$70+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MDW
Jun 3 — Jun 101
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
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 May 4, 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 May 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 7/299:35 pm
ORF
- MDW
2 stops25h 33m
Frontier
Tue 8/1112:11 pm
MDW
- ORF
1 stop22h 10m
Frontier
Deal found 4/29![Frontier logo]()
$312
This Southwest deal was found by Cheapflights users on 5/4. 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 6/36:25 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Tue 6/97:55 am
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 5/4![Southwest logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 6/1712:21 pm
ORF
- MDW
1 stop10h 50m
Frontier
Sun 6/216:00 am
MDW
- ORF
1 stop28h 26m
Frontier
Deal found 5/3![Frontier logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Wed 8/1212:21 pm
ORF
- MDW
1 stop23h 46m
Frontier
Sun 8/1612:11 pm
MDW
- ORF
1 stop22h 10m
Frontier
Deal found 5/1![Frontier logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 6/1712:21 pm
ORF
- MDW
1 stop23h 51m
Frontier
Sat 6/206:00 am
MDW
- ORF
2 stops11h 40m
Frontier
Deal found 5/2![Frontier logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Thu 7/3012:21 pm
ORF
- MDW
1 stop10h 47m
Frontier
Sun 8/212:11 pm
MDW
- ORF
1 stop22h 10m
Frontier
Deal found 4/29![Frontier logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Thu 6/1112:21 pm
ORF
- MDW
1 stop10h 50m
Frontier
Sun 6/146:00 am
MDW
- ORF
1 stop28h 26m
Frontier
Deal found 5/1![Frontier logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 6/1112:21 pm
ORF
- MDW
1 stop10h 50m
Frontier
Mon 6/156:00 am
MDW
- ORF
2 stops13h 40m
Frontier
Deal found 4/30![Frontier logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 6/412:06 pm
ORF
- MDW
1 stop10h 56m
Frontier
Mon 6/812:04 pm
MDW
- ORF
2 stops31h 36m
Frontier
Deal found 5/3![Frontier logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 7/289:35 pm
ORF
- MDW
2 stops14h 32m
Frontier
Tue 8/1112:11 pm
MDW
- ORF
1 stop22h 10m
Frontier
Deal found 4/29![Frontier logo]()
$334
This Southwest deal was found by Cheapflights users on 4/29. 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.
Tue 6/26:25 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Sat 6/66:30 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 4/29![Southwest logo]()
$336
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:20 am
ORF
- MDW
1 stop4h 40m
Delta
Tue 6/210:59 am
MDW
- ORF
1 stop5h 22m
Delta
Deal found 4/30![Delta logo]()
$337
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 May 4, 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 May 4, 2026.
This Southwest deal was found by Cheapflights users on 5/3. 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 6/1011:40 am
ORF
- MDW
Nonstop2h 05m
Southwest
Fri 6/127:40 am
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 5/3![Southwest logo]()
$340
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:17 pm
ORF
- MDW
1 stop4h 58m
Delta
Sun 8/96:05 am
MDW
- ORF
1 stop4h 23m
Delta
Deal found 4/30![Delta logo]()
$383
This Southwest deal was found by Cheapflights users on 5/3. 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 6/1711:40 am
ORF
- MDW
Nonstop2h 05m
Southwest
Sun 6/217:45 am
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 5/3![Southwest logo]()
$340
This Delta deal was found by Cheapflights users on 4/29. 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.
Sat 7/410:58 am
ORF
- MDW
1 stop5h 42m
Delta
Wed 7/811:05 am
MDW
- ORF
1 stop6h 48m
Delta
Deal found 4/29![Delta logo]()
$383
This Southwest deal was found by Cheapflights users on 5/2. 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 7/317:05 am
ORF
- MDW
Nonstop2h 05m
Southwest
Sun 8/27:00 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 5/2![Southwest logo]()
$363
This Southwest deal was found by Cheapflights users on 5/3. 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 6/56:00 am
ORF
- MDW
1 stop5h 35m
Southwest
Sun 6/77:00 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 5/3![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 4/30. 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 7/96:10 pm
ORF
- MDW
1 stop4h 50m
Southwest
Mon 7/137:40 am
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 4/30![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 4/29. 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 7/306:30 am
ORF
- MDW
1 stop5h 25m
Southwest
Sun 8/27:00 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 4/29![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 5/1. 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.
