Best Flights starting from $254
from$254economy
Norfolk (ORF)
Tue, Sep 15
Roundtrip
Chicago (Any)
Sun, Sep 20
from$318economy
Norfolk (ORF)
Wed, Sep 16
Roundtrip
Chicago (Any)
Mon, Sep 21
from$340economy
Norfolk (ORF)
Thu, Sep 17
Roundtrip
Chicago (Any)
Tue, Sep 22
from$340economy
Norfolk (ORF)
Fri, Sep 18
Roundtrip
Chicago (Any)
Wed, Sep 23
from$363economy
Norfolk (ORF)
Sat, Sep 12
Roundtrip
Chicago (Any)
Thu, Sep 17
from$363economy
Norfolk (ORF)
Sun, Sep 13
Roundtrip
Chicago (Any)
Fri, Sep 18
from$363economy
Norfolk (ORF)
Mon, Sep 14
Roundtrip
Chicago (Any)
Sat, Sep 19
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Other Destinations
Norfolk (ORF) to Jacksonville (JAX) in September from $98
From $98
Norfolk (ORF) to New York (LGA) in September from $100
From $100
Norfolk (ORF) to Dallas (Any) in September from $103
From $103
Norfolk (ORF) to Orlando (Any) in September from $108
From $108
Norfolk (ORF) to Islip (ISP) in September from $123
From $123
Norfolk (ORF) to Houston (IAH) in September from $126
From $126
Flights from Other Cities
Atlanta (Any) to Chicago (Any) in September from $69
From $69
Los Angeles (LAX) to Chicago (Any) in September from $93
From $93
Los Angeles (Any) to Chicago (Any) in September from $120
From $120
Orlando (Any) to Chicago (Any) in September from $125
From $125
Minneapolis (MSP) to Chicago (Any) in September from $142
From $142
Jackson (JAN) to Chicago (Any) in September from $157
From $157
✈️ Flight Guide: Norfolk (ORF) → Chicago (Any)
Complete travel information for your September journey
September is a favorable month to fly out of Norfolk International Airport (ORF) to Chicago (All Airports) (CHIA) with shoulder-season demand and lower fares than peak summer. Expect competitive pricing on mid-week departures and early-morning flights that reduce delay risk. Nearby destinations—Virginia Beach, Chesapeake, Williamsburg and Richmond—often feed ORF traffic, so allow extra time if driving from those areas. Book 3–6 weeks ahead for the best September deals and sign up for fare alerts to capture lower ORF to CHIA prices.
Departing from Norfolk (ORF) FAQs
Nonstop and one-stop options typically include major carriers that serve Norfolk International Airport (ORF) with routes into Chicago (All Airports) (CHIA), such as American Airlines and Southwest on seasonal and regular schedules. In September, airlines often adjust frequencies after the summer peak, so check the carriers' schedules for updated nonstop availability and book early for the best fares.
Typical nonstop flight time between Norfolk International Airport (ORF) and Chicago (All Airports) (CHIA) is about 2 hours and 15 minutes to 2 hours and 45 minutes depending on which Chicago airport you use (O'Hare or Midway) and winds. Connecting itineraries often increase total travel time to 4–6+ hours including layovers, so compare nonstop versus one-stop schedules when booking.
September typically sees fewer weather disruptions than winter months, but travelers should monitor airline alerts and Norfolk International Airport (ORF) advisories for maintenance closures or staffing notices. Check the airport website and carrier emails before departure for gate changes, TSA updates, and potential schedule shifts during regional events or hurricane season.
Early morning departures (before 9 AM) from Norfolk International Airport (ORF) generally have lower delay rates and fewer missed connections, especially in September when afternoon thunderstorms can impact regional flights. For cost savings, consider mid-week flights (Tuesday–Thursday) and use price tracking tools to spot lower fares on ORF to CHIA routes.
Norfolk International Airport (ORF) is accessible via I-64 and local shuttle services; long-term and economy parking lots are available with shuttle service to terminals year-round. In September, parking demand is moderate after summer; reserve long-term parking online for the best rates and consider rideshare or regional shuttle if attending local events in Virginia Beach or Williamsburg before your flight.
Arrive prepared in Chicago (All Airports) (CHIA) during September by choosing the airport that best serves your final destination—O'Hare for broader flight options and Midway for faster access to the Near South Side and downtown. Public transit, rideshares, and airport shuttles offer dependable transfers; expect comfortable weather but pack a light jacket for crisp evenings. For the best deals, aim to book transfers and downtown hotels early if your trip coincides with sports or neighborhood festivals in September.
Arriving at Chicago (Any) FAQs
Chicago (All Airports) (CHIA) commonly refers to O'Hare International Airport and Midway International Airport; O'Hare handles more international and long-haul flights while Midway often serves domestic connections. In September, consider which airport is closest to your final destination—downtown Chicago is fastest from Midway, while O'Hare has more frequent nonstop options and greater carrier choice.
