San Diego to Chicago Flight Route Information
| Travel Distance: | 1,726 Miles |
|---|---|
| Airlines Flying This Route: | American Airlines, Spirit Airlines, United Airlines |
| Weekly Flights: | 272 |
| Avg. Flight Duration: | 04.12 Hours |
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11/5/2026 Find Cheap Flights from San Diego to Chicago (SAN to CHI)
SAN - San Diego CHI - Chicago 
Find Cheap Flights from San Diego to Chicago (SAN to CHI)
Fares Starting from $141
SAN - San Diego CHI - Chicago Great deal! This is the lowest price we've seen for this one way route in the last 12 hours. Prices may change and aren't guaranteed for all flights or dates. Click on the price to continue your search and check the latest available fare. Ref. id 202609~Ref:TZ2OCwPHlk2T2pN92IRcJQ
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Cheap Flights from San Diego to Chicago - Compare & Book Our Best Deals
With over 36 daily departures from San Diego to Chicago, this route offers great flexibility for different travel plans. Browse one-way fares from $140.99, round-trip fares from $261.66, and other affordable options across different budgets. Compare flight choices, explore schedules, and book the best San Diego to Chicago deals that fit your budget and travel preferences.
Top Airlines that fly from San Diego to Chicago
Cheap Flight Deals from San Diego to Chicago
SAN San Diego Thu, Nov 5
CHI Chicago
from $141
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SAN San Diego Mon, Nov 9
CHI Chicago
from $141
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SAN San Diego Sat, Oct 17
CHI Chicago
from $146
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SAN San Diego Tue, Oct 20
CHI Chicago
from $146
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SAN San Diego Wed, Oct 21
CHI Chicago
from $146
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SAN San Diego Sat, Oct 24
CHI Chicago
from $146
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SAN San Diego Tue, Oct 27
CHI Chicago
from $146
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SAN San Diego Wed, Oct 28
CHI Chicago
from $146
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SAN San Diego Tue, Nov 3
CHI Chicago
from $146
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SAN San Diego Wed, Nov 4
CHI Chicago
from $146
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*All fares above were last found on: Fares are one way/round trip. Fares incl. all fuel surcharges, taxes & fees and our service fees. Displayed fares are subject to change and cannot be guaranteed at the time of booking. See all booking terms and conditions. 202609~Ref:TZ2OCwPHlk2T2pN92IRcJQ
Insights about cheap flights from San Diego to Chicago – Direct Flights, Duration & Best Travel Time
When it comes to booking cheap flights, having the right information at your fingertips can make all the difference. Dive into the insights for cheap flights from San Diego to Chicago and enhance your travel experience!
Daily Flights
36
Cheapest Month
August, December, October, June, July
Avg. Flight Duration
04.12
Peak Season
September
Distance
1,726 miles
Direct Flights
1098
When is the Cheapest Time to Book Flights from SAN to CHI?
Explore data-powered insights and trends for flights from San Diego to Chicago. Discover average fares, cheap months to fly, when to book, and plan smarter.
What’s the cheapest day of the week to fly from San Diego to Chicago?‡
What is the cheapest month to fly from San Diego to Chicago?‡
‡This information is based on historical data from the last 365 days.
Finding Affordable Flights from San Diego to Chicago
- Plan Ahead - One of the keys to securing cheap flights from San Diego to Chicago is to plan your trip well in advance. Airlines often offer lower prices for those who book tickets months ahead. Keep an eye on special promotions and sales events, which can yield significant savings.
- Flexibility is Key - Being flexible with your travel dates can also lead to substantial cost savings. Consider flying during off-peak seasons or on weekdays when prices tend to be lower.
- Set Price Alerts - To keep tabs on flight prices, consider setting up fare alerts. These alerts will notify you when fares from San Diego to Chicago drop, giving you the opportunity to grab cheap deals.
- Consider Nearby Airports - If Chicago has multiple airports, check the prices at each one. Sometimes, flying into a nearby airport and then taking a short train or bus ride to your destination can be a much cheaper option.
