$71+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
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.The best prices from San Diego to Chicago are usually found in October or September, booked 54 days in advance, depart on a Wednesday or Thursday 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 November 20, 2024.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Popular in | June |
Cheapest in | October |
Round-trip from | $140 (Kiwi.com) |
One-way from | $71 (Cheapflightsfares) |
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 November 20, 2024.
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 November 20, 2024.
This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
This Mytrip deal was found by Cheapflights users on 11/19. 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.
This Frontier deal was found by Cheapflights users on 11/19. 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.
This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
This Delta deal was found by Cheapflights users on 11/19. 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.
This Kissandfly.com deal was found by Cheapflights users on 11/19. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 11/19. 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.
This Southwest deal was found by Cheapflights users on 11/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 11/20. 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.
Find flights from San Diego to Chicago within your budget
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 2,629,791 searches. Data last updated November 20, 2024.
Fly from
Fly to
Route
Depart
Return
Price
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Thu 12/5
10:35 am-11:48 am
1 stop23h 13m
Chicago Midway
Mon 12/9
12:43 pm-7:10 pm
1 stop8h 27m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Sat 2/15
2:08 pm-5:05 am
1 stop12h 57m
Chicago O'Hare Intl
Wed 2/19
6:50 am-11:48 am
1 stop6h 58m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Thu 12/5
5:58 pm-5:30 am
1 stop9h 32m
Chicago O'Hare Intl
Sun 12/8
9:53 pm-8:13 am
1 stop12h 20m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Tue 1/7
7:16 pm-5:30 am
1 stop8h 14m
Chicago O'Hare Intl
Sat 1/11
6:20 am-5:29 pm
1 stop13h 09m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Tue 2/18
11:20 am-11:56 pm
1 stop10h 36m
Chicago O'Hare Intl
Wed 2/26
7:00 am-8:31 pm
1 stop15h 31m
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Thu 12/12
5:09 pm-11:48 am
2 stops16h 39m
Chicago Midway
Mon 12/16
7:15 am-7:10 pm
3 stops13h 55m
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Thu 12/12
6:15 am-5:01 pm
1 stop8h 46m
Chicago Midway
Sat 12/14
9:30 am-2:27 pm
1 stop6h 57m
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Tue 12/24
4:50 pm-10:40 pm
Nonstop3h 50m
Chicago Midway
Wed 1/8
8:40 am-11:20 am
Nonstop4h 40m
San DiegoChicago
SAN - RFD
SANRFD
San Diego
Sat 12/14
7:15 pm-11:55 am
1 stop14h 40m
Chicago Greater Rockford
Thu 12/19
12:40 pm-10:05 am
2 stops23h 25m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Wed 12/11
1:05 pm-5:30 am
1 stop14h 25m
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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
Travel insights for flights from San Diego to Chicago
Get recent, data-driven insights about flights from San Diego to Chicago including ideal travel times, pricing trends, and more.
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 November 15, 2024.
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 54 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, September is the cheapest month in which you can book a flight from San Diego to Chicago (average of $232). Flying from San Diego to Chicago in June is currently the most expensive (average of $308). 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 November 20, 2024.
It’s optimal to fly from San Diego to Chicago in the evening. By choosing this option you can save up to 20% 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 November 18, 2024.
Travelers seeking maximum savings on their San Diego to Chicago flight should consider departing on Monday evenings 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 November 20, 2024.
The most flights from SAN to CHI are scheduled on a Wednesday (29 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (17 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 November 20, 2024.
To help decide which airline to fly from San Diego to Chicago, see what other customers have to say about Spirit Airlines, Delta and Frontier. 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.
Entertainment
Comfort
Overall
Food
Boarding
Crew
Reviews
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
Entertainment
Comfort
Overall
Food
Boarding
Crew
Reviews
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
Entertainment
Comfort
Overall
Food
Boarding
Crew
Reviews
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
Entertainment
Comfort
Overall
Food
Boarding
Crew
Reviews
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
Entertainment
Comfort
Overall
Food
Boarding
Crew
Reviews
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
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.
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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 2,629,791 searches. Data last updated November 20, 2024.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$200 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$100 | Average$226 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$217 | Average$428 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$245 | Average$472 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$251 | Average$357 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$252 | Average$485 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$391 | Average$751 | FlexibilityNo cancel fee | On-time75% |