From Chicago (All Airports) (CHIA), travelers can use the CTA (Blue Line from O'Hare), Metra trains, airport shuttles, rideshare services, and regional buses. In September, traffic is lighter than summer peak, making rail and rideshare reliable choices for quick access to downtown Chicago, suburbs like Naperville, and nearby cities such as Milwaukee.
September in Chicago features numerous events such as neighborhood festivals, early fall sports seasons, and arts programming; arrivals into Chicago (All Airports) (CHIA) should prepare for increased hotel demand during major conventions. If visiting for concerts or the start of the Bears season, book accommodations and airport transfers early to secure the best rates.
September usually brings mild temperatures and lower chance of winter delays, but occasional storms can still disrupt schedules at Chicago (All Airports) (CHIA). Monitor forecasts before travel—airlines typically issue alerts for turbulence or thunderstorms—and allow extra time for connections during busy weekend nights when regional traffic picks up.
Last-minute fares into Chicago (All Airports) (CHIA) in September vary widely and are influenced by event demand and remaining seat inventory. Use fare comparison tools, sign up for price-drop alerts, and check mid-week inbound flights for better odds of discount pricing; however, booking 2–4 weeks out usually yields the best combination of price and schedule options.
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September Events & Festivals to Consider When Flying ORF → CHIA
September brings neighborhood festivals, college football kickoffs, and arts events that can affect ORF and CHIA demand. In Norfolk and nearby Virginia Beach, late-summer festivals wind down while business travel picks up; in Chicago, theater openings, conventions, and sports season greatly increase hotel and transfer demand. If your trip aligns with big events—sports games, trade shows, or music festivals—book flights and lodging well in advance and consider alternate nearby airports or off-peak days to save on fares.
Best Time to Fly ORF to CHIA — September Recommendations
For ORF to CHIA travel in September, fly early morning or mid-week to reduce delay exposure and often secure lower fares. Tuesdays and Wednesdays typically show cheaper tickets, while Friday evenings and Sunday afternoons are busiest and most expensive. Book 3–6 weeks ahead to capture September deals, and use fare-tracking tools to monitor short-term price drops for last-minute windows.
Direct vs Connecting Flights from Norfolk International Airport (ORF) to Chicago (All Airports) (CHIA)
Nonstop flights from Norfolk International Airport (ORF) to Chicago (All Airports) (CHIA) save time and reduce missed-connection risk, usually taking about 2–3 hours. Connecting flights may be cheaper—especially in September shoulder season—but add layover time and possible delay exposure. If price is primary, search one-stop itineraries via major hubs (Charlotte, Atlanta); if time and convenience matter, prioritize nonstop options and book early to secure seats.
Airline Comparison for ORF to CHIA — September Options
Major carriers operating between Norfolk International Airport (ORF) and Chicago (All Airports) (CHIA) include American Airlines, Southwest, and other network partners offering one-stop or seasonal nonstop service. American often provides convenient connections via Charlotte or Philadelphia and a robust loyalty program, while Southwest offers easy change policies and two free checked bags which can lower total trip costs. Compare fare classes, baggage fees, and schedule reliability when booking September travel; use airline-flexible search tools and read recent on-time performance reports to choose the best carrier for your priorities.
Seasonal Travel Tips for ORF to CHIA in September
Pack layered clothing for September: warm afternoons and cool evenings are common in Chicago, while Norfolk may still feel summery—bring a light jacket. Monitor Atlantic hurricane season updates when traveling from Norfolk International Airport (ORF) and allow extra connection time if flights are routed around storms. Use mobile boarding passes, enroll in TSA PreCheck to speed Norfolk airport security lines, and compare O'Hare vs Midway arrival times to choose the most convenient Chicago (All Airports) (CHIA) option. Book mid-week flights and set fare alerts to lock in affordable September tickets.
ORF to CHIA Flight Times & Schedules — September Guide
Nonstop flights from Norfolk International Airport (ORF) to Chicago (All Airports) (CHIA) generally run about 2 hours 15 minutes to 2 hours 45 minutes, depending on the specific Chicago airport and winds. Airlines publish frequent early-morning and midday departures; September schedules often slim down slightly from summer peaks but remain steady as business travel resumes. For connections, typical layovers occur in Charlotte, Philadelphia, or Atlanta and can add 1.5–4 hours to total travel time. Book early-morning flights to minimize delay risk and check real-time schedules 24–48 hours before departure.
How to Find Cheap Flights from Norfolk International Airport (ORF) to Chicago (All Airports) (CHIA) in September
To find cheap flights from Norfolk International Airport (ORF) to Chicago (All Airports) (CHIA) in September, use flexible date searches and target mid-week departures (Tuesday–Thursday) when demand drops. Set price alerts, compare departures to both O'Hare and Midway, and consider one-stop itineraries that may be substantially cheaper than nonstops. Check discount calendars on major travel search engines and book within the 3–6 week window for the best balance of price and schedule. CTA: Compare ORF to CHIA fares now and sign up for alerts to capture price dips.