$112+ Cheap flights from Orlando (MCO) to Midway (MDW)
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 12/17. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Dec 14 — Dec 211
Round-trip
1 adult, Economy
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Find cheap flights from Orlando to Midway 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 Orlando to Chicago Midway are usually found in February or January, booked 90 days in advance, depart on a Saturday or Friday and return on a Friday
Cheap flight deals from Orlando to Midway
Cheapest
Best
Last-minute
One-way
Cheapest flights from Orlando to MidwayExplore the most affordable flight options available from Orlando to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 14, 2026.
Explore the most affordable flight options available from Orlando to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/27:15 am -
1 stop5h 18m
Sat 12/512:28 pm -
1 stop7h 25m
Deal found 11/10![Frontier logo]()
$205
This Mytrip deal was found by Cheapflights users on 11/11. 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.
Thu 12/39:28 am -
1 stop7h 39m
Sat 12/512:28 pm -
1 stop10h 42m
Deal found 11/11![Frontier logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/39:28 am -
1 stop7h 39m
Mon 12/75:02 pm -
1 stop5h 25m
Deal found 11/10![Frontier logo]()
$207
This Frontier deal was found by Cheapflights users on 11/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/312:39 pm -
Nonstop3h 02m
Sun 12/68:37 pm -
Nonstop2h 50m
Deal found 11/12![Frontier logo]()
$208
This Frontier deal was found by Cheapflights users on 11/10. 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.
Wed 12/27:15 am -
1 stop5h 18m
Thu 12/108:37 pm -
Nonstop2h 50m
Deal found 11/10![Frontier logo]()
$209
This Frontier deal was found by Cheapflights users on 11/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/89:58 pm -
1 stop12h 47m
Wed 12/912:28 pm -
1 stop9h 59m
Deal found 11/12![Frontier logo]()
$210
This Cheapflightsfares deal was found by Cheapflights users on 11/11. 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.
Fri 12/47:15 am -
1 stop9h 52m
Sat 12/510:40 am -
1 stop12h 41m
Deal found 11/11![Frontier logo]()
$211
This Cheapflightsfares deal was found by Cheapflights users on 11/11. 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.
Sun 12/135:41 pm -
Nonstop3h 01m
Tue 12/1512:28 pm -
1 stop10h 42m
Deal found 11/11![Frontier logo]()
$212
This Frontier deal was found by Cheapflights users on 11/11. 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.
Sat 11/215:46 pm -
Nonstop3h 01m
Mon 11/308:42 pm -
Nonstop2h 43m
Deal found 11/11![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 12/97:10 am -
1 stop5h 23m
Sun 1/108:30 pm -
Nonstop2h 50m
Deal found 11/9![Frontier logo]()
$214
This Trip.com deal was found by Cheapflights users on 11/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:39 pm -
Nonstop3h 02m
Sun 12/68:37 pm -
Nonstop2h 50m
Deal found 11/12![Frontier logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/144:07 pm -
1 stop20h 26m
Wed 12/1612:28 pm -
1 stop7h 25m
Deal found 11/10![Frontier logo]()
$216
Best flights from Orlando to MidwayDiscover carefully curated flight deals from Orlando to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 14, 2026.
Discover carefully curated flight deals from Orlando to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 14, 2026.
This Southwest deal was found by Cheapflights users on 11/10. 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 1/278:55 pm -
Nonstop3h 00m
Tue 2/23:35 pm -
Nonstop2h 40m
Deal found 11/10![Southwest logo]()
$377
This Southwest deal was found by Cheapflights users on 11/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/229:20 pm -
Nonstop2h 55m
Tue 1/55:20 am -
Nonstop2h 30m
Deal found 11/13![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 11/11. 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 12/56:30 pm -
Nonstop2h 55m
Mon 12/71:15 pm -
Nonstop2h 40m
Deal found 11/11![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 11/9. 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 12/174:00 pm -
Nonstop3h 00m
Sat 1/97:40 am -
Nonstop2h 45m
Deal found 11/9![Southwest logo]()
$392
This Southwest deal was found by Cheapflights users on 11/11. 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 1/72:35 pm -
1 stop5h 10m
Fri 1/156:15 am -
Nonstop2h 45m
Deal found 11/11![Southwest logo]()
$393
This Southwest deal was found by Cheapflights users on 11/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/185:40 pm -
Nonstop2h 50m
Wed 11/258:35 am -
Nonstop2h 50m
Deal found 11/13![Southwest logo]()
$397
This Southwest deal was found by Cheapflights users on 11/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/212:35 pm -
1 stop4h 25m
Sun 11/227:50 am -
2 stops6h 20m
Deal found 11/12![Southwest logo]()
$403
This Southwest deal was found by Cheapflights users on 11/11. 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 2/129:45 am -
Nonstop3h 00m
Sun 2/145:25 am -
Nonstop2h 50m
Deal found 11/11![Southwest logo]()
$403
This Southwest deal was found by Cheapflights users on 11/9. 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 11/259:20 pm -
Nonstop2h 55m
Thu 12/319:40 am -
Nonstop2h 45m
Deal found 11/9![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 11/11. 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 11/2012:55 pm -
1 stop5h 45m
Sun 11/227:50 am -
2 stops6h 20m
Deal found 11/11![Southwest logo]()
$408
This Southwest deal was found by Cheapflights users on 11/9. 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 12/2411:55 am -
Nonstop2h 55m
Thu 12/318:10 am -
1 stop5h 05m
Deal found 11/9![Southwest logo]()
$413
Last-minute flights from Orlando to MidwayDiscover last-minute flight deals from Orlando to Midway. Data last updated November 14, 2026 and is based on user searches.
