$110+ Cheap flights from Virginia Beach, VA 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MDW
Sep 1 — Sep 81
Round-trip
1 adult, Economy
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Find cheap flights from Virginia Beach to Midway with Cheapflights
1. Tell us where you want to go
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Cheapest flights from Virginia Beach to MidwayExplore the most affordable flight options available from Virginia Beach to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 2, 2026.
Explore the most affordable flight options available from Virginia Beach to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:00 am
ORF
- MDW
2 stops17h 44m
Multiple Airlines
Thu 9/246:25 am
MDW
- ORF
1 stop5h 04m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$316
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:45 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Mon 8/246:50 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 7/29![Southwest logo]()
$317
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/41:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Mon 9/76:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Deal found 7/31![Frontier logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/112:57 pm
ORF
- MDW
1 stop9h 56m
Multiple Airlines
Mon 11/27:25 am
MDW
- ORF
2 stops14h 18m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:00 am
ORF
- MDW
2 stops11h 51m
Multiple Airlines
Sat 9/196:25 am
MDW
- ORF
1 stop8h 25m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$322
This Frontier deal was found by Cheapflights users on 7/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/712:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Sun 8/236:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Deal found 7/29![Frontier logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:00 am
ORF
- MDW
2 stops11h 51m
Multiple Airlines
Mon 9/216:46 pm
MDW
- ORF
1 stop16h 43m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1612:10 pm
ORF
- MDW
1 stop22h 41m
Frontier
Thu 8/206:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Deal found 7/30![Frontier logo]()
$330
This Southwest deal was found by Cheapflights users on 8/1. 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 8/298:10 am
ORF
- MDW
Nonstop2h 05m
Southwest
Sun 9/68:40 am
MDW
- ORF
Nonstop2h 15m
Southwest
Deal found 8/1![Southwest logo]()
$331
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:10 am
ORF
- MDW
2 stops8h 30m
Southwest
Sat 10/104:10 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 7/29![Southwest logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/271:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Sun 8/309:26 pm
MDW
- ORF
2 stops17h 45m
Frontier
Deal found 7/30![Frontier logo]()
$335
Best flights from Virginia Beach to MidwayDiscover carefully curated flight deals from Virginia Beach to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 2, 2026.
Discover carefully curated flight deals from Virginia Beach to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 2, 2026.
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:45 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Tue 9/156:25 pm
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 7/28![Southwest logo]()
$322
This KAYAK deal was found by Cheapflights users on 7/28. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1610:05 am
ORF
- MDW
2 stops10h 30m
Southwest
Thu 9/176:50 pm
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 7/28![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 8/1. 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 8/296:25 am
ORF
- MDW
1 stop5h 15m
Southwest
Sun 9/68:40 am
MDW
- ORF
Nonstop2h 15m
Southwest
Deal found 8/1![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:45 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Sun 9/276:55 pm
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 7/28![Southwest logo]()
$345
This Southwest deal was found by Cheapflights users on 8/1. 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 8/298:10 am
ORF
- MDW
Nonstop2h 05m
Southwest
Sat 8/293:15 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 8/1![Southwest logo]()
$345
This Southwest deal was found by Cheapflights users on 7/30. 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.
Mon 9/146:25 am
ORF
- MDW
2 stops7h 00m
Southwest
Wed 9/1612:50 pm
MDW
- ORF
2 stops7h 05m
Southwest
Deal found 7/30![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2510:10 am
ORF
- MDW
1 stop4h 55m
Southwest
Tue 9/296:25 pm
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 7/28![Southwest logo]()
$348
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:45 am
ORF
- MDW
Nonstop2h 10m
Southwest
Fri 10/236:25 pm
MDW
- ORF
1 stop4h 10m
Southwest
Deal found 7/29![Southwest logo]()
$348
This Southwest deal was found by Cheapflights users on 8/1. 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.
Tue 9/16:15 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Fri 9/46:50 pm
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 8/1![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 7/31. 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 10/307:00 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Sun 11/18:00 am
MDW
- ORF
1 stop5h 50m
Southwest
Deal found 7/31![Southwest logo]()
$355
This KAYAK deal was found by Cheapflights users on 7/31. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/211:55 pm
ORF
- MDW
1 stop9h 30m
Southwest
Fri 9/259:00 am
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 7/31![Southwest logo]()
$362
This Southwest deal was found by Cheapflights users on 7/30. 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 9/256:45 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Sun 9/278:50 am
MDW
- ORF
Nonstop2h 15m
Southwest
Deal found 7/30![Southwest logo]()
$366
Last-minute flights from Virginia Beach to MidwayDiscover last-minute flight deals from Virginia Beach to Midway. Data last updated August 2, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia Beach to Midway. Data last updated August 2, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 7/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/712:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Sun 8/236:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Deal found 7/29![Frontier logo]()
$325
This Trip.com deal was found by Cheapflights users on 7/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1512:16 pm
ORF
- MDW
1 stop10h 47m
Frontier
Wed 8/196:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Deal found 7/28![Frontier logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1612:10 pm
ORF
- MDW
1 stop22h 41m
Frontier
Thu 8/206:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Deal found 7/30![Frontier logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:06 pm
ORF
- MDW
2 stops18h 49m
Frontier
Fri 8/216:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Deal found 7/29![Frontier logo]()
$339
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:45 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Mon 8/246:50 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 7/29![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 7/30. 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 8/276:25 am
ORF
- MDW
2 stops7h 00m
Southwest
Thu 8/276:50 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 7/30![Southwest logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/271:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Sun 8/309:26 pm
MDW
- ORF
2 stops17h 45m
Frontier
Deal found 7/30![Frontier logo]()
$335
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:45 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Sat 8/293:15 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 7/29![Southwest logo]()
$338
This Southwest deal was found by Cheapflights users on 8/1. 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 8/298:10 am
ORF
- MDW
Nonstop2h 05m
Southwest
Sat 9/57:45 am
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 8/1![Southwest logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/301:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Sun 9/69:26 pm
MDW
- ORF
2 stops37h 59m
Frontier
Deal found 8/1![Frontier logo]()
$340
One-way flights from Virginia Beach to MidwaySearch for one-way flight options from Virginia Beach to Midway. Find affordable one-way fares based on user searches. Data last updated August 2, 2026.
