Find cheap flights from Chicago Midway Airport to San Diego

MDW - SAN

Find cheap flights from Chicago Midway Airport to San Diego

Round-trip
Economy
Chicago (MDW)
San Diego
Fri 9/25
Fri 10/2
Any month
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Good to know

Low season

September Best time to beat the crowds with an average 27% drop in price.

High season

December Most popular time to fly with an average 26% increase in price.

Average price of a round-trip

$336 (avg. price over the last 2 weeks)

Good deal for a round-trip

$311 or less

When to book flights from Chicago Midway to San Diego

Estimated round-trip price
Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for $197 or less.
  • The cheapest flight from Chicago Midway Airport to San Diego was found 43 days before departure, on average.
  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be November, December and January. The cheapest month to fly is September.
  • Morning departure is around 10% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for booking Chicago Midway Airport to San Diego flights

Which airlines have a flexible cancellation policy for flights from Chicago Midway to San Diego due to COVID-19?

Which airlines apply social distancing measures on flights from Chicago Midway to San Diego due to COVID-19?

Are there San Diego travel restrictions currently due to Coronavirus?

How long does a flight from Chicago Midway Airport to San Diego take?

How many flights are there between Chicago Midway Airport and San Diego?

Which airlines provide the cheapest flights from Chicago Midway Airport to San Diego?

Do I need a passport to fly between Chicago Midway Airport and San Diego?

Which airlines fly most frequently between Chicago Midway Airport and San Diego?

What’s the cheapest day of the week to fly Chicago Midway Airport to San Diego?

How does KAYAK find such low prices on flights from Chicago Midway Airport to San Diego?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to San Diego?

What is the Hacker Fare option on flights from Chicago Midway Airport to San Diego?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to San Diego?

Top airlines flying Chicago Midway to San Diego

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 28,640 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews
Read more about Delta

Book cheap flights from Chicago Midway Airport to San Diego

Recent round-trip flight deals

10/15
Thu
1 stop
Delta
11h 15m
MDW - SAN
10/19
Mon
1 stop
Delta
9h 25m
SAN - MDW
10/22
Thu
2 stops
Multiple Airlines
28h 07m
MDW - SAN
10/31
Sat
2 stops
Multiple Airlines
27h 24m
SAN - MDW
10/1
Thu
1 stop
Delta
11h 15m
MDW - SAN
10/13
Tue
1 stop
Delta
9h 25m
SAN - MDW
9/30
Wed
1 stop
Delta
11h 40m
MDW - SAN
10/3
Sat
1 stop
Delta
9h 25m
SAN - MDW
11/22
Sun
1 stop
Delta
11h 03m
MDW - SAN
12/3
Thu
1 stop
Delta
8h 40m
SAN - MDW
12/1
Tue
1 stop
Delta
7h 51m
MDW - SAN
12/8
Tue
1 stop
Delta
6h 58m
SAN - MDW
10/4
Sun
1 stop
Delta
6h 53m
MDW - SAN
10/7
Wed
1 stop
Delta
7h 10m
SAN - MDW
10/8
Thu
1 stop
Delta
11h 15m
MDW - SAN
10/12
Mon
1 stop
Delta
9h 25m
SAN - MDW
10/4
Sun
1 stop
Delta
11h 15m
MDW - SAN
10/10
Sat
1 stop
Delta
9h 25m
SAN - MDW
12/3
Thu
1 stop
Delta
11h 01m
MDW - SAN
12/7
Mon
1 stop
Delta
8h 40m
SAN - MDW
1/19
Tue
1 stop
Delta
7h 12m
MDW - SAN
1/24
Sun
1 stop
Delta
11h 29m
SAN - MDW
12/4
Fri
1 stop
Delta
8h 47m
MDW - SAN
12/8
Tue
1 stop
Delta
6h 13m
SAN - MDW
9/29
Tue
1 stop
Delta
7h 40m
MDW - SAN
10/3
Sat
1 stop
Delta
7h 10m
SAN - MDW
10/4
Sun
1 stop
Delta
11h 15m
MDW - SAN
10/8
Thu
2 stops
Delta
11h 30m
SAN - MDW
10/11
Sun
1 stop
Delta
6h 53m
MDW - SAN
10/17
Sat
1 stop
Delta
7h 10m
SAN - MDW
10/2
Fri
1 stop
Delta
11h 15m
MDW - SAN
10/5
Mon
1 stop
Delta
9h 25m
SAN - MDW
2/1
Mon
1 stop
Delta
6h 28m
MDW - SAN
3/31
Wed
1 stop
Delta
11h 29m
SAN - MDW
11/20
Fri
1 stop
Delta
11h 03m
MDW - SAN
12/4
Fri
1 stop
Delta
9h 19m
SAN - MDW
2/12
Fri
1 stop
Delta
11h 03m
MDW - SAN
2/16
Tue
1 stop
Delta
11h 29m
SAN - MDW
1/14
Thu
1 stop
Delta
10h 58m
MDW - SAN
1/18
Mon
1 stop
Delta
11h 29m
SAN - MDW
Show more results

Recent one-way flight deals

9/30
Wed
1 stop
Delta
7h 40m
MDW - SAN
11/1
Sun
2 stops
Multiple Airlines
28h 07m
MDW - SAN
11/1
Sun
1 stop
Delta
11h 15m
MDW - SAN
10/4
Sun
1 stop
Delta
6h 53m
MDW - SAN
10/12
Mon
1 stop
Delta
6h 53m
MDW - SAN
10/22
Thu
2 stops
Multiple Airlines
28h 07m
MDW - SAN
10/9
Fri
1 stop
Delta
11h 15m
MDW - SAN
10/8
Thu
2 stops
Multiple Airlines
28h 07m
MDW - SAN
10/2
Fri
3 stops
Multiple Airlines
34h 56m
MDW - SAN
10/16
Fri
2 stops
Volaris
32h 11m
MDW - SAN
9/29
Tue
2 stops
Delta
11h 55m
MDW - SAN
10/11
Sun
1 stop
Delta
6h 53m
MDW - SAN
10/16
Fri
3 stops
Multiple Airlines
40h 35m
MDW - SAN
10/9
Fri
1 stop
Delta
11h 15m
MDW - SAN
10/2
Fri
1 stop
Delta
11h 15m
MDW - SAN
11/25
Wed
1 stop
Delta
7h 51m
MDW - SAN
10/8
Thu
3 stops
Multiple Airlines
76h 07m
MDW - SAN
10/18
Sun
1 stop
Delta
11h 15m
MDW - SAN
10/1
Thu
3 stops
Multiple Airlines
20h 15m
MDW - SAN
10/11
Sun
1 stop
Delta
6h 53m
MDW - SAN
Show more results
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an and someone from our team will get back to you promptly.

^
The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.
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