Find Cheap Flights from San Diego to Chicago Midway (SAN - MDW)

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Good to Know

Low Season:
January
Best time to beat the crowds
2%
expected price decrease
High Season:
July
Most popular time to fly
9%
expected price increase
Average Price:
$400
(avg. price over the last 2 weeks)
Good Deal:
$290
or less (round trip)

When to Book Flights from San Diego to Chicago Midway

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 $290 or less.
The cheapest flight from San Diego to Chicago Midway was found 55 days before departure, on average.
Book at least 6 weeks before departure in order to get a below-average price.
High season is considered to be June, July and August. The cheapest month to fly is January.
Morning departure is around 26% 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 San Diego to Chicago Midway Flights

How long does a flight from San Diego to Chicago Midway take?
An average nonstop flight takes 5h 42m, covering a distance of 1725 miles.
How many flights are there between San Diego and Chicago Midway?
There are 27 (nonstop) flights between San Diego and Chicago Midway per week, averaging 3 per day.
Which airlines provide the cheapest flights from San Diego to Chicago Midway?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($264)
Do I need a passport to fly between San Diego and Chicago Midway?
No.
Which airlines fly most frequently between San Diego and Chicago Midway?
Southwest (3 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly San Diego to Chicago Midway?
For San Diego to Chicago Midway, Friday is the cheapest day to fly on average and Friday is the most expensive. Flying from Chicago Midway back to San Diego, the best deals are generally found on Friday, with Thursday being the most expensive.

Book cheap flights from San Diego to Chicago Midway (round-trip)

Airports
Origin
San Diego
$264
only
$264
Destination
Chicago
$264
only
$264
Fri, Jan 19
SAN
MDW
7h 58m
Tue, Jan 23
MDW
SAN
10h 51m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSY
JFK
Excellent 10.0

Love the new in-cabin wi-fi, USB charging station, and menu of in-flight entertainment and resources on the individual flatscreens.

YUL
MSP
Good 6.0

We got on the plane and it went to where it was supposed to go.

ORF
BOS
Excellent 10.0

Flight attendant Gillian Awesome. Crew was fun and made my kids first flight great.

CMH
DTW
Excellent 8.6

Easy to board.

Delayed due to weather.

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

Fri, Jan 26
SAN
MDW
7h 58m
Mon, Jan 29
MDW
SAN
8h 04m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ORD
MSP
Okay 4.0

I needed to run real fast to the connection flight and gladly got there on time.

DTW
PHL
Excellent 8.0

Made it out of Detroit that same day! Friendly flight attendants!

Flight was delayed. And then cancelled. We were booked into a later flight 8 hours later that was also delayed again due to weather but we did make it out of Detroit that night. Other people were not as lucky.

CUN
MSP
Okay 4.3

The Cancun airport provides a terrible experience for transferring between flights, especially if you need to change from the international terminal to a domestic terminal or vice-versa. There is no way to get between terminals inside security and the free shuttle is slow and overcrowded. Meanwhile, one is forced to run a gauntlet of taxi and shuttle drivers trying to get you to pay them exorbitant fees to drive you to your terminal. Once you finally arrive you discover that there is no dedicated baggage recheck for an international arrival. Just don't buy a ticket that transfers in CUN.

ORF
BOS
Excellent 10.0

Flight attendant Gillian Awesome. Crew was fun and made my kids first flight great.

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

Thu, Feb 1
SAN
MDW
7h 04m
Tue, Feb 6
MDW
SAN
8h 04m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
CMH
DTW
Excellent 8.6

Easy to board.

Delayed due to weather.

MSP
DSM
Good 6.0

The plane went where it was supposed to go.

CUN
MSP
Okay 4.3

The Cancun airport provides a terrible experience for transferring between flights, especially if you need to change from the international terminal to a domestic terminal or vice-versa. There is no way to get between terminals inside security and the free shuttle is slow and overcrowded. Meanwhile, one is forced to run a gauntlet of taxi and shuttle drivers trying to get you to pay them exorbitant fees to drive you to your terminal. Once you finally arrive you discover that there is no dedicated baggage recheck for an international arrival. Just don't buy a ticket that transfers in CUN.

ORF
BOS
Excellent 10.0

Flight attendant Gillian Awesome. Crew was fun and made my kids first flight great.

