Find Cheap Flights from San Diego to Chicago O'Hare International (SAN - ORD)

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Wed 11/22
Wed 11/29
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Good to Know

Low Season:
September
Best time to beat the crowds
2%
expected price decrease
High Season:
March
Most popular time to fly
1%
expected price increase
Average Price:
$1003
(avg. price over the last 2 weeks)
Good Deal:
$600
or less (round trip)

When to Book Flights from San Diego to Chicago O'Hare International

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

Top tips for Finding a Cheap Flight

The cheapest flight from San Diego to Chicago O'Hare International was found 24 days before departure, on average.
Book at least 1 week before departure in order to get a below-average price.
High season is considered to be February, March and April. The cheapest month to fly is September.
Morning departure is around 27% 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 O'Hare International Flights

How long does a flight from San Diego to Chicago O'Hare International take?
An average nonstop flight takes 4h 01m, covering a distance of 1720 miles.
How many flights are there between San Diego and Chicago O'Hare International?
There are 614 (nonstop) flights between San Diego and Chicago O'Hare International per week, averaging 91 per day.
Which airlines provide the cheapest flights from San Diego to Chicago O'Hare International?
In the past 3 days, the cheapest round-trip tickets were found on United ($99), American Airlines ($109) and Spirit Airlines ($113).
Do I need a passport to fly between San Diego and Chicago O'Hare International?
No.
Which airlines fly most frequently between San Diego and Chicago O'Hare International?
Air Canada (12 times daily), United (11 times daily), Alaska 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 O'Hare International?
For San Diego to Chicago O'Hare International, Tuesday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Chicago O'Hare International back to San Diego, the best deals are generally found on Saturday, with Friday being the most expensive.

Book cheap flights from San Diego to Chicago O'Hare International (round-trip)

Airports
Origin
San Diego
$99
only
$99
Destination
Chicago
$99
only
$99
Tue, Jan 30
SAN
ORD
4h 07m
Sat, Feb 3
ORD
SAN
4h 28m
Trip: 5 days
7.5GoodShow reviews
Overall 7.5 Good
Based on 88 reviews
Overall
7.2
Boarding
7.3
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
SAN
ORD
Excellent 10.0

The coffee. Everything else very good.

SAN
ORD
Good 6.0

I had charged 300$ for my extra luggage this morning at the checking ....it never happened to me before usually I paid 100$ but never that much... I will never ever flight with United again for sure.

SAN
ORD
Mediocre 2.0

they canceled the flight and put us on american airlines wich was terrible

SAN
ORD
Excellent 8.0

Got in early, but unfortunately no gate to unload passengers for almost 20 mins

Stewardess told me I had to use overhead bin for my personal item. Personal item met requirements with ease. Did not listen to this woman's command.

SAN
ORD
Excellent 8.3

Seat area had a good deal of trash around it and in the seat back pocket

Sat, Dec 2
SAN
ORD
4h 03m
Tue, Dec 12
ORD
SAN
4h 27m
Trip: 11 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 38 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
SAN
ORD
Excellent 8.3

Nice crew.

We didn't take off on time so I was in anxiety about catching my next flight out of ORD.

SAN
ORD
Excellent 8.6

We have American Credit Card we thought we were told we would be in Group 1 NOT Group 5!

SAN
ORD
Excellent 10.0

Smooth flight- communication from the pilot, free beverage, movies, what more could a person ask for

No leg room.

SAN
ORD
Excellent 9.0

Service in coach was nice and attentive.

SAN
ORD
Excellent 8.0

The flight from San Diego to Chicago went well. We left on time and arrived a little earlier than expected. I was worried about the weather delaying our flight once we go to Chicago but we encounter different problems. as I will explain next.

Mon, Dec 11
SAN
ORD
4h 01m
Wed, Dec 13
ORD
SAN
4h 35m
Trip: 3 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 199 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
Excellent 10.0

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

SAN
ORD
Mediocre 2.0

Nothing

Everything

SAN
ORD
Excellent 10.0

See above also left on time no delays

It was fine

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, Feb 13
SAN
ORD
11h 06m
Sat, Feb 17
ORD
SAN
4h 27m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Feb 28
SAN
ORD
4h 04m
Tue, Mar 6
ORD
SAN
4h 27m
Trip: 7 days
7.5GoodShow reviews
Overall 7.5 Good
Based on 88 reviews
Overall
7.2
Boarding
7.3
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
SAN
ORD
Excellent 8.0

Got in early, but unfortunately no gate to unload passengers for almost 20 mins

Stewardess told me I had to use overhead bin for my personal item. Personal item met requirements with ease. Did not listen to this woman's command.

