$68+ Cheap flights from Midway (MDW) to Orlando (MCO)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Jun 7 — Jun 141
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 February or January, booked 80 days in advance, depart on a Thursday or Friday 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 May 8, 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 May 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/16:00 am
MDW
- MCO
1 stop23h 40m
Frontier
Tue 6/95:10 pm
MCO
- MDW
1 stop6h 01m
Frontier
Deal found 5/5![Frontier logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/26:00 am
MDW
- MCO
1 stop7h 15m
Frontier
Thu 6/47:56 am
MCO
- MDW
1 stop15h 06m
Frontier
Deal found 5/5![Frontier logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Fri 5/293:42 pm
MDW
- MCO
1 stop17h 22m
Multiple Airlines
Wed 6/35:10 pm
MCO
- MDW
1 stop5h 52m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/26:00 am
MDW
- MCO
1 stop7h 15m
Frontier
Mon 6/87:56 am
MCO
- MDW
1 stop28h 16m
Frontier
Deal found 5/5![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 6/212:27 pm
MDW
- MCO
1 stop8h 20m
Frontier
Tue 6/165:25 am
MCO
- MDW
1 stop6h 47m
Frontier
Deal found 5/8![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 5/276:00 am
MDW
- MCO
1 stop23h 40m
Frontier
Wed 6/35:10 pm
MCO
- MDW
1 stop5h 52m
Frontier
Deal found 5/6![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/306:00 am
MDW
- MCO
1 stop7h 15m
Frontier
Wed 6/35:10 pm
MCO
- MDW
1 stop5h 52m
Frontier
Deal found 5/4![Frontier logo]()
$168
This Southwest deal was found by Cheapflights users on 5/7. 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 9/156:15 am
MDW
- MCO
Nonstop2h 30m
Southwest
Tue 9/225:25 pm
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 5/7![Southwest logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 6/312:04 pm
MDW
- MCO
1 stop8h 43m
Frontier
Tue 6/97:25 am
MCO
- MDW
2 stops15h 46m
Frontier
Deal found 5/7![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 5/4. 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.
Thu 5/2812:27 pm
MDW
- MCO
1 stop5h 35m
Frontier
Wed 6/33:10 pm
MCO
- MDW
1 stop7h 52m
Frontier
Deal found 5/4![Frontier logo]()
$171
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 May 8, 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 May 8, 2026.
This Southwest deal was found by Cheapflights users on 5/5. 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 7/158:10 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Tue 7/218:10 pm
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 5/5![Southwest logo]()
$169
This Delta deal was found by Cheapflights users on 5/8. 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.
Thu 5/285:10 pm
MDW
- MCO
1 stop6h 45m
Delta
Sat 5/305:15 pm
MCO
- MDW
1 stop4h 54m
Delta
Deal found 5/8![Delta logo]()
$263
This Southwest deal was found by Cheapflights users on 5/7. 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 6/175:30 pm
MDW
- MCO
1 stop5h 05m
Southwest
Wed 6/2410:20 am
MCO
- MDW
1 stop4h 50m
Southwest
Deal found 5/7![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 5/6. 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 6/212:55 pm
MDW
- MCO
1 stop6h 00m
Southwest
Sat 6/68:15 am
MCO
- MDW
1 stop5h 20m
Southwest
Deal found 5/6![Southwest logo]()
$195
This Southwest deal was found by Cheapflights users on 5/5. 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 5/298:35 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Wed 6/38:55 am
MCO
- MDW
1 stop4h 05m
Southwest
Deal found 5/5![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 5/8. 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.
Mon 6/13:50 pm
MDW
- MCO
1 stop4h 25m
Southwest
Thu 6/410:55 pm
MCO
- MDW
Nonstop2h 45m
Southwest
Deal found 5/8![Southwest logo]()
$249
This Southwest deal was found by Cheapflights users on 5/7. 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 6/612:55 pm
MDW
- MCO
1 stop4h 55m
Southwest
Mon 6/810:55 pm
MCO
- MDW
Nonstop2h 45m
Southwest
Deal found 5/7![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 5/6. 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 6/410:20 am
MDW
- MCO
2 stops7h 10m
Southwest
Mon 6/89:00 am
MCO
- MDW
1 stop4h 20m
Southwest
Deal found 5/6![Southwest logo]()
$300
This Southwest deal was found by Cheapflights users on 5/7. 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.
