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Midway

$70+ Cheap flights from Charlotte (CLT) 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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
CLT — MDW
Aug 16 — Aug 231
Sat 8/16
Sat 8/23
1 adult, Economy
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Cheapflights Tip: The best prices from Charlotte Douglas to Chicago Midway are usually found in October or February, booked 23 days in advance, depart on a Wednesday or Friday and return on a Tuesday

Cheap flight deals from Charlotte to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Charlotte (CLT) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 11, 2025.

Round-trip from

$139
(Southwest)

One-way from

$70
(Southwest)

Popular in

May

Cheapest in

October

Average price

$307

Good round-trip deal

$211 or less

Good one-way deal

$166 or less
From Charlotte Douglas to Chicago Midway
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One-way flight from Charlotte Douglas to Chicago Midway
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Highest demand for flights based on searches. 9% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Charlotte Douglas to Chicago Midway.
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Price to beat on a one-way flight from Charlotte Douglas to Chicago Midway.
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Find flight deals from Charlotte to Midway

Cheapest flights from Charlotte to Midway
Explore the most affordable flight options available from Charlotte to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 11, 2025.

This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/246:30 amCLT - MDW
Nonstop1h 55mSouthwest
Sat 9/275:35 pmMDW - CLT
Nonstop1h 55mSouthwest
Deal found 8/10$139
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/116:00 amCLT - MDW
Nonstop1h 55mSouthwest
Sat 9/135:35 pmMDW - CLT
Nonstop1h 55mSouthwest
Deal found 8/10$141
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/116:00 amCLT - MDW
Nonstop1h 55mSouthwest
Sun 9/1410:10 amMDW - CLT
Nonstop2h 00mSouthwest
Deal found 8/10$143
This Southwest deal was found by Cheapflights users on 8/8. 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 9/55:05 pmCLT - MDW
Nonstop2h 05mSouthwest
Mon 9/86:45 pmMDW - CLT
Nonstop1h 55mSouthwest
Deal found 8/8$153
This Southwest deal was found by Cheapflights users on 8/9. 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 10/46:30 amCLT - MDW
Nonstop1h 55mSouthwest
Sun 10/510:10 amMDW - CLT
Nonstop1h 50mSouthwest
Deal found 8/9$158
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/174:55 pmCLT - MDW
Nonstop2h 05mSouthwest
Sun 10/198:25 pmMDW - CLT
Nonstop1h 50mSouthwest
Deal found 8/10$160
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/36:35 pmCLT - MDW
Nonstop2h 00mSouthwest
Thu 9/49:35 amMDW - CLT
Nonstop1h 55mSouthwest
Deal found 8/11$163
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/46:00 amCLT - MDW
Nonstop1h 55mSouthwest
Sat 9/65:35 pmMDW - CLT
Nonstop1h 55mSouthwest
Deal found 8/9$166
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/106:35 pmCLT - MDW
Nonstop2h 00mSouthwest
Wed 9/176:05 pmMDW - CLT
Nonstop2h 00mSouthwest
Deal found 8/11$169
This Southwest deal was found by Cheapflights users on 8/8. 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 9/126:00 amCLT - MDW
Nonstop1h 55mSouthwest
Sun 9/1410:10 amMDW - CLT
Nonstop2h 00mSouthwest
Deal found 8/8$171
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2410:50 amCLT - MDW
1 stop5h 30mSouthwest
Mon 9/296:45 pmMDW - CLT
Nonstop1h 55mSouthwest
Deal found 8/9$176

Cheapflights Fare Finder

 
Customize your flight search to find flights from Charlotte 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 August 11, 2025.
Use the filters below to find and compare flights from Charlotte to Chicago Midway Airport that are best for you.

