Best Flights starting from $205
from$205economy
Miami (MIA)
Wed, Apr 8
Roundtrip
Chicago (MDW)
Wed, Apr 8
from$225economy
Miami (MIA)
Thu, Apr 9
Roundtrip
Chicago (MDW)
Thu, Apr 9
from$231economy
Miami (MIA)
Tue, Apr 14
Roundtrip
Chicago (MDW)
Tue, Apr 14
from$307economy
Miami (MIA)
Fri, Apr 10
Roundtrip
Chicago (MDW)
Fri, Apr 10
from$346economy
Miami (MIA)
Mon, Apr 13
Roundtrip
Chicago (MDW)
Mon, Apr 13
from$358economy
Miami (MIA)
Sat, Apr 11
Roundtrip
Chicago (MDW)
Sat, Apr 11
from$409economy
Miami (MIA)
Sun, Apr 12
Roundtrip
Chicago (MDW)
Sun, Apr 12
Fields updated — click View Prices to search ↑
Other Options for This Route
Other Destinations
Miami (MIA) to Durham (RDU) in April from $28
From $28
Miami (MIA) to Durham (RDU) in April from $56
From $56
Miami (MIA) to Charlotte (CLT) in April from $78
From $78
Miami (MIA) to Memphis (MEM) in April from $80
From $80
Miami (MIA) to Newark (EWR) in April from $85
From $85
Miami (MIA) to Washington, D.C. (DCA) in April from $98
From $98
Flights from Other Cities
Atlanta (ATL) to Chicago (MDW) in April from $119
From $119
Sarasota (SRQ) to Chicago (MDW) in April from $331
From $331
Calgary (YYC) to Chicago (MDW) in May from $257
From $257
Belize City (Any) to Chicago (MDW) in May from $259
From $259
Sarasota (SRQ) to Chicago (MDW) in May from $331
From $331
Manila (MNL) to Chicago (MDW) in May from $581
From $581
✈️ Flight Guide: Miami (MIA) → Chicago (MDW)
Complete travel information for your April journey
Departing from Miami (MIA) FAQs
Chicago Midway International Airport (MDW) offers on-site parking, off-site lots, and shuttle services year-round. In March expect variable winter-to-spring traffic; book off-site economy lots in advance for the best rates and use Pace buses or ride-shares for predictable transfers to downtown Chicago. Check parking maps and prepay for the lowest rates to save time and money.
For domestic economy flights from Chicago Midway International Airport (MDW) during peak summer months like July, arrive at least 90 minutes before departure to allow time for security, bag drop, and potential crowds. Southwest Airlines is a major carrier at MDW and can have long boarding lines in summer; arriving early reduces stress and gives you better boarding positions. Consider online check-in and TSA PreCheck if available to shorten wait times.
Chicago Midway International Airport (MDW) offers frequent nonstop service to top leisure and business destinations such as Orlando, Las Vegas, Phoenix, Dallas, Denver, and Los Angeles. During November and Thanksgiving travel, expect high frequency flights to Orlando and Phoenix; book as early as possible to secure economy fares. Use fare alerts and flexible dates to find the cheapest economy options for holiday weeks.
January in Chicago can bring winter storms, low visibility, and de-icing delays that impact operations at Chicago Midway International Airport (MDW). Allow extra connection time and monitor flight status closely; airlines may proactively rebook passengers during widespread winter weather. Signing up for airline alerts and checking the Chicago Department of Aviation advisories reduces surprises.
To find the cheapest economy fares from Chicago Midway International Airport (MDW), be flexible with departure dates and times, book 2–8 weeks in advance for domestic routes, and use fare comparison tools and airline sale alerts. Consider mid-week departures, early morning or late-night flights, and low-cost carriers like Southwest, Spirit, or Frontier; always check baggage fees when comparing base fares. Use price-tracking tools to capitalize on flash sales from MDW.
From Chicago Midway International Airport (MDW) travelers commonly fly to Orlando, Las Vegas, Phoenix, Dallas, Denver, Los Angeles, Atlanta, and New York. These cities attract both leisure and business travelers and are frequently served by low-cost carriers and legacy airlines alike. If you're planning a trip, compare fares across carriers and consider alternative airports like Chicago O'Hare International Airport (ORD) for additional schedule options.
Arriving at Chicago (MDW) FAQs
'Cheapest Economy Fare (CHEAP)' represents the lowest available economy-class options across multiple carriers and routing choices rather than a physical airport. When booking an economy cheapest fare, expect basic seat selection and possible ancillary fees for baggage and seat changes; always compare total trip cost including extras. Use fare-aggregator tools and check both budget and legacy carriers to find the best all-in price for your arrival city.
Cheapest economy arrivals from Chicago Midway International Airport (MDW) typically target large leisure and business hubs such as New York City, Los Angeles, Orlando, Miami, Las Vegas, Dallas, Phoenix, and Atlanta. These destinations often have high flight volumes and competitive pricing across carriers, enabling frequent sale fares. Consider alternative airports near your destination (for example, O'Hare for Chicago area or Fort Lauderdale for Miami) to find lower fares.
In August, cheapest economy arrivals can fluctuate as end-of-summer demand drops; some last-minute deals appear for non-holiday routes while family travel remains common earlier in the month. Late-August often offers price reductions for travel after school starts, so set fare alerts for your target route and consider mid-week travel for the best prices. Monitor carrier flash sales and be ready to book quickly when a good deal appears.
