$99+ Cheap flights from Chicago (CHI) to Chesapeake, VA
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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Jul 8 — Jul 151
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Chesapeake 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to Chesapeake are usually found in December or September, booked 61 days in advance, depart on a Saturday or Wednesday and return on a Thursday
Cheap flight deals from Chicago to Chesapeake
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to ChesapeakeExplore the most affordable flight options available from Chicago to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 8, 2026.
Explore the most affordable flight options available from Chicago to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 8, 2026.
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.
Fri 9/410:54 am
MDW
- ORF
1 stop5h 14m
Delta
Thu 9/101:00 pm
ORF
- MDW
1 stop6h 31m
Delta
Deal found 6/8![Delta logo]()
$341
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 7/267:05 am
ORD
- ORF
1 stop27h 10m
Frontier
Fri 7/3112:10 pm
ORF
- ORD
2 stops37h 39m
Frontier
Deal found 6/8![Frontier logo]()
$341
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 8/119:57 pm
ORD
- ORF
2 stops21h 58m
Multiple Airlines
Sat 8/1512:16 pm
ORF
- ORD
1 stop8h 37m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 7/112:04 pm
MDW
- ORF
1 stop22h 22m
Frontier
Tue 7/712:10 pm
ORF
- MDW
2 stops28h 40m
Frontier
Deal found 6/5![Frontier logo]()
$345
This CheapOair deal was found by Cheapflights users on 6/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/149:40 am
ORD
- ORF
2 stops30h 30m
Multiple Airlines
Sat 7/1812:16 pm
ORF
- ORD
1 stop8h 37m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$345
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.
Sat 7/251:50 pm
ORD
- ORF
1 stop20h 25m
Frontier
Fri 7/3112:10 pm
ORF
- ORD
1 stop20h 43m
Frontier
Deal found 6/8![Frontier logo]()
$346
This Southwest deal was found by Cheapflights users on 6/7. 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 6/278:00 am
MDW
- ORF
Nonstop2h 15m
Southwest
Sat 7/410:00 am
ORF
- MDW
2 stops5h 35m
Southwest
Deal found 6/7![Southwest logo]()
$347
This American Airlines deal was found by Cheapflights users on 6/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/297:14 pm
ORD
- ORF
Nonstop2h 25m
American Airlines
Thu 8/66:17 pm
ORF
- ORD
Nonstop2h 42m
American Airlines
Deal found 6/4![American Airlines logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 7/246:05 am
MDW
- ORF
2 stops13h 34m
Frontier
Tue 7/2812:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Deal found 6/5![Frontier logo]()
$348
This CheapOair deal was found by Cheapflights users on 6/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:00 am
ORD
- ORF
2 stops10h 10m
Multiple Airlines
Mon 7/612:10 pm
ORF
- ORD
1 stop8h 43m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 6/306:00 am
MDW
- ORF
1 stop28h 26m
Frontier
Tue 7/712:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Deal found 6/5![Frontier logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 6/241:29 pm
ORD
- ORF
1 stop20h 57m
Frontier
Sun 6/2812:21 pm
ORF
- ORD
1 stop20h 42m
Frontier
Deal found 6/5![Frontier logo]()
$349
Best flights from Chicago to ChesapeakeDiscover carefully curated flight deals from Chicago to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 8, 2026.
Discover carefully curated flight deals from Chicago to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 8, 2026.
This Southwest deal was found by Cheapflights users on 6/7. 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 8/289:00 am
MDW
- ORF
Nonstop2h 10m
Southwest
Sun 8/308:20 am
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 6/7![Southwest logo]()
$347
This United Airlines deal was found by Cheapflights users on 6/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/243:53 pm
ORD
- ORF
1 stop6h 51m
United Airlines
Tue 7/2810:48 am
ORF
- ORD
Nonstop2h 39m
United Airlines
Deal found 6/5![United Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 6/7. 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 9/2410:48 am
MDW
- ORF
1 stop4h 09m
Delta
Mon 9/286:05 am
ORF
- MDW
1 stop4h 02m
Delta
Deal found 6/7![Delta logo]()
$383
This KAYAK deal was found by Cheapflights users on 6/5. 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.
