MDW - MCO

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

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Everything you should know

Cheapest round-trip
$203
Typical prices: $182-$394
Frontier
Wed 12/5Mon 12/10
MDW - MCO • 1 stop
Cheapest non-stop
$206
Typical prices: $183-$401
Frontier
Tue 11/27Tue 12/11
MDW - MCO • Non-stop
Nonstop flights
You can fly direct with Southwest and Frontier. Average duration is 2h 37m
Direct flights
+1
Direct flights
+1
Avoid delays
Most punctual • 86% on-time
Best time • Fewest delays
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 25% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 39% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $159 (round-trip)
Shortest trip • 5h 22m (one-way)
Insights
Insights
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We hope you love your trip to Orlando Airport!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Midway to Orlando (MDW-MCO)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Orlando

Sat, Dec 5 - Thu, Dec 10
Frontier Logo
5:20 pm - 11:14 pmMDW  Chicago Midway-MCO Orlando
4h 54m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
5:01 pm - 7:02 pmMCO  Orlando-MDW Chicago Midway
3h 01mnonstop
$203Frontier
Fri, Nov 27 - Fri, Dec 11
Frontier Logo
1:29 pm - 5:19 pmMDW  Chicago Midway-MCO Orlando
2h 50mnonstop
Frontier Logo
5:01 pm - 7:02 pmMCO  Orlando-MDW Chicago Midway
3h 01mnonstop
$206Frontier
Thu, Dec 3 - Sun, Dec 6
Frontier Logo
8:07 pm - 11:57 pmMDW  Chicago Midway-MCO Orlando
2h 50mnonstop
Frontier Logo
5:01 pm - 7:02 pmMCO  Orlando-MDW Chicago Midway
3h 01mnonstop
$211Frontier
Thu, Dec 3 - Fri, Dec 11
Frontier Logo
2:04 pm - 11:14 pmMDW  Chicago Midway-MCO Orlando
8h 10m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
5:01 pm - 7:02 pmMCO  Orlando-MDW Chicago Midway
3h 01mnonstop
$213Frontier
Tue, Oct 20 - Tue, Oct 27
Southwest Logo
9:05 am - 12:40 pmMDW  Chicago Midway-MCO Orlando
2h 35mnonstop
Southwest Logo
4:45 pm - 6:35 pmMCO  Orlando-MDW Chicago Midway
2h 50mnonstop
$237Southwest
Sat, Nov 7 - Tue, Nov 10
Southwest Logo
4:25 pm - 8:05 pmMDW  Chicago Midway-MCO Orlando
2h 40mnonstop
Southwest Logo
5:40 pm - 7:30 pmMCO  Orlando-MDW Chicago Midway
2h 50mnonstop
$237Southwest
Tue, Oct 27 - Wed, Oct 28
Southwest Logo
11:10 am - 2:45 pmMDW  Chicago Midway-MCO Orlando
2h 35mnonstop
Southwest Logo
6:35 am - 8:25 amMCO  Orlando-MDW Chicago Midway
2h 50mnonstop
$237Southwest
Wed, Oct 28 - Tue, Nov 3
Delta Logo
10:59 am - 4:32 pmMDW  Chicago Midway-MCO Orlando
4h 33m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:30 am - 10:43 amMCO  Orlando-MDW Chicago Midway
6h 13m1 stop Atlanta Hartsfield-Jackson
$257Delta
Sat, Dec 12 - Thu, Dec 17
Delta Logo
1:41 pm - 9:27 pmMDW  Chicago Midway-MCO Orlando
6h 46m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:45 pm - 10:55 pmMCO  Orlando-MDW Chicago Midway
6h 10m1 stop Atlanta Hartsfield-Jackson
$257Delta
Mon, Dec 7 - Sat, Dec 12
Delta Logo
1:41 pm - 7:35 pmMDW  Chicago Midway-MCO Orlando
4h 54m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:45 pm - 10:55 pmMCO  Orlando-MDW Chicago Midway
5h 10m1 stop Atlanta Hartsfield-Jackson
$257Delta
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to Orlando Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Chicago Midway Airport to Orlando Airport with more confidence.

How much is a round-trip flight from Chicago Midway Airport to Orlando Airport?

Round-trip flights from Chicago Midway Airport to Orlando Airport start at $203. Prices are typical for this route right now, with typical round-trip fares ranging from $182 to $394. The lowest price found in the past 5 days was $203 on Frontier.

What's the cheapest day of the week to fly from Chicago Midway Airport to Orlando Airport?

Thursday is the cheapest day of the week to fly from Chicago Midway Airport to Orlando Airport, it is 11% cheaper than the average day. Wednesday is the most expensive day with flight prices 17% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Chicago Midway Airport to Orlando Airport?

