Plan to arrive at least two hours before your flight from SAN to avoid stress, especially during peak traffic times.
$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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — CHI
Jul 6 — Jul 131
1 adult, Economy
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Find cheap flights from San Diego to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from San Diego to Chicago are usually found in August or June, booked 49 days in advance, depart on a Wednesday or Thursday 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 July 1, 2025.
Round-trip from | $166 (Cheapflightsfares) |
|---|---|
One-way from | $91 (Priceline) |
Popular in | December |
Cheapest in | August |
Average price | $322 |
Good round-trip deal | $279 or less |
Good one-way deal | $169 or less |
Find flight deals from San Diego to Chicago
Cheapest flights from San Diego to ChicagoExplore 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 1, 2025.
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 1, 2025.
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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 8/14:44 pmSAN - ORD
Nonstop4h 23mFrontier
Tue 8/51:39 pmORD - SAN
Nonstop4h 20mFrontier
Deal found 6/30![Frontier logo]()
$166
This CheapOair deal was found by Cheapflights users on 6/29. 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 8/288:26 pmSAN - MDW
1 stop25h 58mFrontier
Mon 9/16:31 pmMDW - SAN
1 stop7h 21mFrontier
Deal found 6/29![Frontier logo]()
$167
This Mytrip deal was found by Cheapflights users on 6/29. 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.
Mon 7/215:13 pmSAN - ORD
1 stop10h 50mSpirit Airlines
Wed 7/307:08 amORD - SAN
1 stop12h 47mSpirit Airlines
Deal found 6/29![Spirit Airlines logo]()
$168
This Southwest deal was found by Cheapflights users on 7/1. 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.
Tue 8/510:40 amSAN - MDW
Nonstop4h 00mSouthwest
Tue 8/121:35 pmMDW - SAN
Nonstop4h 10mSouthwest
Deal found 7/1![Southwest logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 6/30. 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.
Sat 7/127:00 pmSAN - ORD
1 stop9h 03mMultiple Airlines
Sun 7/271:39 pmORD - SAN
Nonstop4h 20mMultiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$173
This Mytrip deal was found by Cheapflights users on 6/30. 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 9/48:16 amSAN - RFD
1 stop8h 36mMultiple Airlines
Sun 9/79:16 pmRFD - SAN
1 stop12h 05mMultiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$197
This Alaska Airlines deal was found by Cheapflights users on 6/30. 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.
Tue 9/3011:46 amSAN - ORD
1 stop10h 17mAlaska Airlines
Sat 11/12:54 pmORD - SAN
Nonstop4h 25mAlaska Airlines
Deal found 6/30![Alaska Airlines logo]()
$204
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 1, 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
Fri 8/1
4:44 pm-11:07 pm
Nonstop4h 23m
Chicago O'Hare Intl
Tue 8/5
1:39 pm-3:59 pm
Nonstop4h 20m
$166
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Thu 8/28
8:26 pm-12:24 am
1 stop25h 58m
Chicago Midway
Mon 9/1
6:31 pm-11:52 pm
1 stop7h 21m
$167
San DiegoChicago
SAN - ORD
SANORD
San Diego
Mon 7/21
5:13 pm-6:03 am
1 stop10h 50m
Chicago O'Hare Intl
Wed 7/30
7:08 am-5:55 pm
1 stop12h 47m
$168
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Tue 8/5
10:40 am-4:40 pm
Nonstop4h 00m
Chicago Midway
Tue 8/12
1:35 pm-3:45 pm
Nonstop4h 10m
$171
San DiegoChicago
SAN - ORD
SANORD
San Diego
Sat 7/12
7:00 pm-6:03 am
1 stop9h 03m
Chicago O'Hare Intl
Sun 7/27
1:39 pm-3:59 pm
Nonstop4h 20m
$173
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
7:25 am-9:44 am
Nonstop4h 19m
$196
San DiegoChicago
SAN - RFD
SANRFD
San Diego
Thu 9/4
8:16 am-6:52 pm
1 stop8h 36m
Chicago Greater Rockford
Sun 9/7
9:16 pm-7:21 am
1 stop12h 05m
$197
San DiegoChicago
SAN - ORD
SANORD
San Diego
Fri 7/4
1:10 pm-10:42 pm
1 stop7h 32m
$91
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Sun 8/24
2:09 pm-12:45 am
1 stop8h 36m
$91
San DiegoChicago
SAN - ORD
SANORD
San Diego
Sat 7/19
6:15 am-6:44 pm
1 stop10h 29m
$92
Showing 1-10 of 15 results
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
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 27, 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 July 1, 2025.
It’s optimal to fly from San Diego to Chicago in the afternoon. By choosing this option you can save up to 35% 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 29, 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 July 1, 2025.
The most flights from SAN to CHI are scheduled on a Tuesday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 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 July 1, 2025.
Get a feel of what it's like to fly with Southwest, Delta, 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.
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.6
Boarding
8.2
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentMerlyn,Feb 2025
LAX - SMF
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.6
Boarding
8.2
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentMerlyn,Feb 2025
LAX - SMF
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.6
Boarding
8.2
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentMerlyn,Feb 2025
LAX - SMF
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.6
Boarding
8.2
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentMerlyn,Feb 2025
LAX - SMF
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.6
Boarding
8.2
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentMerlyn,Feb 2025
LAX - SMF
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.6
Boarding
8.2
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentMerlyn,Feb 2025
LAX - SMF
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.
Traveling to a place near San Diego?
Book flights to San Diego if you plan to visit one of these locationsMerrillville
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.
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 July 1, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$92 | Average$180 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$112 | Average$203 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$217 | Average$397 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$245 | Average$460 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$258 | Average$349 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$277 | Average$686 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$284 | Average$448 | FlexibilityNo cancel fee | On-time63% |