$67+ Cheap flights from Chesapeake, VA to Chicago (CHI)
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.
RIC — CHI
Mar 15 — Mar 221
1 adult, Economy
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Find cheap flights from Chesapeake to Chicago 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 Chesapeake to Chicago are usually found in September or October, booked 78 days in advance, depart on a Thursday or Friday and return on a Wednesday
Cheap flight deals from Chesapeake to Chicago
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Best
Last-minute
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Cheapest flights from Chesapeake to ChicagoExplore the most affordable flight options available from Chesapeake to Chicago. 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 Chesapeake to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 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.
Tue 3/107:31 pm
ORF
- ORD
1 stop16h 05m
Multiple Airlines
Tue 3/176:36 pm
ORD
- ORF
1 stop24h 10m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$139
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/911:50 am
ORF
- ORD
1 stop21h 33m
Frontier
Wed 3/187:18 pm
ORD
- ORF
1 stop13h 57m
Frontier
Deal found 2/13![Frontier logo]()
$154
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2311:39 am
ORF
- MDW
1 stop11h 50m
Frontier
Thu 2/267:30 am
MDW
- ORF
1 stop9h 58m
Frontier
Deal found 2/9![Frontier logo]()
$160
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 5/411:19 am
ORF
- ORD
1 stop12h 20m
Frontier
Thu 5/710:25 am
ORD
- ORF
1 stop6h 24m
Frontier
Deal found 2/13![Frontier logo]()
$160
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.
Mon 3/1612:33 pm
ORF
- MDW
1 stop10h 46m
Frontier
Wed 3/186:05 am
MDW
- ORF
1 stop27h 10m
Frontier
Deal found 2/11![Frontier logo]()
$163
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 3/107:31 pm
ORF
- ORD
1 stop16h 51m
Spirit Airlines
Tue 3/176:01 pm
ORD
- ORF
2 stops24h 45m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$169
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.
Fri 3/67:31 pm
ORF
- ORD
1 stop16h 51m
Spirit Airlines
Mon 3/98:16 pm
ORD
- ORF
1 stop21h 10m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$172
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/911:50 am
ORF
- ORD
1 stop21h 33m
Multiple Airlines
Tue 3/176:36 pm
ORD
- ORF
1 stop24h 10m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$173
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 3/37:31 pm
ORF
- ORD
2 stops16h 20m
Multiple Airlines
Wed 3/48:16 pm
ORD
- ORF
1 stop21h 10m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$175
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.
Mon 3/1612:33 pm
ORF
- MDW
1 stop10h 46m
Multiple Airlines
Wed 3/186:05 am
MDW
- ORF
2 stops12h 41m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$177
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/911:50 am
ORF
- ORD
1 stop21h 33m
Multiple Airlines
Wed 3/187:31 pm
ORD
- ORF
2 stops38h 11m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$177
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/272:41 pm
ORF
- ORD
1 stop9h 06m
Multiple Airlines
Wed 3/412:44 pm
ORD
- ORF
1 stop8h 06m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$178
Best flights from Chesapeake to ChicagoDiscover carefully curated flight deals from Chesapeake to Chicago 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 Chesapeake to Chicago 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 2/11. 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.
Mon 3/1612:33 pm
ORF
- MDW
1 stop10h 46m
Frontier
Wed 3/186:05 am
MDW
- ORF
1 stop27h 10m
Frontier
Deal found 2/11![Frontier logo]()
$163
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.
Mon 3/166:15 am
ORF
- ORD
Nonstop2h 35m
United Airlines
Wed 3/187:00 am
ORD
- ORF
1 stop6h 08m
United Airlines
Deal found 2/10![United Airlines logo]()
$213
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.
Mon 3/168:41 pm
ORF
- ORD
2 stops22h 45m
Spirit Airlines
Wed 3/185:05 am
ORD
- ORF
1 stop13h 41m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$214
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.
Wed 3/115:50 am
ORF
- MDW
1 stop7h 12m
Delta
Sat 3/146:34 pm
MDW
- ORF
1 stop4h 50m
Delta
Deal found 2/10![Delta logo]()
$233
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.
