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Cheap flights from Chicago Midway to Orlando Sanford

Compare Chicago Midway to Orlando Sanford flight deals

Find the cheapest month or even day of the year to fly to Orlando Sanford

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Flight deals from Chicago Midway to Orlando Sanford

Looking for a cheap last-minute deal or the best round-trip flight from Chicago Midway to Orlando Sanford? Find the lowest prices on one-way and round-trip tickets right here.
Orlando.C$299 per passenger.Departing Fri, Oct 17, returning Sun, Oct 19.Round-trip flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departing from Chicago Midway on Fri, Oct 17, arriving in Orlando Sanford.Inbound indirect flight with Allegiant Air, departing from Orlando Sanford on Sun, Oct 19, arriving in Chicago Midway.Price includes taxes and charges.From C$299, select.
Orlando.C$311 per passenger.Departing Fri, Aug 22, returning Sun, Aug 24.Round-trip flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departing from Chicago Midway on Fri, Aug 22, arriving in Orlando Sanford.Inbound indirect flight with Allegiant Air, departing from Orlando Sanford on Sun, Aug 24, arriving in Chicago Midway.Price includes taxes and charges.From C$311, select.
Orlando.C$318 per passenger.Departing Fri, Sep 5, returning Sun, Sep 7.Round-trip flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departing from Chicago Midway on Fri, Sep 5, arriving in Orlando Sanford.Inbound indirect flight with Allegiant Air, departing from Orlando Sanford on Sun, Sep 7, arriving in Chicago Midway.Price includes taxes and charges.From C$318, select.
Orlando.C$333 per passenger.Departing Mon, Sep 29, returning Mon, Oct 6.Round-trip flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departing from Chicago Midway on Mon, Sep 29, arriving in Orlando Sanford.Inbound indirect flight with Allegiant Air, departing from Orlando Sanford on Mon, Oct 6, arriving in Chicago Midway.Price includes taxes and charges.From C$333, select.
Orlando.C$345 per passenger.Departing Mon, Nov 17, returning Fri, Nov 21.Round-trip flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departing from Chicago Midway on Mon, Nov 17, arriving in Orlando Sanford.Inbound indirect flight with Allegiant Air, departing from Orlando Sanford on Fri, Nov 21, arriving in Chicago Midway.Price includes taxes and charges.From C$345, select.
Orlando.C$354 per passenger.Departing Fri, Oct 31, returning Sun, Nov 9.Round-trip flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departing from Chicago Midway on Fri, Oct 31, arriving in Orlando Sanford.Inbound indirect flight with Allegiant Air, departing from Orlando Sanford on Sun, Nov 9, arriving in Chicago Midway.Price includes taxes and charges.From C$354, select.
Orlando.C$367 per passenger.Departing Fri, Aug 22, returning Fri, Sep 26.Round-trip flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departing from Chicago Midway on Fri, Aug 22, arriving in Orlando Sanford.Inbound indirect flight with Allegiant Air, departing from Orlando Sanford on Fri, Sep 26, arriving in Chicago Midway.Price includes taxes and charges.From C$367, select.

Find the cheapest month to fly from Chicago Midway to Orlando Sanford

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Orlando Sanford flights are currently cheapest in October.
Aug
from C$311
Sep
from C$318
Oct
from C$299
Nov
from C$345
Dec
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Jan
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Feb
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Mar
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Apr
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May
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Chicago Midway to Orlando Sanford: Alternative routes

Compare routes from Chicago Midway to Orlando below. You may find an airport to fly into that's cheaper, faster, or easier than Orlando Sanford.

Chicago to Orlando: Flight information

The things to know before you go.
Cheapest flight foundC$299
Cheapest month to flyOctober

Finding cheap flights from Chicago Midway to Orlando Sanford: Frequently asked questions

The best price we found for a round-trip flight from Chicago Midway to Orlando Sanford is C$299. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Chicago Midway to Orlando Sanford. But we found flights with one or more stops from C$299.
There are no flights flying from Chicago Midway to Orlando Sanford, as of August 2025.
The cheapest month to fly from Chicago Midway to Orlando Sanford is usually October.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Orlando Sanford Airport on Friday, October 17, 2025.
No airlines currently offer direct flights between Chicago Midway Airport and Orlando Sanford Airport. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Orlando Sanford but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Orlando is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Allegiant Air offers the cheapest flight tickets to Orlando Sanford.

