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Midway

$229+ Cheap flights from Charlottesville (CHO) to Midway (MDW)

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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — MDW
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheap flight deals from Charlottesville to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Charlottesville (CHO) 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 18, 2025.

Round-trip from

$229
(Delta)

Popular in

June

Cheapest in

February

Average price

$389
From Charlottesville Albemarle to Chicago Midway
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Highest demand for flights based on searches. 14% potential increase in price ($64 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Charlottesville to Midway

Cheapest flights from Charlottesville to Midway
Explore the most affordable flight options available from Charlottesville to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2025.

This Delta deal was found by Cheapflights users on 8/17. 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 9/165:40 amCHO - MDW
1 stop7h 08mDelta
Tue 9/236:00 amMDW - CHO
1 stop4h 24mDelta
Deal found 8/17$229
This Delta deal was found by Cheapflights users on 8/18. 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 10/76:01 pmCHO - MDW
1 stop5h 13mDelta
Sat 10/114:23 pmMDW - CHO
1 stop5h 26mDelta
Deal found 8/18$269
This Delta deal was found by Cheapflights users on 8/16. 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.
Thu 10/166:01 pmCHO - MDW
1 stop5h 13mDelta
Tue 10/216:00 amMDW - CHO
1 stop4h 11mDelta
Deal found 8/16$304
This Delta deal was found by Cheapflights users on 8/16. 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 10/44:08 pmCHO - MDW
1 stop6h 02mDelta
Sat 10/114:23 pmMDW - CHO
1 stop5h 26mDelta
Deal found 8/16$309
This Delta deal was found by Cheapflights users on 8/18. 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.
Thu 10/235:35 amCHO - MDW
1 stop7h 18mDelta
Mon 10/275:04 pmMDW - CHO
1 stop4h 45mDelta
Deal found 8/18$344
This Delta deal was found by Cheapflights users on 8/18. 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 9/274:08 pmCHO - MDW
1 stop6h 02mDelta
Sat 10/44:25 pmMDW - CHO
1 stop6h 10mDelta
Deal found 8/18$439
This Delta deal was found by Cheapflights users on 8/17. 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.
Mon 9/225:42 pmCHO - MDW
1 stop4h 54mDelta
Wed 9/246:00 amMDW - CHO
1 stop6h 48mDelta
Deal found 8/17$467
This Delta deal was found by Cheapflights users on 8/17. 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 9/205:40 amCHO - MDW
1 stop5h 07mDelta
Sun 9/286:00 amMDW - CHO
1 stop4h 24mDelta
Deal found 8/17$479
This Delta deal was found by Cheapflights users on 8/16. 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.
Thu 9/255:42 pmCHO - MDW
1 stop4h 54mDelta
Mon 9/296:00 amMDW - CHO
1 stop4h 24mDelta
Deal found 8/16$514
This Delta deal was found by Cheapflights users on 8/18. 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 9/175:42 pmCHO - MDW
1 stop4h 54mDelta
Mon 9/226:00 amMDW - CHO
1 stop4h 24mDelta
Deal found 8/18$519
This Delta deal was found by Cheapflights users on 8/18. 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 11/216:00 amCHO - MDW
1 stop4h 51mDelta
Sun 11/236:00 amMDW - CHO
1 stop7h 28mDelta
Deal found 8/18$579
This Delta deal was found by Cheapflights users on 8/16. 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 11/256:00 amCHO - MDW
1 stop6h 55mDelta
Mon 12/16:00 amMDW - CHO
1 stop7h 28mDelta
Deal found 8/16$599

Cheapflights Fare Finder

 
Customize your flight search to find flights from Charlottesville 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 18, 2025.
Use the filters below to find and compare flights from Charlottesville to Chicago Midway Airport that are best for you.

Fly from

Charlottesville

Fly to

Midway

Route

Depart

Return

Price

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Tue 9/16

5:40 am-11:48 am

1 stop7h 08m

Chicago Midway

Tue 9/23

6:00 am-11:24 am

1 stop4h 24m

$229

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Tue 9/30

5:40 am-11:48 am

1 stop7h 08m

Chicago Midway

Tue 10/7

10:35 am-5:16 pm

1 stop5h 41m

$229

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Tue 10/7

5:35 am-9:40 am

1 stop5h 05m

Chicago Midway

Sat 10/11

6:00 am-11:11 am

1 stop4h 11m

$269

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 10/16

6:01 pm-10:14 pm

1 stop5h 13m

Chicago Midway

Tue 10/21

6:00 am-11:11 am

1 stop4h 11m

$304

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Fri 10/3

5:42 pm-9:36 pm

1 stop4h 54m

Chicago Midway

Mon 10/6

6:00 am-1:50 pm

1 stop6h 50m

$304

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Sat 10/4

4:08 pm-9:10 pm

1 stop6h 02m

Chicago Midway

Sat 10/11

4:23 pm-10:49 pm

1 stop5h 26m

$309

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Fri 10/24

6:01 pm-10:14 pm

1 stop5h 13m

Chicago Midway

Mon 10/27

5:04 pm-10:49 pm

1 stop4h 45m

$344

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Fri 10/31

4:05 pm-10:14 pm

1 stop7h 09m

$234

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 9/11

5:40 am-11:48 am

1 stop7h 08m

$290

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 10/30

5:35 am-9:45 am

1 stop5h 10m

$340

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 12 results
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Best time to book a flight from Charlottesville to Midway

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

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

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

Related info for your journey

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

    For a flight from Charlottesville to Chicago Midway, you will be flying from Albemarle. Charlottesville Albemarle (CHO) is just 7.6 mi from the center of the city. Albemarle is the only Charlottesville airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from Charlottesville Albemarle on a regular basis.

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

    Departing from Charlottesville to Chicago Midway Airport will take you 7h 08m. Charlottesville and Chicago Midway Airport are separated by a distance of 552 mi.

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

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

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

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

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

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

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

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