Helping travelers to find the best flight offers
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from San Diego to Chicago:
We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
The cheapest one-way flight from San Diego to Chicago departs on 05/14/2025, is operated by Spirit Airlines and costs $78
The cheapest roundtrip flight from San Diego to Chicago departs on 05/13/2025, is operated by Spirit Airlines and costs $155
Fastest flight from San Diego to Chicago takes 6h 16m
There are no direct flights on this route.
The distance between San Diego and Chicago is 2786km (1727 miles). There are 16 direct flights from San Diego to Chicago. The time difference between San Diego and Chicago is 2h . Flights from San Diego begin at 6:55 AM. The latest flight from San Diego departs at 5:15 PM.
Unable to find information about the schedule of direct flights from
We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from San Diego to Chicago
Below you will find a list of airlines operating flights on the San Diego — Chicago route and the starting prices for flights of each specific airline on it.
Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from San Diego to Chicago. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
A direct 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.
San Diego — Chicago
04/07/2025
Departure date
Direct flight
WN375
Starting at $471
San Diego — Chicago
04/21/2025
Departure date
Direct flight
WN1169
Starting at $250
San Diego — Chicago
05/13/2025
Departure date
Direct flight
WN495
Starting at $189
San Diego — Chicago
05/13/2025
Departure date
Direct flight
AA2131
Starting at $159
San Diego — Chicago
05/14/2025
Departure date
Direct flight
WN3677
Starting at $225
San Diego — Chicago
05/16/2025
Departure date
Direct flight
AA2065
Starting at $159
San Diego — Chicago
05/17/2025
Departure date
Direct flight
WN495
Starting at $218
San Diego — Chicago
05/17/2025
Departure date
Direct flight
WN233
Starting at $229
San Diego — Chicago
05/18/2025
Departure date
Direct flight
UA2486
Starting at $436
San Diego — Chicago
05/19/2025
Departure date
Direct flight
AA1461
Starting at $159
The cheapest flight ticket from San Diego to Chicago according to data for the last 48 hours costs $78
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: April, March.
The fastest flights from San Diego to Chicago start from 6 hours 16 minutes in the air.
The following airlines operate direct flights on the route San Diego — Chicago: Southwest Airlines, American Airlines, United Airlines
We couldn't find any special offers for flights from San Diego to Chicago