Sun 7/55:00 am
ORD
- ORF
1 stop5h 57m
American Airlines
Thu 7/96:40 am
ORF
- ORD
Nonstop2h 40m
American Airlines
Deal found 6/5![American Airlines logo]()
$415
This JetBlue deal was found by Cheapflights users on 6/6. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/110:56 am
ORD
- ORF
1 stop5h 09m
JetBlue
Wed 9/26:00 am
ORF
- ORD
1 stop8h 39m
JetBlue
Deal found 6/6![JetBlue logo]()
$418
This Southwest deal was found by Cheapflights users on 6/3. 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 10/286:00 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Sat 11/73:10 pm
ORF
- MDW
Nonstop2h 15m
Southwest
Deal found 6/3![Southwest logo]()
$347
This United Airlines deal was found by Cheapflights users on 6/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:00 am
ORD
- ORF
Nonstop2h 30m
United Airlines
Sun 9/206:05 am
ORF
- ORD
Nonstop2h 29m
United Airlines
Deal found 6/7![United Airlines logo]()
$363
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 8/16:00 am
MDW
- ORF
1 stop5h 46m
Delta
Sat 8/156:00 am
ORF
- MDW
1 stop4h 17m
Delta
Deal found 6/8![Delta logo]()
$383
This Southwest deal was found by Cheapflights users on 6/5. 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 10/167:55 am
MDW
- ORF
Nonstop2h 10m
Southwest
Sun 10/187:00 am
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 6/5![Southwest logo]()
$363
This United Airlines deal was found by Cheapflights users on 6/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Sun 7/56:00 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Deal found 6/3![United Airlines logo]()
$363
This Delta deal was found by Cheapflights users on 6/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/187:00 am
ORD
- ORF
1 stop4h 46m
Delta
Sat 7/186:17 pm
ORF
- ORD
1 stop6h 36m
Delta
Deal found 6/4![Delta logo]()
$383
This Southwest deal was found by Cheapflights users on 6/4. 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.
Thu 10/222:00 pm
MDW
- ORF
2 stops8h 55m
Southwest
Wed 10/286:05 am
ORF
- MDW
2 stops7h 40m
Southwest
Deal found 6/4![Southwest logo]()
$377
This Delta deal was found by Cheapflights users on 6/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/511:10 am
ORD
- ORF
1 stop4h 49m
Delta
Sun 11/85:30 am
ORF
- ORD
1 stop5h 37m
Delta
Deal found 6/3![Delta logo]()
$411
This Southwest deal was found by Cheapflights users on 6/4. 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.
Thu 7/167:40 am
MDW
- ORF
Nonstop2h 05m
Southwest
Mon 7/206:10 pm
ORF
- MDW
2 stops7h 00m
Southwest
Deal found 6/4![Southwest logo]()
$378
This United Airlines deal was found by Cheapflights users on 6/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:15 pm
ORD
- ORF
Nonstop2h 26m
United Airlines
Wed 8/266:02 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Deal found 6/3![United Airlines logo]()
$417
This Southwest deal was found by Cheapflights users on 6/3. 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 7/102:45 pm
MDW
- ORF
2 stops7h 55m
Southwest
Tue 7/144:30 pm
ORF
- MDW
2 stops7h 45m
Southwest
Deal found 6/3![Southwest logo]()
$380
This United Airlines deal was found by Cheapflights users on 6/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/276:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Thu 7/3010:48 am
ORF
- ORD
Nonstop2h 39m
United Airlines
Deal found 6/6![United Airlines logo]()
$443
This United Airlines deal was found by Cheapflights users on 6/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:15 am
ORD
- ORF
Nonstop2h 30m
United Airlines
Wed 9/26:02 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Deal found 6/7![United Airlines logo]()
$443
This United Airlines deal was found by Cheapflights users on 6/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1510:55 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Wed 8/196:02 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Deal found 6/7![United Airlines logo]()
$443
Last-minute flights from Chicago to ChesapeakeDiscover last-minute flight deals from Chicago to Chesapeake. Data last updated June 8, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Chesapeake. Data last updated June 8, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 6/241:29 pm
ORD
- ORF
1 stop20h 57m
Frontier
Sun 6/2812:21 pm
ORF
- ORD
1 stop20h 42m
Frontier
Deal found 6/5![Frontier logo]()
$349
This Southwest deal was found by Cheapflights users on 6/7. 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 6/278:00 am
MDW
- ORF
Nonstop2h 15m
Southwest
Sat 7/410:00 am
ORF
- MDW
2 stops5h 35m
Southwest
Deal found 6/7![Southwest logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 6/306:00 am
MDW
- ORF
1 stop28h 26m
Frontier
Tue 7/712:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Deal found 6/5![Frontier logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 7/112:04 pm
MDW
