$113+ Cheap flights from Midway (MDW) to Miami (MIA)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MIA
Oct 7 — Oct 141
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Miami 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 Miami are usually found in October or January, booked 23 days in advance, depart on a Thursday or Sunday and return on a Thursday
Cheap flight deals from Midway to Miami
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midway to MiamiExplore the most affordable flight options available from Midway to Miami. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 7, 2026.
Explore the most affordable flight options available from Midway to Miami. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Sat 10/317:25 am -
1 stop8h 39m
Tue 11/35:05 am -
1 stop13h 42m
Deal found 9/5![Frontier logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 10/296:42 pm -
1 stop14h 47m
Tue 11/35:05 am -
1 stop13h 42m
Deal found 9/4![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Wed 11/116:42 pm -
1 stop26h 07m
Sun 11/1510:55 pm -
1 stop19h 52m
Deal found 9/4![Frontier logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 10/206:21 am -
1 stop14h 08m
Tue 10/275:05 am -
1 stop13h 22m
Deal found 9/5![Frontier logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Wed 10/286:42 pm -
1 stop14h 47m
Tue 11/35:05 am -
1 stop13h 42m
Deal found 9/4![Frontier logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Mon 10/266:15 am -
1 stop8h 10m
Thu 10/294:30 pm -
1 stop8h 17m
Deal found 9/4![Frontier logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Wed 11/46:16 am -
1 stop14h 15m
Sun 11/85:15 am -
1 stop13h 32m
Deal found 9/4![Frontier logo]()
$232
This Priceline deal was found by Cheapflights users on 9/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:25 am -
1 stop9h 04m
Thu 10/14:30 pm -
1 stop8h 14m
Deal found 9/3![Frontier logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 9/266:25 am -
1 stop13h 13m
Thu 10/14:30 pm -
1 stop8h 14m
Deal found 9/3![Frontier logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Tue 9/296:25 am -
1 stop13h 13m
Fri 10/25:32 am -
1 stop19h 12m
Deal found 9/4![Frontier logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 10/246:21 am -
1 stop14h 08m
Mon 10/2610:55 pm -
1 stop19h 32m
Deal found 9/4![Frontier logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/216:21 am -
1 stop6h 57m
Wed 10/285:05 am -
1 stop13h 42m
Deal found 9/3![Frontier logo]()
$243
Best flights from Midway to MiamiDiscover carefully curated flight deals from Midway to Miami that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 7, 2026.
Discover carefully curated flight deals from Midway to Miami that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 7, 2026.
This Southwest deal was found by Cheapflights users on 9/3. 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 11/181:25 pm -
Nonstop3h 00m
Tue 11/242:35 pm -
1 stop7h 30m
Deal found 9/3![Southwest logo]()
$387
This Delta deal was found by Cheapflights users on 9/3. 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.
Fri 12/45:14 pm -
1 stop6h 43m
Mon 12/78:00 am -
1 stop6h 01m
Deal found 9/3![Delta logo]()
$422
This Southwest deal was found by Cheapflights users on 9/3. 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 12/31:20 pm -
2 stops7h 50m
Thu 12/1012:00 pm -
1 stop6h 20m
Deal found 9/3![Southwest logo]()
$404
This Southwest deal was found by Cheapflights users on 9/5. 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.
Sat 10/1712:10 pm -
Nonstop3h 10m
Sat 10/244:00 pm -
Nonstop3h 05m
Deal found 9/5![Southwest logo]()
$405
This Southwest deal was found by Cheapflights users on 9/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/241:50 pm -
1 stop7h 20m
Mon 10/266:40 am -
Nonstop3h 05m
Deal found 9/4![Southwest logo]()
$405
This Southwest deal was found by Cheapflights users on 9/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/58:05 am -
Nonstop3h 15m
Tue 10/138:25 am -
2 stops9h 45m
Deal found 9/4![Southwest logo]()
$410
This Southwest deal was found by Cheapflights users on 9/6. 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 10/67:55 am -
2 stops8h 35m
Mon 10/126:25 am -
2 stops8h 00m
Deal found 9/6![Southwest logo]()
$425
This Southwest deal was found by Cheapflights users on 9/5. 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.
