Best Flights starting from $156
from$156economy
Tampa (TPA)
Tue, Oct 6
Roundtrip
Chicago (Any)
Sat, Oct 10
from$156economy
Tampa (TPA)
Sat, Oct 10
Roundtrip
Chicago (Any)
Wed, Oct 14
from$174economy
Tampa (TPA)
Mon, Oct 5
Roundtrip
Chicago (Any)
Fri, Oct 9
from$174economy
Tampa (TPA)
Wed, Oct 7
Roundtrip
Chicago (Any)
Sun, Oct 11
from$193economy
Tampa (TPA)
Wed, Oct 7
Roundtrip
Chicago (Any)
Sat, Oct 10
from$193economy
Tampa (TPA)
Sat, Oct 10
Roundtrip
Chicago (Any)
Tue, Oct 13
from$199economy
Tampa (TPA)
Fri, Oct 9
Roundtrip
Chicago (Any)
Tue, Oct 13
from$217economy
Tampa (TPA)
Sun, Oct 11
Roundtrip
Chicago (Any)
Thu, Oct 15
from$220economy
Tampa (TPA)
Thu, Oct 8
Roundtrip
Chicago (Any)
Mon, Oct 12
from$231economy
Tampa (TPA)
Mon, Oct 12
Roundtrip
Chicago (Any)
Thu, Oct 15
from$235economy
Tampa (TPA)
Fri, Oct 9
Roundtrip
Chicago (Any)
Mon, Oct 12
from$237economy
Tampa (TPA)
Thu, Oct 8
Roundtrip
Chicago (Any)
Sun, Oct 11
from$240economy
Tampa (TPA)
Tue, Oct 6
Roundtrip
Chicago (Any)
Fri, Oct 9
from$244economy
Tampa (TPA)
Sun, Oct 11
Roundtrip
Chicago (Any)
Wed, Oct 14
Fields updated — click View Prices to search ↑
Other Options for This Route
Other Destinations
Tampa (TPA) to Chicago (ORD) in October from $22
From $22
Tampa (TPA) to Atlanta (Any) in October from $29
From $29
Tampa (TPA) to Houston (IAH) in October from $63
From $63
Tampa (TPA) to Washington, D.C. (BWI) in October from $72
From $72
Tampa (TPA) to Fort Lauderdale (FLL) in October from $78
From $78
Tampa (TPA) to Chicago (MDW) in October from $78
From $78
Flights from Other Cities
Fort Lauderdale (Any) to Chicago (Any) in October from $56
From $56
Miami (Any) to Chicago (Any) in October from $56
From $56
New York (JFK) to Chicago (Any) in October from $63
From $63
Fort Lauderdale (FLL) to Chicago (Any) in October from $64
From $64
Orlando (Any) to Chicago (Any) in October from $74
From $74
New York (Any) to Chicago (Any) in October from $88
From $88
✈️ Flight Guide: Tampa (TPA) → Chicago (Any)
Complete travel information for your October journey
Planning October travel from Tampa International Airport (TPA) to Chicago (All Airports) (CHIA)? October typically brings steady demand from fall getaways and business travel. Book midweek for the best cheap flights TPA to CHIA October fares, and consider early-morning or late-evening nonstops to avoid crowds. Nearby major destinations commonly accessed from TPA include St. Petersburg, Clearwater, Sarasota, Orlando, and Miami for multi-destination trips. CTA: Search Tampa to Chicago flights in October now and set price alerts to catch seasonal deals.
Departing from Tampa (TPA) FAQs
Nonstop flights from Tampa International Airport (TPA) to Chicago O'Hare or Midway typically take about 2 hours 40 minutes to 3 hours depending on the airport (ORD or MDW) and winds. Remember Chicago is in Central Time, one hour behind Tampa’s Eastern Time, so plan your arrival time accordingly. October schedules are stable with multiple daily nonstop options.
Yes — several carriers operate nonstop routes from Tampa International Airport (TPA) to Chicago’s airports in October, including American, Southwest, United, and Delta on select days. Frequency increases on popular travel days like Fridays and Sundays; check airline schedules and book early for best nonstop availability. Consider early-morning and evening options for greater seat availability.
