$100+ 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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MIA
Dec 4 — Dec 111
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 March or February, booked 23 days in advance, depart on a Thursday or Friday and return on a Saturday
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 November 4, 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 November 4, 2026.
This Delta deal was found by Cheapflights users on 11/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/179:30 am -
1 stop7h 13m
Wed 11/188:15 am -
1 stop4h 44m
Deal found 11/4![Delta logo]()
$247
This Frontier deal was found by Cheapflights users on 11/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/231:11 pm -
1 stop6h 05m
Thu 12/316:30 am -
1 stop6h 40m
Deal found 11/3![Frontier logo]()
$248
This Mytrip deal was found by Cheapflights users on 11/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/108:37 pm -
2 stops22h 23m
Tue 12/157:05 am -
1 stop5h 28m
Deal found 11/3![Frontier logo]()
$249
This Frontier deal was found by Cheapflights users on 11/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/208:16 am -
1 stop6h 14m
Fri 11/2010:59 pm -
1 stop9h 34m
Deal found 11/3![Frontier logo]()
$250
This Trip.com deal was found by Cheapflights users on 11/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/239:09 am -
1 stop5h 21m
Fri 11/278:08 am -
1 stop5h 26m
Deal found 11/4![Frontier logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 12/231:11 pm -
1 stop6h 05m
Tue 12/296:30 am -
1 stop6h 40m
Deal found 10/31![Frontier logo]()
$252
This Mytrip deal was found by Cheapflights users on 11/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1212:28 pm -
1 stop6h 32m
Tue 12/153:41 pm -
2 stops19h 04m
Deal found 11/3![Frontier logo]()
$253
This Frontier deal was found by Cheapflights users on 11/1. 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 11/249:09 am -
1 stop5h 21m
Fri 11/278:08 am -
1 stop5h 26m
Deal found 11/1![Frontier logo]()
$254
This CheapOair deal was found by Cheapflights users on 11/1. 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.
Fri 12/115:02 pm -
1 stop20h 34m
Tue 12/157:05 am -
1 stop5h 28m
Deal found 11/1![Frontier logo]()
$255
This Frontier deal was found by Cheapflights users on 11/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/201:06 pm -
1 stop9h 20m
Wed 11/2510:59 pm -
1 stop10h 15m
Deal found 11/3![Frontier logo]()
$256
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 12/206:43 am -
1 stop9h 05m
Fri 12/252:31 pm -
1 stop10h 30m
Deal found 11/1![Frontier logo]()
$257
This Cheapflightsfares deal was found by Cheapflights users on 10/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:15 am -
1 stop8h 49m
Sun 11/2210:59 pm -
1 stop10h 15m
Deal found 10/31![Frontier logo]()
$258
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 November 4, 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 November 4, 2026.
This Southwest deal was found by Cheapflights users on 11/1. 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 1/412:55 pm -
Nonstop3h 00m
Thu 1/712:30 pm -
Nonstop3h 25m
Deal found 11/1![Southwest logo]()
$262
This Delta deal was found by Cheapflights users on 11/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/161:41 pm -
1 stop6h 50m
Tue 1/55:40 am -
1 stop5h 20m
Deal found 11/2![Delta logo]()
$308
This Southwest deal was found by Cheapflights users on 10/30. 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.
Tue 12/11:25 pm -
Nonstop3h 00m
Sat 12/510:15 am -
1 stop7h 15m
Deal found 10/30![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 11/3. 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.
Tue 12/228:15 am -
1 stop5h 50m
Tue 12/296:35 am -
Nonstop3h 10m
Deal found 11/3![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 10/30. 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 12/212:45 pm -
1 stop6h 25m
Sat 12/512:20 pm -
1 stop8h 20m
Deal found 10/30![Southwest logo]()
$317
This KAYAK deal was found by Cheapflights users on 11/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/151:02 pm -
1 stop6h 53m
Thu 12/178:15 am -
1 stop4h 49m
Deal found 11/2![Delta logo]()
$385
This Southwest deal was found by Cheapflights users on 11/2. 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.
Tue 12/11:25 pm -
Nonstop3h 00m
Mon 12/76:40 am -
1 stop5h 40m
Deal found 11/2![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 10/30. 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.
Thu 12/174:00 pm -
1 stop5h 20m
Mon 12/216:35 am -
Nonstop3h 10m
Deal found 10/30![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 10/30. 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 1/65:45 pm -
Nonstop3h 00m
Sun 1/106:15 am -
1 stop9h 30m
Deal found 10/30![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 10/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/138:15 am -
1 stop4h 55m
Mon 1/185:50 am -
2 stops8h 10m
Deal found 10/31![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 10/30. 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.
Thu 1/712:50 pm -
2 stops8h 10m
Sun 1/106:50 am -
2 stops6h 45m
Deal found 10/30![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 10/30. 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.
