Southwest® flights from San Diego to Chicago (O'Hare) from $180*
Fly one-way from San Diego to Chicago (O'Hare) starting at $180. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.
$38 CHEAP FLIGHTS from San Diego to Illinois - KAYAK
The cheapest ticket to Illinois from San Diego found in the last 72 hours was $38 one-way, and $87 round-trip. The most popular route is from San Diego to Chicago O'Hare Intl , and the cheapest round-trip airline ticket found on this route in the last 72 hours was $33.
Cheap Flights from San Diego to Chicago | United Airlines
Find United Airlines cheap flights from San Diego to Chicago. Enjoy a San Diego to Chicago modern flight experience in premium cabins with Wi-Fi.
$33 Cheap Flights from San Diego (SAN) to Chicago (ORD)
Cheap Flights from San Diego (SAN) to Chicago (ORD) start at $33 for one-way and $66 for round trip. Earn your airline miles on top of our rewards!
San Diego to Chicago - 5 ways to travel via train, plane
The best way to get from San Diego to Chicago is to fly which takes 5h 41m and costs $60 - $460. Alternatively, you can train, which costs $190 - $700 and takes 46h 3m, you could also bus, which costs $170 - $1,000 and takes 2 days 3h.
Southwest® flights from San Diego to Chicago (Midway) from …
Fly one-way from San Diego to Chicago (Midway) starting at $171. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.
$41 CHEAP FLIGHTS from San Diego to Chicago (SAN - CHI) - KAYAK
Cheap Flight Deals from San Diego to Chicago (SAN-CHI) Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Diego to Chicago that are departing in the next months.
Direct (non-stop) flights from San Diego to Chicago
San Diego (SAN) to Chicago (ORD) flight schedule. The monthly calendar shows every direct flight departure from San Diego International Airport (SAN) with all airlines. Click on a date to see a list of flights or search for the best prices.
$61+ Flights from San Diego to Illinois | Cheapflights
Explore weekly flight availability from San Diego to Illinois. 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.
Bus from San Diego, CA to Chicago, IL - Greyhound
The journey from San Diego to Chicago can take as little as 49 hours 30 minutes and starts from as little as $258.98. The earliest bus leaves at 7:15 am and the last bus leaves at 7:35 pm . Greyhound schedules 3 buses per day from San Diego to Chicago.