Tue 4/216:05 am
ORF
- MDW
2 stops14h 26m
Multiple Airlines
Fri 4/249:14 am
MDW
- ORF
1 stop6h 37m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$250
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:50 am
ORF
- MDW
2 stops6h 05m
Southwest
Wed 3/41:15 pm
MDW
- ORF
1 stop3h 35m
Southwest
Deal found 2/10![Southwest logo]()
$288
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/155:30 pm
ORF
- MDW
1 stop5h 58m
Delta
Fri 4/175:21 pm
MDW
- ORF
1 stop6h 16m
Delta
Deal found 2/10![Delta logo]()
$233
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 4/3011:19 am
ORF
- ORD
1 stop8h 35m
Multiple Airlines
Mon 5/44:28 pm
ORD
- ORF
2 stops29h 30m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$252
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.
Wed 3/115:00 pm
ORF
- ORD
Nonstop2h 46m
United Airlines
Sat 3/145:45 pm
ORD
- ORF
Nonstop2h 09m
United Airlines
Deal found 2/10![United Airlines logo]()
$256
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.
Tue 4/75:45 am
ORF
- MDW
1 stop4h 08m
Delta
Tue 4/145:21 pm
MDW
- ORF
1 stop6h 16m
Delta
Deal found 2/10![Delta logo]()
$233
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1911:50 am
ORF
- MDW
1 stop8h 57m
Frontier
Sun 3/226:20 am
MDW
- ORF
1 stop7h 35m
Frontier
Deal found 2/11![Frontier logo]()
$264
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.
Thu 4/97:29 pm
ORF
- ORD
1 stop5h 25m
Delta
Sun 4/127:14 pm
ORD
- ORF
1 stop4h 24m
Delta
Deal found 2/10![Delta logo]()
$233
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.
Tue 4/216:25 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Fri 4/245:50 pm
MDW
- ORF
1 stop4h 05m
Southwest
Deal found 2/12![Southwest logo]()
$290
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 3/38:05 pm
ORF
- ORD
1 stop4h 38m
United Airlines
Wed 3/411:05 am
ORD
- ORF
Nonstop2h 17m
United Airlines
Deal found 2/10![United Airlines logo]()
$273
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 3/165:00 pm
ORF
- ORD
1 stop4h 17m
Delta
Thu 3/197:14 pm
ORD
- ORF
1 stop4h 10m
Delta
Deal found 2/10![Delta logo]()
$233
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.
Fri 3/611:25 am
ORF
- MDW
1 stop9h 22m
Frontier
Mon 3/96:15 am
MDW
- ORF
1 stop7h 16m
Frontier
Deal found 2/10![Frontier logo]()
$286
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.
Mon 3/167:20 pm
ORF
- MDW
Nonstop2h 15m
Southwest
Wed 3/186:05 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 2/11![Southwest logo]()
$293
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.
Wed 3/255:00 pm
ORF
- ORD
Nonstop2h 46m
United Airlines
Sat 3/285:45 pm
ORD
- ORF
Nonstop2h 09m
United Airlines
Deal found 2/10![United Airlines logo]()
$293
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:25 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Fri 4/177:00 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 2/10![Southwest logo]()
$304
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.
Sat 4/117:36 pm
ORF
- ORD
1 stop5h 07m
United Airlines
Tue 4/145:48 pm
ORD
- ORF
Nonstop2h 20m
United Airlines
Deal found 2/11![United Airlines logo]()
$303
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/15:45 am
ORF
- MDW
1 stop4h 08m
Delta
Wed 4/812:47 pm
MDW
- ORF
1 stop7h 04m
Delta
Deal found 2/12![Delta logo]()
$283
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/265:24 pm
ORF
- RFD
1 stop16h 53m
Multiple Airlines
Mon 6/297:48 pm
RFD
- ORF
1 stop26h 53m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$385
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.
Wed 3/117:29 pm
ORF
- ORD
1 stop5h 25m
Delta
Sat 3/145:40 pm
ORD
- ORF
1 stop5h 44m
Delta
Deal found 2/10![Delta logo]()
$301
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.
Fri 4/247:00 am
ORF
- RFD
1 stop12h 19m
Multiple Airlines
Sun 4/2610:37 am
RFD
- ORF
1 stop7h 52m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$478
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.
Fri 6/265:24 pm
ORF
- RFD
1 stop16h 53m
Multiple Airlines
Thu 7/21:14 pm
RFD
- ORF
1 stop29h 12m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$553
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 4/18:41 pm
ORF
- RFD
1 stop14h 06m
Multiple Airlines
Sun 4/510:37 am
RFD
- ORF
1 stop8h 09m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$624
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.