SLC
MEX
Good 7.0

They hade entertainment

No food

Mon, Mar 5
SAN
MDW
9h 30m
Tue, Mar 13
MDW
SAN
6h 15m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
YUL
MSP
Good 6.0

We got on the plane and it went to where it was supposed to go.

ORD
MSP
Okay 4.0

I needed to run real fast to the connection flight and gladly got there on time.

MSP
LAS
Good 6.6

comfortable seats

delay delay delay

CUN
MSP
Okay 4.3

The Cancun airport provides a terrible experience for transferring between flights, especially if you need to change from the international terminal to a domestic terminal or vice-versa. There is no way to get between terminals inside security and the free shuttle is slow and overcrowded. Meanwhile, one is forced to run a gauntlet of taxi and shuttle drivers trying to get you to pay them exorbitant fees to drive you to your terminal. Once you finally arrive you discover that there is no dedicated baggage recheck for an international arrival. Just don't buy a ticket that transfers in CUN.

DTW
PHL
Excellent 8.0

Made it out of Detroit that same day! Friendly flight attendants!

Flight was delayed. And then cancelled. We were booked into a later flight 8 hours later that was also delayed again due to weather but we did make it out of Detroit that night. Other people were not as lucky.

Wed, Apr 18
SAN
MDW
5h 55m
Wed, Apr 25
MDW
SAN
6h 56m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
CMH
DTW
Excellent 8.6

Easy to board.

Delayed due to weather.

SLC
MEX
Good 7.0

They hade entertainment

No food

MSP
DSM
Good 6.0

The plane went where it was supposed to go.

MSP
LAS
Good 6.6

comfortable seats

delay delay delay

MSY
JFK
Excellent 10.0

Love the new in-cabin wi-fi, USB charging station, and menu of in-flight entertainment and resources on the individual flatscreens.

Thu, Feb 8
SAN
MDW
7h 04m
Sun, Feb 11
MDW
SAN
8h 09m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSY
JFK
Excellent 10.0

Love the new in-cabin wi-fi, USB charging station, and menu of in-flight entertainment and resources on the individual flatscreens.

SDQ
ATL
Excellent 8.0

Wasted my time on security and lost my flight

ORD
MSP
Okay 4.0

I needed to run real fast to the connection flight and gladly got there on time.

CMH
DTW
Excellent 8.6

Easy to board.

Delayed due to weather.

MSP
DSM
Good 6.0

The plane went where it was supposed to go.

Tue, Apr 10
SAN
MDW
5h 42m
Thu, Apr 12
MDW
SAN
9h 07m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
CUN
MSP
Okay 4.3

The Cancun airport provides a terrible experience for transferring between flights, especially if you need to change from the international terminal to a domestic terminal or vice-versa. There is no way to get between terminals inside security and the free shuttle is slow and overcrowded. Meanwhile, one is forced to run a gauntlet of taxi and shuttle drivers trying to get you to pay them exorbitant fees to drive you to your terminal. Once you finally arrive you discover that there is no dedicated baggage recheck for an international arrival. Just don't buy a ticket that transfers in CUN.

ORD
MSP
Okay 4.0

I needed to run real fast to the connection flight and gladly got there on time.

SDQ
ATL
Excellent 8.0

Wasted my time on security and lost my flight

YUL
MSP
Good 6.0

We got on the plane and it went to where it was supposed to go.

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

Wed, May 2
SAN
MDW
8h 15m
Wed, May 16
MDW
SAN
6h 10m
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

SDQ
ATL
Excellent 8.0

Wasted my time on security and lost my flight

ORD
MSP
Okay 4.0

I needed to run real fast to the connection flight and gladly got there on time.

ORF
BOS
Excellent 10.0

Flight attendant Gillian Awesome. Crew was fun and made my kids first flight great.

MSP
LAS
Good 6.6

comfortable seats

delay delay delay

Thu, May 3
SAN
MDW
5h 42m
Mon, May 7
MDW
SAN
6h 10m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
YUL
MSP
Good 6.0

We got on the plane and it went to where it was supposed to go.

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

SLC
MEX
Good 7.0

They hade entertainment

No food

CUN
MSP
Okay 4.3

The Cancun airport provides a terrible experience for transferring between flights, especially if you need to change from the international terminal to a domestic terminal or vice-versa. There is no way to get between terminals inside security and the free shuttle is slow and overcrowded. Meanwhile, one is forced to run a gauntlet of taxi and shuttle drivers trying to get you to pay them exorbitant fees to drive you to your terminal. Once you finally arrive you discover that there is no dedicated baggage recheck for an international arrival. Just don't buy a ticket that transfers in CUN.

