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Midway

$76+ Cheap flights from Miami (MIA) 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
MIA — MDW
Jun 3 — Jun 101
Wed 6/3
Wed 6/10
1 adult, Economy
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Cheap flight deals from Miami to Midway

Cheapest flights from Miami to Midway
Explore the most affordable flight options available from Miami to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 4, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/30. 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 5/205:22 pm
MIA
-
MDW
1 stop5h 40m
Frontier
Tue 6/212:27 pm
MDW
-
MIA
1 stop9h 20m
Frontier
Deal found 4/30$140
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Wed 6/311:23 am
MIA
-
MDW
1 stop11h 39m
Frontier
Wed 6/1012:04 pm
MDW
-
MIA
1 stop9h 59m
Frontier
Deal found 5/2$143
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Sun 5/2411:23 am
MIA
-
MDW
1 stop11h 39m
Frontier
Mon 6/16:00 am
MDW
-
MIA
1 stop15h 47m
Frontier
Deal found 5/3$151
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2811:23 am
MIA
-
MDW
1 stop11h 39m
Frontier
Thu 6/46:00 am
MDW
-
MIA
1 stop9h 27m
Frontier
Deal found 4/29$153
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Wed 5/278:10 am
MIA
-
MDW
1 stop14h 52m
Multiple Airlines
Sat 5/3011:59 am
MDW
-
MIA
1 stop28h 11m
Multiple Airlines
Deal found 5/1$164
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Wed 5/2011:23 am
MIA
-
MDW
1 stop11h 39m
Multiple Airlines
Sun 5/246:00 am
MDW
-
MIA
1 stop10h 10m
Multiple Airlines
Deal found 5/1$167
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
MIA
-
MDW
1 stop6h 12m
Frontier
Tue 6/1612:27 pm
MDW
-
MIA
1 stop9h 36m
Frontier
Deal found 4/29$176
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/293:45 pm
MIA
-
MDW
2 stops31h 17m
Frontier
Tue 6/212:27 pm
MDW
-
MIA
1 stop9h 20m
Frontier
Deal found 5/4$178
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 6/311:23 am
MIA
-
MDW
1 stop11h 39m
Frontier
Sat 6/136:00 am
MDW
-
MIA
1 stop13h 35m
Frontier
Deal found 4/30$179
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2011:23 am
MIA
-
MDW
1 stop11h 39m
Frontier
Sun 5/246:00 am
MDW
-
MIA
1 stop9h 27m
Frontier
Deal found 4/30$180
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Wed 6/175:26 pm
MIA
-
MDW
1 stop5h 45m
Frontier
Sat 6/206:00 am
MDW
-
MIA
1 stop13h 35m
Frontier
Deal found 5/2$181

Find flight deals from Miami to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Miami (MIA) 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 May 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$140
(Kiwi.com)

One-way from

$76
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$306

Good round-trip deal

$221 or less

Good one-way deal

$178 or less
Provider with most accurate pricing for Miami-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Miami-Chicago Midway flights.
Search Deals
From Miami to Chicago Midway
Search Deals
One-way flight from Miami to Chicago Midway
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Miami to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Miami to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Miami 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 2,558,603 searches. Data last updated May 4, 2026.
Use the filters below to find and compare flights from Miami to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 6/17