For the best fares in October, target midweek departures (Tuesdays and Wednesdays) and book 3–6 weeks in advance to capture lower prices. Avoid peak holiday weekends and Columbus Day weekend, when fares often spike. Use fare alerts and compare aggregators like Google Flights and Skyscanner to catch flash sales and cheap flights TPA to CHIA October deals.
Tampa International Airport (TPA) offers rideshare pickup, rental cars, shuttle services, and express buses year-round; in October services remain fully operational. For faster transfers use the SkyConnect people mover to the rental car center and allow extra time during special events in Tampa. Check TPA’s official site before travel for any construction advisories or holiday service changes.
October is still within Florida’s hurricane season, so while most days are fine, tropical systems or remnants can cause delays or cancellations at Tampa International Airport (TPA). Monitor NOAA advisories and airline notifications, purchase flexible tickets or travel insurance, and prepare for last-minute schedule changes when booking October travel.
Tampa International Airport (TPA) is a gateway to St. Petersburg, Clearwater, Sarasota, Orlando, and the Gulf Coast beaches — popular extensions for leisure travelers flying to Chicago. Many travelers connect to Florida beaches or theme parks before returning to the Midwest; consider flexible baggage and one-way fares if planning multi-city travel in October.
Arriving in Chicago (All Airports) (CHIA) in October from Tampa International Airport (TPA) means cooler weather, lively fall festivals, and steady transit options. The Chicago Marathon and Chicago International Film Festival are often held in October and can affect road access and hotel availability, so book ground transport and lodging early. Popular destinations accessible from CHIA arrivals include downtown Chicago, Evanston, Naperville, Oak Brook, and Milwaukee. CTA trains and rideshares are reliable choices; CTA Blue and Orange Lines provide direct connections to O'Hare and Midway respectively. CTA: Book your October Chicago transit or car rental early for the best rates and to secure your preferred arrival transfer.
Arriving at Chicago (Any) FAQs
Flights from Tampa International Airport (TPA) typically arrive at Chicago O'Hare International Airport or Chicago Midway International Airport; schedule availability depends on airline and fare type. Use the city code Chicago (All Airports) (CHIA) when searching broad results to see options for ORD and MDW. Consider your final destination—downtown Chicago favors ORD for direct airport trains and MDW for quicker access to the south side.
Chicago (All Airports) (CHIA) arrivals can use CTA trains (Blue Line to/from ORD), Orange Line to/from MDW, taxis, rideshares, and Metra commuter services. October weather can be cool and crisp—plan for extra time if you’re traveling to outer suburbs like Naperville or Evanston. For the fastest trip downtown, the Blue Line from O'Hare typically beats rush-hour road traffic.
October in Chicago brings cooler temperatures, possible rain, and event-driven crowds for the Chicago Marathon and film festivals; allow additional transfer time on arrival. Pack layers and a compact umbrella, and check event schedules if you’re arriving near downtown, as road closures may affect ground transportation. Monitor local news and airline alerts for any weather-related adjustments.
If your itinerary includes an international connection into Chicago (All Airports) (CHIA), allow at least 90–120 minutes for customs and baggage claim; for domestic connections between ORD and MDW, provide 2–3 hours due to transfer time and traffic. October is a busy travel month with conferences and fall events, so err on the side of extra time. Check with your airline for minimum connection time policies.
From Chicago (All Airports) (CHIA) you can easily reach downtown Chicago, Evanston, Naperville, Oak Brook, and Milwaukee for regional trips. October is ideal for Midwest road trips to see fall foliage—Lake Geneva and Starved Rock State Park are popular choices within a two-hour drive. Consider car rentals at arrival airports for flexible regional travel plans.
Most airline lounges and airport services operate normally at Chicago O'Hare and Midway in October, though hours may vary during events or holidays. If you need lounge access or special assistance, confirm availability ahead of travel and reserve services where possible. Priority lanes and TSA PreCheck remain valuable for speedy arrivals during October’s event-packed weekends.
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October Events & Festivals — Tampa (TPA) to Chicago (CHIA) Travel Planner
October can be event-heavy for both origin and destination. In Chicago, the Chicago Marathon and Chicago International Film Festival typically occur in October, driving hotel and flight demand near downtown. In Tampa, October features fall festivals, Halloween celebrations, and college football weekends which can raise departure-day traffic at Tampa International Airport (TPA). If traveling during event weekends, book flights and ground transport early, and expect crowds and potential road closures near venues. CTA: Check event calendars for both cities before finalizing October travel dates to CHIA.
