
Stay at this hotel in Chicago. Enjoy free breakfast, WiFi, and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions ...
7.8/10 Good! (2,203 reviews)

Families like: Indoor pools, close to beach, bicycle rentals nearby, extra beds/cribs

Travelers say...
"Rooms were great. Comfortable and spacious."

Reviewed on Apr 23, 2024

Embassy Suites by Hilton Chicago Downtown River North
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 $176 per night from May 12 to May 13
$176
per night
May 12 - May 13
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, WiFi, and room service. Our guests praise the breakfast and the helpful staff in ...
8.2/10 Very Good! (2,409 reviews)

Families like: Indoor pools, close to beach, bicycle rentals nearby, extra beds/cribs

Travelers say...
"Property is getting older. Overall very pleasant."

Reviewed on Apr 27, 2024

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 $173 per night from May 26 to May 27
$173
per night
May 26 - May 27
Stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast, and a 24-hour health club. Our guests praise the breakfast and the helpful staff in our ...
8/10 Very Good! (1,181 reviews)

Families like: Indoor pools, close to beach, bicycle rentals, extra beds/cribs

Travelers say...
"Staff was helpful. Rooms were kept clean. Good area."

Reviewed on Apr 22, 2024

Palmer House a Hilton Hotel
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.

Map To Nearby Hotels

SAT to MDW Route Info

Origin Airport
San Antonio
Destination Airport
Chicago
Number Of Airlines Serving
1
Distance
1037 mi
Shortest Flight Departure Time
4:10PM CDT
Shortest Flight Departure Date
May 5
SAT Address & GPS
Address:
9800 Airport Boulevard
San Antonio TX, 78216
United States
IATA Code:
SAT
Longitude:
-98.472643
Latitude:
29.524937
Time Zone:
America/Chicago
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 Antonio, TX Airport (SAT-San Antonio Intl.) to Chicago, IL Airport (MDW-Midway Intl.) now?
Our Covid-19 Travel Advisor can help you with queries about current travel restrictions and quarantine requirements when traveling by plane from San Antonio, TX Airport (SAT-San Antonio Intl.) to Chicago, IL Airport (MDW-Midway Intl.).
Are there non-stop flights from SAT to Midway Airport?
We’re delighted to inform you that Southwest Airlines will take you directly from Oakland Estates to West Lawn. Book your seat now and enjoy a stress-free, nonstop flight.
What is the shortest flight from San Antonio, TX Airport (SAT-San Antonio Intl.) to Chicago Airport?
Indulge in a miniature bottle of vino and get comfortable in your seat with an interesting movie or book. With the trip from Oakland Estates to West Lawn taking 4 hours and 43 minutes, there’s plenty of time to kick back and enjoy the experience.
How many hours flight from San Antonio, TX Airport (SAT-San Antonio Intl.) to MDW?
The trip from San Antonio Airport to MDW will take around 4 hours and 47 minutes. A few movies, some audiobooks and a decent snooze will help make time fly.
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 SAT to Chicago Airport?
If you’re aiming for a hassle-free journey, buckle up and take off with Southwest Airlines. This air carrier has 112 flights every month from Oakland Estates to West Lawn and is one of the leading airlines operating on this route.

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.