Best Flights starting from $435
from$435economy
Sarasota (SRQ)
Thu, Oct 1
Roundtrip
Chicago (MDW)
Fri, Oct 9
Fields updated — click View Prices to search ↑
Other Options for This Route
Other Destinations
Sarasota (SRQ) to Durango (DRO) in October from $496
From $496
Sarasota (SRQ) to Port Moresby (POM) in October from $6,470
From $6,470
Sarasota (SRQ) to Cincinnati (CVG) in November from $97
From $97
Sarasota (SRQ) to Pittsburgh (PIT) in November from $182
From $182
Sarasota (SRQ) to Greensboro / High Point (GSO) in November from $296
From $296
Sarasota (SRQ) to Boston (BOS) in December from $264
From $264
Flights from Other Cities
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
Orlando (MCO) to Chicago (MDW) in November from $77
From $77
Mobile (MOB) to Chicago (MDW) in November from $165
From $165
Fort Lauderdale (Any) to Chicago (MDW) in November from $203
From $203
✈️ Flight Guide: Sarasota (SRQ) → Chicago (MDW)
Complete travel information for your October journey
Departing from Sarasota (SRQ) FAQs
The CTA Orange Line provides the most budget-friendly, frequent transit link from downtown Chicago to Chicago Midway International Airport (MDW) in about 25–30 minutes. Rideshare services and airport shuttles are widely available and typically take 20–35 minutes depending on traffic; consider leaving extra time during rush hour. If traveling with heavy luggage, door-to-door rideshares or taxis may be more convenient than public transit.
Southwest Airlines is the dominant low-cost carrier at Chicago Midway International Airport (MDW) and often offers the most competitive economy fares on domestic routes. Other carriers with economy options include Spirit and participating legacy carriers on select routes; comparing prices on aggregators like Google Flights and Kayak helps you find the cheapest fare for your dates. Consider booking 3–7 weeks in advance for the lowest domestic economy fares.
Yes — security wait times at Chicago Midway International Airport (MDW) typically increase during peak travel periods such as Thanksgiving, Christmas-New Year, spring break (March–April), and summer holidays (June–August). Weekday mornings and early evenings can also be busy. Check the TSA wait-time feed or the airport's official site on your travel day and arrive 90–120 minutes before domestic flights during busy months to ensure a smooth departure.
January is one of the least busy months for departures from Chicago Midway International Airport (MDW), which often leads to lower economy fares especially on leisure routes to southern and sun destinations like Orlando and Phoenix. Airlines may reduce peak-frequency flights after the December holiday surge; use fare alerts, flexible date searches, and mid-week travel to secure the cheapest economy tickets. Consider subscribing to airline newsletters for Midway-specific sales.
Chicago Midway International Airport (MDW) offers cell-phone waiting lots, on-site daily and hourly parking, and several nearby economy lots with shuttle service for longer trips. For long departures, pre-book off-site parking for savings and confirm shuttle frequencies. Rideshare pickup zones and rental car counters are located on-site, making onward connections to nearby destinations like Milwaukee, Indianapolis, and the Chicago suburbs straightforward.
Departure and arrival processes at Chicago Midway International Airport (MDW) are the same regardless of ticket class, but economy passengers should budget extra time for baggage checks and gate boarding, especially on high-traffic leisure routes such as Orlando (MCO), Las Vegas (LAS), and Dallas (DFW). Southwest's boarding groups can help organize economy travelers; check airline boarding policies and arrive at the gate early during peak seasons.
Arriving at Chicago (MDW) FAQs
Cheapest economy fares usually include a standard carry-on or personal item and may exclude checked baggage or seat selection depending on the airline. On arrival, expect standard disembarkation, and prepare for potential baggage fees and longer waits at the carousel if flights are full or carry-on-heavy. Always check airline-specific economy fare rules before you fly to avoid surprise fees at arrival.
Use flexible-date searches and fare calendars on Google Flights or Kayak to compare MDW-to-Orlando and MDW-to-Las Vegas economy prices. Signing up for airline and aggregator fare alerts, booking on mid-week departures, and looking for flash sales—especially from Southwest at MDW—are effective ways to secure the cheapest economy round-trip fares.
In March, spring break traffic increases at many destinations, which can affect arrival times and baggage wait times, making earlier arrival at the airport advisable. If you have the cheapest economy fare, anticipate packed flights and prioritize early boarding or paid seat selection where possible. Plan ground transfers in advance during high-demand March weekends to avoid long waits.
Major arrival logistics include checking local ground transport (shared shuttles, rideshares, trains) and understanding peak traffic times. For example, Orlando International Airport (MCO) and Las Vegas McCarran/ Harry Reid (LAS) offer robust rental car and shuttle services, while New York area airports may require longer transfer times into Manhattan. Pre-book transfers or use official airport apps for arrival updates.
