$55+ 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Mar 15 — Mar 221
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 70 days in advance, depart on a Wednesday or Tuesday and return on a Thursday
Cheap flight deals from Chicago to Chesapeake
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Best
Last-minute
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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 February 13, 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 February 13, 2026.
This Mytrip deal was found by Cheapflights users on 2/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/55:15 am
ORD
- ORF
1 stop12h 11m
Spirit Airlines
Mon 3/97:31 pm
ORF
- ORD
1 stop16h 51m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/176:36 pm
ORD
- ORF
1 stop24h 10m
Multiple Airlines
Tue 3/248:41 pm
ORF
- ORD
1 stop14h 55m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$140
This Mytrip deal was found by Cheapflights users on 2/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/117:00 am
ORD
- ORF
1 stop10h 26m
Spirit Airlines
Wed 3/188:41 pm
ORF
- ORD
1 stop15h 36m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$144
This Frontier deal was found by Cheapflights users on 2/10. 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.
Thu 2/267:30 am
MDW
- ORF
1 stop9h 58m
Frontier
Mon 3/211:39 am
ORF
- MDW
1 stop11h 50m
Frontier
Deal found 2/10![Frontier logo]()
$160
This Expedia deal was found by Cheapflights users on 2/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/188:00 am
ORD
- ORF
1 stop8h 49m
Frontier
Sun 4/196:43 pm
ORF
- ORD
1 stop20h 34m
Frontier
Deal found 2/12![Frontier logo]()
$160
This Mytrip deal was found by Cheapflights users on 2/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/127:17 am
ORD
- ORF
1 stop11h 29m
Spirit Airlines
Tue 3/178:41 pm
ORF
- ORD
1 stop15h 36m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Thu 3/122:41 pm
MDW
- ORF
1 stop19h 01m
Frontier
Mon 3/1612:33 pm
ORF
- MDW
1 stop8h 14m
Frontier
Deal found 2/10![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/129:15 am
ORD
- ORF
1 stop9h 31m
Multiple Airlines
Wed 3/188:41 pm
ORF
- ORD
1 stop21h 18m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Thu 3/126:05 am
MDW
- ORF
2 stops12h 41m
Multiple Airlines
Mon 3/1612:33 pm
ORF
- MDW
1 stop8h 14m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Thu 3/57:00 am
ORD
- ORF
1 stop10h 26m
Multiple Airlines
Sun 3/811:35 am
ORF
- ORD
1 stop24h 21m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Thu 3/129:15 am
ORD
- ORF
1 stop9h 31m
Multiple Airlines
Mon 3/168:41 pm
ORF
- ORD
1 stop14h 55m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$180
This Expedia deal was found by Cheapflights users on 2/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:30 am
MDW
- ORF
1 stop9h 58m
Frontier
Sun 3/111:32 am
ORF
- MDW
1 stop11h 58m
Frontier
Deal found 2/10![Frontier logo]()
$181
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 February 13, 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 February 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Thu 2/265:16 pm
MDW
- ORF
1 stop16h 21m
Multiple Airlines
Sun 3/17:31 pm
ORF
- MDW
2 stops27h 58m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$191
This CheapOair deal was found by Cheapflights users on 2/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/149:14 am
MDW
- ORF
1 stop7h 35m
Frontier
Sun 5/176:43 pm
ORF
- MDW
1 stop14h 21m
Frontier
Deal found 2/11![Frontier logo]()
$192
This United Airlines deal was found by Cheapflights users on 2/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/236:05 pm
ORD
- ORF
Nonstop2h 09m
United Airlines
Wed 3/255:00 pm
ORF
- ORD
Nonstop2h 46m
United Airlines
Deal found 2/9![United Airlines logo]()
$203
This Delta deal was found by Cheapflights users on 2/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/236:07 pm
MDW
- ORF
1 stop5h 16m
Delta
Sun 3/295:45 am
ORF
- MDW
1 stop4h 08m
Delta
Deal found 2/10![Delta logo]()
$233
This Southwest deal was found by Cheapflights users on 2/11. 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.
