Route guide · 991 miles
Cheap Flights from Chicago to Orlando
MDW → MCO · Nonstop 2h 31m · Live round-trip fares
Looking for cheap flights from Chicago to Orlando? You're in the right place. Airfare Deal tracks live fares on this 991-mile route around the clock. As a rule of thumb, booking 3–6 weeks ahead lands the best prices — and a free fare alert means you never have to keep refreshing the page.
Live fares for MDW → MCO are updating. Use the search below for real-time prices.
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See live fares
Updated daily
Flight time
2h 31m
Nonstop, typical
Distance
991 mi
MDW → MCO
Cheapest month
October 2026
Fares from $118
Nonstop airlines
1
Southwest Airlines
Nonstop flights from Chicago to Orlando
Nonstop service links Chicago and Orlando directly — flights are flown by Southwest Airlines. Expect roughly 2h 31m in the air. If a nonstop is what you want, don't wait too long: booking 3–6 weeks ahead is when these seats are priced most kindly.
Booking insights: Chicago → Orlando
- Distance: 991 miles · nonstop flight time: 2h 31m.
- Cheapest upcoming week in the live data starts around Oct 29, with fares from $118.
- Of the months we're tracking right now, October 2026 has the lowest fares, starting at $118.
- Rule of thumb for this route: the sweet spot is usually 3–6 weeks before departure.
- Tuesday and Wednesday departures usually undercut Friday and Sunday fares on routes like this one.
- Set a free Airfare Deal alert instead of checking daily — the best fares can sell out in hours.
Price trend
Cheapest departure weeks ahead
Departing around Oct 29 is currently the cheapest window — about $40 less than the nearest weeks. Based on recent fares found for this route; prices change quickly.
Cheapest month · Chicago → Orlando
October 2026
Every date's recent round-trip fare, at a glance.
Fares from
$118
Cheapest: Sat, Oct 31 — $118 · Priciest: Oct 25 — $175
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 Orlando: what you need to know
The flight
Chicago to Orlando covers 991 miles, and a nonstop gets it done in about 2h 31m. That's long enough to settle in with a coffee and a downloaded show, short enough that a connection rarely makes sense — a layover usually doubles your travel day to save very little.
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 Orlando (MCO)
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 Orlando airport guide lays out your ground options, from transit and shuttles to rideshares and rental cars. Flying back the other way? Check Orlando to Chicago fares — prices on the return direction often move on a different rhythm.
When to book
Of the months we're currently tracking, October 2026 is coming in cheapest for this route, with fares from $118. As a rule, booking 3–6 weeks ahead lands you in the sweet spot — leave it to the final two weeks and prices usually climb. If you see a fare that works, don't wait around: set a fare alert on this page and we'll watch the price for you.
Good to know before you go
- Morning flights are delayed less often than evening ones — earlier departures have the best on-time record.
- Basic economy fares often exclude checked bags and seat selection. Price the whole trip, not the headline fare.
- Get to the airport two hours before departure; security, not the flight, is the part that runs late.
- If you're traveling with only a carry-on, you can skip the bag-drop line entirely with mobile check-in.
- Download the airline's app before you fly; gate changes and delays show up there first.
Chicago to Orlando flight FAQs
How long is the flight from MDW to MCO?
Nonstop flights from Chicago to Orlando take about 2h 31m and cover roughly 991 miles. One-stop itineraries add 2–4 hours depending on the layover city.
Are there nonstop flights from Chicago to Orlando?
Yes — look for Southwest Airlines on this route. Nonstop seats are usually priced best 3–6 weeks before departure.
What is the cheapest month to fly from Chicago to Orlando?
Of the months we're tracking right now, October 2026 has the lowest fares from Chicago to Orlando, starting at $118. Fares update as new data comes in, so it's worth setting a free alert for your dates.
How much are last minute flights from MDW to MCO?
Book inside the final week and you'll usually pay a premium on MDW to MCO. Fares booked 3–6 weeks ahead are almost always kinder.
What is a good round-trip deal from Chicago to Orlando?
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 Orlando?
The main carriers on this route are Southwest Airlines. Comparing all of them on the live search below usually surfaces the lowest fare 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.
More cheap flights from Chicago
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