Route guide · 775 miles
Cheap Flights from Chicago to Windsor Locks
MDW → BDL · Nonstop 2h 5m · Live round-trip fares
The run from Chicago (MDW) to Windsor Locks (BDL) is 775 miles of sky, and ticket prices on it are anything but steady. One week can cost double the next. Booking about 2–4 weeks in advance — and watching fares with a free Airfare Deal alert — is how regulars on this route keep costs down.
Live fares for MDW → BDL are updating. Use the search below for real-time prices.
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See live fares
Updated daily
Flight time
2h 5m
Nonstop, typical
Distance
775 mi
MDW → BDL
Book ahead
2–4 weeks
Best window, typically
Nonstop airlines
1
Southwest Airlines
Nonstop flights from Chicago to Windsor Locks
The fastest way between the two cities is the nonstop: about 2h 5m for the 775-mile run from MDW to BDL. Those flights are flown by Southwest Airlines. Prices behave best when you book 2–4 weeks out.
Booking insights: Chicago → Windsor Locks
- Distance: 775 miles · nonstop flight time: 2h 5m.
- Cheapest upcoming week in the live data starts around Oct 15, with fares from $299.
- Fares tend to bottom out when you book about 2–4 weeks ahead — earlier than that rarely helps, later usually hurts.
- Tuesday and Wednesday departures usually undercut Friday and Sunday fares on routes like this one.
- A free fare alert beats daily checking: we watch this route and ping you when prices drop.
Cheapest month · Chicago → Windsor Locks
October 2026
Every date's recent round-trip fare, at a glance.
Fares from
$299
Cheapest: Mon, Oct 19 — $299
Get this fare →Recent fares found for specific dates in October 2026. Blank days had no recent fare in our data — ask our team and we'll check them for you.
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Flying from Chicago to Windsor Locks: what you need to know
The flight
The nonstop from MDW to BDL runs about 2h 5m over 775 miles. It's a comfortable mid-range flight: long enough that seat choice matters a little, short enough that paying up for extras rarely does.
Airlines on this route
Southwest Airlines flies this route nonstop. That matters more than it sounds: the cheapest fare on one carrier is rarely the same product as the cheapest on another. Checked-bag fees, free seat selection and change rules all differ, so compare the full trip cost before you pick a winner. See our airline guides for exactly what each carrier charges — then send an enquiry and we'll confirm the all-in price for your dates.
Leaving from Chicago (MDW)
Plan to be at the airport two hours before a domestic departure — ninety minutes can work at smaller airports outside peak times, but security lines are the one variable you can't control. If you're checking a bag, add time rather than cutting it close. Our Chicago airport guide covers terminals, parking and ground transport so you can plan the trip to the airport, not just the flight.
Arriving in Windsor Locks (BDL)
Before you land, know how you're getting from the airport to where you're staying — it's the part of the trip people forget to plan. The Windsor Locks airport guide lays out your ground options, from transit and shuttles to rideshares and rental cars. Flying back the other way? Check Windsor Locks to Chicago fares — prices on the return direction often move on a different rhythm.
When to book
For a trip of 775 miles, booking 2–4 weeks ahead typically lands you in the sweet spot. Leave it to the final two weeks and prices usually climb as the cheapest seats sell out. If your dates are flexible, midweek departures are where the lower fares hide on most domestic routes.
Good to know before you go
- Nonstop time on this route is about 2h 5m — a one-stop itinerary needs to be a lot cheaper to be worth the extra hours.
- Tuesday and Wednesday departures are typically the cheapest days on domestic routes.
- Screenshot your fare before you enquire — prices move, and a saved fare helps our team match or beat it.
- Flexible dates? Search a few days either side — one day can change the fare a lot.
- Morning flights are delayed less often than evening ones — earlier departures have the best on-time record.
Chicago to Windsor Locks flight FAQs
How long is the flight from MDW to BDL?
Plan on about 2h 5m in the air for a nonstop from Chicago to Windsor Locks — the route runs roughly 775 miles. Connecting flights typically add 2–4 hours.
Are there nonstop flights from Chicago to Windsor Locks?
Southwest Airlines typically operate nonstop flights from MDW to BDL. Nonstops are usually cheapest when booked 2–4 weeks ahead of departure.
What is the cheapest month to fly from Chicago to Windsor Locks?
Travelers usually find the gentlest prices away from peak periods — think post-holiday January and the early-fall weeks. Midweek dates inside those windows are cheaper still.
How much are last minute flights from MDW to BDL?
Book inside the final week and you'll usually pay a premium on MDW to BDL. Fares booked 2–4 weeks ahead are almost always kinder.
What is a good round-trip deal from Chicago to Windsor Locks?
A good deal is anything at or below the recent fares shown above. Set a free Airfare Deal alert and we'll ping you the moment fares drop.
Which airlines fly from Chicago to Windsor Locks?
You'll mainly see Southwest Airlines on Chicago to Windsor Locks. Checking each against the live fares below is the surest way to find the lowest price for your dates.
How early should I get to Chicago airport for this flight?
Plan on two hours before departure for a domestic flight — ninety minutes can work at smaller airports outside peak times. If you're checking a bag, earlier is better; the bag-drop line, not the flight, is what runs late.
Do the cheapest fares on this route include a checked bag?
Usually not. Basic economy fares on most airlines include a carry-on but charge extra for checked bags, and seat selection can cost more too. Add up the real total before comparing — a slightly higher regular fare sometimes works out cheaper. Our team confirms the full breakdown with you before you pay.
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