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

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Sat 12/16
Sat 12/23
Any month
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Good to Know

Low Season:
September
Best time to beat the crowds
2%
expected price decrease
High Season:
June
Most popular time to fly
13%
expected price increase
Average Price:
$321
(avg. price over the last 2 weeks)
Good Deal:
$207
or less (round trip)

When to Book Flights from San Diego to Chicago

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 $207 or less.
The cheapest flight from San Diego to Chicago was found 42 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 May, June and July. The cheapest month to fly is September.
Morning departure is around 20% cheaper 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 Flights

How long does a flight from San Diego to Chicago take?
An average nonstop flight takes 3h 55m, covering a distance of 1732 miles.
How many flights are there between San Diego and Chicago?
There are 695 (nonstop) flights between San Diego and Chicago per week, averaging 103 per day.
Which airlines provide the cheapest flights from San Diego to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on Spirit Airlines ($99) and Multiple Airlines ($113)
Do I need a passport to fly between San Diego and Chicago?
No.
Which airlines fly most frequently between San Diego and Chicago?
Air Canada (13 times daily), United (9 times daily), American Airlines (8 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly San Diego to Chicago?
For San Diego to Chicago, Tuesday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Chicago back to San Diego, the best deals are generally found on Tuesday, with Saturday being the most expensive.

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

Airports
Origin
San Diego
$99
only
$99
Destination
Chicago
$99
only
$99
Tue, Jan 23
SAN
ORD
4h 06m
Sat, Jan 27
ORD
SAN
4h 35m
Trip: 5 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 201 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
SAN
ORD
Excellent 10.0

Smooth flight. Best landing I ever experienced. Great crew!

SAN
ORD
Okay 4.6

The crew at the check-in in San Diego was terrific!! Super friendly and great customer service.

Flight delayed by two hours but still told to show up at airport two hours prior to original departure in case it changes. This is unheard of, same thing happened to one of my kids on a different trip, and I will not fly Spirit again.

SAN
ORD
Okay 4.0

They nickel and dime you on seats, bagage and other fees.

SAN
ORD
Mediocre 3.6

i like that they boarded us easily on the plane

not roomy no entertainment no wifi croweded in our row lil snack slection hot on the plane little tray hate the baggage fee

SAN
ORD
Excellent 8.4

My flight included 2 unaccompanied minors. I sat in the rear of the plane near them. There were two female flight attendants who were so great with the kids. I felt they really went beyond what was required to entertain and engage the kids. I was impressed.

Tue, Jan 9
SAN
ORD
4h 07m
Sat, Jan 20
ORD
SAN
15h 04m
Trip: 12 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Jan 27
SAN
ORD
4h 06m
Tue, Jan 30
ORD
SAN
4h 35m
Trip: 4 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 201 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
SAN
ORD
Mediocre 2.0

Very bad service another company's it's butter

SAN
ORD
Mediocre 2.6

nothing

The crew was inconsiderate and rude. They were carrying on loudly and woke me up and when I asked them to be quiet - I and another passenger were sleeping - they said too bad, they could talk if they wanted to.

SAN
ORD
Okay 4.3

Low ticket price

to check in one bag it was $52. My seat was all the way in the back next to the bathrooms.

SAN
ORD
Mediocre 2.0

We left over two hours late due to a "missing tool", and once we arrived in Chicago we sat on the plane for another HOUR before we could get to our gate. During this time, not even a free glass of water was offered. Such a waste of my time. I won't be flying Spirit again!

SAN
ORD
Okay 4.6

The crew at the check-in in San Diego was terrific!! Super friendly and great customer service.

Flight delayed by two hours but still told to show up at airport two hours prior to original departure in case it changes. This is unheard of, same thing happened to one of my kids on a different trip, and I will not fly Spirit again.

Tue, Jan 30
SAN
ORD
4h 06m
Sat, Feb 3
ORD
SAN
4h 35m
Trip: 5 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 201 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
SAN
ORD
Okay 4.6

The crew at the check-in in San Diego was terrific!! Super friendly and great customer service.

Flight delayed by two hours but still told to show up at airport two hours prior to original departure in case it changes. This is unheard of, same thing happened to one of my kids on a different trip, and I will not fly Spirit again.

SAN
ORD
Excellent 10.0

Smooth flight. Best landing I ever experienced. Great crew!

SAN
ORD
Excellent 10.0

See above also left on time no delays

It was fine

SAN
ORD
Okay 4.3

Low ticket price

to check in one bag it was $52. My seat was all the way in the back next to the bathrooms.