Thu 3/126:43 pm
ORF
- RFD
1 stop16h 06m
Multiple Airlines
Sun 3/1510:37 am
RFD
- ORF
1 stop8h 09m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$628
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 4/48:41 pm
ORF
- RFD
1 stop14h 06m
Multiple Airlines
Wed 4/85:46 pm
RFD
- ORF
2 stops15h 50m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$817
Last-minute flights from Chesapeake to ChicagoDiscover last-minute flight deals from Chesapeake to Chicago. Data last updated February 13, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to Chicago. Data last updated February 13, 2026 and is based on user searches.
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2311:39 am
ORF
- MDW
1 stop11h 50m
Frontier
Thu 2/267:30 am
MDW
- ORF
1 stop9h 58m
Frontier
Deal found 2/9![Frontier logo]()
$160
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/272:41 pm
ORF
- ORD
1 stop9h 06m
Multiple Airlines
Wed 3/412:44 pm
ORD
- ORF
1 stop8h 06m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$178
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 3/37:31 pm
ORF
- ORD
2 stops16h 20m
Multiple Airlines
Wed 3/48:16 pm
ORD
- ORF
1 stop21h 10m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$175
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.
Fri 3/67:31 pm
ORF
- ORD
1 stop16h 51m
Spirit Airlines
Mon 3/98:16 pm
ORD
- ORF
1 stop21h 10m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$172
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/911:50 am
ORF
- ORD
1 stop21h 33m
Frontier
Wed 3/187:18 pm
ORD
- ORF
1 stop13h 57m
Frontier
Deal found 2/13![Frontier logo]()
$154
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/911:50 am
ORF
- ORD
1 stop21h 33m
Multiple Airlines
Tue 3/176:36 pm
ORD
- ORF
1 stop24h 10m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$173
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/911:50 am
ORF
- ORD
1 stop21h 33m
Multiple Airlines
Wed 3/187:31 pm
ORD
- ORF
2 stops38h 11m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$177
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 3/107:31 pm
ORF
- ORD
1 stop16h 05m
Multiple Airlines
Tue 3/176:36 pm
ORD
- ORF
1 stop24h 10m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$139
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.
Tue 3/107:31 pm
ORF
- ORD
1 stop16h 51m
Spirit Airlines
Thu 3/125:05 am
ORD
- ORF
1 stop13h 41m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$160
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 3/107:31 pm
ORF
- ORD
1 stop16h 51m
Spirit Airlines
Tue 3/176:01 pm
ORD
- ORF
2 stops24h 45m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$169
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.
Mon 3/1612:33 pm
ORF
- MDW
1 stop10h 46m
Frontier
Wed 3/186:05 am
MDW
- ORF
1 stop27h 10m
Frontier
Deal found 2/11![Frontier logo]()
$163
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.
Mon 3/1612:33 pm
ORF
- MDW
1 stop10h 46m
Multiple Airlines
Wed 3/186:05 am
MDW
- ORF
2 stops12h 41m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$177
One-way flights from Chesapeake to ChicagoSearch for one-way flight options from Chesapeake to Chicago. Find affordable one-way fares based on user searches. Data last updated February 13, 2026.
Search for one-way flight options from Chesapeake to Chicago. Find affordable one-way fares based on user searches. Data last updated February 13, 2026.
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:05 am
ORF
- MDW
1 stop11h 08m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$67
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:05 am
ORF
- ORD
1 stop10h 20m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$67
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:05 am
ORF
- MDW
1 stop11h 08m
Multiple Airlines
Deal found 2/9![Multiple 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.
Mon 3/97:31 pm
ORF
- ORD
1 stop16h 51m
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 3/248:41 pm
ORF
- ORD
1 stop15h 36m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$69
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.
Wed 3/188:41 pm
ORF
- ORD
1 stop15h 36m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$72
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:31 pm
ORF
- ORD
1 stop16h 05m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$73
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/1612:33 pm
ORF
- MDW
1 stop10h 46m
Frontier
Deal found 2/12![Frontier logo]()
$77
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/911:50 am
ORF
- ORD
1 stop21h 33m
Frontier
Deal found 2/13![Frontier logo]()
$77
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.
Sat 4/115:47 pm
ORF
- MDW
1 stop5h 42m
Frontier
Deal found 2/10![Frontier logo]()
$80
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.
