$75 Cheap flights from Midway Intl. to San Diego Intl. (MDW to SAN)

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Find The Best Dates To Fly from Midway Intl. to San Diego Intl.

Amazing MDW to SAN Flight Deals

The cheapest flights to San Diego Intl. found within the past 7 days were $150 round trip and $75 one way. Prices and availability subject to change. Additional terms may apply.

Sat, Jun 8 - Tue, Jun 11
MDW
Chicago
SAN
San Diego
$150 Roundtrip, found 15 hours ago
$150
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Sat, Jun 8 from Chicago to San Diego, returning Tue, Jun 11, priced at $150 found 15 hours ago
Sat, Aug 24 - Mon, Sep 2
MDW
Chicago
SAN
San Diego
$153 Roundtrip, found 4 days ago
$153
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Aug 24 from Chicago to San Diego, returning Mon, Sep 2, priced at $153 found 4 days ago
Sat, Aug 17 - Sat, Aug 24
MDW
Chicago
SAN
San Diego
$154 Roundtrip, found 1 day ago
$154
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Aug 17 from Chicago to San Diego, returning Sat, Aug 24, priced at $154 found 1 day ago
Sat, Jun 8 - Tue, Jun 11
MDW
Chicago
SAN
San Diego
$155 Roundtrip, found 5 days ago
$155
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Jun 8 from Chicago to San Diego, returning Tue, Jun 11, priced at $155 found 5 days ago
Wed, Aug 14 - Sat, Aug 17
MDW
Chicago
SAN
San Diego
$158 Roundtrip, found 1 day ago
$158
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Aug 14 from Chicago to San Diego, returning Sat, Aug 17, priced at $158 found 1 day ago
Fri, Sep 6 - Wed, Sep 11
MDW
Chicago
SAN
San Diego
$160 Roundtrip, found 4 days ago
$160
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Sep 6 from Chicago to San Diego, returning Wed, Sep 11, priced at $160 found 4 days ago
Sat, Jun 1 - Wed, Jun 5
MDW
Chicago
SAN
San Diego
$161 Roundtrip, found 4 days ago
$161
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Jun 1 from Chicago to San Diego, returning Wed, Jun 5, priced at $161 found 4 days ago
Sat, Jun 8 - Tue, Jun 11
MDW
Chicago
SAN
San Diego
$162 Roundtrip, found 6 days ago
$162
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Jun 8 from Chicago to San Diego, returning Tue, Jun 11, priced at $162 found 6 days ago
Sat, Jun 8 - Tue, Jun 11
MDW
Chicago
SAN
San Diego
$167 Roundtrip, found 6 days ago
$167
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Jun 8 from Chicago to San Diego, returning Tue, Jun 11, priced at $167 found 6 days ago
Sat, Aug 17 - Sat, Aug 24
MDW
Chicago
SAN
San Diego
$168 Roundtrip, found 1 day ago
$168
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Aug 17 from Chicago to San Diego, returning Sat, Aug 24, priced at $168 found 1 day ago

Best San Diego Intl. Flight and Hotel Packages

San Diego Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Paradise Point Resort & Spa

Paradise Point Resort & Spa

4 out of 5
per person
Jun 25 - Jun 27
Roundtrip non-stop flight included
Chicago (CHI) to San Diego (SAN)
Winners Circle Resort by VRI Americas

Winners Circle Resort by VRI Americas

3.5 out of 5
Save 100% on your flight
per person
Jul 14 - Jul 19
Roundtrip flight included
Chicago (ORD) to San Diego (SAN)
The Lodge at Torrey Pines

The Lodge at Torrey Pines

5 out of 5
Save 100% on your flight
per person
Jun 25 - Jun 27
Roundtrip non-stop flight included
Chicago (CHI) to San Diego (SAN)
The Wayfarer San Diego

The Wayfarer San Diego

4 out of 5
Save 100% on your flight
per person
Jun 25 - Jun 27
Roundtrip non-stop flight included
Chicago (CHI) to San Diego (SAN)
Westin Carlsbad Resort & Spa

Westin Carlsbad Resort & Spa

4 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 8
Roundtrip non-stop flight included
Chicago (ORD) to San Diego (SAN)
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Frequently asked questions

