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$77+ Cheap flights from San Diego (SAN) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from San Diego to Chicago are usually found in August or September, booked 49 days in advance, depart on a Wednesday or Thursday and return on a Thursday

Cheap flight deals from San Diego to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from San Diego (SAN) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 15, 2025.

Round-trip from

$141
(Southwest)

One-way from

$77
(Alaska Airlines)

Popular in

December

Cheapest in

August

Average price

$257

Good round-trip deal

$205 or less

Good one-way deal

$145 or less
From San Diego to Chicago (CHI)
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One-way flight from San Diego to Chicago (CHI)
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Highest demand for flights based on searches. 16% potential increase in price ($67 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from San Diego to Chicago (CHI).
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Price to beat on a one-way flight from San Diego to Chicago (CHI).
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Find flight deals from San Diego to Chicago

Cheapest flights from San Diego to Chicago
Explore the most affordable flight options available from San Diego to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/231:35 pmSAN - ORD
1 stop6h 45mSouthwest
Wed 10/295:25 pmORD - SAN
1 stop6h 00mSouthwest
Deal found 9/12$141
This KAYAK deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/45:19 pmSAN - ORD
Nonstop4h 40mAlaska Airlines
Tue 10/147:59 pmORD - SAN
Nonstop5h 00mAlaska Airlines
Deal found 9/12$145
This Southwest deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2311:05 amSAN - MDW
1 stop6h 30mSouthwest
Wed 10/297:00 pmMDW - SAN
1 stop6h 20mSouthwest
Deal found 9/12$145
This Trip.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/185:19 pmSAN - ORD
Nonstop4h 40mHawaiian Airlines
Sat 10/2510:00 amORD - SAN
Nonstop5h 00mHawaiian Airlines
Deal found 9/13$146
This SmartFares deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/45:19 pmSAN - ORD
Nonstop4h 40mHawaiian Airlines
Tue 10/77:59 pmORD - SAN
Nonstop5h 00mHawaiian Airlines
Deal found 9/12$147
This eDestinos deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3112:34 pmSAN - ORD
1 stop10h 41mFrontier
Mon 11/36:00 amORD - SAN
1 stop7h 17mFrontier
Deal found 9/14$150
This Hawaiian Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2112:20 pmSAN - ORD
Nonstop4h 39mHawaiian Airlines
Wed 10/227:59 pmORD - SAN
Nonstop5h 00mHawaiian Airlines
Deal found 9/15$153
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/296:30 amSAN - MDW
Nonstop4h 05mSouthwest
Sat 11/11:50 pmMDW - SAN
Nonstop4h 15mSouthwest
Deal found 9/13$153
This Priceline deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/139:14 amSAN - MDW
1 stop6h 08mFrontier
Sat 11/152:57 pmMDW - SAN
1 stop7h 27mFrontier
Deal found 9/13$154
This Gotogate deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/187:00 amSAN - ORD
1 stop24h 36mFrontier
Sat 10/257:05 amORD - SAN
1 stop28h 52mFrontier
Deal found 9/13$155
This Trip.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/292:24 pmSAN - ORD
1 stop7h 48mMultiple Airlines
Sat 11/19:20 amORD - SAN
Nonstop4h 25mMultiple Airlines
Deal found 9/14$156
This Trip.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/292:24 pmSAN - ORD
1 stop7h 48mMultiple Airlines
Wed 11/59:20 amORD - SAN
Nonstop4h 25mMultiple Airlines
Deal found 9/14$157

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Diego to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
Use the filters below to find and compare flights from San Diego to Chicago that are best for you.

Fly from

San Diego

Fly to

Chicago

Route

Depart

Return

Price

San DiegoChicago

SAN - ORD

SANORD

San Diego

Wed 11/5

1:41 pm-7:55 pm

Nonstop4h 14m

Chicago O'Hare Intl

Tue 11/11

8:59 pm-11:19 pm

Nonstop4h 20m

$153

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Wed 11/12

5:00 pm-10:55 pm

Nonstop3h 55m

Chicago Midway

Sat 11/15

7:30 pm-9:50 pm

Nonstop4h 20m

$153

San DiegoChicago

SAN - ORD

SANORD

San Diego

Sat 10/18

5:19 pm-11:59 pm

Nonstop4h 40m

Chicago O'Hare Intl

Wed 10/22

8:20 am-11:20 am

Nonstop5h 00m

$165

San DiegoChicago

SAN - ORD

SANORD

San Diego

Wed 11/12

2:50 pm-10:35 pm

1 stop5h 45m

Chicago O'Hare Intl

Sat 11/15

2:15 pm-9:45 pm

2 stops9h 30m

$168

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Thu 11/13

11:10 am-6:30 pm

1 stop5h 20m

Chicago Midway

Sun 11/16

7:45 am-10:10 am

Nonstop4h 25m

$169

San DiegoChicago

SAN - ORD

SANORD

San Diego

Wed 10/8

8:10 am-2:50 pm

Nonstop4h 40m

Chicago O'Hare Intl

Sat 10/11

3:50 pm-6:50 pm

Nonstop5h 00m

$173

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Sat 10/4

10:20 am-8:20 pm

1 stop8h 00m

Chicago Midway

Tue 10/14

7:10 am-9:30 am

Nonstop4h 20m

$174

San DiegoChicago

SAN - ORD

SANORD

San Diego

Tue 11/25

5:31 pm-11:32 pm

Nonstop4h 01m

Chicago O'Hare Intl

Wed 12/3

3:05 pm-5:33 pm

Nonstop4h 28m

$175

San DiegoChicago

SAN - ORD

SANORD

San Diego

Wed 10/29

12:45 pm-6:59 pm

Nonstop4h 14m

Chicago O'Hare Intl

Sun 11/2

2:54 pm-5:19 pm

Nonstop4h 25m

$175

San DiegoChicago

SAN - ORD

SANORD

San Diego

Thu 11/13

5:49 pm-11:59 pm

Nonstop4h 10m

Chicago O'Hare Intl

Sat 11/15

2:54 pm-5:19 pm

Nonstop4h 25m

$175

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 54 results
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The best insider tips for San Diego to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your San Diego to Chicago trip
Airports
SAN

