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$110+ Cheap flights from Charlottesville (CHO) 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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — MDW
oct. 17 — oct. 241
vie. 10/17
vie. 10/24
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 septiembre 17, 2025.

Round-trip from

$219
(Delta)

One-way from

$110
(Delta)

Popular in

June

Cheapest in

February

Average price

$488
From Charlottesville Albemarle to Chicago Midway
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One-way flight from Charlottesville Albemarle to Chicago Midway
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Highest demand for flights based on searches. 12% potential increase in price ($56 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 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 septiembre 17, 2025.

This Delta deal was found by Cheapflights users on 9/17. 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.
jue. 10/165:35 amCHO - MDW
1 stop5h 05mDelta
mar. 10/215:04 pmMDW - CHO
1 stop4h 45mDelta
Deal found 9/17$219
This Delta deal was found by Cheapflights users on 9/15. 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.
mié. 10/226:01 pmCHO - MDW
1 stop5h 13mDelta
lun. 10/2710:35 amMDW - CHO
1 stop5h 41mDelta
Deal found 9/15$239
This Delta deal was found by Cheapflights users on 9/15. 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.
mar. 9/305:42 pmCHO - MDW
1 stop4h 54mDelta
sáb. 10/44:25 pmMDW - CHO
1 stop6h 10mDelta
Deal found 9/15$249
This Delta deal was found by Cheapflights users on 9/16. 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.
mar. 9/235:40 amCHO - MDW
1 stop7h 08mDelta
mar. 9/306:00 amMDW - CHO
1 stop6h 48mDelta
Deal found 9/16$299
This Delta deal was found by Cheapflights users on 9/16. 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.
jue. 10/235:35 amCHO - MDW
1 stop5h 05mDelta
lun. 10/2710:35 amMDW - CHO
1 stop5h 41mDelta
Deal found 9/16$304
This Delta deal was found by Cheapflights users on 9/15. 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.
sáb. 10/411:55 amCHO - MDW
1 stop4h 31mDelta
sáb. 10/114:23 pmMDW - CHO
1 stop5h 26mDelta
Deal found 9/15$309
This Delta deal was found by Cheapflights users on 9/15. 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.
sáb. 11/111:51 amCHO - MDW
1 stop4h 35mDelta
lun. 11/36:00 amMDW - CHO
1 stop4h 11mDelta
Deal found 9/15$369
This Delta deal was found by Cheapflights users on 9/15. 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.
mar. 10/75:35 amCHO - MDW
1 stop5h 05mDelta
mié. 10/86:00 amMDW - CHO
1 stop4h 11mDelta
Deal found 9/15$383
This Delta deal was found by Cheapflights users on 9/16. 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.
jue. 10/235:35 amCHO - MDW
1 stop5h 05mDelta
dom. 10/266:00 amMDW - CHO
1 stop6h 50mDelta
Deal found 9/16$414
This Delta deal was found by Cheapflights users on 9/15. 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.
vie. 10/245:35 amCHO - MDW
1 stop5h 05mDelta
lun. 10/2710:35 amMDW - CHO
1 stop5h 41mDelta
Deal found 9/15$424

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 septiembre 17, 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

jue. 10/16

5:35 am-9:40 am

1 stop5h 05m

Chicago Midway

mar. 10/21

5:04 pm-10:49 pm

1 stop4h 45m

$219

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

mié. 10/22

6:01 pm-10:14 pm

1 stop5h 13m

Chicago Midway

lun. 10/27

10:35 am-5:16 pm

1 stop5h 41m

$239

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

jue. 10/23

5:35 am-9:40 am

1 stop5h 05m

Chicago Midway

lun. 10/27

10:35 am-5:16 pm

1 stop5h 41m

$239

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

mié. 10/1

5:42 pm-9:36 pm

1 stop4h 54m

Chicago Midway

sáb. 10/4

4:25 pm-11:35 pm

1 stop6h 10m

$249

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

sáb. 10/4

4:08 pm-9:10 pm

1 stop6h 02m

Chicago Midway

sáb. 10/11

4:23 pm-10:49 pm

1 stop5h 26m

$299

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

jue. 10/23

5:35 am-9:40 am

1 stop5h 05m

Chicago Midway

dom. 10/26

6:00 am-11:11 am

1 stop4h 11m

$329

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

vie. 10/24

6:01 pm-10:14 pm

1 stop5h 13m

Chicago Midway

lun. 10/27

10:35 am-5:16 pm

1 stop5h 41m

$369

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

sáb. 11/1

5:35 am-9:45 am

1 stop5h 10m

Chicago Midway

lun. 11/3

6:00 am-11:11 am

1 stop4h 11m

$369

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

mié. 11/12

11:16 am-4:39 pm

1 stop6h 23m

$110

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

mié. 10/1

5:42 pm-9:36 pm

1 stop4h 54m

$120

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 16 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 5h 05m. 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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