SAN
ORD
Excellent 9.0

Every thing the best company ever

Just make the price $10 more dollars per ticket and give free wifi. Thanks

SAN
ORD
Excellent 10.0

Everything was perfect.

SAN
ORD
Mediocre 2.0

Flight was delayed until the next morning because of weather

SAN
ORD
Excellent 8.3

Seat area had a good deal of trash around it and in the seat back pocket

Thu, Jan 11
SAN
ORD
4h 06m
Thu, Jan 18
ORD
SAN
4h 35m
Trip: 8 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 199 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
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

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
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.

Wed, Nov 29
SAN
ORD
4h 01m
Wed, Dec 6
ORD
SAN
4h 35m
Trip: 8 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 199 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
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

Everything

SAN
ORD
Excellent 10.0

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

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.

Sat, Dec 2
SAN
ORD
4h 01m
Wed, Dec 6
ORD
SAN
4h 35m
Trip: 5 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 199 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
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

Very bad service another company's it's butter

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

Thu, Feb 15
SAN
ORD
4h 05m
Sun, Feb 25
ORD
SAN
4h 27m
Trip: 11 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Mar 2
SAN
ORD
4h 04m
Sun, Mar 4
ORD
SAN
4h 27m
Trip: 3 days
7.5GoodShow reviews
Overall 7.5 Good
Based on 88 reviews
Overall
7.2
Boarding
7.3
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
SAN
ORD
Mediocre 2.0

they canceled the flight and put us on american airlines wich was terrible

SAN
ORD
Okay 4.6

United and SAS are really separate and hard to manage reservation. Seats changed from what I purchased and it was uncomfortable. I don't think I will do a mixed airline flight again even though they quote them as a Star Aliance. Also, flying through Chicago ORD is not great. The international terminal is completely separate so you have to take a train, pour out water, enter security (and they don't have a TSA Pre). All around uggh.

SAN
ORD
Mediocre 2.0

Flight was delayed until the next morning because of weather

SAN
ORD
Excellent 10.0

The coffee. Everything else very good.

SAN
ORD
Excellent 8.3

Seat area had a good deal of trash around it and in the seat back pocket

Sat, Mar 24
SAN
ORD
21h 40m
Sun, Apr 8
ORD
SAN
14h 53m
Trip: 16 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 32989 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
CVG
MCO
Okay 4.0

It got me where I needed to go, albeit with a little effort and stress. Crew was pleasant. Thank you.

6 people overbooked, who might not have gotten seats. I was one of them. I recognize there was nothing I could have done either way but it was unpleasant to hear I might not get a seat on a flight I bought a ticket to a month ago, regardless of the price. And the return flight was dismal. Had to wait an extra 3 hours for maintanence on the plane (fine, would rather it get fixed than have an issue in the air) but we were told there would be vouchers worth some amount sent to our email after we landed back in cincinnati. It's been 3 days and I have received no such vouchers. It also turns out I payed $45 for a personal bag that was I guess covered under a personal bag? I recognize this as being partly my fault, but when I went to get my ticket "personal bag" wasn't an option, so I didn't think I had one, or my single backpack actually was $45 to take with me. Was not a terrible experience. Just not a good one.

ATL
LAS
Excellent 8.5

The crew is really nice, attentive, and it's not hard to get their attention. They also don't bother you when you sleep and are overall quiet and courteous.

Not knowing how long until we land. A quick "1 hour till arrival . . . 30min..." would have been appreciated.

SFO
ATL
Okay 5.3

The price of the flight was great, but even with an upgraded seat I will not be flying Frontier again.

I upgraded my girlfriend and I to stretch seating for our 5 hour flights roundtrip from ATL to SFO. I did not realize by upgrading and selecting my seat in row 4 that my seats do not recline. This caused several issues with my bad back and with the fold down tray on the seat in front of me. I had my laptop on the tray, and when the person in front of me leaned his seat back all the way suddenly, it pinched the top of the screen between the tray and the back of his seat and cracked my laptop exterior. The main issue was not being able to "stretch" by not having a reclining seat and experienced major discomfort and back pain both flights.

