$99+ Cheap flights from Midway (MDW) to Orlando (MCO)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Oct 17 — Oct 241
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Orlando with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago Midway to Orlando are usually found in January or February, booked 85 days in advance, depart on a Thursday or Saturday and return on a Friday
Cheap flight deals from Midway to Orlando
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midway to OrlandoExplore the most affordable flight options available from Midway to Orlando. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2026.
Explore the most affordable flight options available from Midway to Orlando. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2026.
This Frontier deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/108:07 pm -
Nonstop2h 50m
Sun 12/135:01 pm -
Nonstop3h 01m
Deal found 9/13![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:21 am -
1 stop14h 09m
Tue 10/139:25 am -
1 stop15h 18m
Deal found 9/12![Frontier logo]()
$201
This CheapOair deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:25 am -
1 stop9h 44m
Thu 10/85:15 pm -
1 stop7h 28m
Deal found 9/16![Frontier logo]()
$202
This Cheapflightsfares deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:21 am -
1 stop10h 00m
Mon 10/262:52 pm -
1 stop9h 51m
Deal found 9/16![Frontier logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/308:42 pm -
Nonstop2h 43m
Thu 12/106:42 pm -
Nonstop3h 00m
Deal found 9/16![Frontier logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:46 pm -
1 stop12h 23m
Wed 10/712:50 pm -
1 stop6h 01m
Deal found 9/15![Frontier logo]()
$205
This Travelocity deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/108:07 pm -
Nonstop2h 50m
Sat 12/126:00 am -
1 stop11h 15m
Deal found 9/14![Frontier logo]()
$206
This Trip.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:15 am -
1 stop10h 06m
Tue 10/2712:54 pm -
1 stop5h 33m
Deal found 9/15![Frontier logo]()
$207
This CheapOair deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:21 am -
1 stop10h 00m
Mon 11/25:03 pm -
1 stop7h 44m
Deal found 9/15![Frontier logo]()
$208
This Expedia deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/29:23 pm -
1 stop11h 27m
Sun 12/65:01 pm -
Nonstop3h 01m
Deal found 9/13![Frontier logo]()
$209
This Expedia deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:42 pm -
1 stop11h 19m
Mon 11/165:03 pm -
1 stop7h 44m
Deal found 9/16![Frontier logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:25 am -
1 stop14h 34m
Wed 12/166:00 am -
1 stop7h 59m
Deal found 9/14![Frontier logo]()
$211
Best flights from Midway to OrlandoDiscover carefully curated flight deals from Midway to Orlando that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 17, 2026.
Discover carefully curated flight deals from Midway to Orlando that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 17, 2026.
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:05 pm -
Nonstop2h 40m
Tue 10/276:35 am -
Nonstop2h 50m
Deal found 9/16![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/11:02 pm -
1 stop6h 38m
Sat 12/56:45 pm -
1 stop5h 10m
Deal found 9/16![Delta logo]()
$239
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:40 pm -
Nonstop2h 35m
Tue 10/2010:05 am -
1 stop5h 40m
Deal found 9/16![Southwest logo]()
$257
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/162:35 pm -
1 stop4h 15m
Wed 10/212:05 pm -
1 stop4h 05m
Deal found 9/16![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/114:25 pm -
Nonstop2h 35m
Sat 11/147:25 am -
Nonstop2h 55m
Deal found 9/16![Southwest logo]()
$283
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:10 pm -
1 stop5h 15m
Mon 11/98:00 pm -
1 stop5h 10m
Deal found 9/16![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/15:10 am -
Nonstop2h 35m
Sat 11/77:25 am -
Nonstop2h 55m
Deal found 9/15![Southwest logo]()
$304
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/44:25 pm -
Nonstop2h 35m
Tue 12/812:55 pm -
Nonstop3h 00m
Deal found 9/15![Southwest logo]()
$304
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/97:55 am -
2 stops7h 25m
Thu 1/142:30 pm -
1 stop5h 05m
Deal found 9/15![Southwest logo]()
$315
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/153:40 pm -
1 stop4h 20m
Thu 10/226:55 am -
Nonstop2h 50m
Deal found 9/15![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/141:35 pm -
1 stop5h 00m
Thu 1/217:00 am -
Nonstop2h 55m
Deal found 9/14![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/189:05 am -
Nonstop2h 40m
Mon 2/223:50 pm -
1 stop4h 50m
Deal found 9/14![Southwest logo]()
$330
Last-minute flights from Midway to OrlandoDiscover last-minute flight deals from Midway to Orlando. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Orlando. Data last updated September 17, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:25 am -
1 stop14h 34m
Wed 12/166:00 am -
1 stop7h 59m
