$103 Find Cheap Flights from Chicago Midway Airport to Orlando - Compare and Save

Among airlines operating Chicago Midway Airport to Orlando flights:

• Southwest: offers free seat selection
• Frontier: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

2 airlines operate flights between Chicago Midway Airport and Orlando. The airlines offering nonstop flights on this route include:

• Southwest
• Frontier

Flights from Chicago Midway Airport to Orlando usually depart from Chicago Midway (MDW) and may arrive at several airports in Orlando area, including Orlando (MCO) and Orlando Sanford Intl (SFB).

Here are some options for this route, based on selected ticket types and cabin classes:

• Southwest: a cabin bag and a checked bag in Economy Class
• Frontier: a cabin bag in Economy Class class

Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

Three cabin classes are available on flights from Chicago Midway Airport to Orlando:

• Economy Class
• Business Class
• First Class

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $159 round-trip via Newark (EWR), compared to $283 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

One-stop flights from Chicago Midway Airport to Orlando most commonly connect through:

• Atlanta Hartsfield-Jackson (ATL) - 88% of one-stop connections
• Baltimore/Washington (BWI) - 3% of one-stop connections
• Cincinnati Cinci./N. Kentucky (CVG) - 3% of one-stop connections
• Newark (EWR) - 3% of one-stop connections

Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 24% on the Chicago Midway Airport to Orlando route. Thursday is the cheapest departure day at $251 round-trip on average, while Wednesday is the most expensive at $330, a difference of $79. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Chicago Midway Airport to Orlando route, 17% of flights were delayed in the past 3 months, with delays averaging 2 hours 41 minutes.

Morning is the busiest departure period on Chicago Midway Airport to Orlando flights, with 51% of flights leaving in that window. Afternoon departures account for 33%, evening flights for 16%, and night flights for 0%.

Some of the most popular sights in Orlando are Universal Orlando Resort, Camping World Stadium and Universal Volcano Bay. These are among the most viewed places in Orlando on KAYAK.

These are the earliest and latest flight times available from Chicago Midway Airport to Orlando:

• Earliest: departs at 5:00 am and lands at 7:37 am
• Latest: departs at 8:50 pm and lands at 11:27 pm.

The flight takes about 2h 37m.

Last-minute fares on this route - booked within 2 weeks of departure - run 6% above the route average of $281. Book 4 weeks before departure for the lowest fares.

A nonstop flight from Chicago Midway Airport to Orlando takes 2h 37m, covering 982 miles.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $203 to $1,534. That means the highest observed fare was about 8x higher than the lowest one.

One-way fares from Chicago Midway Airport to Orlando are currently lower than usual. Average one-way flight prices are about $121, which is 26% below the typical average for this route.

Night flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

Flying via Milwaukee-Mitchell (MKE) gives the shortest average 1-stop total travel time at 4h 14m, compared with 5h 22m via Cincinnati Cinci./N. Kentucky (CVG) and 6h 09m via Atlanta Hartsfield-Jackson (ATL).

Orlando is 1 hour ahead of Chicago Midway Airport (Eastern Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

Since Orlando is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Orlando Airport (MCO) — daily rates from around $1:

· Rent-A-Wreck
· Routes Car & Truck Rentals
· Hertz
· Budget
· Thrifty

Near Orlando Sanford Intl Airport (SFB) — daily rates from around $13:

· Hertz
· Budget
· Dollar
· Alamo
· ADDCAR RENTAL

Round-trip flights from Chicago Midway Airport to Orlando range from $182 to $395, with an average of $281 over the past 12 months. Anything below $182 counts as a good deal.