$104+ 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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MDW
Jul 12 — Jul 191
Round-trip
1 adult, Economy
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Find cheap flights from Virginia Beach to Midway with Cheapflights
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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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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 June 12, 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 June 12, 2026.
This Southwest deal was found by Cheapflights users on 6/9. 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 7/17:00 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Sat 7/48:00 am
MDW
- ORF
Nonstop2h 15m
Southwest
Deal found 6/9![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 6/12. 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 8/125:23 am
ORF
- MDW
1 stop5h 36m
Delta
Sat 8/156:42 pm
MDW
- ORF
1 stop4h 00m
Delta
Deal found 6/12![Delta logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 7/2812:10 pm
ORF
- MDW
1 stop10h 53m
Multiple Airlines
Mon 8/36:05 am
MDW
- ORF
2 stops34h 27m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 6/8. 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 8/1312:38 pm
ORF
- MDW
1 stop6h 55m
Delta
Sun 8/166:42 pm
MDW
- ORF
1 stop4h 00m
Delta
Deal found 6/8![Delta logo]()
$341
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 7/2012:10 pm
ORF
- MDW
1 stop10h 53m
Multiple Airlines
Fri 7/243:28 pm
MDW
- ORF
2 stops28h 11m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/812:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Thu 7/912:11 pm
MDW
- ORF
1 stop22h 04m
Frontier
Deal found 6/8![Frontier logo]()
$344
This Southwest deal was found by Cheapflights users on 6/12. 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 12/96:15 am
ORF
- MDW
2 stops9h 10m
Southwest
Fri 12/112:40 pm
MDW
- ORF
1 stop6h 15m
Southwest
Deal found 6/12![Southwest logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 8/229:56 pm
ORF
- MDW
2 stops17h 11m
Frontier
Tue 8/2512:27 pm
MDW
- ORF
1 stop21h 59m
Frontier
Deal found 6/9![Frontier logo]()
$346
This Southwest deal was found by Cheapflights users on 6/10. 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
Sun 9/136:55 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 6/10![Southwest logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 6/12. 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.
Fri 7/312:21 pm
ORF
- MDW
1 stop10h 50m
Frontier
Mon 7/66:05 am
MDW
- ORF
1 stop28h 10m
Frontier
Deal found 6/12![Frontier logo]()
$349
This Southwest deal was found by Cheapflights users on 6/10. 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 7/217:50 am
ORF
- MDW
Nonstop2h 00m
Southwest
Thu 7/237:00 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 6/10![Southwest logo]()
$350
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 June 12, 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 June 12, 2026.
This Southwest deal was found by Cheapflights users on 6/9. 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 9/1010:15 am
ORF
- MDW
2 stops6h 15m
Southwest
Sun 9/135:00 am
MDW
- ORF
1 stop6h 35m
Southwest
Deal found 6/9![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 6/12. 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.
Sun 8/22:45 pm
ORF
- MDW
2 stops8h 00m
Southwest
Sat 8/156:35 am
MDW
- ORF
1 stop6h 35m
Southwest
Deal found 6/12![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 6/10. 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 9/113:45 pm
ORF
- MDW
2 stops7h 35m
Southwest
Sun 9/136:55 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 6/10![Southwest logo]()
$362
This Southwest deal was found by Cheapflights users on 6/12. 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 7/177:15 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Sat 7/186:30 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 6/12![Southwest logo]()
$363
This Southwest deal was found by Cheapflights users on 6/9. 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 7/410:00 am
ORF
- MDW
2 stops5h 35m
Southwest
Tue 7/77:50 am
MDW
- ORF
2 stops5h 35m
Southwest
Deal found 6/9![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 6/12. 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 9/176:25 am
ORF
- MDW
2 stops8h 20m
Southwest
Sun 9/208:10 am
MDW
- ORF
2 stops6h 50m
Southwest
Deal found 6/12![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 6/11. 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 8/143:45 pm
ORF
- MDW
2 stops7h 35m
Southwest
Sat 8/159:55 am
MDW
- ORF
2 stops10h 00m
Southwest
Deal found 6/11![Southwest logo]()
$377
This Southwest deal was found by Cheapflights users on 6/12. 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 7/137:15 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Mon 7/202:45 pm
MDW
- ORF
2 stops7h 55m
Southwest
Deal found 6/12![Southwest logo]()
$378
This Southwest deal was found by Cheapflights users on 6/12. 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 7/184:40 pm
ORF
- MDW
1 stop7h 35m
Southwest
Mon 7/201:40 pm
MDW
- ORF
1 stop8h 50m
Southwest
Deal found 6/12![Southwest logo]()
$383
This Southwest deal was found by Cheapflights users on 6/12. 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.
