Cheap flights from San Diego (SAN) to Chicago (CHI) from $43

This is the cheapest one-way flight price, found on 9/27. Prices may vary by date and flight preferences.
SAN — CHI
Oct 3 — Oct 101

The best prices from San Diego to Chicago are usually found in January or February, booked 29 days in advance, depart on a Thursday or Wednesday and return on a Tuesday

How to find the cheapest flight from San Diego (SAN) to Chicago (CHI)

All the information you need to plan the best SAN to CHI flight in 2023: compare San Diego to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.

Popular in

June

Cheapest in

January

Round-trip from

$207

One-way from

$68
High demand for flights, 26% potential price rise
Best time to find cheap flights, 22% potential price drop
From San Diego to Chicago (CHI)
One-way flight from San Diego to Chicago (CHI)

SAN - CHI

Price

$207 - $364

CHI

Temperature

23 - 73.4 °F

CHI

Rainfall

1.7 - 4.9 inches

What is the cheapest day to fly round-trip from San Diego to Chicago?

Departing on a Wednesday is a good option for securing a great price. You can expect to save up to 26% when planning your travel around this day of the week.

How far in advance should I book a flight from San Diego to Chicago?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 29 days in advance, which can save you up to 24% on flights from San Diego to Chicago compared to booking the week you need them. Waiting 29 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $465. For sooner than that we have options available in the next 3 days from $563.

What is the cheapest month to fly from San Diego to Chicago?

The best pricing can be found in the month of January. Prices to Chicago from San Diego average $430. You can even find prices in January for less than $430, as users have found deals to Chicago from as low as $168. The month of June appears to be one of the more expensive times to travel to Chicago from San Diego. Flying in the targeted month can save you up to 35%.

When is the cheapest time to fly from San Diego to Chicago (SAN - CHI)?

It’s optimal to fly from San Diego to Chicago in the afternoon. By choosing this option you can save up to 29% on the cost of your flight, compared to a flight in the morning.

Cheap Spirit Airlines flights from San Diego to Chicago

Check out some of the cheapest Spirit Airlines flights we've come across from San Diego to Chicago. Be sure to come back soon if the deals available don't appeal to you at this time.
  • If you’re traveling from San Diego to Chicago, one of the more common airlines traveling that route is Spirit Airlines. San Diego to Chicago flights are typically 23% cheaper than other airlines traveling the same route. Flights from Spirit Airlines typically cost $456.40 RT. The cheapest Spirit Airlines flight found for this route was $222. When traveling from San Diego to Chicago on Spirit Airlines, the most popular airport to depart from is San Diego Airport and the most popular airport to arrive at is Chicago O'Hare Intl Airport. When flying from San Diego to Chicago, Spirit Airlines flights are 13% more popular than any other airline flying that same route.

Cheap Frontier flights from San Diego to Chicago

To aid your search, here are some of the cheapest Frontier flights we've found from San Diego to Chicago. Deals frequently update to provide users with more options.
  • One of the most popular airlines traveling from San Diego to Chicago is Frontier. Flights from Frontier traveling this route typically cost $440.80 RT. This price is typically 19% cheaper than other airlines that offer San Diego to Chicago flights. When booking this route, the cheapest RT price found was $221. San Diego Airport is the most common San Diego airport to take off from when flying to Chicago. Chicago O'Hare Intl Airport is the most popular arrival airport in Chicago. When flying from San Diego to Chicago, Frontier flights are 4% more popular than any other airline flying that same route.

Cheap San Diego to Chicago flights in September & October 2023

The best prices found for SAN to CHI flights for September, October
These are some of the most attractive deals on flights from San Diego to Chicago in 2023. More deals are always being added, so be sure to check back regularly.

San Diego to Chicago 2023 flight deals

Cheap flights to Chicago from San Diego found for this year
These are some of the most attractive deals on flights from San Diego to Chicago in 2023. More deals are always being added, so be sure to check back regularly.

Non-stop flights to Chicago from San Diego

Save time with San Diego to Chicago direct flight deals
To help reduce your travel time, choose from one of these non-stop flights from San Diego to Chicago. Search for alternative flights from San Diego to Chicago by utilizing the search form above.

San Diego to Chicago flights leaving soon

Late deals on return flights to Chicago from San Diego, departing today and this week
Book one of these great deals on flights from San Diego to Chicago. To prevent any unwanted surprises, users should verify their flight info before booking.

One-way flights to Chicago from San Diego

The cheapest one-way flights from San Diego to Chicago
Take a look at some of the best available options we've come across on one-way flights from San Diego to Chicago. Users can also find round-trip San Diego to Chicago flights by using the search form above.

Find flights from San Diego to Chicago within your budget

Use the slider to find flights from San Diego to Chicago that fit your budget.

