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$80+ 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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — CHI
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheapflights Tip: The best prices from San Diego to Chicago are usually found in August or July, booked 49 days in advance, depart on a Wednesday or Thursday and return on a Friday

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 August 18, 2025.

Round-trip from

$152
(CheapOair)

One-way from

$80
(Cheapflightsfares)

Popular in

December

Cheapest in

August

Average price

$259

Good round-trip deal

$228 or less

Good one-way deal

$148 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. 14% potential increase in price ($62 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 August 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 August 18, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 8/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/34:03 pmSAN - ORD
Nonstop4h 22mFrontier
Fri 10/107:15 amORD - SAN
Nonstop4h 22mFrontier
Deal found 8/18$149
This Mytrip deal was found by Cheapflights users on 8/18. 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.
Thu 9/189:03 pmSAN - ORD
1 stop24h 56mFrontier
Sun 9/216:00 amORD - SAN
1 stop7h 09mFrontier
Deal found 8/18$150
This CheapOair deal was found by Cheapflights users on 8/16. 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 10/236:41 amSAN - MDW
1 stop15h 55mFrontier
Mon 10/276:24 pmMDW - SAN
1 stop7h 26mFrontier
Deal found 8/16$152
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 9/52:31 pmSAN - ORD
1 stop6h 09mFrontier
Mon 9/156:00 amORD - SAN
1 stop7h 09mFrontier
Deal found 8/18$153
This Gotogate deal was found by Cheapflights users on 8/17. 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.
Thu 9/412:04 pmSAN - MDW
1 stop25h 49mFrontier
Fri 9/124:48 pmMDW - SAN
1 stop9h 05mFrontier
Deal found 8/17$153
This United Airlines deal was found by Cheapflights users on 8/16. 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.
Sat 9/132:11 pmSAN - ORD
Nonstop4h 14mUnited Airlines
Sat 9/204:00 pmORD - SAN
Nonstop4h 20mUnited Airlines
Deal found 8/16$154
This Trip.com deal was found by Cheapflights users on 8/16. 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 10/1512:20 pmSAN - ORD
Nonstop4h 39mMultiple Airlines
Sun 10/197:15 amORD - SAN
Nonstop4h 22mMultiple Airlines
Deal found 8/16$155
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Tue 10/1412:20 pmSAN - ORD
Nonstop4h 39mMultiple Airlines
Thu 11/136:00 amORD - SAN
1 stop19h 50mMultiple Airlines
Deal found 8/17$156
This Frontier deal was found by Cheapflights users on 8/17. 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.
Mon 8/253:40 pmSAN - ORD
Nonstop4h 23mFrontier
Mon 10/66:00 amORD - SAN
1 stop7h 09mFrontier
Deal found 8/17$157
This Booking.com deal was found by Cheapflights users on 8/18. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/86:35 amSAN - MDW
1 stop7h 18mFrontier
Thu 9/1110:13 amMDW - SAN
1 stop9h 29mFrontier
Deal found 8/18$157
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 10/21:18 pmSAN - ORD
1 stop7h 22mFrontier
Thu 10/94:44 pmORD - SAN
1 stop9h 06mFrontier
Deal found 8/18$158
This Booking.com deal was found by Cheapflights users on 8/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/267:11 pmSAN - MDW
1 stop13h 17mFrontier
Mon 9/294:48 pmMDW - SAN
1 stop9h 05mFrontier
Deal found 8/16$158

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 August 18, 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 - MDW

SANMDW

San Diego

Thu 10/23

6:41 am-12:36 am

1 stop15h 55m

Chicago Midway

Mon 10/27

6:24 pm-11:50 pm

1 stop7h 26m

$152

San DiegoChicago

SAN - ORD

SANORD

San Diego

Tue 9/16

6:15 am-6:51 pm

1 stop10h 36m

Chicago O'Hare Intl

Fri 9/19

9:54 pm-6:30 pm

1 stop22h 36m

$153

San DiegoChicago

SAN - ORD

SANORD

San Diego

Thu 9/11

7:47 pm-11:51 am

1 stop14h 04m

Chicago O'Hare Intl

Tue 9/16

11:15 am-11:34 pm

1 stop14h 19m

$153

San DiegoChicago

SAN - ORD

SANORD

San Diego

Thu 10/30

10:14 am-1:15 am

1 stop13h 01m

Chicago O'Hare Intl

Tue 11/4

2:54 pm-5:19 pm

Nonstop4h 25m

$153

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Thu 9/4

12:04 pm-3:53 pm

1 stop25h 49m

Chicago Midway

Fri 9/12

4:48 pm-11:53 pm

1 stop9h 05m

$153

San DiegoChicago

SAN - ORD

SANORD

San Diego

Sat 9/13

2:11 pm-8:25 pm

Nonstop4h 14m

Chicago O'Hare Intl

Sat 9/20

4:00 pm-6:20 pm

Nonstop4h 20m

$154

San DiegoChicago

SAN - ORD

SANORD

San Diego

Fri 11/7

8:30 am-9:43 pm

1 stop11h 13m

Chicago O'Hare Intl

Sat 11/8

2:54 pm-5:19 pm

Nonstop4h 25m

$154

San DiegoChicago

SAN - ORD

SANORD

San Diego

Sat 11/8

8:00 am-1:54 pm

Nonstop3h 54m

Chicago O'Hare Intl

Sat 11/15

7:15 am-1:28 pm

1 stop8h 13m

$154

San DiegoChicago

SAN - ORD

SANORD

San Diego

Wed 10/22

12:20 pm-6:59 pm

Nonstop4h 39m

Chicago O'Hare Intl

Mon 10/27

2:54 pm-5:19 pm

Nonstop4h 25m

$156

San DiegoChicago

SAN - ORD

SANORD

San Diego

Sat 9/20

6:15 am-9:32 pm

1 stop13h 17m

Chicago O'Hare Intl

Tue 9/23

9:00 am-6:42 pm

1 stop11h 42m

$156

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 53 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 August 8, 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 August 18, 2025.

It’s optimal to fly from San Diego to Chicago in the afternoon. By choosing this option you can save up to 43% 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 August 10, 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 August 18, 2025.

The most flights from SAN to CHI are scheduled on a Monday (58 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (20 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 August 18, 2025.
Get a feel of what it's like to fly with Southwest, United Airlines, and American 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
4,246 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,925 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,038 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,212 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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

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

    Airlines like Frontier, Spirit Airlines, and United Airlines fly from San Diego to Chicago in about 4h 14m. The time it takes to get you to your destination can typically vary by up to 11h 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?

    Spirit Airlines, at $98, 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 72% less than the average price by searching for these airlines.

  • 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 (87%), Austrian Airlines (85%), Cathay Pacific (84%).

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

    On average you can expect to pay $880 for a flight from San Diego to Chicago. The cheapest flight overall is $86 while the most popular route, (San Diego - Chicago O'Hare Intl) is currently priced at $116.

  • 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 $54 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 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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$98Average$181FlexibilityNo cancel feeOn-time65%
FrontierCheapest$117Average$208FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$180Average$384FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$184Average$568FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$239Average$461FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$247Average$433FlexibilityNo cancel feeOn-time63%
DeltaCheapest$267Average$393FlexibilityNo cancel feeOn-timeN/A

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