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$69+ 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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
MIA — MDW
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheapflights Tip: The best prices from Miami to Chicago Midway are usually found in August or July, booked 65 days in advance, depart on a Friday or Thursday and return on a Wednesday

Cheap 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 July 29, 2025.

Round-trip from

$137
(Southwest)

One-way from

$69
(Southwest)

Popular in

June

Cheapest in

August

Average price

$143

Good round-trip deal

$185 or less

Good one-way deal

$158 or less
From Miami to Chicago Midway
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One-way flight from Miami to Chicago Midway
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Highest demand for flights based on searches. 22% potential increase in price ($61 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Miami to Chicago Midway.
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Price to beat on a one-way flight from Miami to Chicago Midway.
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Find 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 July 29, 2025.

This Southwest deal was found by Cheapflights users on 7/29. 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.
Fri 9/1912:35 pmMIA - MDW
Nonstop3h 10mSouthwest
Mon 9/222:10 pmMDW - MIA
Nonstop3h 00mSouthwest
Deal found 7/29$137
This eDestinos deal was found by Cheapflights users on 7/27. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/85:45 amMIA - MDW
1 stop18h 13mFrontier
Sat 10/116:10 amMDW - MIA
1 stop15h 59mFrontier
Deal found 7/27$176
This Delta deal was found by Cheapflights users on 7/27. 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.
Sat 9/68:10 amMIA - MDW
1 stop5h 18mDelta
Sun 9/76:00 amMDW - MIA
1 stop6h 33mDelta
Deal found 7/27$217

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 July 29, 2025.
Use the filters below to find and compare flights from Miami to Chicago Midway Airport that are best for you.

Fly from

Miami

Fly to

Midway

Route

Depart

Return

Price

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 9/19

12:35 pm-2:45 pm

Nonstop3h 10m

Chicago Midway

Mon 9/22

2:10 pm-6:10 pm

Nonstop3h 00m

$137

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 10/8

5:45 am-10:58 pm

1 stop18h 13m

Chicago Midway

Sat 10/11

6:10 am-11:09 pm

1 stop15h 59m

$176

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 9/6

8:10 am-12:28 pm

1 stop5h 18m

Chicago Midway

Sun 9/7

6:00 am-1:33 pm

1 stop6h 33m

$217

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sun 9/21

7:30 am-9:35 am

Nonstop3h 05m

$69

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 10/23

6:53 pm-9:08 pm

Nonstop3h 15m

$71

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sun 10/5

6:00 am-9:40 am

1 stop4h 40m

$109

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

The best insider tips for Miami to Chicago Midway Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Miami to Chicago Midway Airport trip
Airlines
Frontier

Frontier's UpFront Plus offers a guaranteed empty middle seat for extra comfort.


Consider early check-in to secure your place onboard due to frequent overbooking.

Read more about Frontierby Marisa Garcia
Southwest

Enjoy free snacks and non-alcoholic drinks, plus a free drink on special occasions.


Two free checked bags included, even oversized like skis or golf clubs.

Read more about Southwestby Marisa Garcia
Airports
MIA

For a quick check-in at MIA, avoid crowded areas by finding faster security lanes through the check-in area.

Read more about MIAby Ramsey Qubein
MDW

Use the Orange Line train for a quick, affordable trip from MDW to downtown Chicago in under 30 minutes.

Read more about MDWby Ramsey Qubein
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Frontier and Southwest

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on MDW and MIA

Ramsey Qubein

Ramsey Qubein

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

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

How far ahead should I book a flight from Miami to Chicago Midway Airport?

Use this chart to determine the optimal time to book a round-trip flight from Miami to Midway. Price data was last updated on July 25, 2025.

The price you pay for your flight from Miami to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 64 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, April is the cheapest month in which you can book a flight from Miami to Chicago Midway Airport (average of $160). Flying from Miami to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 July 29, 2025.

It’s optimal to fly from Miami to Chicago Midway Airport at noon. By choosing this option you can save up to 23% on the cost of your flight, compared to a flight in the morning.

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 July 27, 2025.

Travelers seeking maximum savings on their Miami to Chicago Midway Airport flight should consider departing on Wednesday 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 July 29, 2025.
Get a feel of what it's like to fly with Southwest, Delta, 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
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Delta
8.0
Very good
7,977 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Frontier
5.9
Fair
3,238 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 0 outbound flights to Chicago Midway per day. 2 airlines have flights to Chicago Midway from Miami on a regular basis.

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

    Currently priced at $137, Southwest will fly you from Miami to Chicago Midway Airport and back. In addition to Southwest, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Frontier and Delta - these airlines can fly you to your destination from $176 and $217, respectively. You may be able to fly from Miami to Chicago Midway Airport for 36% 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 Southwest, which is currently one of the cheapest options available, starting at $69. Frontier flights start at $71 while deals on Delta start at $109 one-way.

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

    While on average a flight from Miami to Chicago Midway Airport is generally $242, our data shows the cheapest flight currently is $68. When looking at the most popular route, (Miami - Chicago Midway), you can expect to pay $137 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, April is the cheapest month in which you can book a flight from Miami to Chicago Midway Airport (average of $160). Flying from Miami to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$86Average$183FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$177Average$324FlexibilityNo cancel feeOn-time63%

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