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$91+ 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 8/2. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from San Diego to Chicago are usually found in June or August, booked 49 days in advance, depart on a Thursday or Wednesday and return on a Wednesday

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 June 12, 2025.

Round-trip from

$172
(FlightHub)

One-way from

$91
(FlightHub)

Popular in

December

Cheapest in

June

Average price

$317

Good round-trip deal

$278 or less

Good one-way deal

$156 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. 10% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This FlightHub deal was found by Cheapflights users on 6/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/87:31 pmSAN - ORD
1 stop8h 32mSpirit Airlines
Tue 7/153:18 pmORD - SAN
1 stop9h 48mSpirit Airlines
Deal found 6/10$172
This FlightHub deal was found by Cheapflights users on 6/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/35:50 pmSAN - ORD
1 stop10h 22mMultiple Airlines
Wed 7/91:39 pmORD - SAN
Nonstop4h 20mMultiple Airlines
Deal found 6/10$174
This FlightHub deal was found by Cheapflights users on 6/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/224:44 pmSAN - ORD
Nonstop4h 23mFrontier
Thu 7/311:39 pmORD - SAN
Nonstop4h 20mFrontier
Deal found 6/11$175
This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2910:45 pmSAN - ORD
Nonstop4h 09mAmerican Airlines
Tue 9/29:55 amORD - SAN
Nonstop4h 20mAmerican Airlines
Deal found 6/11$186
This Southwest deal was found by Cheapflights users on 6/9. 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 8/76:30 pmSAN - MDW
Nonstop4h 00mSouthwest
Tue 8/128:20 amMDW - SAN
Nonstop4h 10mSouthwest
Deal found 6/9$186
This Alaska Airlines deal was found by Cheapflights users on 6/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/207:45 pmSAN - ORD
1 stop9h 18mAlaska Airlines
Tue 10/78:20 amORD - SAN
Nonstop5h 00mAlaska Airlines
Deal found 6/10$219
This CheapOair deal was found by Cheapflights users on 6/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2312:03 pmSAN - MDW
1 stop8h 35mFrontier
Mon 10/274:29 pmMDW - SAN
1 stop9h 21mFrontier
Deal found 6/10$235
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/265:01 pmSAN - ORD
Nonstop4h 13mUnited Airlines
Tue 10/74:10 pmORD - SAN
Nonstop4h 20mUnited Airlines
Deal found 6/10$251
This Southwest deal was found by Cheapflights users on 6/10. 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.
Fri 8/291:20 pmSAN - ORD
1 stop7h 00mSouthwest
Tue 9/21:50 pmORD - SAN
1 stop9h 55mSouthwest
Deal found 6/10$256
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/312:00 pmSAN - ORD
1 stop7h 53mDelta
Sun 11/25:00 amORD - SAN
1 stop8h 58mDelta
Deal found 6/12$257
This Delta deal was found by Cheapflights users on 6/11. 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.
Wed 9/2412:50 pmSAN - MDW
1 stop6h 54mDelta
Thu 10/210:35 amMDW - SAN
1 stop8h 53mDelta
Deal found 6/11$257
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/56:15 amSAN - RFD
1 stop27h 39mMultiple Airlines
Sun 7/1312:44 pmRFD - SAN
1 stop12h 22mMultiple Airlines
Deal found 6/11$282

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 June 12, 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

