$106+ Cheap flights from Orlando (ORL) to Midway (MDW)
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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — MDW
Sep 30 — Oct 71
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
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.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 August 31, 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 August 31, 2026.
This Expedia deal was found by Cheapflights users on 8/27. 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.
Mon 11/2310:23 am -
Nonstop3h 01m
Fri 11/271:29 pm -
Nonstop2h 50m
Deal found 8/27![Frontier logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 8/31. 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 9/912:50 pm -
1 stop6h 01m
Sat 9/126:25 am -
1 stop9h 44m
Deal found 8/31![Frontier logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 9/55:23 pm -
1 stop6h 24m
Sat 9/126:25 am -
1 stop9h 44m
Deal found 8/28![Frontier logo]()
$210
This Super.com deal was found by Cheapflights users on 8/28. 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 12/105:01 pm -
Nonstop3h 01m
Sun 12/138:07 pm -
Nonstop2h 50m
Deal found 8/28![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 9/25:23 pm -
1 stop6h 24m
Sat 9/511:45 am -
1 stop9h 29m
Deal found 8/26![Frontier logo]()
$213
This Trip.com deal was found by Cheapflights users on 8/27. 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 12/115:01 pm -
Nonstop3h 01m
Mon 12/148:07 pm -
Nonstop2h 50m
Deal found 8/27![Frontier logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 9/912:50 pm -
1 stop6h 01m
Thu 9/106:25 am -
1 stop9h 44m
Deal found 8/28![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 9/1212:50 pm -
1 stop6h 01m
Tue 9/156:25 am -
1 stop9h 44m
Deal found 8/26![Frontier logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 9/99:30 am -
1 stop9h 21m
Fri 9/116:25 am -
1 stop9h 44m
Deal found 8/26![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 9/105:19 pm -
1 stop25h 32m
Wed 9/166:25 am -
1 stop9h 44m
Deal found 8/26![Frontier logo]()
$225
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 August 31, 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 August 31, 2026.
This Southwest deal was found by Cheapflights users on 8/26. 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 10/105:30 pm -
Nonstop2h 50m
Sat 10/177:00 pm -
Nonstop2h 35m
Deal found 8/26![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 8/27. 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 10/296:00 am -
1 stop7h 47m
Mon 11/21:27 pm -
1 stop6h 27m
Deal found 8/27![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 8/27. 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 10/218:05 pm -
Nonstop2h 55m
Thu 10/228:40 pm -
Nonstop2h 35m
Deal found 8/27![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 8/26. 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 9/297:35 pm -
Nonstop2h 50m
Wed 9/3012:20 pm -
Nonstop2h 40m
Deal found 8/26![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 8/26. 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 10/2810:40 am -
1 stop5h 00m
Wed 10/285:55 pm -
1 stop4h 15m
Deal found 8/26![Southwest logo]()
$252
This Southwest deal was found by Cheapflights users on 8/27. 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 10/164:00 pm -
1 stop5h 15m
Sun 10/185:25 pm -
Nonstop2h 35m
Deal found 8/27![Southwest logo]()
$323
This Southwest deal was found by Cheapflights users on 8/29. 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 10/37:45 am -
Nonstop2h 50m
Tue 10/277:55 am -
1 stop4h 15m
Deal found 8/29![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 8/29. 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 9/105:15 pm -
Nonstop2h 50m
Sat 9/127:50 am -
1 stop4h 05m
Deal found 8/29![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 8/28. 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 10/110:40 am -
Nonstop2h 50m
Tue 10/67:05 pm -
Nonstop2h 40m
Deal found 8/28![Southwest logo]()
$348
This Southwest deal was found by Cheapflights users on 8/29. 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 9/123:20 pm -
Nonstop2h 50m
Sat 9/193:40 pm -
Nonstop2h 40m
Deal found 8/29![Southwest logo]()
$351
This Southwest deal was found by Cheapflights users on 8/30. 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 9/97:40 am -
Nonstop2h 45m
Sat 9/123:40 pm -
Nonstop2h 40m
Deal found 8/30![Southwest logo]()
$351
This Southwest deal was found by Cheapflights users on 8/29. 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 10/134:20 pm -
1 stop4h 20m
Thu 10/152:15 pm -
Nonstop2h 35m
Deal found 8/29![Southwest logo]()
$354
Last-minute flights from Orlando to MidwayDiscover last-minute flight deals from Orlando to Midway. Data last updated August 31, 2026 and is based on user searches.
Discover last-minute flight deals from Orlando to Midway. Data last updated August 31, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 9/25:23 pm -
1 stop6h 24m
Sat 9/511:45 am -
1 stop9h 29m
Deal found 8/26![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 8/31. 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 9/55:23 pm -
1 stop6h 24m
Fri 9/116:46 pm -
1 stop21h 23m
Deal found 8/31![Frontier logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 8/31. 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 9/55:23 pm -
1 stop6h 24m
Sun 9/66:05 am -
1 stop15h 09m
Deal found 8/31![Frontier logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 9/55:23 pm -
1 stop6h 24m
Sat 9/126:25 am -
1 stop9h 44m
Deal found 8/28![Frontier logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 9/55:23 pm -
1 stop6h 24m
Wed 9/96:25 am -
1 stop9h 44m
Deal found 8/30![Frontier logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 9/912:50 pm -
1 stop6h 01m
Thu 9/106:25 am -
1 stop9h 44m
Deal found 8/28![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 9/912:50 pm -
1 stop6h 01m
Sat 9/126:25 am -
1 stop24h 44m
Deal found 8/26![Frontier logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 9/105:19 pm -
1 stop25h 32m
Wed 9/166:25 am -
1 stop9h 44m
Deal found 8/26![Frontier logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 9/116:50 am -
1 stop12h 01m
Sat 9/126:25 am -
1 stop9h 44m
Deal found 8/26![Frontier logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 9/1212:50 pm -
1 stop6h 01m
Tue 9/156:25 am -
1 stop9h 44m
Deal found 8/26![Frontier logo]()
$219
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 August 31, 2026.
