Best Flights starting from $286
from$286economy
Chicago (ORD)
Thu, Sep 17
Roundtrip
San Diego (SAN)
Sun, Sep 20
from$347economy
Chicago (ORD)
Mon, Sep 14
Roundtrip
San Diego (SAN)
Thu, Sep 17
from$347economy
Chicago (ORD)
Tue, Sep 15
Roundtrip
San Diego (SAN)
Fri, Sep 18
from$347economy
Chicago (ORD)
Wed, Sep 16
Roundtrip
San Diego (SAN)
Sat, Sep 19
from$347economy
Chicago (ORD)
Fri, Sep 18
Roundtrip
San Diego (SAN)
Mon, Sep 21
from$347economy
Chicago (ORD)
Sat, Sep 19
Roundtrip
San Diego (SAN)
Tue, Sep 22
from$347economy
Chicago (ORD)
Sun, Sep 20
Roundtrip
San Diego (SAN)
Wed, Sep 23
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Other Options for This Route
Other Destinations
Chicago (ORD) to Orlando (MCO) in September from $54
From $54
Chicago (ORD) to Fort Lauderdale (FLL) in September from $62
From $62
Chicago (ORD) to Fort Lauderdale (Any) in September from $62
From $62
Chicago (ORD) to Orlando (MCO) in September from $62
From $62
Chicago (ORD) to Philadelphia (PHL) in September from $64
From $64
Chicago (ORD) to Los Angeles (LAX) in September from $68
From $68
Flights from Other Cities
Denver (DEN) to San Diego (SAN) in September from $44
From $44
Denver (Any) to San Diego (SAN) in September from $44
From $44
Denver (DEN) to San Diego (SAN) in September from $77
From $77
Orlando (MCO) to San Diego (SAN) in September from $111
From $111
Sacramento (SMF) to San Diego (SAN) in September from $137
From $137
Dallas (DFW) to San Diego (SAN) in September from $153
From $153
✈️ Flight Guide: Chicago (ORD) → San Diego (SAN)
Complete travel information for your September journey
September departures from Chicago O'Hare International Airport (ORD) to San Diego International Airport (SAN) strike a balance between summer demand and lower autumn fares. Travelers from Chicago, Milwaukee, Indianapolis, and Madison often choose ORD for nonstop service to San Diego, La Jolla, Carlsbad, and Orange County. For best results, book flights 3–8 weeks in advance, check United and other carriers for nonstop options, and use CTA or rideshare to arrive at the terminal early. Need a cheap flight from ORD to SAN in September? Search now and compare nonstop and one-stop itineraries to find the best value.
Departing from Chicago (ORD) FAQs
Chicago O'Hare International Airport (ORD) is accessible by CTA Blue Line, airport shuttles, rideshare services, and taxis. In September, traffic is generally lighter after the summer peak, but allow extra time during early morning rush hours and around major events—plan to arrive 90–120 minutes before domestic flights. For the best fares and on-time arrival, book a CTA or app-based ride and check flight status before departure.
Security wait times at Chicago O'Hare International Airport (ORD) in September typically range from 10 to 40 minutes depending on terminal and time of day. Early weekday mornings and late afternoons can be busier with business travel; use TSA PreCheck or CLEAR when available to speed up screening. Check live TSA wait estimates and your airline's app for gate updates to avoid stress.
Yes, several carriers operate nonstop flights between Chicago O'Hare International Airport (ORD) and San Diego International Airport (SAN) in September, especially United Airlines and some seasonal services by other carriers. Nonstop options are popular for business and leisure travelers heading to San Diego beaches, La Jolla, or downtown. Book early to secure nonstop seats and competitive fares.
At Chicago O'Hare International Airport (ORD), United Airlines primarily operates from Terminals 1 and 2, while American and Delta use Terminals 3 and 2 respectively; gate assignments can change in September with seasonal schedules. Confirm your terminal and gate in your airline app or the ORD website the night before travel to avoid terminal changes. Allow extra time to transfer between terminals if you have connecting flights.
Checked bag fees and allowances vary by airline on routes from Chicago O'Hare International Airport (ORD) to San Diego, but most U.S. carriers allow one carry-on and one personal item free; checked bag fees apply for basic economy fares. In September, pack for mild San Diego weather—light layers and beachwear—and label luggage clearly. Consider an airline credit card to offset baggage fees and check size/weight limits to avoid overweight surcharges.
September in Chicago can bring variable weather—cooler mornings and occasional storms—which may cause delays at Chicago O'Hare International Airport (ORD) but rarely leads to widespread cancellations in late summer. Most disruptions are short-lived; monitor your airline for real-time updates and consider travel insurance for tight connections. If weather impacts your flight, airlines often rebook passengers on the next available nonstop or connecting service.
Arriving at San Diego International Airport (SAN) in September offers pleasant weather, shorter lines than midsummer, and convenient access to coastal highlights like La Jolla, Coronado, Carlsbad, and the Gaslamp Quarter. Travelers flying from Chicago O'Hare International Airport (ORD) should budget 10–30 minutes for ground transport to downtown San Diego, and slightly longer for coastal suburbs. For the best arrival experience, pre-book airport shuttles or rideshares, consider a rental car for exploring North County (Oceanside, Carlsbad), and check Padres game schedules at Petco Park that may affect traffic.
Arriving at San Diego (SAN) FAQs
Nonstop flights between Chicago O'Hare International Airport (ORD) and San Diego International Airport (SAN) typically take about 4 hours and 40 minutes to 5 hours in September depending on wind and routing. Connecting flights vary widely based on layovers, often adding 2–4 hours. For the fastest travel, book a nonstop United or other available direct service and check seasonal departure times.
