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Cheap Flights From Chicago, Illinois (MDW) To Orlando, Florida (MCO)

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Fares from Chicago, IL (MDW)
$258 RT to
Orlando, FL (MCO)
Sorry this deal is over or has been sold out! But here’s another great Airfarewatchdog verified fare for this route!
$258 RT Chicago to Orlando, FL
Airline(s)
Southwest
Seats:
Seats are not available on all flights or all dates of travel. You may need to have flexible travel dates to find this fare. Fares for travel on holidays may be higher.
Adv. Purchase:
14 Days
Available:
Mon-Thur & Sat
Travel Ending:
Thursday, 30 October 2014
More Details:
Non-Stop Flights, No min. stay, Fare can be bought one-way for half the lowest roundtrip price, Spring/Fall travel, No peak summer travel at this price
Last Updated:
Tuesday, 15 April 2014
Our Notes:
Travel April 29 through June 7 and August 25 through October 30, 2014. Blackout Dates Apply: May 22, 23, 26 and September 1, 2014. This is a fare from Southwest - visit Southwest.com to find this fare. Other airlines often match Southwest sales, so search other sites to find the best option.
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All mandatory taxes/fees are included in the price. Tax-inclusive fare may be a few dollars higher or lower depending on the airport you connect through, if any. Baggage fees, if applicable, and other optional fees are not included.

Our Dealhounds found this airfare using flexible date search. This means we searched a range of dates to find you the best price.

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"Great condo with the right expectations" 03/24/2013
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"Virgin Holidays Family of four and Two Adult Friends-To See Halloween, Kennedy, Universal" 01/14/2013
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"5 Year Anniversary" 04/15/2014
"Excellent place to stay for families in Orlando" 04/14/2014

More Flights From Chicago To Orlando (MDW-MCO)

Price
Details
$278 RT Non-Stop Flights. No min. stay. Fare can be bought one-way for half the... (Southwest) See all details »
  • Airline(s):
    Southwest
  • Seats are:
    Seats Are Not Available On All Flights Or All Dates Of Travel. You May Need To Have Flexible Travel Dates To Find This Fare. Fares For Travel On Holidays May Be Higher.
  • Advance Purchase:
    14 Days
  • Available for travel:
    7 Days/week, If Available
  • Travel ending:
    Friday, October 31, 2014
  • More Details:
    Non-Stop Flights, No Min. Stay, Fare Can Be Bought One-way For Half The Lowest Roundtrip Price
  • Last Updated:
    Wednesday, April 16, 2014
  • Our Notes:
    This is a fare from Southwest. Visit Southwest.com to find this fare. Other airlines often match Southwest sales, so search other sites to find your best ...moreoption.
$258 RT Non-Stop Flights. No min. stay. Fare can be bought one-way for half the... (AirTran) See all details »
  • Airline(s):
    AirTran
  • Seats are:
    Seats Are Not Available On All Flights Or All Dates Of Travel. You May Need To Have Flexible Travel Dates To Find This Fare. Fares For Travel On Holidays May Be Higher.
  • Advance Purchase:
    14 Days
  • Available for travel:
    Mon-Thur & Sat
  • Travel ending:
    Thursday, October 30, 2014
  • More Details:
    Non-Stop Flights, No Min. Stay, Fare Can Be Bought One-way For Half The Lowest Roundtrip Price, No Peak Summer Travel At This Price
  • Last Updated:
    Wednesday, April 16, 2014
  • Our Notes:
    CheapAir.com Will Include A Booking Fee Of $9.95

Reviews for Chicago to Orlando (MDW-MCO)

based on 7 reviews
Flown this route before? Write a review
    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Paying for bags and seat selection BAD...Flight and Service GOOD

    by kberna on August 6, 2011

    Flight from Chicago to Orlando

    Airline:
    AirTran
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    August 2010
    Seat Class:
    economy

    We really didn't like paying for our bags to fly or if we wanted a seat sitting next to our children. But the flights were smooth and on-time and the ailine stewards were polite. Checking in went smooth on both ends and we had no problems boarding.

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    up grade seats... nice.

    by FritzFarrago on September 23, 2010

    Flight from Chicago to Orlando

    Airline:
    Air Transat
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    September 2010
    Seat Class:
    economy

    this was on a Boeing 717/ MD95, older plane, but ok... first surprise was, upon internet check-in.. if you wanted to sit in a "chosen" seat you have to pay... naturally everyone with a ticket will get a seat, but if you want to sit with someone, or up front, you pay... we got two of the free seats, naturally next to the engine... no biggie... coming home through, and this was strange in today's air... the plane was half empty and we got exit row seats that would have cost $25 to reserve on line... so much room, next time I may pay for the extra space....