- Bundle and Save - Booking your flight and accommodation together as a package can often result in significant savings. CheapOair offers these bundled deals, so make sure to explore this option.
When should I book flights from SAN to CHI? ‡
‡Got flexible travel dates? Use our flight data from the past year to discover ideal time to fly from San Diego to Chicago. Find out which months and days typically offer lower fares and let CheapOair search for the best options.
CheapOair provides the predicted prices for one-way trips or round-trips with a duration of 7 days for domestic and 14 days for international trips based on historical data and available flight information. Graphs are estimates only. Prices are subject to change and can't be guaranteed until ticketed.
Estimated price for
Round-trip
‡Graphs are estimates only. Based on historical data and available flight information. Prices are subject to change and cannot be guaranteed until ticketed.
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Insights About Flying from San Diego to Chicago
Which is the high season to travel from San Diego to Chicago?
The month of September is considered the high season for flying from SAN to CHI. Traveling during the high season can affect ticket prices and availability, making this data crucial for trip planning.
How many direct flights are available from SAN to CHI?
There are a total of 1098 direct flights from San Diego to Chicago. For travelers seeking convenience and shorter travel times, this data is important when choosing flight options.
Which is the low season to travel from San Diego to Chicago?
August, December, October, June, July is considered the low season for traveling from San Diego to Chicago, Illinois. Travelers looking for cost-effective options and fewer crowds may consider traveling during this period.
How many daily flights are there between San Diego to Chicago?
There are as many as 36 daily flights available for travelers between SAN to CHI. This data offers flexibility in choosing departure times that best suit your schedule.
At what time does the last flight depart to Chicago?
The last flight to Chicago typically departs between 10:00PM - 11:00PM. Travelers who prefer late-night departures will find this information valuable for planning their journey.
What percentage of travelers spent an average of 3 days in Chicago, Illinois?
Approximately 40.22% of travelers spent an average of 3 days exploring Chicago. This information can assist in planning the duration of your stay in Chicago
What percentage of SAN to CHI flyers traveled with kids under 14?
About 9% of passengers on flights from San Diego to Chicago were accompanied by children under the age of 14. This information is useful if you're planning a family trip and want to know how common it is to travel with young children on this route.
What percentage of San Diego to Chicago travelers were over 60 years old?
A notable 13% of travelers were aged 60 or older. This statistic provides insights for senior travelers or those seeking a mature travel demographic.
What percentage of SAN to CHI travelers were millennials?
Millennials make up a significant portion of travelers on this route, accounting for 40% of all passengers. If you're a millennial looking to connect with like-minded travelers, this statistic might interest you.
What percentage of San Diego to Chicago travelers were female?
Almost half of the passengers, approximately 51% were female. Knowing the gender distribution can be useful for solo female travelers or those interested in gender-related travel insights.
What percent of San Diego to Chicago travellers booked first or business class?
3% of travelers booked first or business class on this route.
At what time the earliest flight departs from San Diego?
The earliest flight departs at 7:00AM - 8:00AM.
What is the price range of a San Diego to Chicago flight?
San Diego to Chicago Flight Prices usually vary between 1 - 301.26.
On which days one can have the most flight options in Chicago?
Monday offer the most flight options in Chicago.
§
All flight facts are based on last 3 months' data except the highest and lowest booking months that are based on last 3 months' data.
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Cheap Flights from San Diego to Chicago
Looking for flights from San Diego (SAN) to Chicago (CHI)? Find affordable air travel deals on CheapOair and save big on air tickets online. Known for its history, culture and an excellent art scene, Chicago is an absolute paradise for Shopaholics. Museum lovers should head to the Museum Campus, animal lovers to the Lincoln Park Zoo and photography enthusiasts to the Museum of Photography when in Chicago. Also, you can opt for the Chicago CityPASS an avail discount admission to some of the top museums and attractions. To reach Chicago from San Diego, you may choose amongst the top airlines such as Frontier Airlines, Spirit Airlines, and Virgin America. Your flight from San Diego to Chicago takes about four hours thirty minutes to cover a distance of about 1,729 miles excluding layover time, make sure to carry an IPod or an mp3 player to keep yourself entertained.
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