Mon 6/88:55 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Wed 6/108:00 am
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 5/7![Southwest logo]()
$304
This Southwest deal was found by Cheapflights users on 5/7. 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 7/28:55 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Wed 7/84:40 pm
MCO
- MDW
1 stop4h 10m
Southwest
Deal found 5/7![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 5/8. 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 6/277:35 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Wed 7/19:15 am
MCO
- MDW
1 stop5h 45m
Southwest
Deal found 5/8![Southwest logo]()
$313
Last-minute flights from Midway to OrlandoDiscover last-minute flight deals from Midway to Orlando. Data last updated May 8, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Orlando. Data last updated May 8, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 5/276:00 am
MDW
- MCO
1 stop23h 40m
Frontier
Wed 6/35:10 pm
MCO
- MDW
1 stop5h 52m
Frontier
Deal found 5/6![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 5/4. 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.
Thu 5/2812:27 pm
MDW
- MCO
1 stop5h 35m
Frontier
Wed 6/33:10 pm
MCO
- MDW
1 stop7h 52m
Frontier
Deal found 5/4![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Fri 5/293:42 pm
MDW
- MCO
1 stop17h 22m
Multiple Airlines
Wed 6/35:10 pm
MCO
- MDW
1 stop5h 52m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/306:00 am
MDW
- MCO
1 stop7h 15m
Frontier
Wed 6/35:10 pm
MCO
- MDW
1 stop5h 52m
Frontier
Deal found 5/4![Frontier logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/16:00 am
MDW
- MCO
1 stop23h 40m
Frontier
Tue 6/95:10 pm
MCO
- MDW
1 stop6h 01m
Frontier
Deal found 5/5![Frontier logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/26:00 am
MDW
- MCO
1 stop7h 15m
Frontier
Thu 6/47:56 am
MCO
- MDW
1 stop15h 06m
Frontier
Deal found 5/5![Frontier logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/26:00 am
MDW
- MCO
1 stop7h 15m
Frontier
Mon 6/87:56 am
MCO
- MDW
1 stop28h 16m
Frontier
Deal found 5/5![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 6/212:27 pm
MDW
- MCO
1 stop8h 20m
Frontier
Tue 6/165:25 am
MCO
- MDW
1 stop6h 47m
Frontier
Deal found 5/8![Frontier logo]()
$164
This Southwest deal was found by Cheapflights users on 5/5. 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 6/26:20 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Wed 6/37:15 am
MCO
- MDW
Nonstop2h 55m
Southwest
Deal found 5/5![Southwest logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 6/312:04 pm
MDW
- MCO
1 stop8h 43m
Frontier
Tue 6/97:25 am
MCO
- MDW
2 stops15h 46m
Frontier
Deal found 5/7![Frontier logo]()
$170
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 May 8, 2026.
Search for one-way flight options from Midway to Orlando. Find affordable one-way fares based on user searches. Data last updated May 8, 2026.
This WAYA deal was found by Cheapflights users on 5/6. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
MDW
- MCO
1 stop7h 15m
Frontier
Deal found 5/6![Frontier logo]()
$68
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 8/46:00 am
MDW
- MCO
1 stop26h 45m
Frontier
Deal found 5/7![Frontier logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 6/26:00 am
MDW
- MCO
1 stop7h 15m
Frontier
Deal found 5/6![Frontier logo]()
$70
This Trip.com deal was found by Cheapflights users on 5/8. 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.