Best Time to Fly — TPA to CHIA in October
The best time to fly from Tampa International Airport (TPA) to Chicago (All Airports) (CHIA) in October is midweek (Tuesday–Thursday) and early morning or late evening when fares tend to be lower and airports less crowded. Avoid major event weekends like the Chicago Marathon weekend and Columbus Day long weekend for lower prices and smoother airport experiences. If you need weekend travel, book at least 4–8 weeks in advance. CTA: Use flexible-date search and set fare alerts to lock in the best October rates.
Direct vs Connecting Flights — TPA to CHIA October Guide
Nonstop flights from Tampa International Airport (TPA) to Chicago (All Airports) (CHIA) are faster and minimize missed-connection risk — typically the best choice for tight schedules. Connecting itineraries through hubs such as Atlanta (ATL), Charlotte (CLT), or Dallas (DFW) can be cheaper, offer more schedule flexibility, and open more departure times, but add transfer time and potential delay exposure. In October, consider nonstop flights when traveling on tight schedules or during storm-prone periods; choose connections for potential savings when you have buffer time. CTA: Compare nonstop and connecting fares for your October dates to find the right balance of price and convenience.
Airline Comparison — TPA to CHIA in October: Southwest, American, United, Delta
Southwest: Often competitive on price and baggage-friendly with two free checked bags, frequent nonstops between Tampa International Airport (TPA) and Chicago Midway; ideal for budget-conscious travelers. American Airlines: Regular nonstops to Chicago O'Hare with tight connections through Charlotte and Philadelphia hubs; good for AAdvantage loyalty members. United Airlines: Strong O'Hare presence with multiple daily flights and convenient connections across its hub network. Delta Air Lines: Reliable schedules often routed via Atlanta with solid SkyMiles benefits. For October, compare final prices including baggage and seat selection fees; loyalty members should weigh program value when selecting an airline. CTA: Check full price breakdowns and book the carrier that balances your schedule and loyalty benefits for October travel.
Seasonal Travel Tips — October Travel from TPA to CHIA
Pack layers and a lightweight rain jacket for October travel — daytime in Tampa can be warm, while Chicago often requires sweaters and an insulated jacket, especially at night. Because October is still in the Atlantic hurricane season, monitor NOAA updates and opt for refundable fares or travel insurance if concerned about storm-related disruptions at Tampa International Airport (TPA). Allow extra transfer time for ground transportation in Chicago during event weekends, and enroll in TSA PreCheck or CLEAR to speed security at both departure and arrival airports. CTA: Prepare for variable weather and flexible travel plans when booking Tampa–Chicago trips in October.
Flight Time & Schedules — Tampa International Airport (TPA) to Chicago (All Airports) (CHIA)
Nonstop flights from Tampa International Airport (TPA) to Chicago O'Hare (ORD) or Midway (MDW) generally take between 2 hours 40 minutes and 3 hours. Schedules in October typically include multiple daily nonstops in morning and evening peaks; connecting itineraries through hubs (Charlotte, Atlanta, Dallas) add 1–3 hours depending on layover. Remember Chicago’s Central Time is one hour earlier than Tampa’s Eastern Time, so a 9:00 AM departure from TPA might arrive around 10:40 AM local time. CTA: Check real-time schedules with airlines before booking, and consider nonstops for the fastest travel time.
Cheap Flights — Tampa International Airport (TPA) to Chicago (All Airports) (CHIA) in October
To find cheap flights from Tampa International Airport (TPA) to Chicago (All Airports) (CHIA) in October, book 3–6 weeks in advance and target midweek departures (Tuesday–Thursday). Typical round-trip economy fares in October range from $120–$280 depending on demand and how close to event weekends you travel; use fare comparison tools and set alerts for price drops. Consider flexible dates, alternate Chicago airports (ORD vs MDW), and low-cost carriers like Southwest for the best deals. CTA: Sign up for price alerts and search multiple airport combos (TPA→CHIA) to find the best October savings.