Search for one-way flight options from Orlando to Midway. Find affordable one-way fares based on user searches. Data last updated August 31, 2026.
This Trip.com deal was found by Cheapflights users on 8/30. 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 9/53:21 pm -
1 stop8h 26m
Deal found 8/30![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 9/83:16 pm -
1 stop27h 35m
Deal found 8/30![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 9/105:19 pm -
1 stop25h 32m
Deal found 8/27![Frontier logo]()
$108
This Southwest deal was found by Cheapflights users on 8/26. 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 10/1210:35 pm -
Nonstop2h 50m
Deal found 8/26![Southwest logo]()
$119
This Trip.com deal was found by Cheapflights users on 8/26. 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.
Tue 9/159:30 am -
1 stop9h 16m
Deal found 8/26![Frontier logo]()
$120
This Southwest deal was found by Cheapflights users on 8/27. 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 11/113:50 pm -
1 stop4h 50m
Deal found 8/27![Southwest logo]()
$124
This Trip.com deal was found by Cheapflights users on 8/27. 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.
Tue 9/229:30 am -
1 stop9h 16m
Deal found 8/27![Frontier logo]()
$125
This Super.com deal was found by Cheapflights users on 8/26. 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.
Sun 9/276:00 am -
1 stop6h 59m
Deal found 8/26![Frontier logo]()
$127
This Super.com deal was found by Cheapflights users on 8/29. 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.
Fri 9/1812:50 pm -
1 stop6h 01m
Deal found 8/29![Frontier logo]()
$128
Find flight deals from Orlando to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Orlando (ORL) 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 August 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $204 (Expedia) |
One-way from | $106 (Trip.com) |
Popular in | July |
Cheapest in | January |
Average price | $362 |
Good round-trip deal | $309 or less |
Good one-way deal | $169 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 August 31, 2026.
Use the filters below to find and compare flights from Orlando 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 10/10
5:30 pm-7:20 pm
Nonstop2h 50m
Chicago Midway
Sat 10/17
7:00 pm-10:35 pm
Nonstop2h 35m
$237
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Wed 10/21
8:05 pm-10:00 pm
Nonstop2h 55m
Chicago Midway
Thu 10/22
8:40 pm-12:15 am
Nonstop2h 35m
$237
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Tue 9/29
7:35 pm-9:25 pm
Nonstop2h 50m
Chicago Midway
Wed 9/30
12:20 pm-4:00 pm
Nonstop2h 40m
$247
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Wed 10/28
10:40 am-2:40 pm
1 stop5h 00m
Chicago Midway
Wed 10/28
5:55 pm-11:10 pm
1 stop4h 15m
$252
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Thu 10/29
6:00 am-12:47 pm
1 stop7h 47m
Chicago Midway
Mon 11/2
1:27 pm-8:54 pm
1 stop6h 27m
$257
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Fri 10/16
4:00 pm-8:15 pm
1 stop5h 15m
Chicago Midway
Sun 10/18
5:25 pm-9:00 pm
Nonstop2h 35m
$323
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Sat 10/3
7:45 am-9:35 am
Nonstop2h 50m
Chicago Midway
Tue 10/27
7:55 am-1:10 pm
1 stop4h 15m
$333
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Thu 9/10
5:15 pm-7:05 pm
Nonstop2h 50m
Chicago Midway
Sat 9/12
7:50 am-12:55 pm
1 stop4h 05m
$333
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Thu 10/1
10:40 am-12:30 pm
Nonstop2h 50m
Chicago Midway
Tue 10/6
7:05 pm-10:45 pm
Nonstop2h 40m
$348
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Sat 9/12
3:20 pm-5:10 pm
Nonstop2h 50m
Chicago Midway
Sat 9/19
3:40 pm-7:20 pm
Nonstop2h 40m
$351
Showing 1-10 of 24 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 August.
| 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*1 star |
- Most accurate provider: When it comes to deals on Orlando-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-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Orlando-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Orlando-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-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.
ORL-MDW
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.
Cheapflights Insights
Everything you need to know about your flight from Orlando to Chicago Midway Airport
ORL-MDW
MCO-MDW
What is the cheapest month to book a flight from Orlando to Chicago Midway Airport?
Currently, January is the cheapest month in which you can book a flight from Orlando to Chicago Midway Airport (average of $177). Flying from Orlando to Chicago Midway Airport in June is currently the most expensive (average of $441). 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 ORL 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 August 31, 2026.
It’s typically best to fly out from Orlando to Chicago Midway Airport at noon. Doing so could potentially save you 25% on the flight price compared to flying in the morning, which is usually more expensive.
How much does it cost to fly round-trip from Orlando to Chicago Midway Airport?
Airfare is typical for this route at the moment.
Orlando to Chicago Midway Airport flights typically cost between $186 and $251 in November.The cheapest round-trip price found within the last 5 days was $204 on Frontier (Nov 23-Nov 27).
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 130 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.
How far ahead should I book a flight from Orlando to Chicago Midway Airport?
The price you pay for your flight from Orlando to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 77 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Orlando 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 August 22, 2026.
Travelers seeking maximum savings on their Orlando to Chicago Midway Airport flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 August 31, 2026.
Read through reviews of airlines operating flights from Orlando to Chicago Midway Airport, such as Southwest and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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
Lansing
Merrillville
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 August 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$170 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$184 | Average$348 | FlexibilityNo cancel fee | On-time63% |