There are most likely no direct flights on the San Diego — Chicago route
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In different months, ticket prices from San Diego to Chicago vary: minimum — $82 (November 2026), maximum — $149 (October 2026). Typically, the flight costs $116–$149.
A non-stop flight is the most convenient and comfortable way to fly from San Diego to Chicago, despite the fact that sometimes flights with transfers can cost significantly less.
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Answers to questions about the route that travelers are most interested in.
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There are most likely no direct flights on the San Diego — Chicago route
All airports
San Diego — Chicago
10/31/2026
Departure
Direct flight
UA2343
starting at $295
San Diego — Chicago
11/02/2026
Departure
Direct flight
UA2486
starting at $321
San Diego — Chicago
10/28/2026
Departure
Direct flight
AA2131
starting at $373
San Diego — Chicago
11/04/2026
Departure
Direct flight
AS1446
starting at $253
starting at $295
starting at $373
starting at $253
starting at $138
The route San Diego — Chicago is served by many carriers — 4 in total, including United Airlines, American Airlines, Alaska Airlines, and Frontier Airlines. This gives passengers wide opportunities: from finding the lowest fare (from $138) to selecting flights by schedule or service class. Our service aggregates data from multiple booking systems so you can compare offers in one place. This saves time and money: no need to check dozens of sites — just pick the right option and book online.
The cheapest flight ticket from San Diego to Chicago according to data for the last 48 hours costs $138
Often the best time to buy tickets from San Diego to Chicago is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from San Diego to Chicago can be found flying in these months: November, October.
The fastest flights from San Diego to Chicago start from 15 hours 56 minutes in the air.
The following airlines operate direct flights on the route San Diego — Chicago: United Airlines, American Airlines, Alaska Airlines
The cheapest one-way flight from San Diego to Chicago departs on 11/04/2026, is operated by Frontier Airlines and costs $138
There is no information about the cheapest roundtrip flight from San Diego to Chicago
Fastest flight from San Diego to Chicago takes 15h 56m
There are direct flights on this route 3 days a week: Mo, We, and Sa
The distance between San Diego and Chicago is 2786km (1727 miles). There are 53 direct flights from San Diego to Chicago. The time difference between San Diego and Chicago is 2h. Flights from San Diego begin at 6:15 AM. The latest flight from San Diego departs at 10:59 PM
We couldn't find any special offers for flights from San Diego to Chicago