SAN → ORD
Compare one-way, round-trip and flight + hotel packages from San Diego to Chicago, a nonstop flight of about 4h, with fares from around 235.
San Diego to Chicago is a domestic route covering about 1,719 miles, arriving at O'Hare International Airport (ORD) in United States. Peak travel season in Chicago runs June–August (warm, lakefront festivals), while November–April is usually the quietest and best-value time to visit. The cheapest fares we've tracked on this route include at least one stop.
| Departing from | San Diego International Airport (SAN) |
|---|---|
| Arriving at | O'Hare International Airport (ORD) |
| Distance | 1,719 miles (2,769 km) |
| Nonstop flight time | About 4h |
| Nonstop airlines seen | None in recent fares, expect 1 stop |
| Round-trip fares from | $235 (estimate) |
| Cheapest months | January, September, February |
| Peak season in Chicago | June–August |
| Cheapest hotel months in Chicago | November–April |
| Best time to book | 1 to 3 months ahead |
| Route info updated | October 16, 2026 |
June–August
Warm, lakefront festivals
May & September–October
Mild and comfortable
November–April
Cold, windy and snowy
| Month | Fares from |
|---|---|
| January | $235 |
| February | $245 |
| March | $310 |
| April | $270 |
| May | $280 |
| June | $325 |
| July | $340 |
| August | $335 |
| September | $235 |
| October | $250 |
| November | $280 |
| December | $330 |
The cheapest fares we've tracked on this route include at least one stop. Ducoffs.com compares full-service and low-cost airlines flying between San Diego and Chicago in a single search, including nonstop and one-stop options, so you can weigh price against total travel time.
Fares on this route tend to be lowest in January, September, and February. For the best selection, book about 1 to 3 months before departure and stay flexible by a day or two.
San Diego and Chicago are about 1,719 miles apart. A nonstop flight takes roughly 4h; connecting itineraries usually add 2 to 5 hours.
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.
Based on typical seasonal demand, January, September, and February tend to offer the lowest fares on this route, with estimated round-trip prices starting around $235. Live prices change daily, so run a search for your exact dates.
San Diego and Chicago 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.
The cheapest fares we've tracked recently on this route include at least one stop. Your live search shows any nonstop options available for your dates.
Hotel rates in Chicago are usually lowest in November–April, when demand is quieter, and highest during peak season (June–August). Booking your flight and hotel together can save up to 30%.
This route arrives at O'Hare International Airport (ORD). Your search results also show nearby airports when they offer a cheaper or faster option.
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.
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.
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