Sat 10/310:25 am -
1 stop5h 55m
Sat 10/104:00 pm -
Nonstop3h 05m
Deal found 9/5![Southwest logo]()
$427
This Southwest deal was found by Cheapflights users on 9/6. 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.
Sat 10/108:10 am -
2 stops11h 25m
Wed 10/1411:30 am -
2 stops8h 15m
Deal found 9/6![Southwest logo]()
$431
This Southwest deal was found by Cheapflights users on 9/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/31:25 pm -
Nonstop3h 00m
Mon 12/712:40 pm -
Nonstop3h 15m
Deal found 9/4![Southwest logo]()
$435
This Southwest deal was found by Cheapflights users on 9/6. 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.
Wed 10/2811:35 am -
Nonstop3h 10m
Sun 11/18:05 pm -
1 stop5h 00m
Deal found 9/6![Southwest logo]()
$447
This Southwest deal was found by Cheapflights users on 9/2. 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 9/1211:20 am -
Nonstop3h 00m
Tue 9/154:00 pm -
Nonstop3h 05m
Deal found 9/2![Southwest logo]()
$450
Last-minute flights from Midway to MiamiDiscover last-minute flight deals from Midway to Miami. Data last updated September 7, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Miami. Data last updated September 7, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 9/266:25 am -
1 stop13h 13m
Thu 10/14:30 pm -
1 stop8h 14m
Deal found 9/3![Frontier logo]()
$238
This Priceline deal was found by Cheapflights users on 9/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:25 am -
1 stop9h 04m
Thu 10/14:30 pm -
1 stop8h 14m
Deal found 9/3![Frontier logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Tue 9/296:25 am -
1 stop13h 13m
Fri 10/25:32 am -
1 stop19h 12m
Deal found 9/4![Frontier logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 10/206:21 am -
1 stop14h 08m
Tue 10/275:05 am -
1 stop13h 22m
Deal found 9/5![Frontier logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Tue 10/206:21 am -
1 stop14h 08m
Thu 10/225:15 am -
1 stop13h 30m
Deal found 9/4![Frontier logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/216:21 am -
1 stop6h 57m
Wed 10/285:05 am -
1 stop13h 42m
Deal found 9/3![Frontier logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 10/246:21 am -
1 stop14h 08m
Mon 10/2610:55 pm -
1 stop19h 32m
Deal found 9/4![Frontier logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Mon 10/266:15 am -
1 stop8h 10m
Thu 10/294:30 pm -
1 stop8h 17m
Deal found 9/4![Frontier logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Wed 10/286:42 pm -
1 stop14h 47m
Tue 11/35:05 am -
1 stop13h 42m
Deal found 9/4![Frontier logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 10/296:42 pm -
1 stop14h 47m
Tue 11/35:05 am -
1 stop13h 42m
Deal found 9/4![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Sat 10/317:25 am -
1 stop8h 39m
Tue 11/35:05 am -
1 stop13h 42m
Deal found 9/5![Frontier logo]()
$200
This FlightHub deal was found by Cheapflights users on 9/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:25 am -
1 stop8h 39m
Sat 11/711:45 am -
1 stop7h 02m
Deal found 9/2![Frontier logo]()
$246
One-way flights from Midway to MiamiSearch for one-way flight options from Midway to Miami. Find affordable one-way fares based on user searches. Data last updated September 7, 2026.
Search for one-way flight options from Midway to Miami. Find affordable one-way fares based on user searches. Data last updated September 7, 2026.
This MakeMyTrip deal was found by Cheapflights users on 9/2. 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 MakeMyTrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:21 am -
1 stop6h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$113
This Super.com deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:25 am -
1 stop7h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 9/126:25 am -
1 stop13h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$121
This Priceline deal was found by Cheapflights users on 9/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:50 am -
1 stop8h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 9/226:25 am -
1 stop27h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$125
This CheapOair deal was found by Cheapflights users on 9/2. 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.
