Route guide · 991 miles
Cheap Flights from Orlando to Chicago
MCO → MDW · Nonstop 2h 31m · Live round-trip fares
Flying from Orlando to Chicago doesn't have to drain your wallet. This 991-mile hop takes about 2h 31m nonstop, and fares swing a lot depending on the week you pick. Travelers who book roughly 3–6 weeks out usually come out ahead — set a free alert and let the deals come to you.
Live fares for MCO → MDW are updating. Use the search below for real-time prices.
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Updated daily
Flight time
2h 31m
Nonstop, typical
Distance
991 mi
MCO → MDW
Cheapest month
December 2026
Fares from $116
Nonstop airlines
1
Southwest Airlines
Nonstop flights from Orlando to Chicago
Nonstop flights from Orlando to Chicago are flown by Southwest Airlines. The 991-mile trip takes about 2h 31m gate to gate, and nonstops are usually cheapest when booked 3–6 weeks ahead.
Booking insights: Orlando → Chicago
- Distance: 991 miles · nonstop flight time: 2h 31m.
- Cheapest upcoming week in the live data starts around Nov 4, with fares from $153.
- Of the months we're tracking right now, December 2026 has the lowest fares, starting at $116.
- Fares tend to bottom out when you book about 3–6 weeks ahead — earlier than that rarely helps, later usually hurts.
- If your dates flex by a day or two, shifting to a midweek departure is the easiest saving there is.
- A free fare alert beats daily checking: we watch this route and ping you when prices drop.
Price trend
Cheapest departure weeks ahead
Near-term departures around Nov 4 are currently the cheapest on this route. Based on recent fares found for this route; prices change quickly.
Cheapest month · Orlando → Chicago
December 2026
Every date's recent round-trip fare, at a glance.
Fares from
$116
Cheapest: Wed, Dec 30 — $116 · Priciest: Dec 31 — $136
Get this fare →Recent fares found for specific dates in December 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 Orlando to Chicago: what you need to know
The flight
The nonstop from MCO to MDW runs about 2h 31m over 991 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 Orlando (MCO)
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 Orlando airport guide covers terminals, parking and ground transport so you can plan the trip to the airport, not just the flight.
Arriving in Chicago (MDW)
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 Chicago airport guide lays out your ground options, from transit and shuttles to rideshares and rental cars. Flying back the other way? Check Chicago to Orlando fares — prices on the return direction often move on a different rhythm.
When to book
Of the months we're currently tracking, December 2026 is coming in cheapest for this route, with fares from $116. 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
- 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.
- December 2026 is currently the cheapest tracked month on this route — check those dates first if you're flexible.
- 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.
Orlando to Chicago flight FAQs
How long is the flight from MCO to MDW?
A nonstop from MCO to MDW clocks in at around 2h 31m for the 991-mile trip. If you're connecting, budget an extra 2–4 hours depending on where you stop.
Are there nonstop flights from Orlando to Chicago?
Southwest Airlines typically operate nonstop flights from MCO to MDW. Nonstops are usually cheapest when booked 3–6 weeks ahead of departure.
What is the cheapest month to fly from Orlando to Chicago?
Right now, December 2026 is shaping up cheapest for Orlando to Chicago — we've seen fares from $116 in that month. Prices move fast, so lock in when you see a number you like.
How much are last minute flights from MCO to MDW?
Walking up to this route at the last minute is the expensive way to do it — prices inside 7 days of departure climb fast. The 3–6 weeks booking window is where the value sits.
What is a good round-trip deal from Orlando to Chicago?
A good deal is anything at or below the recent fares shown above. Set a free Flyzento alert and we'll ping you the moment fares drop.
Which airlines fly from Orlando to Chicago?
You'll mainly see Southwest Airlines on Orlando to Chicago. 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 Orlando 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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