$339+ 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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — MDW
Oct 29 — Nov 51
Round-trip
1 adult, Economy
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Find cheap flights from Charlottesville to Midway with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Charlottesville to Midway
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One-way
Cheapest flights from Charlottesville to MidwayExplore 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 September 29, 2026.
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 September 29, 2026.
This Delta deal was found by Cheapflights users on 9/28. 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 11/75:33 pm -
1 stop6h 00m
Wed 11/116:00 am -
1 stop4h 20m
Deal found 9/28![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 9/25. 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.
Sat 11/145:39 pm -
1 stop6h 15m
Sun 11/156:00 am -
1 stop4h 20m
Deal found 9/25![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 9/25. 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.
Tue 10/611:59 am -
1 stop5h 15m
Sat 10/104:19 pm -
1 stop4h 49m
Deal found 9/25![Delta logo]()
$414
This Delta deal was found by Cheapflights users on 9/28. 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 10/235:31 pm -
1 stop6h 02m
Sat 10/246:04 am -
1 stop4h 10m
Deal found 9/28![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 9/28. 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 10/226:00 am -
1 stop5h 03m
Mon 10/2610:59 am -
1 stop4h 46m
Deal found 9/28![Delta logo]()
$421
This Delta deal was found by Cheapflights users on 9/25. 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.
Fri 11/135:39 pm -
1 stop6h 15m
Sun 11/156:00 am -
1 stop4h 20m
Deal found 9/25![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 9/24. 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.
Sat 10/34:20 pm -
1 stop7h 24m
Wed 10/76:04 am -
1 stop4h 10m
Deal found 9/24![Delta logo]()
$494
This Delta deal was found by Cheapflights users on 9/24. 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 9/305:38 pm -
1 stop6h 06m
Mon 10/56:05 am -
1 stop4h 13m
Deal found 9/24![Delta logo]()
$495
This Delta deal was found by Cheapflights users on 9/28. 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 11/57:02 am -
2 stops6h 45m
Sun 11/86:04 am -
1 stop4h 10m
Deal found 9/28![Delta logo]()
$529
Best flights from Charlottesville to MidwayDiscover carefully curated flight deals from Charlottesville to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 29, 2026.
Discover carefully curated flight deals from Charlottesville to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 29, 2026.
This Delta deal was found by Cheapflights users on 9/28. 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 11/75:33 pm -
1 stop6h 00m
Wed 11/116:00 am -
1 stop4h 20m
Deal found 9/28![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 9/27. 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 10/105:33 pm -
1 stop6h 00m
Tue 10/136:04 am -
1 stop4h 10m
Deal found 9/27![Delta logo]()
$414
This Delta deal was found by Cheapflights users on 9/28. 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 11/57:02 am -
2 stops6h 45m
Sun 11/86:04 am -
1 stop4h 10m
Deal found 9/28![Delta logo]()
$529
This Delta deal was found by Cheapflights users on 9/26. 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.
Sat 10/246:00 am -
2 stops7h 47m
Wed 10/2810:59 am -
1 stop4h 46m
Deal found 9/26![Delta logo]()
$529
This Delta deal was found by Cheapflights users on 9/25. 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.
Fri 10/305:31 pm -
1 stop6h 02m
Tue 11/31:27 pm -
2 stops8h 06m
Deal found 9/25![Delta logo]()
$529
This Delta deal was found by Cheapflights users on 9/25. 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 10/2111:59 am -
1 stop5h 15m
Fri 10/235:09 pm -
1 stop5h 35m
Deal found 9/25![Delta logo]()
$577
This Delta deal was found by Cheapflights users on 9/26. 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.
Wed 10/286:00 am -
1 stop5h 03m
Fri 10/306:04 am -
1 stop6h 46m
Deal found 9/26![Delta logo]()
$577
This Delta deal was found by Cheapflights users on 9/24. 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 11/57:02 am -
2 stops10h 45m
Mon 11/95:13 pm -
1 stop5h 30m
Deal found 9/24![Delta logo]()
$604
This Delta deal was found by Cheapflights users on 9/27. 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 10/105:33 pm -
1 stop6h 00m
Fri 10/1612:27 pm -
2 stops9h 02m
Deal found 9/27![Delta logo]()
$639
Last-minute flights from Charlottesville to MidwayDiscover last-minute flight deals from Charlottesville to Midway. Data last updated September 29, 2026 and is based on user searches.
Discover last-minute flight deals from Charlottesville to Midway. Data last updated September 29, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/24. 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 9/305:38 pm -
1 stop6h 06m
Mon 10/56:05 am -
1 stop4h 13m
Deal found 9/24![Delta logo]()
$495
This Delta deal was found by Cheapflights users on 9/24. 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.
Sat 10/34:20 pm -
1 stop7h 24m
Mon 10/56:05 am -
1 stop4h 13m
Deal found 9/24![Delta logo]()
$494
This Delta deal was found by Cheapflights users on 9/27. 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 10/34:20 pm -
1 stop7h 24m
Wed 10/76:04 am -
1 stop4h 10m
Deal found 9/27![Delta logo]()
$574
This Delta deal was found by Cheapflights users on 9/25. 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.
