Cheap flights from MDW to SAN (Midway Intl. to San Diego Intl.)
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Cheap Flights from MDW to SAN starting at $71 One Way, $142 Round Trip
Prices starting at $142 for return flights and $71 for one-way flights to San Diego 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.
MDW
Chicago
SAN
San Diego
$142 Roundtrip, found 3 days ago
$142
Roundtrip
found 3 days ago
MDW
Chicago
SAN
San Diego
$168 Roundtrip, found 2 days ago
$168
Roundtrip
found 2 days ago
MDW
Chicago
SAN
San Diego
$171 Roundtrip, found 3 days ago
$171
Roundtrip
found 3 days ago
MDW
Chicago
SAN
San Diego
$172 Roundtrip, found 2 days ago
$172
Roundtrip
found 2 days ago
MDW
Chicago
SAN
San Diego
$172 Roundtrip, found 2 days ago
$172
Roundtrip
found 2 days ago
Hotel Ideas near San Diego Intl.
Airport Hotels near San Diego Intl.
Sheraton San Diego Resort
1380 Harbor Island Dr, San Diego, CA
$158 nightly
The price is $182 total per night from Aug 26 to Aug 27
$182 total
Aug 26 - Aug 27
Total includes taxes and fees
Stay at this 4-star business-friendly hotel in San Diego. Enjoy free WiFi, 3 outdoor pools, and 5 restaurants. Our guests praise the pool and the restaurant ...
8.2/10 Very Good! (2,927 reviews)
"Exceptional"
Reviewed on Aug 18, 2025
Handlery Hotel
950 Hotel Cir N, San Diego, CA
$101 nightly
The price is $116 total per night from Aug 25 to Aug 26
$116 total
Aug 25 - Aug 26
Total includes taxes and fees
Stay at this 3.5-star business-friendly hotel in San Diego. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the bar in our ...
8/10 Very Good! (1,969 reviews)
"Great value"
Reviewed on Aug 17, 2025
Wyndham San Diego Bayside
1355 N Harbor Drive, San Diego, CA
$174 nightly
The price is $201 total per night from Sep 2 to Sep 3
$201 total
Sep 2 - Sep 3
Total includes taxes and fees
Stay at this 4-star business-friendly hotel in San Diego. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the pool and the restaurant ...
8.2/10 Very Good! (5,859 reviews)
"Location was great definitely had a few food options. The location was very close to the zoo."
Reviewed on Aug 17, 2025
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 San Diego
Handlery Hotel
950 Hotel Cir N, San Diego, CA
$101 nightly
The price is $116 total per night from Aug 25 to Aug 26
$116 total
Aug 25 - Aug 26
Total includes taxes and fees
Stay at this 3.5-star business-friendly hotel in San Diego. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the bar in our ...
8/10 Very Good! (1,969 reviews)
"Great value"
Reviewed on Aug 17, 2025
Wyndham San Diego Bayside
1355 N Harbor Drive, San Diego, CA
$174 nightly
The price is $201 total per night from Sep 2 to Sep 3
$201 total
Sep 2 - Sep 3
Total includes taxes and fees
Stay at this 4-star business-friendly hotel in San Diego. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the pool and the restaurant ...
8.2/10 Very Good! (5,859 reviews)
"Location was great definitely had a few food options. The location was very close to the zoo."
Reviewed on Aug 17, 2025
Hyatt Regency Mission Bay Spa and Marina
1441 Quivira Rd, San Diego, CA
$204 nightly
The price is $235 total per night from Sep 1 to Sep 2
$235 total
Sep 1 - Sep 2
Total includes taxes and fees
Stay at this 4-star spa hotel in San Diego. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.4/10 Very Good! (1,503 reviews)
"Everything was excellent — a truly family-friendly hotel with outstanding customer service. The breakfast was delicious and offered a great variety. The hotel also has a fun play area for the kids, and the pool was clean, relaxing, and perfect for all ages."
Reviewed on Aug 14, 2025
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.
San Diego Hotels With Airport Transportation
Wyndham San Diego Bayside
1355 N Harbor Drive, San Diego, CA
$174 nightly
The price is $201 total per night from Sep 2 to Sep 3
$201 total
Sep 2 - Sep 3
Total includes taxes and fees
Stay at this 4-star business-friendly hotel in San Diego. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the pool and the restaurant ...
8.2/10 Very Good! (5,859 reviews)
"Location was great definitely had a few food options. The location was very close to the zoo."
Reviewed on Aug 17, 2025
Sheraton San Diego Resort
1380 Harbor Island Dr, San Diego, CA
$158 nightly
The price is $182 total per night from Aug 26 to Aug 27
$182 total
Aug 26 - Aug 27
Total includes taxes and fees
Stay at this 4-star business-friendly hotel in San Diego. Enjoy free WiFi, 3 outdoor pools, and 5 restaurants. Our guests praise the pool and the restaurant ...
8.2/10 Very Good! (2,927 reviews)
"Exceptional"
Reviewed on Aug 18, 2025
Holiday Inn Express San Diego Airport - Old Town by IHG
1955 San Diego Ave, San Diego, CA
$136 nightly
The price is $156 total per night from Aug 24 to Aug 25
$156 total
Aug 24 - Aug 25
Total includes taxes and fees
Book a stay at this business-friendly hotel in San Diego. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
9/10 Wonderful! (1,002 reviews)
"Customer representative was very friendly and made check in seamless. Also, he was helpful with recommendations for dinner reservations and transportation."
