$227 Economy Roundtrip to Chicago (TPA-ORD) in Sep from Tampa

September travel from Tampa International Airport (TPA) to O'Hare International Airport (ORD) is a shoulder-season sweet spot: hotel demand in Tampa softens after summer while Chicago begins to cool. Expect multiple daily nonstop flights—ideal for business travelers and weekend getaways—plus competitive fares if you book 3–7 weeks ahead. Because September is peak Atlantic hurricane season, monitor the National Hurricane Center and airline alerts; airlines often publish waivers and rebooking policies during tropical disturbances. For nearby destinations, combine air travel with short transfers to Clearwater Beach, St. Petersburg, and Sarasota for extended Florida stays. Ready to book? Use primary flight search tools and set price alerts to lock in cheap TPA to ORD flights for September.

Departing from Tampa (TPA) FAQs

Nonstop flights from Tampa International Airport (TPA) to O'Hare International Airport (ORD) typically take about 2 hours 35 minutes to 2 hours 50 minutes. Seasonal winds and airline routing can add a few minutes, but most scheduled nonstop services fall in that range. Check real-time flight status the day of travel for gate and departure updates.

Yes, there are multiple daily nonstop flights from Tampa International Airport (TPA) to O'Hare International Airport (ORD) in September offered by carriers such as United, American, and sometimes Southwest. Frequency increases on weekdays and around holiday windows; early morning and late-afternoon departures are most common. Use the airlines' schedules or Google Flights to find current nonstop options and book your preferred time.

For September travel, book 3–7 weeks in advance to find the best fares on the Tampa International Airport (TPA) to O'Hare International Airport (ORD) route, with midweek departures often cheaper than weekends. Being flexible with dates and using price alerts on Google Flights, Skyscanner, or Hopper can capture lower airfares. Consider red-eye or early-morning flights to score the lowest prices.

September falls within the Atlantic hurricane season, so Tampa International Airport (TPA) passengers should monitor weather updates and airline advisories before travel. Airlines may rebook or waive change fees during tropical disturbances; sign up for airline alerts and check the National Hurricane Center and Tampa International Airport (TPA) notices for timely information. Travel insurance that covers weather cancellations is recommended for September bookings.

From Tampa International Airport (TPA), travelers can use rental cars, app-based rideshares (Uber/Lyft), taxis, and the airport's shuttle services to reach downtown Tampa, St. Petersburg, Clearwater Beach, and Sarasota. The TECO streetcar and local bus connections provide budget-friendly access to some areas, while rental cars offer the most flexibility for exploring nearby destinations. Book rides or rental cars in advance, especially on weekends and during shoulder-season events in September.

Arrive at least 90 minutes before domestic departures at Tampa International Airport (TPA) during September to allow time for security, especially if traveling during morning peaks or during weather disruptions. Use TSA PreCheck if available to speed screening, and check airline carry-on and baggage rules because September fares often come with basic economy restrictions. Keep a flexible itinerary and monitor airline notifications due to seasonal weather or schedule adjustments.

September arrivals at O'Hare International Airport (ORD) from Tampa International Airport (TPA) benefit from milder temperatures and consistent ground-transport options. The CTA Blue Line offers a cost-effective link to downtown Chicago, while rideshares and shuttles connect to business hubs in Schaumburg, Naperville, and Oak Brook. Expect normal passenger flows with occasional spikes around local sports events and conferences—book ground transport or a rental car in advance to secure the best rates. For multi-destination trips, consider routing through ORD when visiting Milwaukee or northwest Indiana; compare Midway (MDW) options if price or schedule flexibility matters.

Arriving at Chicago (ORD) FAQs

From O'Hare International Airport (ORD), the most convenient options to downtown Chicago are the CTA Blue Line train, rideshares (Uber/Lyft), taxis, and shuttle services. The Blue Line takes about 45–55 minutes to the Loop and is often the fastest off-peak option for avoiding traffic. In September, mild weather makes either surface transit or the elevated train comfortable; allow extra time during peak morning and evening commutes.

O'Hare International Airport (ORD) can experience seasonal delays in September due to increased airline schedules returning to business frequency after summer and occasional weather systems. However, September typically sees fewer extreme winter weather disruptions than later months. Check the TSA and airline flight status pages before travel, and consider extra connection time if your itinerary is tight.

Yes, consider flying into Chicago Midway International Airport (MDW) as an alternative to O'Hare International Airport (ORD) for potentially lower fares or better schedule options in September. Midway often has competitive prices on carriers like Southwest, and it can be closer to the Near South Side and some western suburbs. Compare total travel time and transit costs, since MDW and ORD have different ground-transport profiles to your final destination.