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Will use Southwest again...and again

    by why on August 23, 2010

    Flight from Chicago to Orlando

    Airline:
    Southwest
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    July 2010
    Seat Class:
    economy

    Southwest knows customer service. I tried them for the first time and the money I saved I spent more time in Disney. My luggage doesn't take a vacation and I'm not paying for that. Last year the major airlines made billions (United and American)...I didn't save a dollar! Make the switch to Midway and SAVE.

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Southwest is a good value

    by suzeyh on August 12, 2010

    Flight from Chicago to Orlando

    Airline:
    Southwest
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    July 2010
    Seat Class:
    economy

    It's great to have no baggage fees and Southwest's prices are certainly hard to beat. However, don't waste your money on the Early Bird Check-in (which is an additional fee of $10/person one way) if you can get to your computer 24 hours prior to boarding. I didn't use the Early Bird leaving Chicago and was in the A boarding group. I used the Early Bird Check leaving Orlando and had nearly the exact same boarding position as the flight out of Chicago. There's $40 my family could have spent elsewhere . . . That said, the flight was on time and we arrived safe and sound.

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Friendly Staff

    by trinamini3 on August 12, 2010

    Flight from Chicago to Orlando

    Airline:
    Southwest
    RT/OW
    Round Trip
    Number of Stops:
    1 stop in Atlanta, Georgia
    Date of Flight:
    August 2010
    Seat Class:
    economy

    Like most times when I fly Southwest, the staff is very pleasant and polite. They have an airiness to their personalities and make a flight enjoyable.

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Just what I expected plus some bonus added humor

    by StephSzklarski on July 30, 2010

    Flight from Chicago to Orlando

    Airline:
    Southwest
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    July 2010
    Seat Class:
    economy

    Fantastic flights each way. Coming home we even at a nature show (weather with lightning). Staff was professional. Service was great at the gate and on-board. We had special needs and challenges. Everything went better than anticipated. Thank you Southwest for brightening our lives.

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Wonderful

    by lindabousk on July 16, 2010

    Flight from Chicago to Orlando

    Airline:
    Southwest
    RT/OW
    One Way
    Number of Stops:
    Many stops
    Date of Flight:
    June 2010
    Seat Class:
    economy

    It was a very enjoyable flight with no complaints.

    Southwest Airlines can't be beat as far as service & better yet - price!

Flown this route before? Write a review
Sample Fares found by other travelers within the past 72 hours
Price From/To Depart/Return Airline
$452 Flight from Midway to Orlando (MDW-MCO) Fri, Apr 18 - Sun, Apr 20 Delta Air Lines
$458 Flight from Midway to Orlando (MDW-MCO) Sat, Apr 19 - Mon, Apr 21 Delta Air Lines
$460 Flight from Midway to Orlando (MDW-MCO) Tue, Apr 22 - Fri, Apr 25 Delta Air Lines
$471 Flight from Midway to Orlando (MDW-MCO) Wed, Apr 16 - Sat, Apr 19 Delta Air Lines
$496 Flight from Midway to Orlando (MDW-MCO) Thu, Apr 17 - Fri, Apr 18 Delta Air Lines
$607 Flight from Midway to Orlando (MDW-MCO) Sat, Apr 26 - Fri, May 2 AirTran
$616 Flight from Midway to Orlando (MDW-MCO) Wed, Apr 23 - Sat, Apr 26 AirTran
$621 Flight from Midway to Orlando (MDW-MCO) Fri, Apr 25 - Fri, May 2 Delta Air Lines
$621 Flight from Midway to Orlando (MDW-MCO) Fri, Apr 18 - Sat, Apr 26 Delta Air Lines
$694 Flight from Midway to Orlando (MDW-MCO) Fri, Apr 18 - Sun, Apr 27 Delta Air Lines
There are approximately 69 flights covering the route from Midway Airport in Chicago to Orlando International Airport in Orlando, provided by as many as 3 airlines.

The following airlines sometimes offer nonstop cheap flights from Chicago to Orlando:

Transwest Air

As an alternative to flying from Chicago, you may also want to try searching for cheap flights from Chicago (ORD).
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