Thu 6/187:15 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Mon 6/227:00 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 5/1![Southwest logo]()
$381
This Southwest deal was found by Cheapflights users on 4/29. 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 8/1212:15 pm
ORF
- MDW
2 stops7h 50m
Southwest
Sun 8/166:05 am
MDW
- ORF
2 stops8h 55m
Southwest
Deal found 4/29![Southwest logo]()
$387
Last-minute flights from Virginia Beach to MidwayDiscover last-minute flight deals from Virginia Beach to Midway. Data last updated May 4, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia Beach to Midway. Data last updated May 4, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 5/2112:06 pm
ORF
- MDW
1 stop10h 56m
Frontier
Sat 5/2311:59 am
MDW
- ORF
1 stop22h 12m
Frontier
Deal found 4/30![Frontier logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 5/2112:06 pm
ORF
- MDW
1 stop10h 56m
Multiple Airlines
Sat 5/236:00 am
MDW
- ORF
2 stops11h 49m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:20 am
ORF
- MDW
1 stop4h 40m
Delta
Tue 6/210:59 am
MDW
- ORF
1 stop5h 22m
Delta
Deal found 4/30![Delta logo]()
$337
This Southwest deal was found by Cheapflights users on 5/4. 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 5/276:25 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Fri 5/297:00 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 5/4![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 4/29. 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.
Tue 6/26:25 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Sat 6/66:30 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 4/29![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 5/4. 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 6/36:25 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Tue 6/97:55 am
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 5/4![Southwest logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 6/412:06 pm
ORF
- MDW
1 stop10h 56m
Frontier
Mon 6/812:04 pm
MDW
- ORF
2 stops31h 36m
Frontier
Deal found 5/3![Frontier logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Thu 6/1112:21 pm
ORF
- MDW
1 stop10h 50m
Frontier
Sun 6/146:00 am
MDW
- ORF
1 stop28h 26m
Frontier
Deal found 5/1![Frontier logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 6/1112:21 pm
ORF
- MDW
1 stop10h 50m
Frontier
Mon 6/156:00 am
MDW
- ORF
2 stops13h 40m
Frontier
Deal found 4/30![Frontier logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 6/1712:21 pm
ORF
- MDW
1 stop10h 50m
Frontier
Sun 6/216:00 am
MDW
- ORF
1 stop28h 26m
Frontier
Deal found 5/3![Frontier logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 6/1712:21 pm
ORF
- MDW
1 stop23h 51m
Frontier
Sat 6/206:00 am
MDW
- ORF
2 stops11h 40m
Frontier
Deal found 5/2![Frontier logo]()
$323
This Southwest deal was found by Cheapflights users on 4/29. 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 6/1711:40 am
ORF
- MDW
Nonstop2h 05m
Southwest
Thu 6/187:00 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 4/29![Southwest 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 May 4, 2026.
Search for one-way flight options from Virginia Beach to Midway. Find affordable one-way fares based on user searches. Data last updated May 4, 2026.
This Trip.com deal was found by Cheapflights users on 5/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:06 pm
ORF
- MDW
1 stop10h 56m
Frontier
Deal found 5/1![Frontier logo]()
$70
This Trip.com deal was found by Cheapflights users on 4/30. 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.