Tue 4/75:00 pm
MDW
- ORF
1 stop3h 55m
Southwest
Tue 4/146:25 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Deal found 2/11![Southwest logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Wed 2/1812:44 pm
ORD
- ORF
1 stop28h 44m
Multiple Airlines
Tue 2/241:02 pm
ORF
- ORD
1 stop29h 44m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Thu 3/55:16 pm
MDW
- ORF
1 stop15h 59m
Frontier
Sun 3/87:31 pm
ORF
- MDW
1 stop18h 37m
Frontier
Deal found 2/10![Frontier logo]()
$199
This United Airlines deal was found by Cheapflights users on 2/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/176:05 pm
ORD
- ORF
Nonstop2h 09m
United Airlines
Tue 3/248:00 am
ORF
- ORD
Nonstop2h 33m
United Airlines
Deal found 2/10![United Airlines logo]()
$203
This CheapOair deal was found by Cheapflights users on 2/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/133:31 pm
ORD
- ORF
1 stop6h 27m
Multiple Airlines
Sun 5/176:43 pm
ORF
- ORD
1 stop20h 34m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$193
This Delta deal was found by Cheapflights users on 2/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/227:14 pm
ORD
- ORF
1 stop4h 10m
Delta
Wed 3/255:00 pm
ORF
- ORD
1 stop4h 17m
Delta
Deal found 2/10![Delta logo]()
$233
This Frontier deal was found by Cheapflights users on 2/10. 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.
Fri 5/19:14 am
MDW
- ORF
1 stop7h 35m
Frontier
Fri 5/811:19 am
ORF
- MDW
1 stop9h 12m
Frontier
Deal found 2/10![Frontier logo]()
$215
This CheapOair deal was found by Cheapflights users on 2/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/712:44 pm
ORD
- ORF
1 stop8h 06m
Multiple Airlines
Sat 3/143:26 pm
ORF
- ORD
1 stop9h 12m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$223
This Southwest deal was found by Cheapflights users on 2/12. 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 3/259:20 am
MDW
- ORF
1 stop6h 10m
Southwest
Sat 3/287:20 pm
ORF
- MDW
Nonstop2h 15m
Southwest
Deal found 2/12![Southwest logo]()
$275
This Frontier deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/89:14 am
MDW
- ORF
1 stop7h 35m
Frontier
Sun 5/1011:19 am
ORF
- MDW
1 stop12h 00m
Frontier
Deal found 2/13![Frontier logo]()
$235
This United Airlines deal was found by Cheapflights users on 2/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/115:45 pm
ORD
- ORF
Nonstop2h 09m
United Airlines
Wed 3/188:00 am
ORF
- ORD
Nonstop2h 33m
United Airlines
Deal found 2/11![United Airlines logo]()
$263
This CheapOair deal was found by Cheapflights users on 2/13. 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.
Fri 3/134:18 pm
ORD
- ORF
1 stop21h 13m
Frontier
Mon 3/1612:33 pm
ORF
- ORD
1 stop11h 06m
Frontier
Deal found 2/13![Frontier logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 2/174:43 pm
ORD
- ORF
1 stop24h 43m
Multiple Airlines
Tue 2/241:02 pm
ORF
- ORD
1 stop29h 44m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$238
This United Airlines deal was found by Cheapflights users on 2/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/134:00 pm
ORD
- ORF
1 stop6h 46m
United Airlines
Sun 3/156:15 am
ORF
- ORD
Nonstop2h 35m
United Airlines
Deal found 2/10![United Airlines logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
Sat 4/183:31 pm
ORD
- ORF
1 stop6h 27m
Multiple Airlines
Sun 4/198:27 pm
ORF
- ORD
2 stops22h 24m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:30 am
MDW
- ORF
2 stops32h 23m
Multiple Airlines
Sun 5/176:43 pm
ORF
- MDW
1 stop14h 21m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
Sat 4/186:00 am
MDW
- ORF
2 stops12h 32m
Multiple Airlines
Sun 4/1911:19 am
ORF
- MDW
1 stop12h 00m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$279
Last-minute flights from Chicago to ChesapeakeDiscover last-minute flight deals from Chicago to Chesapeake. Data last updated February 13, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Chesapeake. Data last updated February 13, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 2/10. 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.