Sat 5/3011:59 am
MDW
- MCO
1 stop6h 03m
Frontier
Deal found 5/8![Frontier logo]()
$80
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/16:00 am
MDW
- MCO
1 stop23h 40m
Frontier
Deal found 5/5![Frontier logo]()
$81
This Southwest deal was found by Cheapflights users on 5/8. 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 6/26:20 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Deal found 5/8![Southwest logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 7/2812:11 pm
MDW
- MCO
1 stop8h 55m
Frontier
Deal found 5/5![Frontier logo]()
$88
This Super.com deal was found by Cheapflights users on 5/4. 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 5/2812:27 pm
MDW
- MCO
1 stop5h 35m
Frontier
Deal found 5/4![Frontier logo]()
$89
This Southwest deal was found by Cheapflights users on 5/8. 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 7/143:00 pm
MDW
- MCO
1 stop3h 55m
Southwest
Deal found 5/8![Southwest logo]()
$90
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 May 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $148 (Kiwi.com) |
One-way from | $68 (WAYA) |
Popular in | June |
Cheapest in | February |
Average price | $295 |
Good round-trip deal | $285 or less |
Good one-way deal | $139 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 2,558,603 searches. Data last updated May 8, 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
Quickest round-trip
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Wed 7/15
8:10 pm-11:45 pm
Nonstop2h 35m
Orlando
Tue 7/21
8:10 pm-10:00 pm
Nonstop2h 50m
$169
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Wed 6/17
5:30 pm-11:35 pm
1 stop5h 05m
Orlando
Wed 6/24
10:20 am-2:10 pm
1 stop4h 50m
$189
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Tue 6/2
12:55 pm-7:55 pm
1 stop6h 00m
Orlando
Sat 6/6
8:15 am-12:35 pm
1 stop5h 20m
$195
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Fri 5/29
8:35 pm-12:10 am
Nonstop2h 35m
Orlando
Wed 6/3
8:55 am-12:00 pm
1 stop4h 05m
$199
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Mon 6/1
3:50 pm-9:15 pm
1 stop4h 25m
Orlando
Thu 6/4
10:55 pm-12:40 am
Nonstop2h 45m
$249
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Thu 5/28
5:10 pm-12:55 am
1 stop6h 45m
Orlando
Sat 5/30
5:15 pm-9:09 pm
1 stop4h 54m
$263
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Sat 6/6
12:55 pm-6:50 pm
1 stop4h 55m
Orlando
Mon 6/8
10:55 pm-12:40 am
Nonstop2h 45m
$289
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Thu 6/4
10:20 am-6:30 pm
2 stops7h 10m
Orlando
Mon 6/8
9:00 am-12:20 pm
1 stop4h 20m
$300
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Mon 6/8
8:55 pm-12:30 am
Nonstop2h 35m
Orlando
Wed 6/10
8:00 am-9:50 am
Nonstop2h 50m
$304
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Thu 7/2
8:55 pm-12:30 am
Nonstop2h 35m
Orlando
Wed 7/8
4:40 pm-7:50 pm
1 stop4h 10m
$309
Showing 1-10 of 20 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 May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- 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 79 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, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Orlando Airport (average of $196). Flying from Chicago Midway Airport to Orlando Airport in June is currently the most expensive (average of $419). 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 May 8, 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 at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 12% 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 May 2, 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 16% of weekly flights between Chicago and Orlando have experienced delays in the past year, with the average delay time being 140 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?
Tuesday 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 15% 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 May 8, 2026.
See what other customers who have flown with Southwest,Delta, andFrontier 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.
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
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
Clermont
Sanford
Celebration
Winter Haven
Leesburg
Sebastian
Apopka
Titusville
Lake Mary
Daytona Beach Shores
Altamonte Springs
Flagler Beach
The Villages
Four Corners
Davenport
Cocoa
Lady Lake
Haines City
Palatka
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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 May 8, 2026.
Midway and Orlando flights
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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 May 8, 2026.
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Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Midway to Orlando
Discover the top 3 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 2,558,603 searches. Data last updated May 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$72 | Average$192 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$98 | Average$529 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$196 | Average$389 | FlexibilityNo cancel fee | On-time63% |