PSP
DEN
Mediocre 3.3

My flight crew. Received call concerning my bag in Atlanta, although I was still in Denver.

Long line to check in, anxiety about missing flight Had to pay for my carry on Missed my connecting flight, announcements were not clear Was told I to pay a rebooking fee for a flight two days later Frontier does not offer stand by Spent $285 with another airline to get to Atlanta on time

DEN
ATL
Mediocre 2.0

I did not make the flight due to unclear announcements.

Fri, Dec 8
SAN
ORD
4h 01m
Mon, Dec 11
ORD
SAN
4h 35m
Trip: 4 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 199 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
SAN
ORD
Mediocre 3.3

The delayed flight ruined any positive feedback

Flight was delayed by 2 hours The seats couldn't be adjusted no television

SAN
ORD
Excellent 10.0

See above also left on time no delays

It was fine

SAN
ORD
Mediocre 2.0

Very bad service another company's it's butter

SAN
ORD
Okay 4.0

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

SAN
ORD
Mediocre 2.0

Nothing

Everything

Thu, Nov 30
SAN
ORD
4h 01m
Mon, Dec 4
ORD
SAN
4h 35m
Trip: 5 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 199 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
Okay 4.0

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

SAN
ORD
Excellent 10.0

See above also left on time no delays

It was fine

SAN
ORD
Excellent 10.0

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

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.

Thu, Mar 1
SAN
ORD
4h 05m
Sun, Mar 4
ORD
SAN
4h 28m
Trip: 4 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 199 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 2.0

Nothing

Everything

SAN
ORD
Mediocre 3.3

The delayed flight ruined any positive feedback

Flight was delayed by 2 hours The seats couldn't be adjusted no television

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
Okay 4.0

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

Thu, Apr 5
SAN
ORD
4h 05m
Mon, Apr 9
ORD
SAN
4h 28m
Trip: 5 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 199 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

Everything

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

See above also left on time no delays

It was fine

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.

Wed, Apr 11
SAN
ORD
4h 05m
Sun, Apr 15
ORD
SAN
4h 15m
Trip: 5 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 199 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 4.0

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

SAN
ORD
Mediocre 3.3

The delayed flight ruined any positive feedback

Flight was delayed by 2 hours The seats couldn't be adjusted no television

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.

Fri, May 4
SAN
ORD
4h 12m
Mon, May 7
ORD
SAN
4h 15m
Trip: 4 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 199 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
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 2.0

Very bad service another company's it's butter

SAN
ORD
Mediocre 3.3

The delayed flight ruined any positive feedback

Flight was delayed by 2 hours The seats couldn't be adjusted no television

SAN
ORD
Mediocre 2.0

Nothing

Everything

Wed, Mar 28
SAN
ORD
4h 05m
Sun, Apr 1
ORD
SAN
4h 28m
Trip: 5 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 199 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
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 2.6

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 4.6

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

Thu, Nov 23
SAN
ORD
5h 49m
Sun, Nov 26
ORD
SAN
4h 27m
Trip: 4 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 38 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
SAN
ORD
Mediocre 2.0

Nothing

The customer service and the lack of assistance from the airline ground staff was horrible .

SAN
ORD
Excellent 8.3

Nice crew.

We didn't take off on time so I was in anxiety about catching my next flight out of ORD.

SAN
ORD
Okay 4.3

Thank god for the classical music station channel 1. Flight going back was better in comfort, space and entertainment options. But still will choose airline more carefully the next time I fly.

Plane was small and tight. Didn't have room for small duffle bag but accepted putting under my seat, even though I don't understand people trying to get on with two bags. Wifi not free in airport and didn't work. Wifi also not free on plane. Movie was nothing i wanted to see.

SAN
ORD
Excellent 8.6

We have American Credit Card we thought we were told we would be in Group 1 NOT Group 5!

SAN
ORD
Excellent 8.0

Overall, I'm pleased with BA.

This flight didn't have the individual TV screens.

Thu, May 24
SAN
ORD
4h 12m
Sun, May 27
ORD
SAN
4h 15m
Trip: 4 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 199 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
Okay 4.0

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

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
Excellent 10.0

See above also left on time no delays

It was fine

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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.