4:00 pm-10:17 pm

1 stop7h 17m

Chicago Midway

Wed 6/24

9:17 am-6:04 pm

1 stop7h 47m

$219

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 5/27

6:40 am-8:50 am

Nonstop3h 10m

Chicago Midway

Wed 6/3

7:55 am-11:55 am

Nonstop3h 00m

$249

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 7/1

11:45 am-3:55 pm

1 stop5h 10m

Chicago Midway

Tue 7/7

11:45 am-3:45 pm

Nonstop3h 00m

$264

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 5/30

7:00 am-9:15 am

Nonstop3h 15m

Chicago Midway

Sat 6/6

3:30 pm-10:25 pm

1 stop5h 55m

$276

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 6/24

6:00 am-9:50 am

1 stop4h 50m

Chicago Midway

Wed 6/24

11:45 am-3:45 pm

Nonstop3h 00m

$327

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 5/28

6:05 am-8:20 am

Nonstop3h 15m

Chicago Midway

Sun 5/31

11:35 am-7:15 pm

1 stop6h 40m

$331

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 5/28

6:20 am-11:50 am

2 stops6h 30m

Chicago Midway

Tue 6/2

12:50 pm-9:10 pm

2 stops7h 20m

$335
Quickest round-trip

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 10/9

6:40 am-8:45 am

Nonstop3h 05m

Chicago Midway

Tue 10/13

12:25 pm-4:20 pm

Nonstop2h 55m

$360

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 10/8

5:25 pm-10:50 pm

2 stops6h 25m

Chicago Midway

Tue 10/13

12:25 pm-4:20 pm

Nonstop2h 55m

$365

MiamiChicago

MIA - MDW

MIAMDW

Miami

Tue 6/16

6:00 am-12:25 pm

2 stops7h 25m

Chicago Midway

Tue 6/23

11:25 am-9:20 pm

2 stops8h 55m

$367

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Miami 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 Miami to Midway in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
eDreamsPrice Accuracy2 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Miami-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 Miami-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Miami-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Miami-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 Miami-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 Miami to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Miami with our price prediction graph.
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 Miami to Chicago Midway Airport

What is the cheapest month to book a flight from Miami to Chicago Midway Airport?

Currently, January is the cheapest month in which you can book a flight from Miami to Chicago Midway Airport (average of $128). Flying from Miami to Chicago Midway Airport in March is currently the most expensive (average of $368). 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 MIA to MDW?

Find hourly flight availability from Miami 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 May 4, 2026.

It’s optimal to fly from Miami to Chicago Midway Airport in the evening. By choosing this option you can save up to 48% on the cost of your flight, compared to a flight in the afternoon.

What is the cheapest day to fly from Miami to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Miami to Midway. Price data was last updated on May 2, 2026.

Travelers seeking maximum savings on their Miami to Chicago Midway Airport flight should consider departing on Sunday at noon 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.

How much does it cost to fly round-trip from Miami to Chicago Midway Airport?

The best insider tips for Miami to Chicago Midway Airport flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Miami to Chicago Midway Airport trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW and MIA

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

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 May 4, 2026.
Get a feel of what it's like to fly with Southwest and Frontier from Miami to Chicago Midway Airport by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,307 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,307 reviews
Southwest
7.9
Good
4,307 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.6
Fair
2,965 reviews
Southwest
7.9
Good
4,307 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Miami to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Miami to Chicago Midway?

    For a flight from Miami to Chicago Midway, you will be flying from Miami. Miami (MIA) is just 6.1 mi from the center of the city. Miami is the only Miami airport and it handles 1 outbound flight to Chicago Midway per day. 2 airlines have flights to Chicago Midway from Miami on a regular basis.

  • How long is the flight from Miami to Chicago Midway Airport?

    Airlines like Delta and Southwest fly from Miami to Chicago Midway Airport in about 3h 10m. The time it takes to get you to your destination can typically vary by up to 4h 07m. There are 1183 mi between Miami and Chicago Midway Airport. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Miami to Chicago Midway Airport round-trip?

    Currently priced at $58, Frontier will fly you from Miami to Chicago Midway Airport and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Southwest for as low as $177. You may be able to fly from Miami to Chicago Midway Airport for 75% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Miami to Chicago Midway Airport one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $54. Southwest flights start at $79 while deals on Delta start at $109 one-way.

  • What are the most reliable airlines from Miami to Chicago Midway Airport?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Miami to Chicago Midway Airport on time: Volaris (70%), Southwest (57%), Frontier (57%).

  • What are the cheapest flights from Miami to Chicago Midway Airport?

    While on average a flight from Miami to Chicago Midway Airport is generally $267, our data shows the cheapest flight currently is $99. When looking at the most popular route, (Miami - Chicago Midway), you can expect to pay $199 for that flight.

  • Can I find deals for flights from Miami to Midway that include hotel bookings?

    Yes. In addition to deals on Miami to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Miami to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Miami to Midway.

  • Can I find deals for business class flights from Miami to Midway?

    Yes. Cheapflights offers flight deals from Miami to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Miami to Chicago Midway Airport?

    Currently, January is the cheapest month in which you can book a flight from Miami to Chicago Midway Airport (average of $128). Flying from Miami to Chicago Midway Airport in March is currently the most expensive (average of $368). 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.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Miami to Midway

Discover the top 2 airlines that operate flights from Miami 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 2,558,603 searches. Data last updated May 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$135FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$177Average$307FlexibilityNo cancel feeOn-time63%

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