Flying from Chicago Midway International Airport (MDW) to Orlando Sanford International Airport (SFB): what you need to know

  • The timezone in Orlando is UTC-4, which is one hour ahead of Chicago.

  • Your MDW to SFB flight won't wait if you're late, so get to the airport with time to spare. Arrive up to one hour in advance for domestic flights and two hours ahead when you're travelling internationally.

  • Travelling during a peak month such as July? Major public holidays and other popular seasons can lead to longer queues at check-in and security. Play things extra safe and get there up to four hours ahead of an international flight and two hours before a domestic departure.

  • If you want to include a stop along the way, just deselect 'Direct flights only' when searching for your ticket from Chicago Midway International Airport to Orlando Sanford International Airport. These are the top stopovers between MDW and SFB:

    • Asheville Regional Airport

    • Nashville International Airport

    • Louisville International Airport-Standiford Field

How to find the cheapest flights from Chicago Midway International Airport (MDW) to Orlando Sanford International Airport (SFB)

  • At the moment, C$150 is the lowest price we've found for a one-way Chicago Midway International Airport to Orlando Sanford International Airport flight. The best price for a return plane ticket is C$299. Keep in mind that fares could change due to demand when booking.

  • Don't wait until the last moment. You're more likely to find cheap tickets from MDW to SFB if you book in advance. Airlines often offer some fantastic early bird deals.

  • The 'Whole month' search tool shows you the cheapest flights from Chicago Midway International Airport to Orlando Sanford International Airport throughout the entire month. It's a great way to find a bargain if your travel plans aren't set in stone.

  • You don't need to check back in every day to find out if fares have gone down when you create a Price Alert. We'll send you an update as soon as a special offer becomes available on cheap flights from MDW to SFB.

  • Tailor your trip with filters. Select your departure and arrival times, total journey duration and airlines. You can also sort your results by 'Best,' 'Fastest' or 'Cheapest' flights from Chicago Midway International Airport to Orlando Sanford International Airport.

Handy information about Chicago Midway International Airport (MDW)

  • MDW is located at 5700 South Cicero.

  • Of all flights leaving Chicago Midway International Airport, 77.88% arrive on time at their destination.

  • Central Chicago to Chicago Midway International Airport is approximately 19 kilometres. Depending on traffic, it'll take about 20 minutes to get there if you're driving, ride-sharing or catching a cab.

  • Expect a trip time of roughly 45 minutes when using public transport.

  • Taking an early flight from Chicago Midway International Airport to Orlando Sanford International Airport? Avoid the stress of rushing to the airport (and sneak in some extra precious sleep) by picking one of these stays near MDW:

Arriving at Orlando Sanford International Airport (SFB)

Getting from Orlando Sanford International Airport (SFB) to central Orlando

  • From Orlando Sanford International Airport, Orlando is approximately 48 kilometres away. It takes around 35 minutes to reach the centre driving.

  • If you're travelling on public transport, expect a journey time of roughly 2 hours 5 minutes.

When to fly to Orlando Sanford International Airport (SFB)

  • It's time to plan your travel dates for your flight from Chicago Midway International Airport to Orlando Sanford International Airport. July is the most popular month to head to Orlando. If you prefer a quieter vibe, go in February.

  • When reserving your flight from Chicago Midway International Airport to Orlando Sanford International Airport, consider the type of weather you like. July is the warmest month in Orlando, with temperatures ranging from 23ºC (73ºF) to 34ºC (93ºF).

  • If you like travelling in cooler conditions, search for a cheap ticket from MDW to SFB in January. Average temperatures are between 7ºC (45ºF) and 23ºC (73ºF) then.

Explore more of United States

  • Orlando is easy to fall in love with, but there are so many other parts of United States you'll want to see. About 209 kilometres north of Orlando, a visit to Jacksonville will fill your itinerary to the brim. Start with attractions like Jacksonville Zoo and Gardens, The Cummer Museum of Art & Gardens and Friendship Fountain.

  • If you're interested in discovering another major destination in United States, consider Miami, about 338 kilometres south of Orlando. Wynwood Walls, Vizcaya Museum and Gardens and American Airlines Arena are among the biggest draws.

Plan the rest of your trip from Chicago to Orlando

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.