Mon 9/286:25 am -
1 stop9h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$126
This Super.com deal was found by Cheapflights users on 9/6. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:25 am -
1 stop7h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Frontier logo]()
$127
This Super.com deal was found by Cheapflights users on 9/4. 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.
Sat 9/191:06 pm -
1 stop7h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$128
Find flight deals from Midway to Miami
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Miami (MIA). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $200 (Kiwi.com) |
One-way from | $113 (MakeMyTrip) |
Popular in | September |
Cheapest in | October |
Average price | $426 |
Good round-trip deal | $334 or less |
Good one-way deal | $185 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Miami that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 7, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Miami that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Wed 10/14
11:35 am-3:45 pm
Nonstop3h 10m
Miami
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$189
Quickest round-trip
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Tue 11/3
1:25 pm-5:25 pm
Nonstop3h 00m
Miami
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$189
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Mon 10/5
8:05 am-12:20 pm
Nonstop3h 15m
Miami
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$190
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Wed 10/7
4:30 pm-10:15 pm
1 stop4h 45m
Miami
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$199
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Mon 10/5
6:05 am-1:05 pm
1 stop6h 00m
Miami
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$200
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Sat 10/17
1:27 pm-9:16 pm
1 stop6h 49m
Miami
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$200
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Sat 10/10
12:10 pm-4:20 pm
Nonstop3h 10m
Miami
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$213
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Sat 10/3
12:10 pm-4:20 pm
Nonstop3h 10m
Miami
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$229
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Fri 10/9
2:50 pm-10:40 pm
2 stops6h 50m
Miami
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$244
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Fri 10/23
8:05 am-12:20 pm
Nonstop3h 15m
Miami
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$249
Showing 1-10 of 23 resultsSorted by cheapest first
Compare providers for flights from Midway to Miami
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 Miami in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| 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-Miami 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-Miami flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Miami flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Miami 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-Miami 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 Miami
Have a flexible travel schedule? Discover the best time to fly to Miami from Midway with our price prediction graph.
MDW-MIA
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 Miami
Prices
Delays
How far ahead should I book a flight from Chicago Midway Airport to Miami?
The best time to book flights from Chicago Midway Airport to Miami is 22 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Chicago Midway Airport to Miami?
Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Miami (average of $181). Flying from Chicago Midway Airport to Miami in September is currently the most expensive (average of $426). 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 MIA?
Find hourly flight availability from Midway to Miami. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 7, 2026.
When flying from Chicago Midway Airport to Miami, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 67% versus a flight in the evening.
How often are flights from Chicago to Miami delayed?
About 23% of weekly flights between Chicago and Miami have experienced delays in the past year, with the average delay time being 131 minutes.
What is the most punctual flight time for Chicago to Miami flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night 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 Monday 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 Miami flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 17% of flights being delayed.
The best insider tips for Chicago Midway Airport to Miami 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 Miami trip
Our travel experts
Reviews of airlines servicing Miami
Get insights into the airlines that provide service to Miami. 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 Miami. Reviews last updated September 7, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andAmerican Airlines from Chicago Midway Airport to Miami to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
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 Miami. 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 Miami?
Book flights to Miami if you plan to visit one of these locationsSunny Isles Beach
Hollywood
Dania Beach
Boynton Beach
Miami Springs
Miramar
Plantation
Sunrise
Doral
Hialeah
Tamarac
Lake Worth
Kendall
Fisher Island
Bonita Springs
Deerfield Beach
North Palm Beach
Oakland Park
Palm Beach
Marathon
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Top 4 airlines flying from Midway to Miami
Discover the top 4 airlines that operate flights from Midway to Miami. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$59 | Average$231 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$134 | Average$387 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$203 | Average$395 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$249 | Average$423 | FlexibilityNo cancel fee | On-time63% |