- ORF
1 stop22h 22m
Frontier
Tue 7/712:10 pm
ORF
- MDW
2 stops28h 40m
Frontier
Deal found 6/5![Frontier logo]()
$345
This CheapOair deal was found by Cheapflights users on 6/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:00 am
ORD
- ORF
2 stops10h 10m
Multiple Airlines
Mon 7/612:10 pm
ORF
- ORD
1 stop8h 43m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$348
This American Airlines deal was found by Cheapflights users on 6/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/17:09 pm
ORD
- ORF
Nonstop2h 26m
American Airlines
Mon 7/66:40 am
ORF
- ORD
Nonstop2h 40m
American Airlines
Deal found 6/4![American Airlines logo]()
$350
This Southwest deal was found by Cheapflights users on 6/3. 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 7/107:00 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Tue 7/147:00 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Deal found 6/3![Southwest logo]()
$350
This CheapOair deal was found by Cheapflights users on 6/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/149:40 am
ORD
- ORF
2 stops30h 30m
Multiple Airlines
Sat 7/1812:16 pm
ORF
- ORD
1 stop8h 37m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 7/246:05 am
MDW
- ORF
2 stops13h 34m
Frontier
Tue 7/2812:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Deal found 6/5![Frontier logo]()
$348
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.
Sat 7/251:50 pm
ORD
- ORF
1 stop20h 25m
Frontier
Fri 7/3112:10 pm
ORF
- ORD
1 stop20h 43m
Frontier
Deal found 6/8![Frontier logo]()
$346
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 7/267:05 am
ORD
- ORF
1 stop27h 10m
Frontier
Fri 7/3112:10 pm
ORF
- ORD
2 stops37h 39m
Frontier
Deal found 6/8![Frontier logo]()
$341
This American Airlines deal was found by Cheapflights users on 6/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/297:14 pm
ORD
- ORF
Nonstop2h 25m
American Airlines
Thu 8/66:17 pm
ORF
- ORD
Nonstop2h 42m
American Airlines
Deal found 6/4![American Airlines logo]()
$347
One-way flights from Chicago to ChesapeakeSearch for one-way flight options from Chicago to Chesapeake. Find affordable one-way fares based on user searches. Data last updated June 8, 2026.
Search for one-way flight options from Chicago to Chesapeake. Find affordable one-way fares based on user searches. Data last updated June 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/3. 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.
Tue 9/16:00 am
MDW
- ORF
1 stop28h 26m
Frontier
Deal found 6/3![Frontier logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/47:05 am
ORD
- ORF
1 stop27h 10m
Frontier
Deal found 6/4![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 6/3. 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.
Fri 8/285:30 pm
ORD
- ORF
1 stop26h 31m
Frontier
Deal found 6/3![Frontier logo]()
$111
This Southwest deal was found by Cheapflights users on 6/7. 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 8/48:50 am
MDW
- ORF
Nonstop2h 15m
Southwest
Deal found 6/7![Southwest logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 6/3. 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.
Tue 9/15:30 pm
ORD
- ORF
1 stop26h 31m
Frontier
Deal found 6/3![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 6/3. 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.
Sat 8/296:00 am
MDW
- ORF
1 stop28h 26m
Frontier
Deal found 6/3![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 6/3. 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.
Mon 8/311:50 pm
ORD
- ORF
1 stop20h 36m
Frontier
Deal found 6/3![Frontier logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 6/3. 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 9/212:04 pm
MDW
- ORF
1 stop22h 22m
Frontier
Deal found 6/3![Frontier logo]()
$121
This Priceline deal was found by Cheapflights users on 6/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/299:26 am
ORD
- ORF
1 stop6h 49m
Frontier
Deal found 6/3![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 8/55:13 pm
ORD
- ORF
1 stop26h 26m
Frontier
Deal found 6/5![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2112:11 pm
MDW
- ORF
1 stop22h 04m
Frontier
Deal found 6/4![Frontier logo]()
$125
This Super.com deal was found by Cheapflights users on 6/7. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/75:13 pm
ORD
- ORF
1 stop26h 26m
Frontier
Deal found 6/7![Frontier logo]()
$125
Find flight deals from Chicago to Chesapeake
Keep the following information in mind while searching for Chicago to Chesapeake flight deals. Data was last updated June 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $341 (Delta) |
One-way from | $99 (Kiwi.com) |
Popular in | March |
Cheapest in | December |
Average price | $389 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Chesapeake 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 8, 2026.
