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Midway

$234+ 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 3/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — MDW
Mar 29 — Apr 51
Sun 3/29
Sun 4/5
1 adult, Economy
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Cheap 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 February 27, 2026.

This Delta deal was found by Cheapflights users on 2/24. 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 4/175:54 pm
CHO
-
MDW
1 stop5h 34m
Delta
Sat 4/1810:41 am
MDW
-
CHO
1 stop4h 44m
Delta
Deal found 2/24$258
This Delta deal was found by Cheapflights users on 2/25. 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 4/235:54 pm
CHO
-
MDW
1 stop5h 34m
Delta
Sat 4/255:21 pm
MDW
-
CHO
1 stop4h 34m
Delta
Deal found 2/25$304
This Delta deal was found by Cheapflights users on 2/24. 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 9/163:05 pm
CHO
-
MDW
1 stop7h 41m
Delta
Mon 9/216:00 am
MDW
-
CHO
1 stop7h 29m
Delta
Deal found 2/24$314
This Delta deal was found by Cheapflights users on 2/24. 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 3/256:06 pm
CHO
-
MDW
1 stop5h 25m
Delta
Wed 4/16:00 am
MDW
-
CHO
1 stop4h 14m
Delta
Deal found 2/24$338
This Delta deal was found by Cheapflights users on 2/25. 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 5/272:25 pm
CHO
-
MDW
1 stop7h 44m
Delta
Sat 5/305:10 pm
MDW
-
CHO
1 stop5h 34m
Delta
Deal found 2/25$339
This Delta deal was found by Cheapflights users on 2/23. 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 3/316:06 pm
CHO
-
MDW
1 stop5h 25m
Delta
Sat 4/44:30 pm
MDW
-
CHO
1 stop5h 18m
Delta
Deal found 2/23$344
This Delta deal was found by Cheapflights users on 2/26. 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 3/176:06 pm
CHO
-
MDW
1 stop5h 25m
Delta
Tue 3/246:00 am
MDW
-
CHO
1 stop4h 13m
Delta
Deal found 2/26$354
This Delta deal was found by Cheapflights users on 2/23. 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 5/142:25 pm
CHO
-
MDW
1 stop7h 44m
Delta
Mon 5/256:23 am
MDW
-
CHO
1 stop6h 23m
Delta
Deal found 2/23$384
This Delta deal was found by Cheapflights users on 2/26. 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 3/106:06 pm
CHO
-
MDW
1 stop5h 25m
Delta
Tue 3/176:00 am
MDW
-
CHO
1 stop4h 13m
Delta
Deal found 2/26$389
This Delta deal was found by Cheapflights users on 2/24. 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 4/235:54 pm
CHO
-
MDW
1 stop5h 34m
Delta
Sun 4/266:00 am
MDW
-
CHO
1 stop4h 17m
Delta
Deal found 2/24$419

Find 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 February 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$258
(Delta)

One-way from

$234
(Delta)

Popular in

September

Cheapest in

January

Average price

$384
Provider with most accurate pricing for Charlottesville Albemarle-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Charlottesville Albemarle-Chicago Midway flights.
Search Deals
From Charlottesville Albemarle to Chicago Midway
Search Deals
One-way flight from Charlottesville Albemarle to Chicago Midway
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 27, 2026.
Use the filters below to find and compare flights from Charlottesville to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 4/23

5:54 pm-10:28 pm

1 stop5h 34m

Chicago Midway

Sat 4/25

5:21 pm-10:55 pm

1 stop4h 34m

$304

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Wed 3/25

6:06 pm-10:31 pm

1 stop5h 25m

Chicago Midway

Wed 4/1

6:00 am-11:14 am

1 stop4h 14m

$338

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Tue 3/10

6:06 pm-10:31 pm

1 stop5h 25m

Chicago Midway

Tue 3/17

6:00 am-11:13 am

1 stop4h 13m

$389

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Tue 3/24

6:00 am-9:56 am

1 stop4h 56m

Chicago Midway

Wed 3/25

6:00 am-1:46 pm

1 stop6h 46m

$457

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Mon 6/8

5:30 pm-9:45 pm

1 stop5h 15m

Chicago Midway

Tue 6/16

6:00 am-11:16 am

1 stop4h 16m

$479

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Sun 4/12

6:08 pm-10:31 pm

1 stop5h 23m

Chicago Midway

Tue 4/14

6:00 am-11:17 am

1 stop4h 17m

$487

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Fri 6/5

2:25 pm-9:09 pm

1 stop7h 44m

Chicago Midway

Mon 6/8

5:25 pm-10:48 pm

1 stop4h 23m

$559

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Mon 3/9

6:06 pm-10:31 pm

1 stop5h 25m

Chicago Midway

Thu 3/12

6:00 am-11:13 am

1 stop4h 13m

$607

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Mon 3/9

6:06 pm-10:31 pm

1 stop5h 25m

Chicago Midway

Mon 3/16

10:45 am-5:25 pm

1 stop5h 40m

$734

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Wed 6/17

3:05 pm-9:45 pm

1 stop7h 40m

Chicago Midway

Sun 6/21

6:00 am-2:28 pm

1 stop7h 28m

$744

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/26

Showing 1-10 of 22 resultsSorted by cheapest first
1
2
3
  • Most accurate provider: When it comes to deals on Charlottesville-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 Charlottesville-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Charlottesville-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Charlottesville-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 Charlottesville-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 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, March is the cheapest month in which you can book a flight from Charlottesville to Chicago Midway Airport (average of $57). Flying from Charlottesville to Chicago Midway Airport in January is currently the most expensive (average of $139). 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 34m. 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, March is the cheapest month in which you can book a flight from Charlottesville to Chicago Midway Airport (average of $57). Flying from Charlottesville to Chicago Midway Airport in January is currently the most expensive (average of $139). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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