Thu 2/267:30 am
MDW
- ORF
1 stop9h 58m
Frontier
Mon 3/211:39 am
ORF
- MDW
1 stop11h 50m
Frontier
Deal found 2/10![Frontier logo]()
$160
This Expedia deal was found by Cheapflights users on 2/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:30 am
MDW
- ORF
1 stop9h 58m
Frontier
Sun 3/111:32 am
ORF
- MDW
1 stop11h 58m
Frontier
Deal found 2/10![Frontier logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/212:44 pm
ORD
- ORF
1 stop22h 21m
Multiple Airlines
Thu 3/511:46 am
ORF
- ORD
1 stop11h 53m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$185
This Mytrip deal was found by Cheapflights users on 2/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/55:15 am
ORD
- ORF
1 stop12h 11m
Spirit Airlines
Mon 3/97:31 pm
ORF
- ORD
1 stop16h 51m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Thu 3/57:00 am
ORD
- ORF
1 stop10h 26m
Multiple Airlines
Sun 3/811:35 am
ORF
- ORD
1 stop24h 21m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$171
This Mytrip deal was found by Cheapflights users on 2/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/117:00 am
ORD
- ORF
1 stop10h 26m
Spirit Airlines
Wed 3/188:41 pm
ORF
- ORD
1 stop15h 36m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$144
This Mytrip deal was found by Cheapflights users on 2/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/127:17 am
ORD
- ORF
1 stop11h 29m
Spirit Airlines
Tue 3/178:41 pm
ORF
- ORD
1 stop15h 36m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Thu 3/122:41 pm
MDW
- ORF
1 stop19h 01m
Frontier
Mon 3/1612:33 pm
ORF
- MDW
1 stop8h 14m
Frontier
Deal found 2/10![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/129:15 am
ORD
- ORF
1 stop9h 31m
Multiple Airlines
Wed 3/188:41 pm
ORF
- ORD
1 stop21h 18m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Thu 3/126:05 am
MDW
- ORF
2 stops12h 41m
Multiple Airlines
Mon 3/1612:33 pm
ORF
- MDW
1 stop8h 14m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Thu 3/129:15 am
ORD
- ORF
1 stop9h 31m
Multiple Airlines
Mon 3/168:41 pm
ORF
- ORD
1 stop14h 55m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/176:36 pm
ORD
- ORF
1 stop24h 10m
Multiple Airlines
Tue 3/248:41 pm
ORF
- ORD
1 stop14h 55m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$140
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 February 13, 2026.
Search for one-way flight options from Chicago to Chesapeake. Find affordable one-way fares based on user searches. Data last updated February 13, 2026.
This Trip.com deal was found by Cheapflights users on 2/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:14 am
MDW
- ORF
1 stop7h 35m
Frontier
Deal found 2/11![Frontier logo]()
$55
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/259:14 am
MDW
- ORF
1 stop7h 35m
Frontier
Deal found 2/11![Frontier logo]()
$59
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Sat 5/98:00 am
ORD
- ORF
1 stop8h 49m
Frontier
Deal found 2/10![Frontier logo]()
$60
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Sat 5/29:14 am
MDW
- ORF
1 stop12h 45m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$62
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Wed 2/257:00 am
MDW
- ORF
1 stop26h 51m
Frontier
Deal found 2/10![Frontier logo]()
$68
This Mytrip deal was found by Cheapflights users on 2/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/105:15 am
ORD
- ORF
1 stop12h 11m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$68
This Mytrip deal was found by Cheapflights users on 2/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/245:05 am
ORD
- ORF
1 stop13h 41m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/98:16 pm
ORD
- ORF
1 stop21h 10m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$71
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
Wed 3/116:36 pm
ORD
- ORF
1 stop24h 10m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$73
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Thu 2/266:25 am
MDW
- ORF
1 stop27h 12m
Frontier
Deal found 2/10![Frontier logo]()
$74
This Trip.com deal was found by Cheapflights users on 2/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/28:00 am
ORD
- ORF
1 stop8h 49m
Frontier
Deal found 2/11![Frontier logo]()
$76
This Expedia deal was found by Cheapflights users on 2/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:06 am
ORD
- ORF
1 stop11h 26m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$78
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 February 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $139 (Mytrip) |
One-way from | $55 (Trip.com) |
Popular in | April |
Cheapest in | December |
Average price | $361 |
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 February 13, 2026.
