ORD → SAN

Find and Compare the Cheapest Ways to Fly from Chicago to San Diego

Compare one-way, round-trip and flight + hotel packages from Chicago to San Diego, a nonstop flight of about 4h, with fares from around 260. Nonstop fares seen from Alaska.

Chicago to San Diego flight facts

Chicago to San Diego is a domestic route covering about 1,719 miles, arriving at San Diego International Airport (SAN) in United States. Peak travel season in San Diego runs June–September (sunny, warm beach weather), while December–February is usually the quietest and best-value time to visit. Nonstop fares we've tracked on this route come from Alaska.

Key facts for flights from Chicago to San Diego
Departing fromO'Hare International Airport (ORD)
Arriving atSan Diego International Airport (SAN)
Distance1,719 miles (2,769 km)
Nonstop flight timeAbout 4h
Nonstop airlines seenAlaska
Round-trip fares from$260 (estimate)
Cheapest monthsJanuary, February, September
Peak season in San DiegoJune–September
Cheapest hotel months in San DiegoDecember–February
Best time to book1 to 3 months ahead
Route info updatedOctober 16, 2026

When to visit San Diego

  • Peak season

    June–September

    Sunny, warm beach weather

  • Shoulder season

    March–May & October–November

    Mild and pleasant

  • Off-peak season

    December–February

    Cool with light rain

Estimated round-trip fares by month, Chicago to San Diego

Estimated lowest round-trip fare per month
MonthFares from
January$260
February$265
March$300
April$295
May$285
June$330
July$340
August$355
September$265
October$285
November$305
December$355

Flying from Chicago to San Diego

Airlines Flying this Route

Nonstop fares we've tracked on this route come from Alaska. Ducoffs.com compares full-service and low-cost airlines flying between Chicago and San Diego in a single search, including nonstop and one-stop options, so you can weigh price against total travel time.

Best Time to Book Flights from Chicago to San Diego

Fares on this route tend to be lowest in January, February, and September. For the best selection, book about 1 to 3 months before departure and stay flexible by a day or two.

Average Travel Duration

Chicago and San Diego are about 1,719 miles apart. A nonstop flight takes roughly 4h; connecting itineraries usually add 2 to 5 hours.

Chicago to San Diego flight questions

How can I find the absolute cheapest flight from Chicago to San Diego?

The best way to secure budget rates is by comparing multiple airlines simultaneously and checking flexible dates. Ducoffs.com scans available partner networks to bring you real-time pricing options.

What is the cheapest month to fly from Chicago to San Diego?

Based on typical seasonal demand, January, February, and September tend to offer the lowest fares on this route, with estimated round-trip prices starting around $260. Live prices change daily, so run a search for your exact dates.

How long is the flight from Chicago to San Diego?

Chicago and San Diego are about 1,719 miles apart. A nonstop flight takes roughly 4h, while connecting itineraries usually add 2 to 5 hours depending on the layover.

Which airlines fly nonstop from Chicago to San Diego?

Recent nonstop fares we've tracked on this route come from Alaska. Schedules change by season, so your live search shows every airline flying your dates.

When are hotels cheapest in San Diego?

Hotel rates in San Diego are usually lowest in December–February, when demand is quieter, and highest during peak season (June–September). Booking your flight and hotel together can save up to 30%.

Which airport do I fly into for San Diego?

This route arrives at San Diego International Airport (SAN). Your search results also show nearby airports when they offer a cheaper or faster option.

How far in advance should I book a flight to San Diego?

For this route, booking about 1 to 3 months before departure usually gives the best balance of price and seat selection. Mid-week departures are often cheaper than weekend flights.

Is it cheaper to bundle flights and hotels together?

Yes. Bundling your travel components can save you up to 30% compared to booking flights and hotels separately, as airlines and properties offer exclusive package discounts.