  • January is the cheapest month to fly from Chicago Midway Airport to Orlando Airport at $170 round-trip.
  • June ($439) and July ($425) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 158% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Chicago Midway Airport to Orlando Airport the cheapest?

Flights from Chicago Midway Airport to Orlando Airport are cheapest 4 weeks before departure. Booking in this window typically costs about 25% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from Midway to Orlando

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Stefanie Waldek

Stefanie Waldek

Expert on Frontier, MDW and MCO

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Key details for Chicago Midway Airport to Orlando Airport flights

Low season

August

Cheapest flight

$115
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly with an average 8% increase in price.
Flight from Chicago Midway Airport to Orlando Airport

When to book flights from Midway to Orlando

Are your dates flexible? Find out the best times to travel from Midway to Orlando based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago Midway Airport to Orlando Airport flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • What can I do after alighting in Orlando?

    Terminals A, B & C and the Gate Areas of the MCO offer numerous shops, and restaurants. The airport's city park atmosphere offers amazing views of the world. You may enjoy scenic views of downtown Orlando at the Terminal Top Parking garage. You may also relax at one of the Orlando International Airport lounges located in Gates 30-59 and other airport areas.

  • Can I smoke in the terminals of both airports?

    Orlando International Airport is a non-smoking facility according to State law. Similarly, Chicago Midway Airport does allow smoking inside the terminals. However, you can smoke outside the terminal building facility.

  • Where can I leave my luggage at Orlando International Airport?

    There is a “Hold My Luggage” spot in level 1 of terminal B. Here, you can drop/pick your luggage, store your luggage for a day/several days and luggage transfer services to your hotel or city.

  • Can I request a wheelchair at MCO?

    Yes, you should notify your airline during booking so that they arrange for assistance from their skycaps. Skycaps offers disability assistance services including wheelchair assistance, luggage transportation and other travel related needs.

  • Which airlines offer extra legroom and free seat selection on Chicago Midway Airport to Orlando Airport flights?

    Among airlines operating Chicago Midway Airport to Orlando Airport flights:

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

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

  • What airlines are available from Chicago Midway Airport to Orlando Airport?

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

    • Southwest
    • Frontier

  • Which airports can I use when flying from Chicago Midway Airport to Orlando Airport?

    Flights from Chicago Midway Airport to Orlando Airport usually depart from Chicago Midway (MDW) and arrive at Orlando (MCO).

  • Which airlines include bags at no extra cost on Chicago Midway Airport to Orlando Airport flights?

    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.

  • What cabin classes can I book on flights from Chicago Midway Airport to Orlando Airport?

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

    • Economy Class
    • Business Class
    • First Class

  • How much can I save by taking a layover when flying from Chicago Midway Airport to Orlando Airport?

    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.

  • What is the standard checked-bag allowance on flights from Chicago Midway Airport to Orlando Airport?

    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.

  • Which aircraft model is used most often on flights from Chicago Midway Airport to Orlando Airport?

    The Airbus A321neo family is used most often on this route, operated mainly by Frontier and United Airlines. Other aircraft seen on the route include Airbus A320-100/200 variants.

  • Which airports do connecting flights from Chicago Midway Airport to Orlando Airport pass through?

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

    • Atlanta Hartsfield-Jackson (ATL) - 93% of one-stop connections
    • Cincinnati Cinci./N. Kentucky (CVG) - 4% of one-stop connections
    • Newark (EWR) - 4% of one-stop connections

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

  • Can I save money by using flexible dates for flights from Chicago Midway Airport to Orlando Airport?

    Yes. Being flexible with your travel dates can save you up to 24% on the Chicago Midway Airport to Orlando Airport 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.

  • At what point is a flight considered delayed from Chicago Midway Airport to Orlando Airport?

    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 Airport route, 17% of flights were delayed in the past 3 months, with delays averaging 2 hours 41 minutes.

  • How are flight departures from Chicago Midway Airport to Orlando Airport spread across the day?

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

  • What popular places can I visit in Orlando Airport?

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

  • What are the earliest and latest flights from Chicago Midway Airport to Orlando Airport?

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

    • 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.

  • How expensive are last-minute Chicago Midway Airport to Orlando Airport flights?

    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.

  • How long is a flight from Chicago Midway Airport to Orlando Airport?

    A nonstop flight from Chicago Midway Airport to Orlando Airport takes 2h 37m, covering 990 miles.

  • Do I need a passport to fly from Chicago Midway Airport to Orlando Airport?

    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.

  • Have flight prices from Chicago Midway Airport to Orlando Airport changed much recently?

    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.