Plan to arrive at least two hours before your flight from SAN to avoid stress, especially during peak traffic times.

Read more about SANby Blane Bachelor
ORD

Use the 'L' train for a reliable and quick way to reach downtown Chicago from ORD, avoiding traffic delays.

Read more about ORDby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Blane Bachelor

Blane Bachelor

Expert on SAN

Blane Bachelor

Blane Bachelor

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more

Best time to book a flight from San Diego to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from San Diego with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from San Diego to Chicago

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

Use this chart to determine the optimal time to book a round-trip flight from San Diego to Chicago. Price data was last updated on September 12, 2025.

The price you pay for your flight from San Diego to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 49 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from San Diego to Chicago?

Currently, August is the cheapest month in which you can book a flight from San Diego to Chicago (average of $245). Flying from San Diego to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from SAN to CHI?

Find hourly flight availability from San Diego to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

It’s optimal to fly from San Diego to Chicago in the afternoon. By choosing this option you can save up to 47% on the cost of your flight, compared to a flight in the morning.

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

Use this chart to determine the cheapest time to fly round-trip from San Diego to Chicago. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their San Diego to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from San Diego to Chicago

Explore weekly flight availability from San Diego to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 15, 2025.

The most flights from SAN to CHI are scheduled on a Sunday (56 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (37 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated September 15, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and United Airlines from San Diego to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.0

Food

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.0

Food

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,242 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.0

Food

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,929 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.0

Food

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.0

Food

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Frontier
5.8
Fair
3,172 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.0

Food

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

Related info for your journey

Find useful and relevant information for your journey from San Diego to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • 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 48 flights from San Diego to Chicago per day from 8 different airlines.

  • How long is the flight from San Diego to Chicago?

    Airlines like Hawaiian Airlines, Southwest, and Alaska Airlines fly from San Diego to Chicago in about 3h 55m. The time it takes to get you to your destination is usually consistent. Airlines will cover a distance of 1725 mi. Generally, flights for this route are nonstop.

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

    Spirit Airlines, at $99, was found to be the cheapest airline from San Diego to Chicago.Alternate airlines to your destination round-trip include Frontier and Hawaiian Airlines. You may be able to fly from San Diego to Chicago for 71% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from San Diego to Chicago one-way?

    One-way options have recently been found by users for as low as $77 on Alaska Airlines. Other airlines that offer cheap prices include Frontier from $82 and Hawaiian Airlines from $87 one-way.

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

    While some choose either San Diego - Chicago Midway or San Diego - Chicago Greater Rockford, San Diego - Chicago O'Hare Intl is the most popular route 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: Royal Jordanian (85%), Austrian Airlines (84%), United Airlines (84%).

  • What are the cheapest flights from San Diego to Chicago?

    On average you can expect to pay $911 for a flight from San Diego to Chicago. The cheapest flight overall is $74 while the most popular route, (San Diego - Chicago O'Hare Intl) is currently priced at $131.

  • Where are the most common layover locations when flying from San Diego to Chicago?

    San Diego to Chicago flights have a layover in Las Vegas most of the time.

  • What are some popular things to do or see while on a layover in Las Vegas?

    The majority of Las Vegas visitors spend their time at Fremont Street Experience, Fountains of Bellagio, and The Colosseum at Caesars Palace. Fremont Street Experience, Fountains of Bellagio, and The Colosseum at Caesars Palace can be accessed by traveling approximately 5.9 mi, 2.3 mi, and 2.6 mi, respectively from Las Vegas Harry Reid Intl. Travelers can rent a car at Las Vegas Harry Reid Intl for an average daily rate of $59 to make sightseeing during their layover a little easier.

  • Where are the least popular layover locations for San Diego to Chicago flights?

    Flights departing from San Diego and landing in Chicago layover in Denver least frequently.

  • Can I find deals for flights from San Diego to Chicago that include hotel bookings?

    Yes. In addition to deals on San Diego to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Diego to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Diego to Chicago.

  • Can I find deals for business class flights from San Diego to Chicago?

    Yes. Cheapflights offers flight deals from San Diego to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from San Diego to Chicago?

    Currently, August is the cheapest month in which you can book a flight from San Diego to Chicago (average of $245). Flying from San Diego to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for San Diego to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from San Diego to Chicago

Discover the top 8 airlines that operate flights from San Diego to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$99Average$178FlexibilityNo cancel feeOn-time65%
FrontierCheapest$118Average$209FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$137Average$197FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$139Average$392FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$167Average$376FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$216Average$458FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$232Average$427FlexibilityNo cancel feeOn-time63%
DeltaCheapest$267Average$390FlexibilityNo cancel feeOn-timeN/A

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