Reviewed on Aug 14, 2025
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 San Diego Hotels
Pleasant Inn
5550 Clairemont Mesa Blvd, San Diego, CA
$94 nightly
The price is $107 total per night from Aug 24 to Aug 25
$107 total
Aug 24 - Aug 25
Total includes taxes and fees
Stay at this hotel in San Diego. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the convenient parking in our ...
8.4/10 Very Good! (1,109 reviews)
"Convenient comfortable and clean. I will return"
Reviewed on Aug 17, 2025
E-Z 8 Motel Old Town
4747 Pacific Highway, San Diego, CA
$75 nightly
The price is $86 total per night from Aug 19 to Aug 20
$86 total
Aug 19 - Aug 20
Total includes taxes and fees
Book a stay at this business-friendly hotel in San Diego. Enjoy free parking, WiFi (surcharge), and a 24-hour front desk. Our guests praise the helpful staff ...
6.2/10 (2,137 reviews)
"God did"
Reviewed on Aug 12, 2025
Kings Inn San Diego
1333 Hotel Cir S, San Diego, CA
$90 nightly
The price is $103 total per night from Aug 24 to Aug 25
$103 total
Aug 24 - Aug 25
Total includes taxes and fees
Stay at this hotel in San Diego. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (3,352 reviews)
"I love their pool. The rooms are nice but not soundproof from outdoor noise or neighbors. Its a bit outdated. But the rates are good and our stays are always comfortable. Its so close to old town."
Reviewed on Aug 16, 2025
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 San Diego
Bahia Resort Hotel
998 W Mission Bay Dr, San Diego, CA
$236 nightly
The price is $272 total per night from Sep 1 to Sep 2
$272 total
Sep 1 - Sep 2
Total includes taxes and fees
Stay at this 3.5-star beach resort in San Diego. Enjoy a beach locale, breakfast (surcharge), and 24-hour room service. Our guests praise the pool and the restaurant ...
8.6/10 Excellent! (1,661 reviews)
"Good service"
Reviewed on Aug 12, 2025
The Dana on Mission Bay
1710 W Mission Bay Dr, San Diego, CA
$169 nightly
The price is $194 total per night from Aug 24 to Aug 25
$194 total
Aug 24 - Aug 25
Total includes taxes and fees
Stay at this 3.5-star business-friendly hotel in San Diego. Enjoy 2 outdoor pools, a marina, and 2 hot tubs. Our guests praise the pool and the restaurant in ...
8.8/10 Excellent! (3,643 reviews)
"Front desk communication about amenities: "It would be beneficial if the front desk staff could proactively inform guests about the food and beverage options available at the second pool area upon arrival." Late flight guest accommodations: "For guests with late-night flights or delayed flights, ..."
Reviewed on Aug 18, 2025
Catamaran Resort and Spa
3999 Mission Boulevard, San Diego, CA
$247 nightly
The price is $284 total per night from Aug 24 to Aug 25
$284 total
Aug 24 - Aug 25
Total includes taxes and fees
Book a stay at this beach resort in San Diego. Enjoy free WiFi, a full-service spa, and a beach locale. Our guests praise the helpful staff and the clean rooms ...
8.2/10 Very Good! (1,018 reviews)
Families like: Outdoor pool, game room, on the beach, bicycle rentals
Travelers say...
"Would definitely recommend and I will be back when visiting SD"
Reviewed on Aug 15, 2025
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.
MDW to SAN Route Info
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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
SAN Address & GPS
Address:
Airport Drive
San Diego CA, 92101
United States
IATA Code:
SAN
Longitude:
-117.197312
Latitude:
32.731938
Time Zone:
America/Los_Angeles
Other Flights from Midway Intl. Airport (MDW)
Other Flights to San Diego Intl. Airport (SAN)
- O'Hare Intl. Airport (ORD)
- Chicago Executive Airport (PWK)
- Dupage Airport (DPA)
- Kenosha Regional Airport (ENW)
- South Bend Intl. Airport (SBN)
- Greater Rockford Airport (RFD)
- General Mitchell Intl. Airport (MKE)
- Waukesha County Airport (UES)
- Goshen Municipal Airport (GSH)
- Purdue University Airport (LAF)
Top Trending
Flights
- BOS to MCO
- JFK to LAS
- LAX to SJO
- JFK to LAX
- DCA to LAX
- LAX to JFK
- LGA to FLL
- LAX to ORD
- LAX to IAD
- LAX to DFW
- SEA to SAN
- JFK to FLL
- BWI to DFW
- LAX to MCO
- SFO to SNA
- SNA to SFO
- SNA to LAS
- LAX to DCA
- DTW to LAX
- ORD to LAX
- SFO to LAX
- PHL to MCO
- JFK to SFO
- LAX to HND
- LAX to LHR
- LAX to SGN
- BWI to LAX
- SFO to JFK
- SFO to PDX
- DCA to BOS
Frequently asked questions
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.