  • How are flight prices from Chicago Midway Airport to Orlando Airport looking right now?

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

  • How do delay rates compare for morning and evening flights from Chicago Midway Airport to Orlando Airport?

    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.

  • How much time can I save by choosing a different layover airport from Chicago Midway Airport to Orlando Airport?

    Flying via Cincinnati Cinci./N. Kentucky (CVG) gives the shortest average 1-stop total travel time at 5h 22m, compared with 6h 11m via Atlanta Hartsfield-Jackson (ATL) and 17h 11m via Newark (EWR).

  • What is the time difference between Chicago Midway Airport and Orlando Airport?

    Orlando Airport 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.

  • What car rental options are available at Orlando Airport (MCO)?

    Orlando Airport (MCO) hosts 5 major car rental companies, with daily rates starting from around $1 for economy cars. Top options include:
    · Rent-A-Wreck
    · Routes Car & Truck Rentals
    · Hertz
    · Budget
    · Thrifty

  • How much should I expect to pay for a Chicago Midway Airport to Orlando Airport flight?

    Round-trip flights from Chicago Midway Airport to Orlando Airport range from $182 to $394, with an average of $281 over the past 12 months. Anything below $182 counts as a good deal.

Your guide to booking Chicago Midway Airport to Orlando Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Thursday departure instead of Wednesday. On this route, Thursday flights average $251 - about $79 less than Wednesday (24% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 4 weeks before you fly. On this route, that window historically saves about 25% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago Midway Airport to Orlando Airport trip for January. Fares historically average $170 round-trip in that month - typically $269 less than the most expensive month, which is June (based on the last 12 months).
  • If arriving on time is high on your priority list, Frontier is the strongest pick on this route. 86% of Frontier flights from Chicago Midway Airport to Orlando Airport arrived on time in the past 3 months, slightly above the route's average on-time arrival rate of 83%. When flights on this route do arrive late, the average delay is 2 hours 41 minutes, so choosing a carrier with strong on-time performance can make a difference on tight schedules.
  • If you have the time, taking a 1-stop flight through Newark Airport (EWR) can be cheaper than flying direct. The cheapest layover option averages $159 round-trip on this route - about $124 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Orlando Airport.
    - Hyatt Regency Orlando International Airport
    - Ramada by Wyndham Suites Orlando Airport
    - Marriott Orlando Airport Lakeside
  • When flying from Chicago Midway Airport (MDW) to Orlando, the most popular airport of arrival is Orlando (MCO) Airport which is 8.6 miles away. This airport is centrally located southeast of downtown Orlado. Other possible airports of arrival include Orlando Sanford (SFB), St. Petersburg (PIE), Sarasota/Bradenton (SRQ and Tampa (TPA). However, these airports may have service from only a few airlines, making MCO the best option for Chicago Midway Airport to Orlando flights.
  • If you want to leave your car at the MDW airport, the long term parking option is available west of S. Cicero Avenue and north of 55th Street. In addition, there are free shuttle buses that connect the long term parking location and the main terminal building. You can call the Midway’s Parking Garage office for assistance for your parking needs.
  • There are two pet relief areas in Chicago Midway International Airport. The centrally located indoor facility iis fitted with fake grass and a pet sitting space. The outdoor facility, located before flight check-in and security, has benches and bags for travelers with pets. Despite the fact that the outdoor relief area is outside the airport’s secure area, you can just walk there in 3 minutes making pet travel easy. The airport also provides waste bags to pet owners.
  • On arrival, The Orlando International Airport has 7 seven pet relief areas. There are three outdoor areas and 4 indoor pet relief areas. Head to North Cell Lot to locate one indoor relief area and two others near the Main Terminal. The other four outdoor pet relief areas are located at the exit of Gates 1-29, 30-59, 70-99, and 100-129. Both pet relief areas are fenced, so you can let your furry companion roam free.
  • If you have a hidden disability, MCO has innovative services to help travelers with hidden disabilities, be it hearing challenges, dementia, etc. The Sunflower Lanyard program is designed to help those with hidden disorders enjoy a fulfilling flight experience at the airport.

Prefer to fly direct from Chicago Midway Airport to Orlando Airport?

 
Find which airlines fly direct from Chicago Midway Airport to Orlando Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Orlando

Monday

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Tuesday

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Southwest

Wednesday

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Thursday

Southwest

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Friday

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Saturday

Southwest

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Sunday

Southwest

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See more direct flights

Direct returns

Orlando to Chicago Midway

Monday

Southwest

Southwest

Tuesday

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Wednesday

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Thursday

Southwest

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Friday

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Saturday

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Sunday

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Everything you need to know for your flight from Midway to Orlando

Other airlines flying to Orlando