Sun 7/198:05 pm
ORF
- MDW
1 stop5h 20m
Southwest
Sat 7/259:15 am
MDW
- ORF
1 stop5h 00m
Southwest
Deal found 6/12![Southwest logo]()
$383
This Southwest deal was found by Cheapflights users on 6/9. 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 7/106:00 pm
ORF
- MDW
2 stops7h 10m
Southwest
Fri 7/172:40 pm
MDW
- ORF
2 stops8h 00m
Southwest
Deal found 6/9![Southwest logo]()
$393
Last-minute flights from Virginia Beach to MidwayDiscover last-minute flight deals from Virginia Beach to Midway. Data last updated June 12, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia Beach to Midway. Data last updated June 12, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/9. 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 7/17:00 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Sat 7/48:00 am
MDW
- ORF
Nonstop2h 15m
Southwest
Deal found 6/9![Southwest logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 6/12. 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.
Fri 7/312:21 pm
ORF
- MDW
1 stop10h 50m
Frontier
Mon 7/66:05 am
MDW
- ORF
1 stop28h 10m
Frontier
Deal found 6/12![Frontier logo]()
$349
This Delta deal was found by Cheapflights users on 6/8. 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 7/412:55 pm
ORF
- MDW
1 stop5h 12m
Delta
Wed 7/812:41 pm
MDW
- ORF
1 stop5h 12m
Delta
Deal found 6/8![Delta logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/812:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Thu 7/912:11 pm
MDW
- ORF
1 stop22h 04m
Frontier
Deal found 6/8![Frontier logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/1212:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Wed 7/1512:11 pm
MDW
- ORF
1 stop22h 04m
Frontier
Deal found 6/8![Frontier logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 7/2012:10 pm
ORF
- MDW
1 stop10h 53m
Multiple Airlines
Fri 7/243:28 pm
MDW
- ORF
2 stops28h 11m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 6/10. 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 7/217:50 am
ORF
- MDW
Nonstop2h 00m
Southwest
Thu 7/237:00 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 6/10![Southwest logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 7/2112:10 pm
ORF
- MDW
1 stop10h 53m
Multiple Airlines
Thu 7/2312:11 pm
MDW
- ORF
2 stops10h 42m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 7/2812:10 pm
ORF
- MDW
1 stop10h 53m
Multiple Airlines
Mon 8/36:05 am
MDW
- ORF
2 stops34h 27m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 6/11. 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 7/2912:25 pm
ORF
- MDW
1 stop6h 30m
Southwest
Sun 8/27:00 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 6/11![Southwest logo]()
$360
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 June 12, 2026.
Search for one-way flight options from Virginia Beach to Midway. Find affordable one-way fares based on user searches. Data last updated June 12, 2026.
