Best Flights starting from $280
from$280economy
Savannah (SAV)
Tue, Oct 13
Roundtrip
Chicago (MDW)
Sat, Oct 17
from$303economy
Savannah (SAV)
Thu, Oct 15
Roundtrip
Chicago (MDW)
Mon, Oct 19
from$305economy
Savannah (SAV)
Sat, Oct 17
Roundtrip
Chicago (MDW)
Wed, Oct 21
from$347economy
Savannah (SAV)
Wed, Oct 14
Roundtrip
Chicago (MDW)
Sun, Oct 18
from$347economy
Savannah (SAV)
Fri, Oct 16
Roundtrip
Chicago (MDW)
Tue, Oct 20
from$390economy
Savannah (SAV)
Sun, Oct 18
Roundtrip
Chicago (MDW)
Thu, Oct 22
from$395economy
Savannah (SAV)
Mon, Oct 12
Roundtrip
Chicago (MDW)
Fri, Oct 16
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Other Options for This Route
Other Destinations
Savannah (SAV) to San Juan (Any) in October from $453
From $453
Savannah (SAV) to Cancun (CUN) in October from $641
From $641
Savannah (SAV) to Dublin (DUB) in October from $713
From $713
Savannah (SAV) to Cairo (CAI) in October from $4,816
From $4,816
Savannah (SAV) to New York (Any) in November from $84
From $84
Savannah (SAV) to Washington, D.C. (IAD) in November from $214
From $214
Flights from Other Cities
Orlando (MCO) to Chicago (MDW) in October from $85
From $85
Mobile (MOB) to Chicago (MDW) in October from $165
From $165
Fort Lauderdale (Any) to Chicago (MDW) in October from $228
From $228
Tampa (Any) to Chicago (MDW) in October from $317
From $317
Mexico City (MEX) to Chicago (MDW) in October from $385
From $385
Sarasota (SRQ) to Chicago (MDW) in October from $435
From $435
✈️ Flight Guide: Savannah (SAV) → Chicago (MDW)
Complete travel information for your October journey
October is a favorable month to fly from Savannah/Hilton Head International Airport (SAV) to Chicago Midway International Airport (MDW). Fall temperatures in Savannah are typically mild, making it an attractive time to visit Hilton Head Island, Savannah Historic District, nearby Charleston, or to begin a Midwest trip. For travelers targeting Chicago attractions—downtown Chicago, the Loop, Wrigleyville, and suburbs like Naperville and Evanston—book early weekdays for the best SAV to MDW fares. Use price alerts and compare Southwest, Delta, American, and United itineraries to find cheap flights in October. CTA: Compare October SAV to MDW fares and book now to lock in the best deals.
Departing from Savannah (SAV) FAQs
October departures from Savannah/Hilton Head International Airport (SAV) are typically smooth with mild fall weather and fewer summer crowds. Expect on-time performance to be good, but check morning and evening peak times for domestic connections. For the best fares to Chicago Midway International Airport (MDW), compare weekday flights and sign up for price alerts.
Direct nonstop service between Savannah/Hilton Head International Airport (SAV) and Chicago Midway International Airport (MDW) may be offered seasonally by carriers like Southwest; availability can change by year. If nonstop is unavailable, popular one-stop itineraries route through Atlanta (ATL) or Charlotte (CLT). Always check current schedules when booking October travel.
A nonstop flight from Savannah/Hilton Head International Airport (SAV) to Chicago Midway International Airport (MDW) typically takes about 2 hours and 10 minutes. One-stop itineraries through hubs like Atlanta add 2–4 hours of total travel time depending on layovers. Check specific airline schedules for exact block time when booking in October.
In October, driving, rideshare, and taxis remain the most convenient options to reach Savannah/Hilton Head International Airport (SAV). Downtown Savannah is roughly a 20–25 minute drive; Hilton Head Island, Charleston, and Jacksonville remain accessible for connecting travelers. Reserve parking in advance for popular fall weekends and consider booking airport shuttles if coming from nearby cities.
October typically brings mild temperatures to the Savannah area and a reduced likelihood of hurricane impacts compared with peak season, so weather delays are less common. However, occasional storms or regional weather patterns can cause disruptions—especially for connecting flights. Always check your airline's flight status and airport advisories before departure.
Pack layers for early-morning and evening temperature swings, arrive 90 minutes before domestic departures during busy fall weekends, and sign up for airline alerts for the SAV to MDW route. Consider nearby destinations like Hilton Head Island, Charleston, and Atlanta if extending your trip. Book early to secure the best SAV to MDW fares for October travel.
Arriving at Chicago Midway International Airport (MDW) in October offers convenient access to downtown Chicago and nearby destinations. Expect crisp fall conditions; pack a light jacket and prepare for cooler evenings. The CTA Orange Line provides an affordable and direct link to the Loop, while taxis and rideshares serve the broader metropolitan area, including Naperville, Evanston, and Milwaukee day trips. For event-heavy weekends such as festival or marathon dates, plan extra transit time and pre-book rides where possible. CTA passes and rental car reservations can help ensure smooth onward travel—compare options and book in advance for the best rates.
Arriving at Chicago (MDW) FAQs
Chicago Midway International Airport (MDW) offers quick access to downtown Chicago via the CTA Orange Line, which runs frequently and is a cost-effective option for October arrivals. Taxis, rideshares, and rental cars are readily available at the terminal, and travel times to downtown typically range from 20–35 minutes depending on traffic. If you plan to visit nearby suburbs such as Oak Lawn, Cicero, Naperville, or Evanston, consider renting a car or booking a rideshare.