Tue 10/611:59 am -
1 stop5h 15m
Sat 10/104:19 pm -
1 stop4h 49m
Deal found 9/25![Delta logo]()
$414
This Delta deal was found by Cheapflights users on 9/25. 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 10/2111:59 am -
1 stop5h 15m
Fri 10/235:09 pm -
1 stop5h 35m
Deal found 9/25![Delta logo]()
$577
This Delta deal was found by Cheapflights users on 9/28. 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 10/226:00 am -
1 stop5h 03m
Mon 10/2610:59 am -
1 stop4h 46m
Deal found 9/28![Delta logo]()
$421
This Delta deal was found by Cheapflights users on 9/28. 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 10/235:31 pm -
1 stop6h 02m
Sat 10/246:04 am -
1 stop4h 10m
Deal found 9/28![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 9/25. 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 10/285:31 pm -
1 stop6h 02m
Mon 11/24:19 pm -
1 stop4h 41m
Deal found 9/25![Delta logo]()
$339
One-way flights from Charlottesville to MidwaySearch for one-way flight options from Charlottesville to Midway. Find affordable one-way fares based on user searches. Data last updated September 29, 2026.
Search for one-way flight options from Charlottesville to Midway. Find affordable one-way fares based on user searches. Data last updated September 29, 2026.
This Delta deal was found by Cheapflights users on 9/28. 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 10/75:31 pm -
1 stop6h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Delta logo]()
$378
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:00 am -
1 stop5h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Delta logo]()
$403
This Delta deal was found by Cheapflights users on 9/25. 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.
Fri 11/66:00 am -
2 stops7h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Delta logo]()
$525
This Delta deal was found by Cheapflights users on 9/28. 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.
Sun 10/46:00 am -
1 stop4h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Delta logo]()
$570
This Delta deal was found by Cheapflights users on 9/25. 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.
Mon 10/125:31 pm -
1 stop6h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Delta logo]()
$650
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 September 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $339 (Delta) |
Popular in | August |
Cheapest in | January |
Average price | $500 |
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 7,457,451 searches. Data last updated September 29, 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
Cheapest round-trip
CharlottesvilleChicago
CHO Charlottesville Albemarle - MDW Chicago Midway
CHOMDW
Charlottesville Albemarle
Sat 11/7
5:33 pm-10:33 pm
1 stop6h 00m
Chicago Midway
Wed 11/11
6:00 am-11:20 am
1 stop4h 20m
$339
CharlottesvilleChicago
CHO Charlottesville Albemarle - MDW Chicago Midway
CHOMDW
Charlottesville Albemarle
Wed 10/7
5:31 pm-10:33 pm
1 stop6h 02m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$378
Quickest round-trip
CharlottesvilleChicago
CHO Charlottesville Albemarle - MDW Chicago Midway
CHOMDW
Charlottesville Albemarle
Thu 10/8
6:00 am-10:03 am
1 stop5h 03m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$403
CharlottesvilleChicago
CHO Charlottesville Albemarle - MDW Chicago Midway
CHOMDW
Charlottesville Albemarle
Sat 10/10
5:33 pm-10:33 pm
1 stop6h 00m
Chicago Midway
Tue 10/13
6:04 am-11:14 am
1 stop4h 10m
$414
CharlottesvilleChicago
CHO Charlottesville Albemarle - MDW Chicago Midway
CHOMDW
Charlottesville Albemarle
Fri 11/6
6:00 am-12:47 pm
2 stops7h 47m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$525
CharlottesvilleChicago
CHO Charlottesville Albemarle - MDW Chicago Midway
CHOMDW
Charlottesville Albemarle
Thu 11/5
7:02 am-12:47 pm
2 stops6h 45m
Chicago Midway
Sun 11/8
6:04 am-11:14 am
1 stop4h 10m
$529
CharlottesvilleChicago
CHO Charlottesville Albemarle - MDW Chicago Midway
CHOMDW
Charlottesville Albemarle
Sat 10/24
6:00 am-12:47 pm
2 stops7h 47m
Chicago Midway
Wed 10/28
10:59 am-4:45 pm
1 stop4h 46m
$529
CharlottesvilleChicago
CHO Charlottesville Albemarle - MDW Chicago Midway
CHOMDW
Charlottesville Albemarle
Fri 10/30
5:31 pm-10:33 pm
1 stop6h 02m
Chicago Midway
Tue 11/3
1:27 pm-10:33 pm
2 stops8h 06m
$529
CharlottesvilleChicago
CHO Charlottesville Albemarle - MDW Chicago Midway
CHOMDW
Charlottesville Albemarle
Wed 10/21
11:59 am-4:14 pm
1 stop5h 15m
Chicago Midway
Fri 10/23
5:09 pm-11:44 pm
1 stop5h 35m
$577
CharlottesvilleChicago
CHO Charlottesville Albemarle - MDW Chicago Midway
CHOMDW
Charlottesville Albemarle
Wed 10/28
6:00 am-10:03 am
1 stop5h 03m
Chicago Midway
Fri 10/30
6:04 am-1:50 pm
1 stop6h 46m
$577
Showing 1-10 of 12 resultsSorted by cheapest first
- 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.
CHO-MDW
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.
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.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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