Deal found 9/14![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:46 pm -
1 stop12h 23m
Wed 10/712:50 pm -
1 stop6h 01m
Deal found 9/15![Frontier logo]()
$205
This CheapOair deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:25 am -
1 stop9h 44m
Thu 10/85:15 pm -
1 stop7h 28m
Deal found 9/16![Frontier logo]()
$202
This Expedia deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:25 am -
1 stop9h 44m
Tue 10/204:53 pm -
1 stop7h 50m
Deal found 9/15![Frontier logo]()
$206
This CheapOair deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:25 am -
1 stop9h 44m
Fri 10/94:53 pm -
1 stop6h 29m
Deal found 9/15![Frontier logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:21 am -
1 stop14h 09m
Tue 10/139:25 am -
1 stop15h 18m
Deal found 9/12![Frontier logo]()
$201
This Mytrip deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:40 pm -
1 stop12h 28m
Tue 10/2712:54 pm -
1 stop5h 33m
Deal found 9/16![Frontier logo]()
$212
This CheapOair deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:21 am -
1 stop10h 00m
Mon 11/25:03 pm -
1 stop7h 44m
Deal found 9/15![Frontier logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:21 am -
2 stops12h 01m
Tue 10/2712:54 pm -
1 stop5h 33m
Deal found 9/14![Frontier logo]()
$210
This Justfly.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:22 am -
1 stop9h 59m
Tue 10/2712:54 pm -
1 stop5h 33m
Deal found 9/16![Frontier logo]()
$214
This Trip.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:15 am -
1 stop10h 06m
Tue 10/2712:54 pm -
1 stop5h 33m
Deal found 9/15![Frontier logo]()
$207
This Cheapflightsfares deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:21 am -
1 stop10h 00m
Mon 10/262:52 pm -
1 stop9h 51m
Deal found 9/16![Frontier logo]()
$203
One-way flights from Midway to OrlandoSearch for one-way flight options from Midway to Orlando. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
Search for one-way flight options from Midway to Orlando. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This Expedia deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:21 am -
1 stop10h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Frontier logo]()
$99
This CheapOair deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:16 am -
1 stop10h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Frontier logo]()
$100
This CheapOair deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:25 am -
1 stop9h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$101
This Super.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:16 am -
1 stop10h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$102
This Expedia deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/112:28 pm -
1 stop7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$104
This Jetabroad deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:15 am -
1 stop10h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:21 am -
1 stop12h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$107
This Trip.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:21 am -
1 stop23h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/148:07 pm -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$109
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/283:25 pm -
Nonstop2h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$110
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:55 am -
Nonstop2h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$111
Find flight deals from Midway to Orlando
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Orlando (MCO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $170 (Frontier) |
One-way from | $99 (Expedia) |
Popular in | July |
Cheapest in | January |
Average price | $373 |
Good round-trip deal | $352 or less |
Good one-way deal | $174 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Orlando that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 17, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Orlando Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoOrlando
MDW Chicago Midway - MCO Orlando
MDWMCO
Chicago Midway
Wed 11/11
3:00 pm-6:40 pm
Nonstop2h 40m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$110
ChicagoOrlando
MDW Chicago Midway - MCO Orlando
MDWMCO
Chicago Midway
Wed 12/9
1:15 pm-4:55 pm
Nonstop2h 40m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$174
Quickest round-trip
ChicagoOrlando
MDW Chicago Midway - MCO Orlando
MDWMCO
Chicago Midway
Sat 11/7
5:00 am-8:35 am
Nonstop2h 35m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$174
ChicagoOrlando
MDW Chicago Midway - MCO Orlando
MDWMCO
Chicago Midway
Wed 3/10
6:00 am-12:41 pm
1 stop5h 41m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$184
ChicagoOrlando
MDW Chicago Midway - MCO Orlando
MDWMCO
Chicago Midway
Thu 10/22
3:45 pm-7:20 pm
Nonstop2h 35m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$195
ChicagoOrlando
MDW Chicago Midway - MCO Orlando
MDWMCO
Chicago Midway
Sun 11/8
9:55 am-1:35 pm