Search for one-way flight options from Virginia Beach to Midway. Find affordable one-way fares based on user searches. Data last updated August 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/181:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Deal found 7/29![Frontier logo]()
$110
This Trip.com deal was found by Cheapflights users on 7/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/251:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Deal found 7/30![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/261:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Deal found 7/29![Frontier logo]()
$119
This Trip.com deal was found by Cheapflights users on 7/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Deal found 7/29![Frontier logo]()
$122
This Frontier deal was found by Cheapflights users on 7/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/291:18 pm
ORF
- MDW
1 stop5h 28m
Frontier
Deal found 7/29![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/291:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Deal found 7/30![Frontier logo]()
$124
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/271:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Deal found 7/30![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/301:20 pm
ORF
- MDW
1 stop22h 35m
Frontier
Deal found 7/30![Frontier logo]()
$126
This Frontier deal was found by Cheapflights users on 7/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/271:18 pm
ORF
- MDW
1 stop5h 28m
Frontier
Deal found 7/29![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/221:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Deal found 7/29![Frontier logo]()
$128
Find flight deals from Virginia Beach to Midway
Keep the following information in mind while searching for Virginia Beach to Midway flight deals. Data was last updated August 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $312 (Trip.com) |
One-way from | $110 (Kiwi.com) |
Popular in | May |
Cheapest in | September |
Average price | $466 |
Cheapflights Fare Finder
Customize your flight search to find flights from Virginia Beach 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 2, 2026.
Use the filters below to find and compare flights from Virginia Beach to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Fri 9/11
6:45 pm-7:50 pm
Nonstop2h 05m
Chicago Midway
Tue 9/15
6:25 pm-9:35 pm
Nonstop2h 10m
$322
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Wed 9/16
10:05 am-7:35 pm
2 stops10h 30m
Chicago Midway
Thu 9/17
6:50 pm-10:00 pm
Nonstop2h 10m
$332
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Sat 8/29
6:25 am-10:40 am
1 stop5h 15m
Chicago Midway
Sun 9/6
8:40 am-11:55 am
Nonstop2h 15m
$341
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Thu 9/24
6:45 pm-7:50 pm
Nonstop2h 05m
Chicago Midway
Sun 9/27
6:55 pm-10:05 pm
Nonstop2h 10m
$345
Quickest round-trip
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Sat 8/29
8:10 am-9:15 am
Nonstop2h 05m
Chicago Midway
Sat 8/29
3:15 pm-6:15 pm
Nonstop2h 00m
$345
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Mon 9/14
6:25 am-12:25 pm
2 stops7h 00m
Chicago Midway
Wed 9/16
12:50 pm-8:55 pm
2 stops7h 05m
$347
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Fri 9/25
10:10 am-2:05 pm
1 stop4h 55m
Chicago Midway
Tue 9/29
6:25 pm-9:35 pm
Nonstop2h 10m
$348
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Thu 10/22
7:45 am-8:55 am
Nonstop2h 10m
Chicago Midway
Fri 10/23
6:25 pm-11:35 pm
1 stop4h 10m
$348
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Tue 9/1
6:15 pm-7:20 pm
Nonstop2h 05m
Chicago Midway
Fri 9/4
6:50 pm-10:00 pm
Nonstop2h 10m
$352
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Fri 10/30
7:00 pm-8:10 pm
Nonstop2h 10m
Chicago Midway
Sun 11/1
8:00 am-2:50 pm
1 stop5h 50m
$355
Showing 1-10 of 20 resultsSorted by cheapest first
Best time to book a flight from Virginia Beach to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Virginia Beach with our price prediction graph.
ORF-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.
Cheapflights Insights
Everything you need to know about your flight from Virginia Beach to Chicago Midway Airport
V1B-MDW
ORF-MDW
What is the cheapest time of day to fly from V1B to MDW?
Find hourly flight availability from Virginia Beach 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 2, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 13% on flights from Virginia Beach to Chicago Midway Airport by exploring options for tickets in the afternoon.
How much does it cost to fly round-trip from Virginia Beach to Chicago Midway Airport?
Airfare is below average for this route at the moment.
Virginia Beach to Chicago Midway Airport flights typically cost between $466 and $468 in August.The cheapest round-trip price found within the last 5 days was $312 on Frontier (Aug 15-Aug 19).
What is the cheapest day to fly from Virginia Beach to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from Virginia Beach to Midway. Price data was last updated on August 1, 2026.
Travelers seeking maximum savings on their Virginia Beach to Chicago Midway Airport flight should consider departing on Saturday at noon when fares are most often at their lowest. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 2, 2026.
Peruse reviews from past customers who have flown with Southwest and Frontier from Virginia Beach to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Virginia Beach 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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Alternative routes for Virginia Beach to Midway
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Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 2, 2026.
Virginia Beach and Midway flights
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Top 2 airlines flying from Virginia Beach to Midway
Discover the top 2 airlines that operate flights from Virginia Beach 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 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$154 | Average$340 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$397 | FlexibilityNo cancel fee | On-time63% |