During December holidays, expect longer queues at arrivals and baggage claim, and potential delays. Pre-booking ground transport, upgrading to priority baggage if available, and packing essentials in a carry-on can streamline your arrival. Allow extra time for transfers to nearby major cities and consider arriving outside peak holiday travel days to avoid the busiest times.
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Events & Festivals Affecting MDW Economy Fares — Plan Around Major Dates
Major events that can increase economy fares out of Chicago Midway International Airport (MDW) include: Lollapalooza and Taste of Chicago (July), Chicago Marathon (October), Thanksgiving and Christmas holidays (Nov–Dec), and spring break weeks (March). Destination-side events—such as Orlando’s theme-park holidays, Las Vegas conventions, and Phoenix spring training—also raise demand and economy fares. To find the cheapest economy tickets, avoid peak festival weekends or book months in advance. CTA: Check your travel dates against major event calendars and adjust to secure cheaper MDW economy flights.
Best Time to Fly from Chicago Midway International Airport (MDW) for Cheap Economy Fares
The best times to find cheap economy fares from Chicago Midway International Airport (MDW) are typically January, February, and September — months with lower leisure demand. Book domestic economy flights 3–7 weeks in advance for the best prices; for peak summer or holiday travel, book 2–4 months ahead. Use flexible-date tools, sign up for fare alerts, and consider flying mid-week to reduce costs. CTA: Run a flexible-date search for MDW routes now to discover the cheapest months for your trip.
Direct vs Connecting Flights from Chicago Midway International Airport (MDW) — Economy Trade-Offs
Direct flights from Chicago Midway International Airport (MDW) save time but can be pricier in economy class. Connecting itineraries often lower total cost, especially when using low-cost carriers or booking mixed-carrier routes; however, connections increase total travel time and risk of missed connections. For short hops (under 3 hours), prioritize direct economy flights for convenience; for longer or cross-country travel, consider a one-stop itinerary if it shaves substantial cost. CTA: Compare direct and connecting economy options for your MDW departure to balance price with travel time.
Airline Comparison for Economy Travelers Departing Chicago Midway International Airport (MDW)
Southwest Airlines: best for flexible economy travelers from Chicago Midway International Airport (MDW) with two free checked bags on many fares and an open seating/boarding group system; great for domestic leisure routes. Spirit: often cheapest base fare but adds fees for carry-ons, seat selection, and checked bags—watch out for add-on costs.American/United/Delta: limited presence at MDW on some routes; may offer more traditional loyalty benefits and wider connections but sometimes at higher economy base fares. Compare total price including baggage and seat fees to determine the best economy option for your MDW itinerary. CTA: Run a multi-carrier search to find the true cheapest economy option out of MDW and account for ancillary fees.
Seasonal Travel Tips for Economy Passengers from Chicago Midway International Airport (MDW)
Winter (Dec–Feb): Expect delays from snow; book earlier and allow additional time at Chicago Midway International Airport (MDW). Pack essentials in a carry-on and consider travel insurance for holiday trips. Spring (Mar–May): Watch spring break demand and book early for highly trafficked routes; flexible dates yield best economy fares. Summer (Jun–Aug): Peak season—reserve economy seats months in advance; consider early-morning flights to avoid delays. Fall (Sep–Nov): Best time for off-peak savings—target September and early November for cheapest fares. Always verify baggage policies for economy tickets and use fare alerts to monitor price drops. CTA: Set seasonal fare alerts for MDW routes to capture the cheapest economy prices when they appear.
Flight Times & Schedules — Chicago Midway International Airport (MDW) Economy Routes
Typical non-stop flight times from Chicago Midway International Airport (MDW) in economy class: to Milwaukee ~50–70 minutes, to Indianapolis ~60–80 minutes, to Dallas/Fort Worth (DFW) ~2.5–3 hours, to Denver (DEN) ~2.5 hours, to Phoenix (PHX) ~3.5 hours, to Las Vegas (LAS) ~3.5–4 hours, to Orlando (MCO) ~3 hours. Schedules vary seasonally — expect increased frequency on leisure routes in summer and spring break. For cheapest economy fares, target midweek flights and off-peak hours (early morning or late evening). CTA: Check live MDW schedules and filter by lowest fares to find economy flights that match your timeframe.
Cheap Flights Guide — Chicago Midway International Airport (MDW) to Top Destinations in Economy
To find the cheapest economy flights from Chicago Midway International Airport (MDW), search flexible dates, compare carriers (Southwest often leads on price), and set fare alerts for target routes such as MDW–Orlando (MCO) and MDW–Las Vegas (LAS). Use LSI keywords in searches: budget flights, low-cost carriers, economy seat deals, Midway flight sales. Consider early-morning departures, mid-week travel, and booking 3–8 weeks in advance for domestic routes. For international or long-haul, mix-and-match carriers and use nearby airports like Chicago O'Hare International Airport (ORD) for additional options. CTA: Start a price alert now for the cheapest MDW economy fares and compare routes across multiple aggregators.