Plan for traffic when heading to SAN. Arrive early to avoid stress, especially during peak hours like 4:00-6:15 a.m. and 9:30 a.m.-12:30 p.m.
$98+ 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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — CHI
May 4 — May 111
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 October or September, booked 83 days in advance, depart on a Thursday or Wednesday and return on a Tuesday
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 April 29, 2025.
Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $213 (FlightHub) |
One-way from | $98 (Cheapflightsfares) |
Popular in | December |
Cheapest in | October |
Average price | $399 |
Good round-trip deal | $350 or less |
Good one-way deal | $175 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 April 29, 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 April 29, 2025.
This Frontier deal was found by Cheapflights users on 4/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/14:53 pmSAN - ORD
Nonstop4h 23mFrontier
Fri 8/81:40 pmORD - SAN
Nonstop4h 20mFrontier
Deal found 4/28![Frontier logo]()
$213
This Expedia deal was found by Cheapflights users on 4/28. 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.
Tue 6/38:48 pmSAN - ORD
1 stop6h 37mSpirit Airlines
Fri 6/1311:50 amORD - SAN
1 stop13h 39mSpirit Airlines
Deal found 4/28![Spirit Airlines logo]()
$214
This Cheapflightsfares deal was found by Cheapflights users on 4/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/96:25 amSAN - MDW
1 stop6h 23mFrontier
Mon 5/128:03 pmMDW - SAN
1 stop6h 10mFrontier
Deal found 4/27![Frontier logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Tue 7/2911:40 amSAN - ORD
1 stop6h 06mMultiple Airlines
Tue 8/51:40 pmORD - SAN
Nonstop4h 20mMultiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$216
This American Airlines deal was found by Cheapflights users on 4/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/312:49 pmSAN - ORD
Nonstop4h 17mAmerican Airlines
Sat 6/77:10 amORD - SAN
Nonstop4h 20mAmerican Airlines
Deal found 4/28![American Airlines logo]()
$237
This Southwest deal was found by Cheapflights users on 4/27. 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.
Wed 5/287:35 amSAN - MDW
Nonstop3h 55mSouthwest
Wed 6/44:45 pmMDW - SAN
Nonstop4h 20mSouthwest
Deal found 4/27![Southwest logo]()
$237
This Mytrip deal was found by Cheapflights users on 4/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/86:15 amSAN - RFD
1 stop12h 31mMultiple Airlines
Sun 5/119:36 pmRFD - SAN
1 stop24h 17mMultiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$241
This United Airlines deal was found by Cheapflights users on 4/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/3010:30 pmSAN - ORD
Nonstop4h 10mUnited Airlines
Thu 6/54:20 pmORD - SAN
Nonstop4h 22mUnited Airlines
Deal found 4/28![United Airlines logo]()
$277
This eDestinos deal was found by Cheapflights users on 4/28. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/56:25 amSAN - MDW
1 stop12h 28mMultiple Airlines
Mon 6/96:25 amMDW - SAN
2 stops27h 14mMultiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$285
This Alaska Airlines deal was found by Cheapflights users on 4/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/157:45 pmSAN - ORD
1 stop9h 18mAlaska Airlines
Tue 9/232:07 pmORD - SAN
1 stop8h 11mAlaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$296
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2310:10 pmSAN - MDW
1 stop8h 35mDelta
Mon 10/279:30 amMDW - SAN
1 stop6h 42mDelta
Deal found 4/28![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/286:20 amSAN - ORD
1 stop8h 29mDelta
Fri 7/411:00 amORD - SAN
1 stop9h 05mDelta
Deal found 4/28![Delta logo]()
$334
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 April 29, 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 5/30
5:43 pm-5:25 am
1 stop9h 42m
Chicago O'Hare Intl
Sun 6/1
10:00 am-11:56 pm
2 stops15h 56m
$213
San DiegoChicago
SAN - ORD
SANORD
San Diego
Thu 6/19
4:53 pm-10:56 pm
Nonstop4h 03m
Chicago O'Hare Intl
Sun 6/22
1:56 pm-4:08 pm
Nonstop4h 12m
$215
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Fri 5/9
6:25 am-2:48 pm
1 stop6h 23m
Chicago Midway
Mon 5/12
8:03 pm-12:13 am
1 stop6h 10m
$215
San DiegoChicago
SAN - ORD
SANORD
San Diego
Sat 6/14
4:53 pm-10:56 pm
Nonstop4h 03m
Chicago O'Hare Intl
Tue 6/17
10:31 am-11:29 pm
2 stops14h 58m
$218
San DiegoChicago
SAN - ORD
SANORD
San Diego
Sat 5/31
6:15 am-12:31 pm
Nonstop4h 16m
Chicago O'Hare Intl
Sat 5/31
9:33 pm-11:59 pm
Nonstop4h 26m
$237
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Wed 5/28
7:35 am-1:30 pm
Nonstop3h 55m
Chicago Midway
Wed 6/4
4:45 pm-7:05 pm
Nonstop4h 20m
$237
San DiegoChicago
SAN - RFD
SANRFD
San Diego
Thu 5/8
6:15 am-8:46 pm
1 stop12h 31m
Chicago Greater Rockford
Sun 5/11
9:36 pm-7:53 pm
1 stop24h 17m
$241
San DiegoChicago
SAN - ORD
SANORD
San Diego
Fri 5/30
10:30 pm-4:40 am
Nonstop4h 10m
Chicago O'Hare Intl
Thu 6/5
4:20 pm-6:42 pm
Nonstop4h 22m
$277
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Thu 6/5
6:25 am-8:53 pm
1 stop12h 28m
Chicago Midway
Mon 6/9
6:25 am-7:39 am
2 stops27h 14m
$285
San DiegoChicago
SAN - ORD
SANORD
San Diego
Wed 5/21
8:25 am-11:56 pm
2 stops13h 31m
Chicago O'Hare Intl
Wed 5/28
2:09 pm-9:19 pm
2 stops9h 10m
$325
Showing 1-10 of 28 results
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 April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy- | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on San Diego-Chicago flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on San Diego-Chicago flight deals on Cheapflights vs. CheapOair >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 CheapOair the most. CheapOair 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.
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 April 25, 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 83 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 April 29, 2025.
It’s optimal to fly from San Diego to Chicago in the afternoon. By choosing this option you can save up to 18% 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 March 30, 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 mornings 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 April 29, 2025.
The most flights from SAN to CHI are scheduled on a Tuesday (49 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (19 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 April 29, 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.
Crew
8.5
Boarding
8.2
Comfort
7.9
Entertainment
7.1
Food
7.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
Crew
8.5
Boarding
8.2
Comfort
7.9
Entertainment
7.1
Food
7.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
Crew
8.5
Boarding
8.2
Comfort
7.9
Entertainment
7.1
Food
7.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
Crew
8.5
Boarding
8.2
Comfort
7.9
Entertainment
7.1
Food
7.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
Crew
8.5
Boarding
8.2
Comfort
7.9
Entertainment
7.1
Food
7.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
Crew
8.5
Boarding
8.2
Comfort
7.9
Entertainment
7.1
Food
7.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton
Browse thousands of different options on Cheapflights for your next trip
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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 April 29, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$94 | Average$195 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$110 | Average$203 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$222 | Average$426 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$251 | Average$470 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$258 | Average$386 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$332 | Average$471 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$391 | Average$767 | FlexibilityNo cancel fee | On-time75% |