Route

Chicago to Windsor Locks flights

Direct and connecting flights from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL). Compare airlines, aircraft types, and fares on one page.

01 / OVERVIEW

Booking tips for ChicagoWindsor Locks

For most economy fares on Chicago to Windsor Locks, booking roughly three to eight weeks ahead tends to hit the sweet spot on price, with last-minute fares rising sharply in the final two weeks. Tuesday, Wednesday, and Saturday departures are usually cheaper than Fridays and Sundays, and early-morning or late-evening flights often undercut midday slots. If you are traveling light, the difference between a basic economy fare with carry-on only and a standard fare with a checked bag can be significant. Compare both options before booking, and also check whether MDW or BDL has a nearby alternative airport that might offer better fares on the same dates.

OPERATORS ON THIS ROUTELast 90 days · top 1
CarrierSightings / 90dSafety events
Southwest Airlines3 sightingsNo recorded events

Planning MDWBDL

MDW to BDL is a short-haul route of 1,246 km (774 mi). See the return BDLMDW route.

Alternative airports near Chicago: Chicago (CGX)14 km, Chicago (ORD)25 km, Gary (GYY)34 km.

Alternative airports near Windsor Locks: Hartford (HFD)23 km, Westfield (BAF)24 km, Chicopee Falls (CEF)31 km.

03 / AIRCRAFT MIX
04 / FAQ

Frequently asked questions about ChicagoWindsor Locks

How long does the flight from Chicago to Windsor Locks take?

Flight time from Chicago (MDW) to Windsor Locks (BDL) depends on routing, aircraft type, and whether the flight is direct or connecting. A direct flight typically reflects great-circle distance plus winds, while one-stop options can add several hours depending on the layover airport. Check the exact duration in the search results above, where we show block time per itinerary along with stop count.

Which airlines fly from Chicago to Windsor Locks?

Airline availability for MDW to BDL changes by season and sometimes week to week as carriers adjust capacity. Our search above pulls live schedules and returns the airlines currently selling this route, both direct and connecting. Codeshare and interline itineraries are included, so you may see results operated by one carrier but sold by another.

Are there direct flights from Chicago to Windsor Locks?

Direct (nonstop) availability on MDW to BDL varies by date, day of week, and season. Busy city pairs usually have multiple daily nonstops, while thinner routes may only have direct service a few days per week or only during peak seasons. Use our search above with flexible dates to see which days actually have nonstop options.

What is the cheapest month to fly from Chicago to Windsor Locks?

Prices on MDW to BDL shift with seasonality, school holidays, and major events at both ends. Our 12-month price calendar below the search results shows the lowest fare found per departure date, which makes it easy to spot the cheapest weeks at a glance. Flexibility of a few days around your target date often unlocks significantly lower fares.

Plan the rest of your trip to Windsor Locks

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05 / EXPLORE MORE