Use the filters below to find and compare flights from Chicago to Chesapeake that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Fri 8/28
9:00 am-12:10 pm
Nonstop2h 10m
Norfolk
Sun 8/30
8:20 am-9:25 am
Nonstop2h 05m
$347
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Wed 10/28
6:00 pm-9:05 pm
Nonstop2h 05m
Norfolk
Sat 11/7
3:10 pm-4:25 pm
Nonstop2h 15m
$347
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Fri 7/24
3:53 pm-11:44 pm
1 stop6h 51m
Norfolk
Tue 7/28
10:48 am-12:27 pm
Nonstop2h 39m
$360
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Fri 9/18
7:00 am-10:30 am
Nonstop2h 30m
Norfolk
Sun 9/20
6:05 am-7:34 am
Nonstop2h 29m
$363
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Fri 10/16
7:55 am-11:05 am
Nonstop2h 10m
Norfolk
Sun 10/18
7:00 am-8:05 am
Nonstop2h 05m
$363
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Fri 7/3
6:45 am-10:07 am
Nonstop2h 22m
Norfolk
Sun 7/5
6:00 am-7:28 am
Nonstop2h 28m
$363
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 10/22
2:00 pm-11:55 pm
2 stops8h 55m
Norfolk
Wed 10/28
6:05 am-12:45 pm
2 stops7h 40m
$377
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 7/16
7:40 am-10:45 am
Nonstop2h 05m
Norfolk
Mon 7/20
6:10 pm-12:10 am
2 stops7h 00m
$378
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Fri 7/10
2:45 pm-11:40 pm
2 stops7h 55m
Norfolk
Tue 7/14
4:30 pm-11:15 pm
2 stops7h 45m
$380
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 9/24
10:48 am-3:57 pm
1 stop4h 09m
Norfolk
Mon 9/28
6:05 am-9:07 am
1 stop4h 02m
$383
Showing 1-10 of 37 resultsSorted by cheapest first
Best time to book a flight from Chicago to Chesapeake
Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Chicago with our price prediction graph.
ORD-ORF
MDW-ORF
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 Chicago to Chesapeake
CHI-C6E
ORD-ORF
MDW-ORF
What is the cheapest time of day to fly from CHI to C6E?
Find hourly flight availability from Chicago to Chesapeake. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 8, 2026.
One of the essential ways to save on airfare from Chicago to Chesapeake is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the morning could potentially save you up to 7% on airfare.
Weekly flight availability from Chicago to Chesapeake
Explore weekly flight availability from Chicago to Chesapeake. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 8, 2026.
The most flights from CHI to C6E are scheduled on a Thursday (30 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (19 on average).
How much does it cost to fly round-trip from Chicago to Chesapeake?
What is the cheapest day to fly from Chicago to Chesapeake?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Chesapeake. Price data was last updated on June 8, 2026.
Travelers seeking maximum savings on their Chicago to Chesapeake flight should consider departing on Sunday mornings when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Chesapeake
Get insights into the airlines that provide service to Chesapeake. 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 Chesapeake. Reviews last updated June 8, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican Airlines from Chicago to Chesapeake 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.
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
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 Chicago to Chesapeake. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Chesapeake
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Complete your trip
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Find flights from Chicago to Chesapeake, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Chesapeake flights
Browse other Chicago and Chesapeake flight options. Last updated on June 8, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on June 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Chesapeake flights
Consider these flights traveling from Chicago to Chesapeake.
Top 3 airlines flying from Chicago to Chesapeake
Discover the top 3 airlines that operate flights from Chicago to Chesapeake. 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 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$174 | Average$361 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$217 | Average$400 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$236 | Average$448 | FlexibilityNo cancel fee | On-time71% |