Tue 7/8

7:31 pm-6:03 am

1 stop8h 32m

Chicago O'Hare Intl

Tue 7/15

3:18 pm-11:06 pm

1 stop9h 48m

$172

San DiegoChicago

SAN - ORD

SANORD

San Diego

Thu 7/3

5:50 pm-6:12 am

1 stop10h 22m

Chicago O'Hare Intl

Wed 7/9

1:39 pm-3:59 pm

Nonstop4h 20m

$174

San DiegoChicago

SAN - ORD

SANORD

San Diego

Tue 7/22

4:44 pm-11:07 pm

Nonstop4h 23m

Chicago O'Hare Intl

Thu 7/31

1:39 pm-3:59 pm

Nonstop4h 20m

$175

San DiegoChicago

SAN - ORD

SANORD

San Diego

Fri 8/29

10:45 pm-4:54 am

Nonstop4h 09m

Chicago O'Hare Intl

Tue 9/2

9:55 am-12:15 pm

Nonstop4h 20m

$186

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Thu 8/7

6:30 pm-12:30 am

Nonstop4h 00m

Chicago Midway

Tue 8/12

8:20 am-10:30 am

Nonstop4h 10m

$186

San DiegoChicago

SAN - ORD

SANORD

San Diego

Mon 9/15

5:01 pm-11:14 pm

Nonstop4h 13m

Chicago O'Hare Intl

Wed 9/17

1:30 pm-3:50 pm

Nonstop4h 20m

$211

San DiegoChicago

SAN - ORD

SANORD

San Diego

Wed 8/20

7:45 pm-7:03 am

1 stop9h 18m

Chicago O'Hare Intl

Sat 10/4

10:00 am-1:00 pm

Nonstop5h 00m

$219

San DiegoChicago

SAN - ORD

SANORD

San Diego

Fri 8/29

1:20 pm-10:20 pm

1 stop7h 00m

Chicago O'Hare Intl

Tue 9/2

1:50 pm-9:45 pm

1 stop9h 55m

$256

San DiegoChicago

SAN - ORD

SANORD

San Diego

Fri 10/31

2:00 pm-11:53 pm

1 stop7h 53m

Chicago O'Hare Intl

Sun 11/2

5:00 am-11:58 am

1 stop8h 58m

$257

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Fri 8/1

10:15 pm-8:44 am

1 stop8h 29m

Chicago Midway

Fri 8/8

7:21 pm-11:29 pm

1 stop6h 08m

$267

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 28 results
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2
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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 June 9, 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 June 12, 2025.

It’s optimal to fly from San Diego to Chicago in the afternoon. By choosing this option you can save up to 33% 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 June 8, 2025.

Travelers seeking maximum savings on their San Diego to Chicago flight should consider departing on Thursday 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 June 12, 2025.

The most flights from SAN to CHI are scheduled on a Thursday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
To help decide which airline to fly from San Diego to Chicago, see what other customers have to say about Alaska Airlines, Southwest and Delta. 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
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 46 flights from San Diego to Chicago per day from 7 different airlines.

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

    Spirit Airlines, at $172, was found to be the cheapest airline from San Diego to Chicago.Alternate airlines to your destination round-trip include Frontier and American Airlines. You may be able to fly from San Diego to Chicago for 54% 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 $91 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $99 and United Airlines from $106 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 (96%), Aer Lingus (96%), Qatar Airways (94%).

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

    On average you can expect to pay $1,208 for a flight from San Diego to Chicago. The cheapest flight overall is $102 while the most popular route, (San Diego - Chicago O'Hare Intl) is currently priced at $118.

  • 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. Phoenix sees the next most layovers on San Diego to Chicago flights.

  • 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, The Colosseum at Caesars Palace, and Fountains of Bellagio. Fremont Street Experience, The Colosseum at Caesars Palace, and Fountains of Bellagio can be accessed by traveling approximately 5.9 mi, 2.6 mi, and 2.3 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 $55 to make sightseeing during their layover a little easier.

  • What are some popular points of interest to see during a layover in Phoenix?

    The majority of Phoenix visitors spend their time at Chase Field, Desert Ridge Marketplace, and Phoenix Symphony Hall. Chase Field, Desert Ridge Marketplace, and Phoenix Symphony Hall are located about 4.0 mi, 16.7 mi, and 4.3 mi, respectively from Phoenix Sky Harbor Intl. Travelers can rent a car at Phoenix Sky Harbor Intl for an average daily rate of $50 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 San Diego?

Book flights to San Diego if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
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 7 airlines flying from San Diego to Chicago

Discover the top 7 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$92Average$188FlexibilityNo cancel feeOn-time65%
FrontierCheapest$109Average$200FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$217Average$403FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$238Average$460FlexibilityNo cancel feeOn-time69%
DeltaCheapest$258Average$357FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$306Average$457FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$391Average$751FlexibilityNo cancel feeOn-time75%

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