Fly from

Any airport

Fly to

Any airport

Budget

$85 - $224

Route

Depart

Return

Price

San DiegoChicago Midway

SAN - MDW

SANMDW

San Diego

Sat 11/11

1 stop9h 22m

Chicago Midway

Wed 11/15

1 stop8h 34m

San DiegoChicago O'Hare Intl

SAN - ORD

SANORD

San Diego

Mon 10/30

1 stop13h 27m

Chicago O'Hare Intl

Tue 11/7

1 stop10h 16m

San DiegoChicago Midway

SAN - MDW

SANMDW

San Diego

Sat 12/2

1 stop7h 28m

Chicago Midway

Tue 12/12

1 stop7h 33m

San DiegoChicago Midway

SAN - MDW

SANMDW

San Diego

Sat 10/28

1 stop9h 27m

Chicago Midway

Sat 11/4

1 stop20h 14m

San DiegoChicago O'Hare Intl

SAN - ORD

SANORD

San Diego

Tue 12/5

1 stop14h 22m

Chicago O'Hare Intl

Tue 12/12

1 stop13h 20m

San DiegoChicago Midway

SAN - MDW

SANMDW

San Diego

Tue 11/14

1 stop8h 50m

Chicago Midway

Wed 11/15

2 stops14h 40m

San DiegoChicago O'Hare Intl

SAN - ORD

SANORD

San Diego

Mon 10/30

1 stop13h 27m

Chicago O'Hare Intl

Tue 11/7

2 stops10h 13m

San DiegoChicago O'Hare Intl

SAN - ORD

SANORD

San Diego

Tue 12/5

1 stop12h 30m

Chicago O'Hare Intl

Sat 12/9

2 stops11h 26m

San DiegoChicago O'Hare Intl

SAN - ORD

SANORD

San Diego

Sat 11/11

Nonstop4h 08m

Chicago O'Hare Intl

Wed 11/15

Nonstop4h 19m

Flights are sorted by cheapest first

Deals found on 9/27

Reviews of airlines servicing Chicago

To help decide which airline to fly from San Diego to Chicago, see what other customers have to say about Spirit Airlines, Frontier and American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.1
Very good
1,394 reviews

Entertainment

7.2

Food

7.2

Comfort

8.0

Overall

8.1

Boarding

8.3

Crew

8.6

Reviews

1 / 10

I appreciated that we departed & arrived on time. I was very cold on the plane, despite wearing 2 jackets, & will bring a blanket next time. I appreciated the hot tea & cookie I was served. I also appreciated that our luggage was not lost or damaged.

Alaska Airlines
8.1
Very good
1,394 reviews
Alaska Airlines
8.1
Very good
1,394 reviews

Entertainment

7.2

Food

7.2

Comfort

8.0

Overall

8.1

Boarding

8.3

Crew

8.6

Reviews

1 / 10

I appreciated that we departed & arrived on time. I was very cold on the plane, despite wearing 2 jackets, & will bring a blanket next time. I appreciated the hot tea & cookie I was served. I also appreciated that our luggage was not lost or damaged.

Delta
7.9
Good
3,023 reviews
Alaska Airlines
8.1
Very good
1,394 reviews

Entertainment

7.2

Food

7.2

Comfort

8.0

Overall

8.1

Boarding

8.3

Crew

8.6

Reviews

1 / 10

I appreciated that we departed & arrived on time. I was very cold on the plane, despite wearing 2 jackets, & will bring a blanket next time. I appreciated the hot tea & cookie I was served. I also appreciated that our luggage was not lost or damaged.

Southwest
7.6
Good
1,521 reviews
Alaska Airlines
8.1
Very good
1,394 reviews

Entertainment

7.2

Food

7.2

Comfort

8.0

Overall

8.1

Boarding

8.3

Crew

8.6

Reviews

1 / 10

I appreciated that we departed & arrived on time. I was very cold on the plane, despite wearing 2 jackets, & will bring a blanket next time. I appreciated the hot tea & cookie I was served. I also appreciated that our luggage was not lost or damaged.

LATAM Airlines
7.5
Good
448 reviews
Alaska Airlines
8.1
Very good
1,394 reviews

Entertainment

7.2

Food

7.2

Comfort

8.0

Overall

8.1

Boarding

8.3

Crew

8.6

Reviews

1 / 10

I appreciated that we departed & arrived on time. I was very cold on the plane, despite wearing 2 jackets, & will bring a blanket next time. I appreciated the hot tea & cookie I was served. I also appreciated that our luggage was not lost or damaged.

Allegiant Air
7.5
Good
103 reviews
Alaska Airlines
8.1
Very good
1,394 reviews

Entertainment

7.2

Food

7.2

Comfort

8.0

Overall

8.1

Boarding

8.3

Crew

8.6

Reviews

1 / 10

I appreciated that we departed & arrived on time. I was very cold on the plane, despite wearing 2 jackets, & will bring a blanket next time. I appreciated the hot tea & cookie I was served. I also appreciated that our luggage was not lost or damaged.

