Cheap direct flights from Chicago MDW
7 current round-trip routes with prices below typical for MDW. Tap a card to see live fares for those dates.
Refreshed within the last 72 hours · Updated 20 October 2026
Summary
There are 7 active direct-flight deals from Chicago Midway International (MDW) with prices below the typical fare for each route, covering Nashville, Philadelphia, Miami, Long Beach and Omaha. The cheapest is $227 round-trip to Nashville (BNA) for 21 Jan → 29 Jan (8 nights), 17% below the typical fare for that route. Average savings across the 7 deals is 4% off typical fares. Prices are refreshed daily from live Google Flights data. Updated 20 October 2026.
Southwest
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Frequently asked questions
What's the cheapest direct flight from MDW right now?
$227 round-trip to Nashville (BNA) for 21 Jan 2027 → 29 Jan 2027, which is 17% below the typical fare on that route.
Which destinations have deals from MDW?
7 destinations have active deals: Nashville (BNA) from $227; Philadelphia (PHL) from $279; Miami (MIA) from $429; Long Beach (LGB) from $428; Omaha (OMA) from $407; Pittsburgh (PIT) from $413; Memphis (MEM) from $421.
How recent are these prices?
Each deal is backed by a live fare we verified within the last 72 hours. Routes without recent cached data don't appear on this page — start a search for a missing destination and the next refresh will pick up the deal.
Are these prices for direct flights only?
Yes. Never Layover only shows nonstop fares — no layovers, no connections. Every deal on this page is a single-leg outbound + single-leg return.