Can I catch a flight from Midway Intl. Airport (MDW) to San Diego Airport right now?
For information on any present San Diego Airport travel advice and quarantine requirements, visit our Covid-19 Travel Advisor. Check before you book your flight, so you don’t get caught out en route.
Are there direct flights from Midway Intl. Airport (MDW) to San Diego Airport?
If you’re not a huge fan of layovers, it’s smart to arrange your flight from Chicago Airport to SAN in advance. Southwest Airlines is the only air carrier that operates nonstop flights on this route.
If I am not able to travel due to COVID-19, can I change my booking to a later date?
For more info about changing your flight to San Diego Airport, please visit our Customer Service Portal.
How long is the flight from Midway Airport to San Diego Airport?
With the flight from MDW to San Diego Intl. Airport (SAN) taking around 4 hours and 18 minutes, there’ll be time to get lots of things done in the air. Take advantage of your trip by bringing that novel you always wanted to read, seeing what in-flight entertainment is on offer or catching up on some rest. You might even find you’re able to squeeze in all three before the plane lands.
What is the flight distance from Midway Airport to SAN?
Covering 1,750 mi between Midway Airport and Midway Airport calls for a glass of bubbly and a few good movies. Adjust your seat, pull a blanket over you and just enjoy the ride.
What airlines fly from Midway Airport to SAN?
With Southwest Airlines, you won’t have to stress about annoying layovers or hanging around waiting for your connecting flight. This popular airline will fly you straight from Chicago to San Diego County on one of the 104 flights offered on this route every month.
What airlines have practices regarding COVID-19 in place and use social distancing?
From the moment you enter the departure terminal to when you leave the arrivals terminal, if you’re flying with Southwest Airlines, Alaska Airlines or United Airlines you can be sure that COVID-19 measures and social distancing rules have been adhered to. Many airlines have introduced capped capacity flights and keeping the middle seat empty.
What is the best day to buy a plane ticket?
This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that is when prices are generally at their highest.
What are the cheapest days to fly?
Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2021, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.
How far in advance can you book a flight?
Trying to figure out how early you should book your flight? It’s possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

 

Traveling From
Midway Intl.
Traveling To
San Diego Intl.
Shortest Flight Time
4 hours 15 mins
Earliest Departure Time
12:15PM CDT
Latest Departure Time
8:05PM CDT
Lowest Flight Price
$150

Route Info

Flight path for flights from Chicago Midway International Airport to San Diego International Airport.


Origin:
MDW - Chicago Midway International Airport
Destination:
SAN - San Diego International Airport
Distance:
1,734.00 miles


Discover our best flights from Chicago MDW to San Diego SAN. 

With 20 airlines to choose from on Travelocity, you can easily find the best option for you. Use our filters to sort by price, compare airlines, and find the most convenient flight times. 

 

Find our best return flights from Chicago MDW to San Diego SAN at the right price  

Airfares to San Diego SAN from Chicago MDW currently cost between $150 and $168. It’s usually cheaper to book a round trip than two separate one-way flights. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way flights from Chicago MDW to San Diego SAN 

If you want to be flexible about when you return, or keep your travel options open ended, a one-way flight could be just the ticket! You’ll find one-way airfares from Chicago MDW to San Diego SAN on Travelocity starting at $75. Prices and availability subject to change. Additional terms may apply. 

 

Get to San Diego SAN from Chicago MDW quicker with direct flights. 

Get to San Diego faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to SAN from MDW to take around 4 hour(s) 15 min(s).  

 

Find our cheapest airfares for flights from Chicago MDW to San Diego SAN

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to SAN from MDW. Our Price Match Promise means if you find a lower rate on Travelocity.com or on another US-based website within 24 hours of booking, we’ll credit or refund the difference.  

 

Get our best airfare deals for your flight from Chicago MDW to San Diego SAN today 

If you’re flexible about when you travel, June is usually the cheapest month to fly from Chicago MDW to San Diego SAN. If you need to be more specific, search by date and arrival and departure times.Then, compare prices across different airlines, and sort results by lowest price first. 

 

Book flexible airline tickets for flights to San Diego SAN from Chicago MDW 

Some airlines let you change your travel dates without charging a fee. Use our ‘no change fee’ filter to see which flights to SAN from MDW have this option.  

 

Travel with confidence when you book flights to San Diego SAN from Chicago MDW with Travelocity 

We’ve secured fantastic deals with all the main airline carriers and it’s easy to compare, choose, and book with Travelocity. With 24/7 customer service and our free 'App', we’ll always keep you moving. 

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.