Related info for your journey

Useful info, stats and facts about San Diego to Chicago flights.

What airport do you fly from for flights from San Diego to Chicago?

If you book a flight to Chicago from San Diego, you will be flying from San Diego, which is the city’s only airport. San Diego (SAN) is located 2.6 mi from the center of San Diego. There are 29 flights from San Diego to Chicago per day from 6 different airlines.

Can I find flights from San Diego to Chicago for under $100 on Cheapflights?

Yes, there are multiple flights from San Diego to Chicago for under $100. The cheapest flight booked recently is on Frontier for just $85, but on average you can expect to pay $103.

Are there nonstop flights from San Diego to Chicago for under $300 on Cheapflights?

Cheapflights has at least 20 direct flights from San Diego to Chicago under $300. A good price for a nonstop flight from San Diego to Chicago is less than $310.

Are there last-minute flights available from San Diego to Chicago for under $200?

There are currently 20+ open flights from San Diego to Chicago within the next 7 days for less than $200.

What days are nonstop flights available from San Diego to Chicago?

Nonstop flights are available for this route on the following days: Sunday, Monday, Tuesday, Thursday, Friday, Saturday.

How many flights depart from San Diego to Chicago on average per day?

38 flight departures from San Diego to Chicago per day on average.
Early Morning (Midnight to 6am) - 11% of flight departures
Morning (6am - Noon) - 45% of flight departures
Afternoon (Noon - 6pm) - 29% of flight departures
Evening (6pm - Midnight) - 16% of flight departures

How long is the flight from San Diego to Chicago?

Airlines like Frontier and Spirit Airlines fly from San Diego to Chicago in about 9h 22m. The time it takes to get you to your destination can typically vary by up to 5h. Airlines will cover a distance of 1729 mi. Both multi-stop and nonstop flights can be found to your destination and back.

What are the cheapest airlines flying from San Diego to Chicago round-trip?

Frontier, at $85, was found to be the cheapest airline from San Diego to Chicago. An alternate airline flying to your destination would be Spirit Airlines. You may be able to fly from San Diego to Chicago for 80% less than the average price by searching for these airlines.

What are the most popular routes from San Diego to Chicago?

What are the most popular airlines that fly from San Diego to Chicago?

What are the most reliable airlines from San Diego to Chicago?

Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from San Diego to Chicago on time: Japan Airlines (96%), Austrian Airlines (93%), SWISS (88%).

What are the cheapest flights from San Diego to Chicago?

On average you can expect to pay $953 for a flight from San Diego to Chicago. The cheapest flight overall is $130 while the most popular route, (San Diego - Chicago O'Hare Intl) is currently priced at $110.

What does SAN to ORD mean?

Great question - SAN to ORD just means San Diego Airport to Chicago O'Hare Intl Airport. Now you’ll know what these unique codes when you look for flights! Ready for more IATA code knowledge? These are related airports for your current travel destination: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

Top 6 airlines flying from San Diego to Chicago

The chart below displays the airlines Cheapflights users traveling from San Diego to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$89Average$203FlexibilityNo cancel feeOn-time62%
Search Frontier flights
Spirit AirlinesCheapest$115Average$227FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights
United AirlinesCheapest$221Average$441FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Alaska AirlinesCheapest$222Average$456FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights
DeltaCheapest$240Average$503FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
American AirlinesCheapest$242Average$452FlexibilityNo cancel feeOn-time71%
Search American Airlines flights

Hourly flight availability from San Diego to Chicago

See what time of day planes typically take off from San Diego to Chicago
49%of flight departuresEarly morningMidnight to 6 am
25%of flight departuresMorning6 am to noon
23%of flight departuresAfternoonNoon to 6 pm
3%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from San Diego to Chicago

See how many times per day planes take to the skies headed from San Diego to Chicago
Sunday31daily flights
Monday32daily flights
Tuesday27daily flights
Wednesday25daily flights
Thursday31daily flights
Friday32daily flights
Saturday25daily flights

Fly with Cheapflights

What makes Cheapflights the go-to destination for all your flight needs

How does Cheapflights help users find flights from San Diego to Chicago?

When you search for this flight from San Diego to Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from San Diego to Chicago?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from San Diego to Chicago.

Can Cheapflights find flights from San Diego to Chicago with no change fees?

Yes! Cheapflights helps users easily find flights from San Diego to Chicago with no change fees.

Can Cheapflights notify me if prices for flights from San Diego to Chicago become cheaper?

Yes! Start tracking prices for San Diego to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, navigate to the search form above to perform a search, which will then prompt you for a valid email address to use the tool.

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