This Trip.com deal was found by Cheapflights users on 6/12. 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 9/812:21 pm
ORF
- MDW
1 stop10h 50m
Frontier
Deal found 6/12![Frontier logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 8/412:10 pm
ORF
- MDW
1 stop22h 41m
Frontier
Deal found 6/10![Frontier logo]()
$111
This Southwest deal was found by Cheapflights users on 6/8. 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 8/56:15 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 6/8![Southwest logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 8/512:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Deal found 6/9![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 8/1012:10 pm
ORF
- MDW
1 stop22h 41m
Frontier
Deal found 6/12![Frontier logo]()
$122
This Trip.com deal was found by Cheapflights users on 6/8. 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 9/512:00 pm
ORF
- MDW
1 stop11h 11m
Frontier
Deal found 6/8![Frontier logo]()
$124
This Delta deal was found by Cheapflights users on 6/8. 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 12/86:05 pm
ORF
- MDW
1 stop5h 05m
Delta
Deal found 6/8![Delta logo]()
$125
This Frontier deal was found by Cheapflights users on 6/9. 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.
Wed 8/1912:21 pm
ORF
- MDW
1 stop10h 50m
Frontier
Deal found 6/9![Frontier logo]()
$126
This Frontier deal was found by Cheapflights users on 6/10. 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.
Sat 8/812:16 pm
ORF
- MDW
1 stop10h 47m
Frontier
Deal found 6/10![Frontier logo]()
$127
This Frontier deal was found by Cheapflights users on 6/10. 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.
Sat 7/2512:16 pm
ORF
- MDW
1 stop10h 47m
Frontier
Deal found 6/10![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 June 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $337 (Southwest) |
One-way from | $104 (Trip.com) |
Popular in | May |
Cheapest in | September |
Average price | $375 |
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 June 12, 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
Thu 9/10
10:15 am-3:30 pm
2 stops6h 15m
Chicago Midway
Sun 9/13
5:00 am-12:35 pm
1 stop6h 35m
$347
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Sun 8/2
2:45 pm-9:45 pm
2 stops8h 00m
Chicago Midway
Sat 8/15
6:35 am-2:10 pm
1 stop6h 35m
$359
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Fri 9/11
3:45 pm-10:20 pm
2 stops7h 35m
Chicago Midway
Sun 9/13
6:55 pm-10:00 pm
Nonstop2h 05m
$362
Quickest round-trip
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Fri 7/17
7:15 pm-8:20 pm
Nonstop2h 05m
Chicago Midway
Sat 7/18
6:30 pm-9:35 pm
Nonstop2h 05m
$363
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Sat 7/4
10:00 am-2:35 pm
2 stops5h 35m
Chicago Midway
Tue 7/7
7:50 am-2:25 pm
2 stops5h 35m
$367
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Thu 9/17
6:25 am-1:45 pm
2 stops8h 20m
Chicago Midway
Sun 9/20
8:10 am-4:00 pm
2 stops6h 50m
$373
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Fri 8/14
3:45 pm-10:20 pm
2 stops7h 35m
Chicago Midway
Sat 8/15
9:55 am-8:55 pm
2 stops10h 00m
$377
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Mon 7/13
7:15 pm-8:20 pm
Nonstop2h 05m
Chicago Midway
Mon 7/20
2:45 pm-11:40 pm
2 stops7h 55m
$378
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Sat 7/18
4:40 pm-11:15 pm
1 stop7h 35m
Chicago Midway
Mon 7/20
1:40 pm-11:30 pm
1 stop8h 50m
$383
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Sun 7/19
8:05 pm-12:25 am
1 stop5h 20m
Chicago Midway
Sat 7/25
9:15 am-3:15 pm
1 stop5h 00m
$383
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 June 12, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 16% on flights from Virginia Beach to Chicago Midway Airport by exploring options for tickets at noon.
How much does it cost to fly round-trip from Virginia Beach to Chicago Midway Airport?
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 June 8, 2026.
Travelers seeking maximum savings on their Virginia Beach to Chicago Midway Airport flight should consider departing on Sunday afternoons 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 June 12, 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.
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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
Hammond
Porter
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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 June 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$154 | Average$340 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$380 | FlexibilityNo cancel fee | On-time63% |