Use the filters below to find and compare flights from Chicago to Chesapeake that are best for you.
Fly from
Chicago
Fly to
Chesapeake
Route
Depart
Return
Price
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 2/26
5:16 pm-10:37 am
1 stop16h 21m
Norfolk
Sun 3/1
7:31 pm-10:29 pm
2 stops27h 58m
$191
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 5/14
9:14 am-5:49 pm
1 stop7h 35m
Norfolk
Sun 5/17
6:43 pm-8:04 am
1 stop14h 21m
$192
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Wed 2/18
12:44 pm-6:28 pm
1 stop28h 44m
Norfolk
Tue 2/24
1:02 pm-5:46 pm
1 stop29h 44m
$192
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Wed 5/13
3:31 pm-10:58 pm
1 stop6h 27m
Norfolk
Sun 5/17
6:43 pm-2:17 pm
1 stop20h 34m
$193
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 3/5
5:16 pm-10:15 am
1 stop15h 59m
Norfolk
Sun 3/8
7:31 pm-1:08 pm
1 stop18h 37m
$199
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Mon 3/23
6:05 pm-9:14 pm
Nonstop2h 09m
Norfolk
Wed 3/25
5:00 pm-6:46 pm
Nonstop2h 46m
$203
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Tue 3/17
6:05 pm-9:14 pm
Nonstop2h 09m
Norfolk
Tue 3/24
8:00 am-9:33 am
Nonstop2h 33m
$203
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Fri 5/1
9:14 am-5:49 pm
1 stop7h 35m
Norfolk
Fri 5/8
11:19 am-7:31 pm
1 stop9h 12m
$215
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Sat 3/7
12:44 pm-9:50 pm
1 stop8h 06m
Norfolk
Sat 3/14
3:26 pm-11:38 pm
1 stop9h 12m
$223
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Mon 3/23
6:07 pm-12:23 am
1 stop5h 16m
Norfolk
Sun 3/29
5:45 am-8:53 am
1 stop4h 08m
$233
Showing 1-10 of 44 results
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
How far ahead should I book a flight from Chicago to Chesapeake?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Chesapeake. Price data was last updated on February 6, 2026.
The best time to book flights from Chicago to Chesapeake is 68 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Chicago to Chesapeake?
Currently, January is the cheapest month in which you can book a flight from Chicago to Chesapeake (average of $130). Flying from Chicago to Chesapeake in December is currently the most expensive (average of $265). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
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 February 13, 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 afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 15% on airfare.
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 February 7, 2026.
Travelers seeking maximum savings on their Chicago to Chesapeake flight should consider departing on Wednesday at noon when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 February 13, 2026.
The most flights from CHI to C6E are scheduled on a Friday (24 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).
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 February 13, 2026.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American 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.
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Chesapeake by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Chesapeake by cabin class
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 February 13, 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 February 13, 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 5 airlines flying from Chicago to Chesapeake
Discover the top 5 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 February 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$78 | Average$222 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$102 | Average$234 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$207 | Average$391 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$213 | Average$372 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$229 | Average$395 | FlexibilityNo cancel fee | On-time71% |