San Diego International Airport (SAN) offers multiple ground transportation options to downtown San Diego including ride-hailing, taxis, shuttle buses, and the Metropolitan Transit System (MTS) trolley via shuttle connections. In September, travel times to downtown are typically 10–20 minutes without heavy traffic; evening and weekend congestion can add time. For cost savings, use shared shuttles or public transit, and book rides in advance if arriving during peak Padres game times.
San Diego International Airport (SAN) serves the greater San Diego region and provides easy access to La Jolla, Coronado, Carlsbad, Oceanside, Tijuana (cross-border trips), and Anaheim/Los Angeles area connections. In September, these destinations are popular for beach visits, surfing, and theme parks. Renting a car or arranging transfers in advance helps you reach coastal communities and inland attractions efficiently.
September typically marks the transition from peak summer schedules to more regular fall timetables at San Diego International Airport (SAN), with some carriers reducing frequency while maintaining key nonstop routes. Expect reliable daily service to and from Chicago O'Hare International Airport (ORD) on major airlines with possible adjustments to evening or red-eye flights. Always confirm your flight time 24–48 hours before departure to avoid surprises.
When arriving at San Diego International Airport (SAN) in September, prepare for mild weather and quick access to beaches—pack a light layer and sunscreen. Use mobile baggage tracking and follow signs for ground transportation to reach downtown San Diego, La Jolla, or Coronado quickly. If you're visiting during a Padres home game or holiday weekend, reserve rides or parking in advance to avoid delays.
As of September, San Diego International Airport (SAN) follows current federal and state public health guidance; most COVID-19 travel restrictions have been lifted, but airlines or destinations may have their own recommendations. Travelers should check the latest CDC and State of California advisories for testing or mask guidance before travel. Keep a digital copy of vaccination or testing records if required by your airline or destination.
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September Events & Festivals Near San Diego International Airport (SAN)
September in San Diego brings pleasant weather and a mix of local events: Major League Baseball regular season continues with San Diego Padres home games at Petco Park, Labor Day weekend activities at Mission Beach and Pacific Beach, and neighborhood festivals such as La Jolla art and food events that often fall in early fall. These events attract visitors from Los Angeles, Orange County, and the Bay Area, so expect higher hotel rates and busy weekend traffic—book accommodations and airport transfers early. CTA: Check Padres schedules and local festival calendars before booking your ORD to SAN trip in September.
Best Time to Fly ORD to SAN — September Travel Advice
For September travel from Chicago O'Hare International Airport (ORD) to San Diego International Airport (SAN), midweek departures (Tuesday–Thursday) and early-morning flights usually offer the best balance of price and reliability. Book 3–8 weeks in advance for the most competitive fares; last-minute demand is lower than summer but can still affect prices around Labor Day. If flexibility permits, target non-peak hours (late morning or mid-afternoon) to avoid busiest boarding periods and to find better seat availability.
Direct vs Connecting Flights: ORD to SAN in September
Choosing a nonstop flight from Chicago O'Hare International Airport (ORD) to San Diego International Airport (SAN) in September usually saves 1–3 hours compared to connecting itineraries and reduces the risk of missed connections. Connecting flights can be cheaper, particularly on low-cost carriers or when using frequent flyer award space, but add complexity and potential delay exposure at layover airports like Denver or Phoenix. If your priority is speed and convenience, opt for nonstop service; if price is the primary concern, compare connecting options while allowing generous connection times.
Airline Comparison for ORD to SAN — September Options
United Airlines often offers multiple nonstop flights between Chicago O'Hare International Airport (ORD) and San Diego International Airport (SAN) with premium seat options and strong loyalty benefits for MileagePlus members. Alaska Airlines may provide competitive fares and customer service with convenient west-coast connections; American and Delta typically offer one-stop options via their hubs. Southwest may operate similar routes from other Chicago airports—review departure airport before booking. Compare total trip cost including baggage, seat selection, and change fees to choose the best carrier for your September trip.
Seasonal Travel Tips for ORD to SAN in September
Pack light layers for San Diego in September—mornings can be cool near the coast while afternoons stay warm. Book early for Padres game nights and long weekends, and opt for early-morning flights from Chicago O'Hare International Airport (ORD) to reduce delay risk. Consider mobile boarding passes, TSA PreCheck, and rental car reservations if you plan to explore North County (Carlsbad, Oceanside). For the best beach days, target mid-September when summer crowds diminish but water temperatures remain pleasant.
Flight Time & Schedules: Chicago O'Hare International Airport (ORD) to San Diego International Airport (SAN) in September
Nonstop flight time from Chicago O'Hare International Airport (ORD) to San Diego International Airport (SAN) averages 4 hours 40 minutes to 5 hours in September, with most departures scheduled in morning, midday, and evening windows. Major carriers commonly operate 1–4 nonstop frequencies per day depending on demand; connecting options via Denver, Phoenix, or Dallas add 1–3 hours of total travel time. Check morning departures for lower delay risk and evening flights for flexible fares; always verify times 48 hours before travel due to seasonal adjustments.
Cheap Flights ORD to SAN in September — Booking Tips & Deals
To score cheap flights from Chicago O'Hare International Airport (ORD) to San Diego International Airport (SAN) in September, book 3–8 weeks in advance and aim for Tuesdays or Wednesdays when leisure demand is lighter. Use fare-aggregation tools and airline newsletters for flash sales, compare nonstop versus one-stop itineraries, and consider early-morning departures for lower prices. Low-cost carrier options and basic economy fares can save money but watch baggage restrictions—add checked bags to compare total trip cost. CTA: Search now for September deals on nonstop ORD to SAN flights and set fare alerts.