Mon 4/133:54 pm
ORF
- ORD
1 stop8h 42m
Frontier
Deal found 2/13![Frontier logo]()
$80
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 3/258:41 pm
ORF
- ORD
1 stop20h 58m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$81
Find flight deals from Chesapeake to Chicago
Keep the following information in mind while searching for Chesapeake to Chicago 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 (Kiwi.com) |
One-way from | $67 (Kiwi.com) |
Popular in | April |
Cheapest in | September |
Average price | $318 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chesapeake to Chicago 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 Chesapeake to Chicago that are best for you.
Fly from
Chesapeake
Fly to
Chicago
Route
Depart
Return
Price
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Mon 3/16
12:33 pm-10:19 pm
1 stop10h 46m
Chicago Midway
Wed 3/18
6:05 am-10:15 am
1 stop27h 10m
$163
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Mon 3/16
6:15 am-7:50 am
Nonstop2h 35m
Chicago O'Hare Intl
Wed 3/18
7:00 am-2:08 pm
1 stop6h 08m
$213
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Mon 3/16
8:41 pm-6:26 pm
2 stops22h 45m
Chicago O'Hare Intl
Wed 3/18
5:05 am-7:46 pm
1 stop13h 41m
$214
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Wed 3/11
5:50 am-12:02 pm
1 stop7h 12m
Chicago Midway
Sat 3/14
6:34 pm-12:24 am
1 stop4h 50m
$233
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Wed 4/15
5:30 pm-10:28 pm
1 stop5h 58m
Chicago Midway
Fri 4/17
5:21 pm-12:37 am
1 stop6h 16m
$233
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Tue 4/7
5:45 am-8:53 am
1 stop4h 08m
Chicago Midway
Tue 4/14
5:21 pm-12:37 am
1 stop6h 16m
$233
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Thu 4/9
7:29 pm-11:54 pm
1 stop5h 25m
Chicago O'Hare Intl
Sun 4/12
7:14 pm-12:38 am
1 stop4h 24m
$233
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Mon 3/16
5:00 pm-8:17 pm
1 stop4h 17m
Chicago O'Hare Intl
Thu 3/19
7:14 pm-12:24 am
1 stop4h 10m
$233
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Tue 4/21
6:05 am-7:31 pm
2 stops14h 26m
Chicago Midway
Fri 4/24
9:14 am-4:51 pm
1 stop6h 37m
$250
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Thu 4/30
11:19 am-6:54 pm
1 stop8h 35m
Chicago O'Hare Intl
Mon 5/4
4:28 pm-10:58 pm
2 stops29h 30m
$252
Showing 1-10 of 56 results
Best time to book a flight from Chesapeake to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Chesapeake with our price prediction graph.
ORF-MDW
ORF-ORD
ORF-RFD
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 Chesapeake to Chicago
C6E-CHI
ORF-MDW
ORF-ORD
ORF-RFD
How far ahead should I book a flight from Chesapeake to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Chesapeake to Chicago. Price data was last updated on February 6, 2026.
To ensure you get the cheapest price possible for a flight from Chesapeake to Chicago, you should look to book at least 78 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Chesapeake to Chicago?
Currently, May is the cheapest month in which you can book a flight from Chesapeake to Chicago (average of $108). Flying from Chesapeake to Chicago in July is currently the most expensive (average of $266). 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 C6E to CHI?
Find hourly flight availability from Chesapeake to Chicago. 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.
A simple way to save on the total cost of your ticket is to fly from Chesapeake to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 12% on your trip compared to booking a flight in the evening.
What is the cheapest day to fly from Chesapeake to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Chesapeake to Chicago. Price data was last updated on February 7, 2026.
Travelers seeking maximum savings on their Chesapeake to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chesapeake to Chicago
Explore weekly flight availability from Chesapeake to Chicago. 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 C6E to CHI are scheduled on a Friday (26 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).
How much does it cost to fly round-trip from Chesapeake to Chicago?
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated February 13, 2026.
Read through reviews of airlines operating flights from Chesapeake to Chicago, such as Southwest, United Airlines, and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Chesapeake to Chicago. 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?
Book flights to Chicago if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Chesapeake to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on February 13, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chesapeake to Chicago by cabin class
Find flights from Chesapeake to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chesapeake and Chicago flights
Browse other Chesapeake and Chicago flight options. Last updated on February 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Chesapeake to Chicago
Discover the top 6 airlines that operate flights from Chesapeake to Chicago. 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$92 | Average$303 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$108 | Average$260 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$172 | Average$208 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$364 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$208 | Average$361 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$216 | Average$386 | FlexibilityNo cancel fee | On-time69% |