Sat 6/612:00 pm
ORF
- MDW
1 stop11h 02m
Frontier
Deal found 4/30![Frontier logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 5/3012:00 pm
ORF
- MDW
1 stop11h 02m
Frontier
Deal found 5/2![Frontier logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 5/2612:06 pm
ORF
- MDW
1 stop24h 03m
Frontier
Deal found 4/29![Frontier logo]()
$88
This Trip.com deal was found by Cheapflights users on 5/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2312:00 pm
ORF
- MDW
1 stop11h 02m
Frontier
Deal found 5/1![Frontier logo]()
$93
This Frontier deal was found by Cheapflights users on 4/29. 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.
Thu 5/2812:06 pm
ORF
- MDW
1 stop10h 56m
Frontier
Deal found 4/29![Frontier logo]()
$96
This Frontier deal was found by Cheapflights users on 4/29. 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.
Wed 8/1912:21 pm
ORF
- MDW
1 stop10h 50m
Frontier
Deal found 4/29![Frontier logo]()
$101
This Trip.com deal was found by Cheapflights users on 5/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/212:06 pm
ORF
- MDW
1 stop10h 56m
Frontier
Deal found 5/1![Frontier logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 5/3112:06 pm
ORF
- MDW
1 stop24h 03m
Frontier
Deal found 5/3![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Mon 6/2912:21 pm
ORF
- MDW
1 stop23h 51m
Frontier
Deal found 5/1![Frontier logo]()
$110
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 May 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $312 (Kiwi.com) |
One-way from | $70 (Trip.com) |
Popular in | May |
Cheapest in | September |
Average price | $429 |
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 May 4, 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
Wed 6/10
11:40 am-12:45 pm
Nonstop2h 05m
Chicago Midway
Fri 6/12
7:40 am-10:45 am
Nonstop2h 05m
$340
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Wed 6/17
11:40 am-12:45 pm
Nonstop2h 05m
Chicago Midway
Sun 6/21
7:45 am-10:55 am
Nonstop2h 10m
$340
Quickest round-trip
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Fri 7/31
7:05 am-8:10 am
Nonstop2h 05m
Chicago Midway
Sun 8/2
7:00 pm-10:00 pm
Nonstop2h 00m
$363
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Fri 6/5
6:00 am-10:35 am
1 stop5h 35m
Chicago Midway
Sun 6/7
7:00 pm-10:00 pm
Nonstop2h 00m
$373
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Thu 7/9
6:10 pm-10:00 pm
1 stop4h 50m
Chicago Midway
Mon 7/13
7:40 am-10:45 am
Nonstop2h 05m
$373
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Thu 7/30
6:30 am-10:55 am
1 stop5h 25m
Chicago Midway
Sun 8/2
7:00 pm-10:00 pm
Nonstop2h 00m
$373
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Thu 6/18
7:15 pm-8:20 pm
Nonstop2h 05m
Chicago Midway
Mon 6/22
7:00 pm-10:00 pm
Nonstop2h 00m
$381
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Fri 8/7
6:17 pm-10:15 pm
1 stop4h 58m
Chicago Midway
Sun 8/9
6:05 am-11:28 am
1 stop4h 23m
$383
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Sat 7/4
10:58 am-3:40 pm
1 stop5h 42m
Chicago Midway
Wed 7/8
11:05 am-6:53 pm
1 stop6h 48m
$383
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Wed 8/12
12:15 pm-7:05 pm
2 stops7h 50m
Chicago Midway
Sun 8/16
6:05 am-4:00 pm
2 stops8h 55m
$387
Showing 1-10 of 19 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 May 4, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 18% on flights from Virginia Beach to Chicago Midway Airport by exploring options for tickets at noon.
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 May 2, 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.
How much does it cost to fly round-trip from Virginia Beach to Chicago Midway Airport?
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 May 4, 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
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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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Alternative routes for Virginia Beach to Midway
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Complete your trip
Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Virginia Beach to Midway by cabin class
Find flights from Virginia Beach to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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 May 4, 2026.
Virginia Beach and Midway flights
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Popular flight searches
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Virginia Beach to Midway flights
Consider these flights traveling from Virginia Beach to Midway.
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 May 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$154 | Average$340 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$372 | FlexibilityNo cancel fee | On-time63% |