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$154+ 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 8/7. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — CHI
Aug 28 — Sep 41
Fri 8/28
Fri 9/4
1 adult, Economy
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Find cheap flights from San Diego to Chicago with Cheapflights

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Cheapflights Tip: The best prices from San Diego to Chicago are usually found in February or January, booked 44 days in advance, depart on a Friday or Wednesday and return on a Thursday

Cheap 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 July 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:25 am
SAN
-
ORD
1 stop25h 36m
Multiple Airlines
Thu 11/122:25 pm
ORD
-
SAN
Nonstop4h 41m
Multiple Airlines
Deal found 7/28$271
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:00 am
SAN
-
ORD
1 stop6h 37m
Frontier
Fri 9/112:46 pm
ORD
-
SAN
2 stops27h 12m
Frontier
Deal found 7/28$272
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/179:03 pm
SAN
-
ORD
1 stop6h 35m
Frontier
Fri 9/251:01 pm
ORD
-
SAN
1 stop6h 59m
Frontier
Deal found 7/28$273
This Priceline deal was found by Cheapflights users on 7/28. 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.
Sun 8/168:51 pm
SAN
-
ORD
1 stop6h 46m
Frontier
Wed 8/199:20 am
ORD
-
SAN
1 stop8h 21m
Frontier
Deal found 7/28$274
This Southwest deal was found by Cheapflights users on 7/28. 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.
Mon 8/249:00 pm
SAN
-
MDW
1 stop6h 50m
Southwest
Wed 8/2610:30 am
MDW
-
SAN
2 stops6h 55m
Southwest
Deal found 7/28$274
This Frontier deal was found by Cheapflights users on 7/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:51 pm
SAN
-
ORD
1 stop6h 46m
Frontier
Mon 8/319:20 am
ORD
-
SAN
1 stop8h 21m
Frontier
Deal found 7/27$275
This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:15 am
SAN
-
ORD
1 stop9h 25m
Delta
Sat 8/296:00 am
ORD
-
SAN
1 stop9h 16m
Delta
Deal found 7/27$277
This Southwest deal was found by Cheapflights users on 7/28. 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 9/172:55 pm
SAN
-
MDW
1 stop6h 55m
Southwest
Thu 9/245:30 pm
MDW
-
SAN
1 stop6h 40m
Southwest
Deal found 7/28$277
This Frontier deal was found by Cheapflights users on 7/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/53:03 pm
SAN
-
ORD
1 stop12h 34m
Frontier
Tue 8/117:29 am
ORD
-
SAN
1 stop8h 39m
Frontier
Deal found 7/27$278
This Southwest deal was found by Cheapflights users on 7/27. 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.
Sat 8/221:50 pm
SAN
-
MDW
1 stop6h 25m
Southwest
Mon 8/246:15 am
MDW
-
SAN
Nonstop4h 05m
Southwest
Deal found 7/27$278
This Expedia deal was found by Cheapflights users on 7/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/283:45 pm
SAN
-
ORD
1 stop19h 51m
Multiple Airlines
Sun 8/308:17 pm
ORD
-
SAN
Nonstop4h 43m
Multiple Airlines
Deal found 7/28$279
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:25 am
SAN
-
RFD
1 stop27h 58m
Multiple Airlines
Sun 8/239:35 pm
RFD
-
SAN
1 stop24h 39m
Multiple Airlines
Deal found 7/24$279

Find 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 July 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$272
(Kiwi.com)

One-way from

$154
(Flightnetwork)

Popular in

July

Cheapest in

February

Average price

$369

Good round-trip deal

$318 or less

Good one-way deal

$203 or less
Provider with most accurate pricing for San Diego-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Diego-Chicago (CHI) flights.
Search Deals
From San Diego to Chicago (CHI)
Search Deals
One-way flight from San Diego to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($60 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from San Diego to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from San Diego to Chicago (CHI).
Search Deals

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 July 29, 2026.
Use the filters below to find and compare flights from San Diego to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Sat 8/29

