$94 Cheap flights from San Diego Intl. to Midway Intl. (SAN to MDW)

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

Compare Flight Prices from San Diego to Chicago

Affordable Airfare Tickets from SAN to MDW Airport

The cheapest flights to Midway Intl. found within the past 7 days were $191 round trip and $94 one way. Prices and availability subject to change. Additional terms may apply.

Sat, May 17 - Sat, May 31
SAN
San Diego
MDW
Chicago
$191 Roundtrip, found 13 hours ago
$191
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Sat, May 17 from San Diego to Chicago, returning Sat, May 31, priced at $191 found 13 hours ago
Sun, Jun 1 - Tue, Jun 3
SAN
San Diego
MDW
Chicago
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Jun 1 from San Diego to Chicago, returning Tue, Jun 3, priced at $198 found 1 day ago
Wed, May 7 - Mon, May 12
SAN
San Diego
MDW
Chicago
$200 Roundtrip, found 5 hours ago
$200
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Wed, May 7 from San Diego to Chicago, returning Mon, May 12, priced at $200 found 5 hours ago
Mon, May 12 - Sat, May 31
SAN
San Diego
MDW
Chicago
$201 Roundtrip, found 13 hours ago
$201
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Mon, May 12 from San Diego to Chicago, returning Sat, May 31, priced at $201 found 13 hours ago
Mon, May 5 - Mon, May 5
SAN
San Diego
MDW
Chicago
$205 Roundtrip, found 11 hours ago
$205
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Mon, May 5 from San Diego to Chicago, returning Mon, May 5, priced at $205 found 11 hours ago
Mon, May 12 - Mon, May 12
SAN
San Diego
MDW
Chicago
$206 Roundtrip, found 3 days ago
$206
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, May 12 from San Diego to Chicago, returning Mon, May 12, priced at $206 found 3 days ago
Thu, May 8 - Mon, May 12
SAN
San Diego
MDW
Chicago
$208 Roundtrip, found 5 hours ago
$208
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Thu, May 8 from San Diego to Chicago, returning Mon, May 12, priced at $208 found 5 hours ago
Mon, May 5 - Mon, May 12
SAN
San Diego
MDW
Chicago
$210 Roundtrip, found 5 hours ago
$210
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Mon, May 5 from San Diego to Chicago, returning Mon, May 12, priced at $210 found 5 hours ago
Mon, May 12 - Sun, May 25
SAN
San Diego
MDW
Chicago
$211 Roundtrip, found 13 hours ago
$211
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Mon, May 12 from San Diego to Chicago, returning Sun, May 25, priced at $211 found 13 hours ago
Sun, Jun 1 - Sat, Jun 7
SAN
San Diego
MDW
Chicago
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Jun 1 from San Diego to Chicago, returning Sat, Jun 7, priced at $218 found 1 day ago

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Regal Inn - Chicago O'Hare Airport

Regal Inn - Chicago O'Hare Airport

2 out of 5
per person
Jun 6 - Jun 8
found 22 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Chicago (ORD)
DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
per person
Jun 6 - Jun 8
found 22 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Chicago (ORD)
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

4 out of 5
per person
Jun 6 - Jun 8
found 22 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Chicago (ORD)
Courtyard by Marriott Chicago Wood Dale

Courtyard by Marriott Chicago Wood Dale

3 out of 5
per person
Jun 6 - Jun 8
found 22 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Chicago (ORD)
Wyndham Garden Elk Grove Village/O'Hare

Wyndham Garden Elk Grove Village/O'Hare

3 out of 5
per person
Jun 6 - Jun 8
found 22 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Chicago (ORD)
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Frequently asked questions

Can I catch a flight from San Diego Intl. Airport (SAN) to Midway Intl. Airport (MDW) right now?
For information on any present Chicago Airport quarantine requirements and travel advice, go to the Covid-19 Travel Advisor. Look before you book your flight, so you don’t get caught out en route.
Are there direct flights from SAN to Midway Intl. Airport (MDW)?
Wander wisely and pick up a direct flight from San Diego Intl. Airport (SAN) to Chicago Airport with Southwest Airlines. This air carrier is the smart choice if you’re hoping to touchdown in Chicago as speedily as possible.
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 MDW, please visit our Customer Service Portal.
How long is the flight from SAN to Chicago Airport?
Flights between San Diego County and Chicago take roughly 3 hours and 55 minutes in total. Make the most of that time in the air by reading, resting, watching a film or doing all three.
What is the flight distance from SAN to Chicago Airport?
Between San Diego Intl. Airport (SAN) and Chicago Airport, the flight distance is approximately 1,750 mi. So, buckle up and settle in. You’ve got some important decisions to make — watch an in-flight movie, read a good book or catch up on your beauty sleep?
What airlines fly from San Diego Airport to Midway Airport?
Ready to book the ticket for your next awesome adventure? Want to travel from San Diego County to Chicago as fast as possible? Book one of the 104 nonstop flights offered by Southwest Airlines each month, and you’ll be hitting the tarmac before you can utter ‘Are we there yet?’
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, Delta or Volaris 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.

Flight information from San Diego to Chicago

 

Traveling From
San Diego Intl.
Traveling To
Midway Intl.
Shortest Flight Time
4 hours 0 mins
Earliest Departure Time
6:30AM PDT
Latest Departure Time
5:55PM PDT
Lowest Flight Price
$191

Route Info

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


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


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

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 San Diego SAN to Chicago MDW at the right price  

Airfares to Chicago MDW from San Diego SAN currently cost between $191 and $218. 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 San Diego SAN to Chicago MDW 

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 San Diego SAN to Chicago MDW on Travelocity starting at $94. Prices and availability subject to change. Additional terms may apply. 

 

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

Get to Chicago faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to MDW from SAN to take around 4 hour(s) 0 min(s).  

 

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

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to MDW from SAN. 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 San Diego SAN to Chicago MDW today 

If you’re flexible about when you travel, May is usually the cheapest month to fly from San Diego SAN to Chicago MDW. 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 Chicago MDW from San Diego SAN 

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

 

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