ORF
BOS
Excellent 10.0

Flight attendant Gillian Awesome. Crew was fun and made my kids first flight great.

Sat, Jun 2
SAN
MDW
8h 15m
Mon, Jun 11
MDW
SAN
7h 43m
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ORF
BOS
Excellent 10.0

Flight attendant Gillian Awesome. Crew was fun and made my kids first flight great.

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

MSP
DSM
Good 6.0

The plane went where it was supposed to go.

DTW
PHL
Excellent 8.0

Made it out of Detroit that same day! Friendly flight attendants!

Flight was delayed. And then cancelled. We were booked into a later flight 8 hours later that was also delayed again due to weather but we did make it out of Detroit that night. Other people were not as lucky.

SLC
MEX
Good 7.0

They hade entertainment

No food

Tue, Jun 19
SAN
MDW
6h 08m
Tue, Jun 26
MDW
SAN
7h 13m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ORF
BOS
Excellent 10.0

Flight attendant Gillian Awesome. Crew was fun and made my kids first flight great.

MSP
LAS
Good 6.6

comfortable seats

delay delay delay

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

ORD
MSP
Okay 4.0

I needed to run real fast to the connection flight and gladly got there on time.

SLC
MEX
Good 7.0

They hade entertainment

No food

Thu, Jul 26
SAN
MDW
10h 15m
Tue, Jul 31
MDW
SAN
7h 23m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
CMH
DTW
Excellent 8.6

Easy to board.

Delayed due to weather.

MSY
JFK
Excellent 10.0

Love the new in-cabin wi-fi, USB charging station, and menu of in-flight entertainment and resources on the individual flatscreens.

SDQ
ATL
Excellent 8.0

Wasted my time on security and lost my flight

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

MSP
DSM
Good 6.0

The plane went where it was supposed to go.

Fri, May 25
SAN
MDW
8h 47m
Tue, May 29
MDW
SAN
7h 20m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSP
DSM
Good 6.0

The plane went where it was supposed to go.

DTW
PHL
Excellent 8.0

Made it out of Detroit that same day! Friendly flight attendants!

Flight was delayed. And then cancelled. We were booked into a later flight 8 hours later that was also delayed again due to weather but we did make it out of Detroit that night. Other people were not as lucky.

MSP
LAS
Good 6.6

comfortable seats

delay delay delay

MSY
JFK
Excellent 10.0

Love the new in-cabin wi-fi, USB charging station, and menu of in-flight entertainment and resources on the individual flatscreens.

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

Thu, Mar 1
SAN
MDW
6h 12m
Mon, Mar 5
MDW
SAN
6h 15m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ORD
MSP
Okay 4.0

I needed to run real fast to the connection flight and gladly got there on time.

ORF
BOS
Excellent 10.0

Flight attendant Gillian Awesome. Crew was fun and made my kids first flight great.

MSY
JFK
Excellent 10.0

Love the new in-cabin wi-fi, USB charging station, and menu of in-flight entertainment and resources on the individual flatscreens.

SDQ
ATL
Excellent 8.0

Wasted my time on security and lost my flight

SLC
MEX
Good 7.0

They hade entertainment

No food

Fri, Mar 23
SAN
MDW
8h 46m
Tue, Mar 27
MDW
SAN
8h 45m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSP
LAS
Good 6.6

comfortable seats

delay delay delay

YUL
MSP
Good 6.0

We got on the plane and it went to where it was supposed to go.

MSY
JFK
Excellent 10.0

Love the new in-cabin wi-fi, USB charging station, and menu of in-flight entertainment and resources on the individual flatscreens.

CMH
DTW
Excellent 8.6

Easy to board.

Delayed due to weather.

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

Fri, Jun 29
SAN
MDW
8h 46m
Sun, Jul 1
MDW
SAN
7h 26m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SDQ
ATL
Excellent 8.0

Wasted my time on security and lost my flight

ORD
MSP
Okay 4.0

I needed to run real fast to the connection flight and gladly got there on time.

SLC
MEX
Good 7.0

They hade entertainment

No food

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

MSP
DSM
Good 6.0

The plane went where it was supposed to go.

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*
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.

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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.

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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.

San Diego to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from San Diego
Flight Price $264
Distance 1725 miles
Airlines Delta