SAN
ORD
Mediocre 2.0

Very bad service another company's it's butter

Wed, Jan 17
SAN
ORD
8h 32m
Wed, Jan 24
ORD
SAN
15h 04m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jan 9
SAN
ORD
3h 55m
Wed, Jan 17
ORD
SAN
4h 35m
Trip: 9 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 201 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
SAN
ORD
Okay 4.3

Low ticket price

to check in one bag it was $52. My seat was all the way in the back next to the bathrooms.

SAN
ORD
Mediocre 2.0

Very bad service another company's it's butter

SAN
ORD
Mediocre 2.0

Nothing

Everything

SAN
ORD
Okay 4.0

They nickel and dime you on seats, bagage and other fees.

SAN
ORD
Mediocre 2.6

nothing

The crew was inconsiderate and rude. They were carrying on loudly and woke me up and when I asked them to be quiet - I and another passenger were sleeping - they said too bad, they could talk if they wanted to.

Wed, Jan 17
SAN
ORD
6h 25m
Sat, Jan 20
ORD
SAN
15h 04m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jan 10
SAN
ORD
3h 55m
Wed, Jan 17
ORD
SAN
4h 35m
Trip: 8 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 201 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
SAN
ORD
Excellent 10.0

Smooth flight. Best landing I ever experienced. Great crew!

SAN
ORD
Mediocre 2.0

Very bad service another company's it's butter

SAN
ORD
Mediocre 2.0

We left over two hours late due to a "missing tool", and once we arrived in Chicago we sat on the plane for another HOUR before we could get to our gate. During this time, not even a free glass of water was offered. Such a waste of my time. I won't be flying Spirit again!

SAN
ORD
Mediocre 2.0

Nothing

They were late for every flight. I paid to change to an earlier flight home and it was delayed so long that I got home around the same time. When I called customer service they were very unhelpful, I will never fly this airline again.

SAN
ORD
Mediocre 2.0

Nothing

Everything

Tue, Feb 6
SAN
ORD
11h 06m
Tue, Feb 13
ORD
SAN
7h 48m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jan 17
SAN
ORD
4h 06m
Wed, Jan 24
ORD
SAN
4h 35m
Trip: 8 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 201 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
SAN
ORD
Mediocre 2.0

We left over two hours late due to a "missing tool", and once we arrived in Chicago we sat on the plane for another HOUR before we could get to our gate. During this time, not even a free glass of water was offered. Such a waste of my time. I won't be flying Spirit again!

SAN
ORD
Okay 4.3

Low ticket price

to check in one bag it was $52. My seat was all the way in the back next to the bathrooms.

SAN
ORD
Mediocre 2.0

Nothing

They were late for every flight. I paid to change to an earlier flight home and it was delayed so long that I got home around the same time. When I called customer service they were very unhelpful, I will never fly this airline again.

SAN
ORD
Mediocre 3.6

i like that they boarded us easily on the plane

not roomy no entertainment no wifi croweded in our row lil snack slection hot on the plane little tray hate the baggage fee

SAN
ORD
Mediocre 2.0

Very bad service another company's it's butter

Wed, Feb 14
SAN
ORD
11h 06m
Wed, Feb 21
ORD
SAN
8h 18m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jan 23
SAN
ORD
4h 06m
Wed, Jan 31
ORD
SAN
4h 35m
Trip: 9 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 201 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
SAN
ORD
Okay 4.6

The crew at the check-in in San Diego was terrific!! Super friendly and great customer service.

Flight delayed by two hours but still told to show up at airport two hours prior to original departure in case it changes. This is unheard of, same thing happened to one of my kids on a different trip, and I will not fly Spirit again.

SAN
ORD
Mediocre 2.0

Nothing

They were late for every flight. I paid to change to an earlier flight home and it was delayed so long that I got home around the same time. When I called customer service they were very unhelpful, I will never fly this airline again.

SAN
ORD
Excellent 10.0

Smooth flight. Best landing I ever experienced. Great crew!

SAN
ORD
Excellent 10.0

See above also left on time no delays

It was fine

SAN
ORD
Mediocre 3.6

i like that they boarded us easily on the plane

not roomy no entertainment no wifi croweded in our row lil snack slection hot on the plane little tray hate the baggage fee

Wed, Feb 21
SAN
ORD
11h 06m
Wed, Feb 28
ORD
SAN
8h 39m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jan 24
SAN
ORD
4h 06m
Wed, Jan 31
ORD
SAN
4h 35m
Trip: 8 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 201 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
SAN
ORD
Excellent 10.0

Smooth flight. Best landing I ever experienced. Great crew!