Nonstop2h 40m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$195
ChicagoOrlando
MDW Chicago Midway - MCO Orlando
MDWMCO
Chicago Midway
Sat 10/3
1:50 pm-5:25 pm
Nonstop2h 35m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$198
ChicagoOrlando
MDW Chicago Midway - MCO Orlando
MDWMCO
Chicago Midway
Wed 9/30
6:20 pm-10:05 pm
Nonstop2h 45m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$198
ChicagoOrlando
MDW Chicago Midway - MCO Orlando
MDWMCO
Chicago Midway
Tue 9/29
9:40 am-1:15 pm
Nonstop2h 35m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$198
ChicagoOrlando
MDW Chicago Midway - MCO Orlando
MDWMCO
Chicago Midway
Wed 2/10
6:00 am-1:37 pm
1 stop6h 37m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$205
Showing 1-10 of 23 resultsSorted by cheapest first
Compare providers for flights from Midway to Orlando
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Orlando in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Orlando Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Orlando Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Orlando Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Orlando Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Orlando Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Midway to Orlando
Have a flexible travel schedule? Discover the best time to fly to Orlando from Midway with our price prediction graph.
MDW-MCO
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Orlando Airport
Prices
Delays
How far ahead should I book a flight from Chicago Midway Airport to Orlando Airport?
The price you pay for your flight from Chicago Midway Airport to Orlando Airport may vary depending on when you book. For the best chance of a lower fare, look to book 84 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Chicago Midway Airport to Orlando Airport?
Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Orlando Airport (average of $207). Flying from Chicago Midway Airport to Orlando Airport in July is currently the most expensive (average of $497). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MDW to MCO?
Find hourly flight availability from Midway to Orlando. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2026.
One of the essential ways to save on airfare from Chicago Midway Airport to Orlando Airport is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 17% on airfare.
What is the cheapest day to fly from Chicago Midway Airport to Orlando Airport?
Use this chart to determine the cheapest time to fly round-trip from Midway to Orlando. Price data was last updated on September 12, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Orlando Airport flight should consider departing on Monday at noon when fares are most often at their lowest. Wednesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
How often are flights from Chicago to Orlando delayed?
About 17% of weekly flights between Chicago and Orlando have experienced delays in the past year, with the average delay time being 136 minutes.
What is the most punctual flight time for Chicago to Orlando flights?
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Wednesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Orlando flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 17% of flights being delayed.
The best insider tips for Chicago Midway Airport to Orlando Airport flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Orlando Airport trip
Our travel experts
Reviews of airlines servicing Orlando
Get insights into the airlines that provide service to Orlando. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Orlando. Reviews last updated September 17, 2026.
See what other customers who have flown with Southwest and Frontier from Chicago Midway Airport to Orlando Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Midway to Orlando. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Orlando Airport?
Book flights to Orlando Airport if you plan to visit one of these locationsLake Buena Vista
Titusville
Winter Haven
Celebration
River Ranch
Four Corners
Sebastian
Leesburg
Ormond Beach
Flagler Beach
Daytona Beach Shores
Cocoa
Clermont
Altamonte Springs
The Villages
Lake Mary
Davenport
Haines City
Palatka
DeLand
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Other flights to Orlando
Explore flights to Orlando departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 17, 2026.
Midway and Orlando flights
Browse other Midway and Orlando flight options. Last updated on September 17, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on September 17, 2026.
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Top 2 airlines flying from Midway to Orlando
Discover the top 2 airlines that operate flights from Midway to Orlando. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$66 | Average$206 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$215 | Average$425 | FlexibilityNo cancel fee | On-time63% |