Discover last-minute flight deals from Orlando to Midway. Data last updated November 14, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 11/11. 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.
Sat 11/215:46 pm -
Nonstop3h 01m
Mon 11/308:42 pm -
Nonstop2h 43m
Deal found 11/11![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/27:15 am -
1 stop5h 18m
Sat 12/512:28 pm -
1 stop7h 25m
Deal found 11/10![Frontier logo]()
$205
This Frontier deal was found by Cheapflights users on 11/10. 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.
Wed 12/27:15 am -
1 stop5h 18m
Thu 12/108:37 pm -
Nonstop2h 50m
Deal found 11/10![Frontier logo]()
$209
This Mytrip deal was found by Cheapflights users on 11/11. 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.
Thu 12/39:28 am -
1 stop7h 39m
Sat 12/512:28 pm -
1 stop10h 42m
Deal found 11/11![Frontier logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/39:28 am -
1 stop7h 39m
Mon 12/75:02 pm -
1 stop5h 25m
Deal found 11/10![Frontier logo]()
$207
This Frontier deal was found by Cheapflights users on 11/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/312:39 pm -
Nonstop3h 02m
Sun 12/68:37 pm -
Nonstop2h 50m
Deal found 11/12![Frontier logo]()
$208
This Cheapflightsfares deal was found by Cheapflights users on 11/11. 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.
Fri 12/47:15 am -
1 stop9h 52m
Sat 12/510:40 am -
1 stop12h 41m
Deal found 11/11![Frontier logo]()
$211
This Trip.com deal was found by Cheapflights users on 11/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:39 pm -
Nonstop3h 02m
Sun 12/68:37 pm -
Nonstop2h 50m
Deal found 11/12![Frontier logo]()
$215
This Frontier deal was found by Cheapflights users on 11/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/89:58 pm -
1 stop12h 47m
Wed 12/912:28 pm -
1 stop9h 59m
Deal found 11/12![Frontier logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 12/97:10 am -
1 stop5h 23m
Sun 1/108:30 pm -
Nonstop2h 50m
Deal found 11/9![Frontier logo]()
$214
This Cheapflightsfares deal was found by Cheapflights users on 11/11. 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.
Sun 12/135:41 pm -
Nonstop3h 01m
Tue 12/1512:28 pm -
1 stop10h 42m
Deal found 11/11![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/144:07 pm -
1 stop20h 26m
Wed 12/1612:28 pm -
1 stop7h 25m
Deal found 11/10![Frontier logo]()
$216
One-way flights from Orlando to MidwaySearch for one-way flight options from Orlando to Midway. Find affordable one-way fares based on user searches. Data last updated November 14, 2026.
Search for one-way flight options from Orlando to Midway. Find affordable one-way fares based on user searches. Data last updated November 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/174:31 pm -
1 stop7h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/13![Frontier logo]()
$112
This CheapOair deal was found by Cheapflights users on 11/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:15 am -
1 stop5h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![Frontier logo]()
$113
This Orbitz deal was found by Cheapflights users on 11/14. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/205:46 pm -
Nonstop3h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/14![Frontier logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 11/14. 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 1/53:49 pm -
1 stop25h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/14![Frontier logo]()
$115
This Kissandfly.com deal was found by Cheapflights users on 11/11. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:46 pm -
Nonstop3h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![Frontier logo]()
$117
This Super.com deal was found by Cheapflights users on 11/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:46 pm -
Nonstop3h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![Frontier logo]()
$118
This Super.com deal was found by Cheapflights users on 11/11. 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.