SAN
ORD
Okay 4.6

The crew at the check-in in San Diego was terrific!! Super friendly and great customer service.

Flight delayed by two hours but still told to show up at airport two hours prior to original departure in case it changes. This is unheard of, same thing happened to one of my kids on a different trip, and I will not fly Spirit again.

SAN
ORD
Mediocre 2.0

Nothing

They were late for every flight. I paid to change to an earlier flight home and it was delayed so long that I got home around the same time. When I called customer service they were very unhelpful, I will never fly this airline again.

SAN
ORD
Mediocre 2.6

nothing

The crew was inconsiderate and rude. They were carrying on loudly and woke me up and when I asked them to be quiet - I and another passenger were sleeping - they said too bad, they could talk if they wanted to.

SAN
ORD
Mediocre 3.6

i like that they boarded us easily on the plane

not roomy no entertainment no wifi croweded in our row lil snack slection hot on the plane little tray hate the baggage fee

Tue, Feb 6
SAN
ORD
4h 06m
Tue, Feb 13
ORD
SAN
15h 04m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jan 24
SAN
ORD
4h 06m
Wed, Jan 31
ORD
SAN
4h 35m
Trip: 8 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 201 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
SAN
ORD
Mediocre 3.6

i like that they boarded us easily on the plane

not roomy no entertainment no wifi croweded in our row lil snack slection hot on the plane little tray hate the baggage fee

SAN
ORD
Okay 4.3

Low ticket price

to check in one bag it was $52. My seat was all the way in the back next to the bathrooms.

SAN
ORD
Mediocre 2.0

Nothing

Everything

SAN
ORD
Mediocre 2.0

Very bad service another company's it's butter

SAN
ORD
Mediocre 2.0

Nothing

They were late for every flight. I paid to change to an earlier flight home and it was delayed so long that I got home around the same time. When I called customer service they were very unhelpful, I will never fly this airline again.

Tue, Jan 9
SAN
ORD
21h 49m
Tue, Jan 16
ORD
SAN
4h 35m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jan 30
SAN
ORD
4h 06m
Wed, Feb 7
ORD
SAN
4h 35m
Trip: 9 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 201 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
SAN
ORD
Okay 4.6

The crew at the check-in in San Diego was terrific!! Super friendly and great customer service.

Flight delayed by two hours but still told to show up at airport two hours prior to original departure in case it changes. This is unheard of, same thing happened to one of my kids on a different trip, and I will not fly Spirit again.

SAN
ORD
Excellent 10.0

See above also left on time no delays

It was fine

SAN
ORD
Mediocre 2.0

Nothing

They were late for every flight. I paid to change to an earlier flight home and it was delayed so long that I got home around the same time. When I called customer service they were very unhelpful, I will never fly this airline again.

SAN
ORD
Mediocre 2.0

Nothing

Everything

SAN
ORD
Mediocre 2.0

We left over two hours late due to a "missing tool", and once we arrived in Chicago we sat on the plane for another HOUR before we could get to our gate. During this time, not even a free glass of water was offered. Such a waste of my time. I won't be flying Spirit again!

Wed, Jan 10
SAN
ORD
3h 55m
Wed, Jan 17
ORD
SAN
15h 04m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jan 31
SAN
ORD
4h 06m
Wed, Feb 7
ORD
SAN
4h 35m
Trip: 8 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 201 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
SAN
ORD
Okay 4.3

Low ticket price

to check in one bag it was $52. My seat was all the way in the back next to the bathrooms.

SAN
ORD
Mediocre 2.0

We left over two hours late due to a "missing tool", and once we arrived in Chicago we sat on the plane for another HOUR before we could get to our gate. During this time, not even a free glass of water was offered. Such a waste of my time. I won't be flying Spirit again!

SAN
ORD
Mediocre 2.0

Nothing

They were late for every flight. I paid to change to an earlier flight home and it was delayed so long that I got home around the same time. When I called customer service they were very unhelpful, I will never fly this airline again.

SAN
ORD
Excellent 8.4

My flight included 2 unaccompanied minors. I sat in the rear of the plane near them. There were two female flight attendants who were so great with the kids. I felt they really went beyond what was required to entertain and engage the kids. I was impressed.

SAN
ORD
Mediocre 2.0

Very bad service another company's it's butter

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.

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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.