When arriving at O'Hare International Airport (ORD) in September, expect efficient immigration and baggage facilities for domestic flights, plentiful ground-transport options, and standard security screening if connecting. Weather in September is generally mild with cooler evenings, so walking between terminals or to ground transportation is comfortable. For business travelers, ORD is a major hub with many lounges and quick connections to suburbs like Naperville and Schaumburg, plus easy rail access to downtown Chicago.

From O'Hare International Airport (ORD), travelers commonly access downtown Chicago, the North Shore suburbs (Evanston, Skokie), Oak Brook and Schaumburg business parks, and destinations across northeastern Illinois such as Naperville or Gary, Indiana. Milwaukee and the greater Milwaukee area are also convenient for multi-city itineraries. Use rail and rental car options at ORD to reach these nearby major cities efficiently.

September in Chicago often features major sports fixtures (MLB regular season for the Chicago Cubs and White Sox), concerts, and corporate conferences that can raise hotel and airfare prices near O'Hare International Airport (ORD). Weekend games and downtown conventions may increase demand, so book hotels and flights early if you plan travel around event dates. Use event calendars and ticketing sites to confirm dates before you book.

1.0.2509.12

September Events & Festivals — Tampa and Chicago Highlights for Travelers on the TPA–ORD Route

September in Tampa: Expect MLB games with the Tampa Bay Rays at Tropicana Field, local food and arts festivals, and Hispanic Heritage Month events that may increase short-term demand. Nearby destinations like Clearwater Beach and St. Petersburg host smaller cultural happenings and offer beach-laden alternatives for travelers seeking sun. September in Chicago: Cooler evenings welcome outdoor concerts, late-season baseball with the Chicago Cubs and White Sox drawing fans across the region, and a variety of neighborhood festivals and culinary events. Major conferences and corporate meetings also take place in Chicago in September; book flights and hotels early around known event dates to avoid price spikes.

Best Time to Fly TPA to ORD in September — Cheapest Days, Weather Considerations, and Booking Windows

The best time to fly from Tampa International Airport (TPA) to O'Hare International Airport (ORD) in September is midweek (Tuesday–Thursday) with early-morning departures to reduce delay risk and typically capture lower fares. Book 3–7 weeks before travel for a balance of price and availability; last-minute September fares can be volatile due to weather. If you're worried about tropical systems, choose refundable fares or flexible tickets and monitor airline policy pages for waivers. For leisure travelers, late-September often offers the best combination of cooler Chicago weather and discounted hotel rates.

Direct vs Connecting Flights on the TPA–ORD Route — Pros, Cons, and When to Choose Each in September

Choosing a nonstop flight from Tampa International Airport (TPA) to O'Hare International Airport (ORD) typically saves time and reduces the risk of missed connections; nonstop options often cost slightly more but are preferred by business travelers. Connecting flights—commonly routing through Atlanta (ATL), Orlando (MCO), or Dallas/Fort Worth (DFW)—can be cheaper or provide better schedule fit, but they increase travel time and baggage-handling touchpoints. In September, prioritize nonstop flights if weather-related rebookings are a concern; choose connecting itineraries if you need to lower costs or if nonstop seats are sold out.

Airline Comparison for TPA to ORD — United, American, Southwest (September Insights)

United Airlines: Strong nonstop frequency into O'Hare International Airport (ORD) from Tampa International Airport (TPA), tight connection options at ORD, and robust MileagePlus perks; fares range from basic economy to first class. American Airlines: Offers competitive schedules with potential one-stop routes through Charlotte (CLT) or Dallas (DFW); AAdvantage benefits and premium-cabin options are available. Southwest Airlines: Often cheaper overall with free checked bags and a user-friendly change policy; may route to Chicago Midway (MDW) or offer market-dependent service to ORD. For September travel, compare total costs (fares + baggage + transfer time) and use airline apps or loyalty status to secure upgrades and waivers during storm-affected travel.

Seasonal Travel Tips for TPA–ORD in September — Packing, Weather, and Safety Advice

Packing & Clothing: Pack lightweight, breathable clothing for Tampa International Airport (TPA) departures and a light jacket for cooler Chicago evenings upon arrival at O'Hare International Airport (ORD). Hurricane & Weather Prep: September is peak Atlantic hurricane season—subscribe to airline and airport alerts, consider refundable fares, and add trip insurance if your itinerary is weather-sensitive. Airport Tips: Use TSA PreCheck or CLEAR at Tampa International Airport (TPA) if available to speed security and arrive at O'Hare International Airport (ORD) with local transit options planned; the CTA Blue Line is often the fastest route to downtown Chicago. Health & Safety: Carry a small health kit, stay hydrated on short domestic flights, and follow local public-health recommendations. Book early for events and set fare alerts to take advantage of September shoulder-season deals.