October in Chicago usually brings crisp fall weather with daytime highs in the 50s–60s°F (10–20°C) and cooler evenings. Be prepared for wind and occasional rain; layering is recommended. Monitor local forecasts before you travel, especially if you plan outdoor activities in the city or nearby day trips to Wisconsin or Indiana.
October is a moderate travel month for Chicago; you may encounter higher passenger volumes during special events like festivals or the Chicago Marathon, which can increase ground transport times. Weather-related delays are less frequent than winter months but can still occur. To reduce stress, allow extra time for ground transportation and monitor your airline's status alerts.
From Chicago Midway International Airport (MDW) you can quickly reach downtown Chicago for attractions like Millennium Park, the Art Institute, and Navy Pier. Nearby cities and top destinations accessible from MDW include Naperville, Evanston, Oak Brook, Milwaukee (north), and northwest Indiana communities like Gary and Hammond. October is ideal for fall foliage drives to suburban parks and lakeshore areas.
After arriving at Chicago Midway International Airport (MDW), follow signs to baggage claim and ground transportation; CTA Orange Line access is well-marked for quick trips to downtown. October crowds can be lighter than summer but heavier on event weekends—allow at least 45–60 minutes from touchdown to exiting the terminal. Use real-time transit apps and book rideshares early during events to secure reliable transport.
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October Events & Festivals – Savannah/Hilton Head (SAV) and Chicago Midway (MDW) Travel Guide
October features several high-traffic events that can impact SAV and MDW travel. In Savannah, cultural and university events such as SCAD-related film and arts programming can increase hotel demand and airport traffic; nearby Hilton Head and Charleston also attract fall visitors. In Chicago, October often brings major draws like the Chicago International Film Festival, the Chicago Marathon (occasionally scheduled in October), and numerous fall food and beer festivals—these can raise demand on arrivals at Chicago Midway International Airport (MDW). When planning October travel, check event calendars, book flights and hotels early, and allow extra time for ground transport on event weekends. CTA: Review local event calendars and adjust SAV to MDW travel dates to avoid peak crowds.
Best Time to Fly SAV to MDW in October – Save Money & Avoid Delays
For October trips from Savannah/Hilton Head International Airport (SAV) to Chicago Midway International Airport (MDW), the best time to fly for value and reliability is midweek (Tuesday–Thursday) and outside holiday weekends. Early morning nonstop flights often avoid weather-driven delays and congested evening periods. If you want lower fares, search flexible dates and consider flights departing on Tuesday or Wednesday. CTA: Compare midweek SAV to MDW fares for October and book the optimal itinerary today.
Direct vs Connecting Flights from Savannah/Hilton Head (SAV) to Chicago Midway (MDW) in October
Choosing between a direct nonstop and a connecting flight from Savannah/Hilton Head International Airport (SAV) to Chicago Midway International Airport (MDW) in October depends on priorities. Nonstops (when available) save time—typically around 2 hours 10 minutes—and reduce the risk of missed connections. Connecting flights often offer lower fares and more schedule options but add layover time and potential delay exposure, especially during busy event weekends. If speed and convenience are priorities, book a nonstop; if you need flexibility or a lower fare, consider a single-connection itinerary. CTA: Compare nonstop and one-stop SAV to MDW options now and choose what fits your schedule and budget.
Airline Comparison for SAV to MDW (October) – Southwest, Delta, American, United
Major carriers on the SAV to MDW route differ by pricing model and perks. Southwest often provides competitive round-trip fares and two free checked bags but operates primarily to Midway for Chicago service; Delta, American, and United typically route through their hubs (e.g., ATL, CLT, ORD) offering more connections. Delta and American may provide tighter schedules for one-stop connections, while Southwest can offer straightforward nonstop options when available. Compare total trip cost including baggage and seat selection fees. CTA: Compare October SAV to MDW fares across carriers and pick the best combination of price, schedule, and baggage policy.
Seasonal Travel Tips for Flying SAV to MDW in October
Pack for variable weather when traveling from Savannah/Hilton Head International Airport (SAV) to Chicago Midway International Airport (MDW) in October—Savannah will be mild while Chicago can be chilly and windy. Dress in layers, bring a compact travel umbrella, and keep essentials in your carry-on in case of checked-bag delays. Book refundable or changeable fares if your itinerary aligns with event dates, and download airline apps for real-time updates. Consider late-afternoon arrivals to avoid early-morning traffic and use public transit like the CTA Orange Line from MDW for cost-efficient downtown transfers. CTA: Prepare your October packing list and check live flight alerts before departing SAV.
SAV to MDW Flight Time & Schedule Guide for October
A nonstop flight from Savannah/Hilton Head International Airport (SAV) to Chicago Midway International Airport (MDW) usually takes about 2 hours and 10 minutes. If nonstops are unavailable, one-stop itineraries through hubs like Atlanta (ATL) or Charlotte (CLT) generally total 4–6 hours, including layovers. October schedules are stable with reduced summer frequency; early-morning and evening flights are popular for connecting passengers. To optimize travel time, search for morning nonstops or single-connection itineraries with short layovers, and confirm the published block time when booking. CTA: Check live October schedules and choose the best flight duration for your trip.
How to Find Cheap Flights from Savannah/Hilton Head International Airport (SAV) to Chicago Midway International Airport (MDW) in October
To find cheap flights from Savannah/Hilton Head International Airport (SAV) to Chicago Midway International Airport (MDW) in October, search 3–8 weeks ahead for the best midweek fares and use fare alerts to monitor price drops. Consider low-cost carriers and flexible dates—weekday departures and red-eye options can yield savings. Compare baggage fees, change policies, and total trip cost across Southwest, Delta, American, and United. Use aggregate search engines and check airline direct promotions for last-minute sales. CTA: Compare SAV to MDW October fares now and sign up for price alerts to capture the best deals.