Cheapest economy arrival fares typically include only a personal item; carry-on baggage and checked bags often incur additional fees on low-cost carriers. Seat assignment may be limited or assigned at check-in, so if seat selection is important, factor that into the total price. Always review the fare rules before booking and compare the all-in total across airlines to avoid surprises at the airport.
Most cheapest economy fares are non-refundable and have limited or expensive change options, though policies vary by carrier and have become more flexible since the pandemic. In November, during holiday travel, airlines may restrict changes or charge higher fees; some carriers offer waivers for schedule changes. Consider purchasing refundable fares or travel protection if plans are uncertain around Thanksgiving.
To ensure a smooth arrival when flying the cheapest economy option, arrive prepared with digital boarding passes, minimal carry-on luggage, and clear immigration/arrival documents for international trips. Choose arrival times outside peak hours when possible and research local ground transportation options (trains, buses, ride-shares) beforehand. Sign up for flight status alerts and confirm baggage policies to avoid delays at the airport.
1.0.2603.04
Major Events & Festivals Impacting Flights from Chicago Midway International Airport (MDW)
Events and festivals both at origin (Chicago) and major destination cities can significantly affect flight prices out of Chicago Midway International Airport (MDW). Chicago events like Lollapalooza (August), the Chicago Marathon (October), and Taste of Chicago (summer) raise ticket prices; similarly destination festivals (e.g., Mardi Gras in New Orleans, SXSW in Austin, or New Year’s Eve events in New York and Las Vegas) drive up fares. To secure the cheapest economy fares, avoid traveling on event weekends, target adjacent weekdays, or book months in advance. Use event calendars and fare-aggregator tools to spot inflated dates and plan accordingly.
Best Time to Fly from Chicago Midway International Airport (MDW) for Cheapest Economy Fares
The best time to fly for cheapest economy fares from Chicago Midway International Airport (MDW) is typically mid-week (Tuesday–Thursday) and during off-peak months such as January and September. Early morning and red-eye flights often cost less than peak afternoon and weekend departures. Book domestic economy fares 2–8 weeks in advance for the best balance of price and availability; for holiday travel, secure tickets 2–4 months ahead. Set fare alerts and compare flexible-date calendars to capture the optimal purchase moment.
Direct vs Connecting Flights from Chicago Midway International Airport (MDW) — Choosing Cheapest Economy Itineraries
Direct flights from Chicago Midway International Airport (MDW) provide convenience and lower missed-connection risk but can be pricier in peak travel periods. Connecting itineraries often deliver the cheapest economy fares, especially when routing through hubs like Dallas Love Field (DAL), Denver (DEN), or Atlanta (ATL). However, connecting trips increase total travel time and carry the risk of missed connections — avoid self-connecting separate tickets if time buffers are tight. For budget travelers, a single connecting flight on one ticket usually offers the best combination of cost savings and protection.
Airline Comparison for Cheapest Economy Fares at Chicago Midway International Airport (MDW)
At Chicago Midway International Airport (MDW), Southwest Airlines dominates with broad route coverage and inclusive two-free-bag policies on many fare types, which can make their economy fares more valuable despite slightly higher base prices. Spirit and Frontier often present the lowest base fares but charge for carry-on and checked baggage and seat selection, which raises the all-in cost. American and United offer legacy-carrier schedules and more connectivity but may be more expensive in basic economy classes. When comparing airlines for the cheapest economy option, always tally ancillary fees, convenience factors (direct vs connecting), and the value of included services like bags and seat selection.
Seasonal Travel Tips for Cheapest Economy Flights from Chicago Midway International Airport (MDW)
Seasonal travel affects both price and travel experience for cheap economy flyers from Chicago Midway International Airport (MDW). Winter: expect weather-related delays and de-icing; book earlier and allow extra connection time. Spring: shoulder-season deals are common but watch spring-break peaks. Summer: high-demand period — early-morning flights and mid-week travel save money. Fall: often the cheapest time to travel with pleasant weather and fewer crowds. Always compare all-in costs, check baggage policies for cheapest economy fares, and use flexible-date searches to find seasonal bargains.
Flight Times & Schedules from Chicago Midway International Airport (MDW) — Economy Route Durations
Typical nonstop flight durations from Chicago Midway International Airport (MDW) include: to Orlando ~2h 30m, to Las Vegas ~4h 15m, to Phoenix ~3h 50m, to Dallas ~2h 30m, to Los Angeles ~4h 20m, to Denver ~2h 30m, and to New York (LaGuardia/JFK/Newark) ~2h 10–2h 30m depending on routing. Southwest frequently schedules multiple daily flights to many of these destinations with strong early-morning and evening options. For international travel, most cheapest economy itineraries will route via major hubs like Dallas Love Field (DAL), Denver (DEN), or Atlanta (ATL). Consider buffer time for connections and add at least 60–90 minutes for domestic connections when booking cheapest economy fares to avoid missed flights.
Cheap Flights from Chicago Midway International Airport (MDW) — Cheapest Economy Fare Strategies
Finding cheap flights from Chicago Midway International Airport (MDW) requires a combination of flexible dates, fare tracking, and awareness of low-cost carrier windows. Southwest is a major player at MDW, but also compare Spirit, Frontier, American, and United for total price including baggage and seat fees. For the cheapest economy fares, target mid-week travel, early-morning departures, and off-peak months like January and September. Use price alerts, split-ticketing only when safe for connections, and evaluate nearby airports such as Chicago O'Hare International Airport (ORD) and Gary/Chicago International Airport (GYY) to widen your low-fare options.