Tue 12/225:29 pm -
Nonstop3h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![Frontier logo]()
$122
This Super.com deal was found by Cheapflights users on 11/10. 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.
Tue 12/17:15 am -
1 stop5h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Frontier logo]()
$123
This CheapOair deal was found by Cheapflights users on 11/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/295:29 pm -
Nonstop3h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![Frontier logo]()
$124
Find flight deals from Orlando to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Orlando (MCO) to Midway (MDW). 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 November 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $205 (Kiwi.com) |
One-way from | $112 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $347 |
Good round-trip deal | $282 or less |
Good one-way deal | $174 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Orlando to Midway 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 November 14, 2026.
Use the filters below to find and compare flights from Orlando Airport to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Sat 1/30
10:25 am-12:20 pm
Nonstop2h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$189
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Tue 12/1
9:25 am-11:20 am
Nonstop2h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$194
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Thu 11/26
7:10 am-9:05 am
Nonstop2h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$194
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Thu 12/24
7:20 pm-9:20 pm
Nonstop3h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$194
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Tue 2/2
6:55 pm-9:05 pm
Nonstop3h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$194
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Tue 12/8
5:40 pm-7:35 pm
Nonstop2h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$194
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Wed 12/9
9:25 am-11:20 am
Nonstop2h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$195
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Sat 12/5
10:30 am-2:10 pm
1 stop4h 40m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$200
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Wed 1/27
8:55 pm-10:55 pm
Nonstop3h 00m
Chicago Midway
Tue 2/2
3:35 pm-7:15 pm
Nonstop2h 40m
$377
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Tue 12/22
9:20 pm-11:15 pm
Nonstop2h 55m
Chicago Midway
Tue 1/5
5:20 am-8:50 am
Nonstop2h 30m
$387
Showing 1-10 of 19 resultsSorted by cheapest first
Compare providers for flights from Orlando to Midway
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 Orlando to Midway in November.
| 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*3 stars |
- Most accurate provider: When it comes to deals on Orlando Airport-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Orlando Airport-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Orlando Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Orlando Airport-Chicago Midway 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 Orlando Airport-Chicago Midway 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 Orlando to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Orlando with our price prediction graph.
MCO-MDW
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.
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Everything you need to know about your flight from Orlando Airport to Chicago Midway Airport
Prices
Delays
How far ahead should I book a flight from Orlando Airport to Chicago Midway Airport?
Booking 89 days in advance of your planned departure date is, on average, the best time to get cheap flights from Orlando Airport to Chicago Midway Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Orlando Airport to Chicago Midway Airport?
Currently, February is the cheapest month in which you can book a flight from Orlando Airport to Chicago Midway Airport (average of $164). Flying from Orlando Airport to Chicago Midway Airport in June is currently the most expensive (average of $475). 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 MCO to MDW?
Find hourly flight availability from Orlando to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 14, 2026.
A simple way to save on the total cost of your ticket is to fly from Orlando Airport to Chicago Midway Airport in the evening. If you’re flexible enough to do this you can expect to save up to 29% on your trip compared to booking a flight in the morning.
What is the cheapest day to fly from Orlando Airport to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from Orlando to Midway. Price data was last updated on November 14, 2026.
Travelers seeking maximum savings on their Orlando Airport to Chicago Midway Airport flight should consider departing on Saturday evenings when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
How often are flights from Orlando to Chicago delayed?
About 24% of weekly flights between Orlando and Chicago have experienced delays in the past year, with the average delay time being 129 minutes.
What is the most punctual flight time for Orlando to Chicago flights?
Historically, flights departing in the morning 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 Orlando to Chicago flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 24% of flights being delayed.
The best insider tips for Orlando Airport to Chicago Midway 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 Orlando Airport to Chicago Midway Airport trip
Our travel experts
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated November 14, 2026.
See what other customers who have flown with Southwest and Frontier from Orlando Airport to Chicago Midway 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
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Related info for your journey
Find useful and relevant information for your journey from Orlando to Midway. 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 Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Midway
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Top 2 airlines flying from Orlando to Midway
Discover the top 2 airlines that operate flights from Orlando to Midway. 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 November 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$190 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$217 | Average$400 | FlexibilityNo cancel fee | On-time63% |