6:20 am-5:05 pm

2 stops8h 45m

Chicago Midway

Sat 9/5

1:45 pm-5:10 pm

1 stop5h 25m

$278

San DiegoChicago

SAN - RFD

SANRFD

San Diego

Thu 8/20

6:25 am-12:23 pm

1 stop27h 58m

Chicago Greater Rockford

Sun 8/23

9:35 pm-8:14 pm

1 stop24h 39m

$279
Quickest round-trip

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Tue 9/22

10:40 pm-4:30 am

Nonstop3h 50m

Chicago Midway

Fri 9/25

6:15 am-8:20 am

Nonstop4h 05m

$279

San DiegoChicago

SAN - ORD

SANORD

San Diego

Fri 10/30

6:15 am-4:40 pm

1 stop8h 25m

Chicago O'Hare Intl

Mon 11/2

3:30 pm-8:14 pm

1 stop6h 44m

$282

San DiegoChicago

SAN - RFD

SANRFD

San Diego

Tue 9/1

6:25 am-1:19 pm

1 stop28h 54m

Chicago Greater Rockford

Fri 9/4

12:09 pm-11:44 pm

1 stop13h 35m

$282

San DiegoChicago

SAN - ORD

SANORD

San Diego

Thu 10/8

4:55 pm-10:59 pm

Nonstop4h 04m

Chicago O'Hare Intl

Sun 10/11

7:05 am-9:32 am

Nonstop4h 27m

$287

San DiegoChicago

SAN - ORD

SANORD

San Diego

Sun 9/27

5:45 pm-11:59 pm

Nonstop4h 14m

Chicago O'Hare Intl

Mon 9/28

7:20 am-10:00 am

Nonstop4h 40m

$287

San DiegoChicago

SAN - ORD

SANORD

San Diego

Wed 9/2

6:15 am-4:17 pm

1 stop8h 02m

Chicago O'Hare Intl

Wed 9/9

6:10 am-1:18 pm

1 stop9h 08m

$287

San DiegoChicago

SAN - ORD

SANORD

San Diego

Fri 11/6

7:02 am-1:23 pm

Nonstop4h 21m

Chicago O'Hare Intl

Mon 11/9

7:25 am-10:04 am

Nonstop4h 39m

$287

San DiegoChicago

SAN - ORD

SANORD

San Diego

Mon 9/14

4:55 pm-10:59 pm

Nonstop4h 04m

Chicago O'Hare Intl

Fri 9/18

1:30 pm-3:49 pm

Nonstop4h 19m

$287

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 56 resultsSorted by cheapest first
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Compare providers for flights from San Diego to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from San Diego to Chicago in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
CheapOairPrice Accuracy3 starsTrust Score*3 stars
Super.comPrice Accuracy-Trust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on San Diego-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Diego-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Diego-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San Diego-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San Diego-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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

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

Currently, February is the cheapest month in which you can book a flight from San Diego to Chicago (average of $247). Flying from San Diego to Chicago in July is currently the most expensive (average of $382). 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 July 29, 2026.

It’s optimal to fly from San Diego to Chicago in the afternoon. By choosing this option you can save up to 21% on the cost of your flight, compared to a flight at noon.

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 July 29, 2026.

The most flights from SAN to CHI are scheduled on a Monday (56 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (34 on average).

How much does it cost to fly round-trip from San Diego to Chicago?

Airfare is typical for this route at the moment.
San Diego to Chicago flights typically cost between $247 and $357 in September.
The cheapest round-trip price found within the last 5 days was $272 on Frontier (Sep 3-Sep 11).

How often are flights from San Diego to Chicago delayed?

About 11% of weekly flights between San Diego and Chicago have experienced delays in the past year, with the average delay time being 184 minutes.

What is the most punctual flight time for San Diego to Chicago flights?

Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on San Diego to Chicago flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 7% of flights being delayed.

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

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 90 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 July 25, 2026.

Travelers seeking maximum savings on their San Diego to Chicago flight should consider departing on Sunday 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.

The best insider tips for San Diego to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your San Diego to Chicago trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

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 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

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 July 29, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, andUnited 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.
Southwest
8.0
Very good
4,228 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,228 reviews
Southwest
8.0
Very good
4,228 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Alaska Airlines
7.9
Good
12,727 reviews
Southwest
8.0
Very good
4,228 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
10,052 reviews
Southwest
8.0
Very good
4,228 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,839 reviews
Southwest
8.0
Very good
4,228 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Frontier
5.6
Fair
2,749 reviews
Southwest
8.0
Very good
4,228 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

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 45 flights from San Diego to Chicago per day from 6 different airlines.

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

    Airlines like Southwest, Delta, and United Airlines fly from San Diego to Chicago in about 4h 04m. The time it takes to get you to your destination can typically vary by up to 4h 41m. Airlines will cover a distance of 1719 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 $118, was found to be the cheapest airline from San Diego to Chicago.Alternate airlines to your destination round-trip include Hawaiian Airlines and Alaska Airlines. You may be able to fly from San Diego to Chicago for 59% 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 $67 on Frontier. Other airlines that offer cheap prices include American Airlines from $79 and Alaska Airlines from $79 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: ITA Airways (93%), Austrian Airlines (89%), SWISS (88%).

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

    On average you can expect to pay $1,344 for a flight from San Diego to Chicago. The cheapest flight overall is $151 while the most popular route, (San Diego - Chicago O'Hare Intl) is currently priced at $240.

  • 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, February is the cheapest month in which you can book a flight from San Diego to Chicago (average of $247). Flying from San Diego to Chicago in July is currently the most expensive (average of $382). 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
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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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 6 airlines flying from San Diego to Chicago

Discover the top 6 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 July 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$118Average$252FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$139Average$197FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$156Average$322FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$157Average$347FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$163Average$362FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$205Average$372FlexibilityNo cancel feeOn-time63%

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