Fly from

Charlotte

Fly to

Midway

Route

Depart

Return

Price

CharlotteChicago

CLT - MDW

CLTMDW

Charlotte Douglas

Wed 9/24

6:30 am-7:25 am

Nonstop1h 55m

Chicago Midway

Sat 9/27

5:35 pm-8:30 pm

Nonstop1h 55m

$139

CharlotteChicago

CLT - MDW

CLTMDW

Charlotte Douglas

Thu 9/11

6:00 am-6:55 am

Nonstop1h 55m

Chicago Midway

Sat 9/13

5:35 pm-8:30 pm

Nonstop1h 55m

$141

CharlotteChicago

CLT - MDW

CLTMDW

Charlotte Douglas

Thu 9/11

6:00 am-6:55 am

Nonstop1h 55m

Chicago Midway

Sun 9/14

10:10 am-1:10 pm

Nonstop2h 00m

$143

CharlotteChicago

CLT - MDW

CLTMDW

Charlotte Douglas

Fri 9/5

5:05 pm-6:10 pm

Nonstop2h 05m

Chicago Midway

Mon 9/8

6:45 pm-9:40 pm

Nonstop1h 55m

$153

CharlotteChicago

CLT - MDW

CLTMDW

Charlotte Douglas

Sat 10/4

6:30 am-7:25 am

Nonstop1h 55m

Chicago Midway

Sun 10/5

10:10 am-1:00 pm

Nonstop1h 50m

$158

CharlotteChicago

CLT - MDW

CLTMDW

Charlotte Douglas

Fri 10/17

4:55 pm-6:00 pm

Nonstop2h 05m

Chicago Midway

Sun 10/19

8:25 pm-11:15 pm

Nonstop1h 50m

$160

CharlotteChicago

CLT - MDW

CLTMDW

Charlotte Douglas

Wed 9/3

6:35 pm-7:35 pm

Nonstop2h 00m

Chicago Midway

Thu 9/4

9:35 am-12:30 pm

Nonstop1h 55m

$163

CharlotteChicago

CLT - MDW

CLTMDW

Charlotte Douglas

Thu 9/4

6:00 am-6:55 am

Nonstop1h 55m

Chicago Midway

Sat 9/6

5:35 pm-8:30 pm

Nonstop1h 55m

$166

CharlotteChicago

CLT - MDW

CLTMDW

Charlotte Douglas

Wed 9/10

6:35 pm-7:35 pm

Nonstop2h 00m

Chicago Midway

Wed 9/17

6:05 pm-9:05 pm

Nonstop2h 00m

$169

CharlotteChicago

CLT - MDW

CLTMDW

Charlotte Douglas

Fri 9/12

6:00 am-6:55 am

Nonstop1h 55m

Chicago Midway

Sun 9/14

10:10 am-1:10 pm

Nonstop2h 00m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 23 results
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The best insider tips for Charlotte 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 Charlotte to Chicago Midway Airport trip
Airports
CLT

Arrive early at CLT as security wait times can peak from 5 pm to 6 pm. Check the airport app for current wait times.

Read more about CLTby Taryn White
MDW

Use the Orange Line train from MDW for a quick, 30-minute ride to downtown Chicago. It's affordable and runs almost 24 hours.

Read more about MDWby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

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
Taryn White

Taryn White

Expert on CLT

Taryn White

Taryn White

Taryn White is a freelance travel writer, digital creator, and travel advisor who has visited nearly 100 countries and all 50 states. She’s familiar with many airports and enjoys beach hopping, boutique hotels, spa experiences, and exploring local culture. Her work has appeared in Travel + Leisure, Condé Nast Traveler, National Geographic, Smithsonian Magazine, AFAR, and more.

Read more

Best time to book a flight from Charlotte to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Charlotte 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 Charlotte to Chicago Midway Airport

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

Use this chart to determine the optimal time to book a round-trip flight from Charlotte to Midway. Price data was last updated on August 8, 2025.

The best time to book flights from Charlotte to Chicago Midway Airport is 23 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 Charlotte to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Charlotte to Chicago Midway Airport (average of $160). Flying from Charlotte 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 CLT to MDW?

Find hourly flight availability from Charlotte to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 11, 2025.

One of the essential ways to save on airfare from Charlotte to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight at noon could potentially save you up to 32% on airfare.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated August 11, 2025.
See what other customers who have flown with Southwest, Delta, and Frontier from Charlotte to Chicago Midway Airport have to say. 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
4,248 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,979 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.8
Fair
3,221 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Related info for your journey

Find useful and relevant information for your journey from Charlotte 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 Charlotte to Chicago Midway?

    If you book a flight to Chicago Midway from Charlotte, you will be flying from Douglas, which is the city’s only airport. Charlotte Douglas (CLT) is located 5.7 mi from the center of Charlotte. There is 1 flight from Douglas to Chicago Midway per day from 3 different airlines.

  • What is the cheapest airline to fly from Charlotte to Chicago Midway Airport round-trip?

    Flying on Southwest is currently your cheapest option to Chicago Midway Airport, with prices starting at $139. Southwest is currently priced 48% below the average price you’ll pay for this route.

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

    On average you can expect to pay $274 for a flight from Charlotte to Chicago Midway Airport. The cheapest flight overall is $71 while the most popular route, (Charlotte Douglas - Chicago Midway) is currently priced at $123.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Charlotte 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 Charlotte to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Charlotte to Chicago Midway Airport (average of $160). Flying from Charlotte 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Charlotte to Midway

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Top 3 airlines flying from Charlotte to Midway

Discover the top 3 airlines that operate flights from Charlotte 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 August 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$77Average$151FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$216FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$158Average$284FlexibilityNo cancel feeOn-time63%

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