Fri 1/85:45 pm -
Nonstop3h 00m
Mon 1/1112:30 pm -
Nonstop3h 25m
Deal found 10/30![Southwest logo]()
$445
Last-minute flights from Midway to MiamiDiscover last-minute flight deals from Midway to Miami. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Miami. Data last updated November 4, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 10/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:15 am -
1 stop8h 49m
Sun 11/2210:59 pm -
1 stop10h 15m
Deal found 10/31![Frontier logo]()
$258
This Delta deal was found by Cheapflights users on 11/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/179:30 am -
1 stop7h 13m
Wed 11/188:15 am -
1 stop4h 44m
Deal found 11/4![Delta logo]()
$247
This Frontier deal was found by Cheapflights users on 11/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/208:16 am -
1 stop6h 14m
Fri 11/2010:59 pm -
1 stop9h 34m
Deal found 11/3![Frontier logo]()
$250
This Frontier deal was found by Cheapflights users on 11/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/201:06 pm -
1 stop9h 20m
Wed 11/2510:59 pm -
1 stop10h 15m
Deal found 11/3![Frontier logo]()
$256
This Trip.com deal was found by Cheapflights users on 11/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/239:09 am -
1 stop5h 21m
Fri 11/278:08 am -
1 stop5h 26m
Deal found 11/4![Frontier logo]()
$251
This Frontier deal was found by Cheapflights users on 11/1. 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 11/249:09 am -
1 stop5h 21m
Fri 11/278:08 am -
1 stop5h 26m
Deal found 11/1![Frontier logo]()
$254
This Mytrip deal was found by Cheapflights users on 11/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/108:37 pm -
2 stops22h 23m
Tue 12/157:05 am -
1 stop5h 28m
Deal found 11/3![Frontier logo]()
$249
This CheapOair deal was found by Cheapflights users on 11/1. 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.
Fri 12/115:02 pm -
1 stop20h 34m
Tue 12/157:05 am -
1 stop5h 28m
Deal found 11/1![Frontier logo]()
$255
This Mytrip deal was found by Cheapflights users on 11/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1212:28 pm -
1 stop6h 32m
Tue 12/153:41 pm -
2 stops19h 04m
Deal found 11/3![Frontier logo]()
$253
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 12/206:43 am -
1 stop9h 05m
Fri 12/252:31 pm -
1 stop10h 30m
Deal found 11/1![Frontier logo]()
$257
This Priceline deal was found by Cheapflights users on 11/3. 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.
Wed 12/231:11 pm -
1 stop6h 05m
Tue 12/296:30 am -
1 stop6h 40m
Deal found 11/3![Frontier logo]()
$248
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 November 4, 2026.
Search for one-way flight options from Midway to Miami. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This Frontier deal was found by Cheapflights users on 11/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:09 am -
1 stop5h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$100
This Trip.com deal was found by Cheapflights users on 11/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1212:28 pm -
1 stop6h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$101
This Super.com deal was found by Cheapflights users on 11/1. 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 12/226:43 am -
1 stop9h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$104
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/251:16 pm -
1 stop9h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$106
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:08 am -
1 stop14h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Mon 12/145:02 pm -
1 stop20h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/812:28 pm -
1 stop23h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Wed 1/65:21 pm -
1 stop28h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Tue 12/112:33 pm -
1 stop27h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/45:02 pm -
1 stop23h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$112
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 November 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $247 (Delta) |
One-way from | $100 (Frontier) |
Popular in | September |
Cheapest in | March |
Average price | $435 |
Good round-trip deal | $419 or less |
Good one-way deal | $178 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 November 4, 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
Mon 12/21
7:20 pm-11:30 pm
Nonstop3h 10m
Miami
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$114
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Tue 12/1
1:02 pm-8:55 pm
1 stop6h 53m
Miami
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$124
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Sat 11/14
11:27 am-6:40 pm
1 stop6h 13m
Miami
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$124
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Thu 11/26
5:40 am-4:05 pm
2 stops9h 25m
Miami
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$129
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Wed 12/9
1:25 pm-5:25 pm
Nonstop3h 00m
Miami
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$149
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Tue 12/15
1:25 pm-5:25 pm
Nonstop3h 00m
Miami
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$149
Quickest round-trip
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Sat 1/16
3:45 pm-7:40 pm
Nonstop2h 55m
Miami
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$209
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Fri 1/15
7:15 pm-11:15 pm
Nonstop3h 00m
Miami
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$209
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Mon 1/4
12:55 pm-4:55 pm
Nonstop3h 00m
Miami
Thu 1/7
12:30 pm-2:55 pm
Nonstop3h 25m
$262
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Tue 11/17
1:31 pm-9:26 pm
1 stop6h 55m
Miami
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$279
Showing 1-10 of 22 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 November.
| 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 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Miami (average of $275). Flying from Chicago Midway Airport to Miami in September is currently the most expensive (average of $517). 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 November 4, 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 66% versus a flight in the evening.
What is the cheapest day to fly from Chicago Midway Airport to Miami?
Use this chart to determine the cheapest time to fly round-trip from Midway to Miami. Price data was last updated on October 31, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Miami flight should consider departing on Sunday at noon when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
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 135 minutes.
What is the most punctual flight time for Chicago to Miami flights?
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Friday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to 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 November 4, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andFrontier 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.
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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 locationsHollywood
Sunny Isles Beach
Doral
Boynton Beach
Dania Beach
Kendall
Miami Springs
Florida City
Plantation
Miramar
Sunrise
Hialeah
Lake Worth
Tamarac
North Miami
Fisher Island
Miami Lakes
North Palm Beach
Oakland Park
Davie
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Other flights to Miami
Explore flights to Miami departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on November 4, 2026.
Midway and Miami flights
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Top 3 airlines flying from Midway to Miami
Discover the top 3 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 November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$59 | Average$253 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$134 | Average$387 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$249 | Average$439 | FlexibilityNo cancel fee | On-time63% |