Price observed over the last 3 months for a round trip.
Compare all flight tickets and find cheap flights from San Diego to Chicago
The cheapest flights right now
San Diego – Chicago
Outbound – Dec 6, 2026
direct
3h 50m Return – Dec 13, 2026
direct
4h 25m $340
yesterday
San Diego – Chicago
Outbound – Dec 5, 2026
direct
4h 18m Return – Dec 12, 2026
direct
4h 45m $342
yesterday
* Prices are in USD per passenger, including taxes, for a round trip. Prices are based on searches carried out within the last 72 hours. Please note that availability and ticket prices are subject to change and should not be considered as the final price quoted.
Cheapest flight tickets
$204
Average price of a round trip
$249
Average flight ticket price recorded over the last 3 months for a round trip.
Flight duration
4h21
A flight from San Diego to Chicago takes on average 4h21.
Best time
June
According to user searches, the ideal month to go to Chicago is June.
The best flight deals for a week
San Diego – Chicago
Outbound – Dec 6, 2026
direct
3h 50m Return – Dec 13, 2026
direct
4h 25m $340
yesterday
San Diego – Chicago
Outbound – Dec 5, 2026
direct
4h 18m Return – Dec 12, 2026
direct
4h 45m $342
yesterday
* Prices are in USD per passenger, including taxes, for a round trip. Prices are based on searches carried out within the last 72 hours. Please note that availability and ticket prices are subject to change and should not be considered as the final price quoted.
Tips for finding a cheap flight from San Diego to Chicago
Check out our tips for booking your flight to Chicago (USA) from San Diego (USA) at the cheapest possible price.
Usually, the cheapest month to pick up a ticket on this route is July, with an average flight ticket price of $128 (calculation over the last two years). The most touristic season corresponds to the months of October, September and July.
For the cheapest flights, it is advisable to buy your ticket at least 24 days before the departure date.
The airline offering the cheapest flight tickets is Alaska Airlines. A ticket from the airline Alaska Airlines to Chicago costs on average $252.
The airlines that offer the most flights are American Airlines, Alaska Airlines and United Airlines.
Price of flight tickets from San Diego to Chicago
Here is some information and tips to know before booking your flight:
- Flight ticket prices range from $204 to $390
- The average price of a flight ticket is about $249
- Prices are lowest for stays in the month of July
- The month in which booking a ticket is cheaper is: October
info departure city :
San Diego, USA
airports :
Lindbergh Field (SAN)
Montgomery Field (MYF)
NAS (NZY)
local time :
San Diego is a city in the country USA, the time zone is [[timezone]]. In San Diego, it is currently {fromLocalTime}, the temperature is on average 27°C, with a minimum of 25°C and a maximum of 29°C.
The city of San Diego has 3 airport(s): Lindbergh Field, Montgomery Field and NAS
destination info :
Chicago, USA
airports :
Chicago-Merrill C. Meigs Field Airport (CGX)
Chicago FSS (CHI)
Chicago-Midway International Airport (MDW)
Chicago-O'Hare International Airport (ORD)
local time :
Chicago is in the country USA, the time zone is [[timezone]]. In Chicago, it is currently {toLocalTime}, the temperature is on average 11°C, with a minimum of 7°C and a maximum of 14°C.
The city of Chicago (CHI) has 4 airport(s): Chicago-Merrill C. Meigs Field, Chicago FSS, Chicago-Midway and Chicago-O'Hare
Useful info about Chicago
What is the least touristic period to go to Chicago?
If you want to visit Chicago during the least touristic period, choose the month of June.
What is the most popular time to travel to Chicago?
In Chicago, the most popular month is October. It is during this period that the prices offered by airlines are also the highest.
When should I book my flight from San Diego to Chicago?
According to our data, it is recommended to book your flight 24 days before your departure. If you book your flight ticket 4 weeks before your departure, you may find a price below average. You can also choose morning flights that are 6% cheaper than afternoon and evening flights. The cheapest day to book a flight from San Diego to Chicago is Saturday.
What are the arrival and destination airports when traveling between San Diego and Chicago?
When you leave, you can leave from Lindbergh Field, and you will arrive at Chicago-Midway or Chicago-O'Hare.
How to reach San Diego airport from the city centre?
The airport Lindbergh Field is located 4 km, Montgomery Field is located 10 km or NAS is located 6 km from the city centre. You can access it by using public transportation, taking a taxi, or renting a car.
Are there other means of transportation to go from San Diego to Chicago?
Airplane is the only means of transportation listed on Liligo for this journey.
Are there big differences in weather between San Diego and Chicago?
In summer, the average temperature is 22°C in Chicago and 21°C in San Diego. The average rainfall in summer is 145 mm in Chicago and 4 mm in San Diego. In summer, it is warmer in Chicago and it rains less in San Diego. In winter, it is colder in San Diego and it rains more in Chicago.