TPA to ORD Flight Time & Schedules — Average Duration, Nonstop Options, and Frequency in September

Average nonstop flight time from Tampa International Airport (TPA) to O'Hare International Airport (ORD) is roughly 2 hours 35–50 minutes. Major carriers operate multiple daily nonstops: United often schedules morning and evening departures to align with hub connections at ORD, American offers early-afternoon options, and Southwest may provide alternative schedules into Midway (MDW) or occasional O'Hare service. Peak travel windows in September include morning business departures and late-afternoon flights; weekends can be slightly pricier. For best connections and to minimize delay risk, choose flights early in the day and verify schedules within 24–48 hours of departure.

How to Find Cheap TPA to ORD Flights in September — Deals, Alerts & Alternatives

Find cheap Tampa International Airport (TPA) to O'Hare International Airport (ORD) flights in September by booking 3–7 weeks ahead, flying on Tuesday–Thursday, and using price alerts. Check alternative arrival airports such as Chicago Midway International Airport (MDW) for Southwest-only sales; sometimes the total door-to-door cost is lower when factoring transit times. Use Google Flights and Skyscanner to compare flexible dates and set email or app alerts. Apply promo codes, loyalty points, or standby options for last-minute savings; if traveling during potential hurricane conditions, prioritize refundable fares or add travel insurance. Book now to secure competitive September fares on the TPA–ORD route.

Tue, Sep 1

Roundtrip

Sat, Sep 5

Sat, Sep 5

Roundtrip

Wed, Sep 9

Wed, Sep 2

Roundtrip

Sun, Sep 6

Fri, Sep 4

Roundtrip

Tue, Sep 8

Sun, Sep 6

Roundtrip

Thu, Sep 10

Thu, Sep 3

Roundtrip

Mon, Sep 7

Tue, Sep 1

Roundtrip

Mon, Sep 14

Wed, Sep 2

Roundtrip

Tue, Sep 15

Fri, Sep 4

Roundtrip

Thu, Sep 17

Sat, Sep 5

Roundtrip

Fri, Sep 18

Thu, Sep 3

Roundtrip

Wed, Sep 16

Other Options for This Route

Other Destinations

Flights from Other Cities

Departing from Tampa (TPA) FAQs

How long is the flight from Tampa International Airport (TPA) to O'Hare International Airport (ORD) in September?

Are there direct flights from Tampa International Airport (TPA) to O'Hare International Airport (ORD) in September?

What is the best time to book cheap TPA to ORD flights for travel in September?

Does Tampa International Airport (TPA) have hurricane-related travel advisories in September?

What ground transportation options are available from Tampa International Airport (TPA) to downtown Tampa and nearby beaches?

What airport tips should I know for departing Tampa International Airport (TPA) in September?

Arriving at Chicago (ORD) FAQs

What are the best ways to get from O'Hare International Airport (ORD) to downtown Chicago in September?

Is O'Hare International Airport (ORD) affected by seasonal delays in September?

Are there cheaper alternatives to flying into O'Hare International Airport (ORD) from Tampa in September?

What should travelers expect arrival-wise at O'Hare International Airport (ORD) in September?

Which nearby destinations are commonly accessed from O'Hare International Airport (ORD)?

Are there any September events near O'Hare International Airport (ORD) that affect hotel and flight prices?

September Events & Festivals — Tampa and Chicago Highlights for Travelers on the TPA–ORD Route

Best Time to Fly TPA to ORD in September — Cheapest Days, Weather Considerations, and Booking Windows

Direct vs Connecting Flights on the TPA–ORD Route — Pros, Cons, and When to Choose Each in September

Airline Comparison for TPA to ORD — United, American, Southwest (September Insights)

Seasonal Travel Tips for TPA–ORD in September — Packing, Weather, and Safety Advice

TPA to ORD Flight Time & Schedules — Average Duration, Nonstop Options, and Frequency in September

How to Find Cheap TPA to ORD Flights in September — Deals, Alerts & Alternatives

Flight Options & Prices:

Cheap economy Flights: TPA to ORD in September - Route 3

Flight Options & Prices:

Cheap economy Flights: TPA to ORD in September - Route 4

Flight Options & Prices:

Cheap economy Flights: TPA to ORD in September - Route 5

Flight Options & Prices:

Cheap economy Flights: TPA to ORD in September - Route 6

Flight Options & Prices:

Cheap economy Flights: TPA to ORD in September - Route 7

Flight Options & Prices:

Cheap economy Flights: TPA to ORD in September - Route 8

Flight Options & Prices:

Cheap economy Flights: TPA to ORD in September - Route 9

Flight Options & Prices:

Cheap economy Flights: TPA to ORD in September - Route 10

Flight Options & Prices:

Cheap economy Flights: TPA to ORD in September - Route 11

Flight Options & Prices:

Why Choose Economy Class Flights from Tampa (TPA) to Chicago (ORD)?