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Chesapeake

$76+ Cheap flights from O'Hare Intl (ORD) 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — RIC
Aug 19 — Aug 261
Wed 8/19
Wed 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Chesapeake are usually found in January or May, booked 62 days in advance, depart on a Saturday or Wednesday and return on a Thursday

Cheap flight deals from O'Hare Intl to Chesapeake

Cheapest flights from O'Hare Intl to Chesapeake
Explore the most affordable flight options available from O'Hare Intl to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 20, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 8/68:52 pm
ORD
-
ORF
2 stops37h 29m
Frontier
Mon 8/1012:10 pm
ORF
-
ORD
1 stop8h 43m
Frontier
Deal found 7/17$280
This Kiwi.com deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 8/105:13 pm
ORD
-
ORF
2 stops17h 02m
Frontier
Sat 8/1512:16 pm
ORF
-
ORD
1 stop8h 37m
Frontier
Deal found 7/18$281
This CheapOair deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 10/94:49 pm
ORD
-
ORF
1 stop23h 41m
Frontier
Sun 10/116:25 pm
ORF
-
ORD
1 stop6h 30m
Frontier
Deal found 7/20$284
This CheapOair deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 8/75:13 pm
ORD
-
ORF
1 stop26h 26m
Frontier
Tue 8/119:34 pm
ORF
-
ORD
1 stop26h 36m
Frontier
Deal found 7/17$288
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/41:50 pm
ORD
-
ORF
1 stop20h 25m
Frontier
Sat 8/812:16 pm
ORF
-
ORD
1 stop8h 37m
Frontier
Deal found 7/16$289
This Kiwi.com deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 8/41:50 pm
ORD
-
ORF
1 stop20h 25m
Frontier
Thu 8/612:10 pm
ORF
-
ORD
1 stop8h 43m
Frontier
Deal found 7/15$290
This Kiwi.com deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 8/227:11 am
ORD
-
ORF
1 stop28h 14m
Frontier
Sat 8/291:20 pm
ORF
-
ORD
1 stop7h 48m
Frontier
Deal found 7/15$292
This CheapOair deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 8/55:13 pm
ORD
-
ORF
1 stop26h 26m
Frontier
Wed 8/1212:10 pm
ORF
-
ORD
1 stop8h 43m
Frontier
Deal found 7/15$293

Find flight deals from O'Hare Intl to Chesapeake

Keep the following information in mind while searching for O'Hare Intl to Chesapeake flight deals. Data was last updated July 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$280
(Kiwi.com)

One-way from

$76
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$388
Provider with most accurate pricing for Chicago (CHI)-Norfolk flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Norfolk flights.
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From Chicago O'Hare Intl to Chesapeake
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One-way flight from Chicago O'Hare Intl to Chesapeake
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in July 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl 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 July 20, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Chesapeake that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 8/27

6:15 pm-9:48 pm

Nonstop2h 33m

Norfolk

Thu 9/3

1:00 pm-2:34 pm

Nonstop2h 34m

$337

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 8/25

10:55 am-2:17 pm

Nonstop2h 22m

Norfolk

Sun 8/30

6:00 am-10:58 am

1 stop5h 58m

$350
Quickest round-trip

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 12/11

6:15 pm-9:32 pm

Nonstop2h 17m

Norfolk

Tue 12/15

5:15 pm-6:45 pm

Nonstop2h 30m

$350

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 8/14

10:55 am-2:17 pm

Nonstop2h 22m

Norfolk

Sun 8/16

10:41 am-2:27 pm

1 stop4h 46m

$373

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 1/8

7:15 am-10:46 am

Nonstop2h 31m

Norfolk

Sun 1/17

5:12 pm-11:42 pm

1 stop7h 30m

$373

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sun 12/20

5:55 pm-12:14 am

1 stop5h 19m

Norfolk

Sat 12/26

12:30 pm-6:32 pm

1 stop7h 02m

$383

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 8/4

6:45 am-10:07 am

Nonstop2h 22m

Norfolk

Thu 8/6

10:45 am-2:29 pm

1 stop4h 44m

$413

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 8/15

6:30 am-2:14 pm

1 stop6h 44m

Norfolk

Wed 8/19

1:00 pm-2:34 pm

Nonstop2h 34m

$427

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 8/15

8:45 am-2:14 pm

1 stop4h 29m

Norfolk

Tue 8/18

6:00 am-10:58 am

1 stop5h 58m

$437

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 8/8

3:53 pm-11:44 pm

1 stop6h 51m

Norfolk

Tue 8/11

6:10 pm-11:22 pm

1 stop6h 12m

$437

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/15

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

Best time to book a flight from O'Hare Intl to Chesapeake

Have a flexible travel schedule? Discover the best time to fly to Chesapeake from O'Hare Intl with our price prediction graph.
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 O'Hare Intl Airport to Chesapeake

What is the cheapest time of day to fly from ORD to C6E?

Find hourly flight availability from O'Hare Intl 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 July 20, 2026.

It’s typically best to fly out from Chicago O'Hare Intl Airport to Chesapeake in the morning. Doing so could potentially save you 7% on the flight price compared to flying in the afternoon, which is usually more expensive.

Weekly flight availability from Chicago O'Hare Intl Airport to Chesapeake

Explore weekly flight availability from O'Hare Intl 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 July 20, 2026.

The most flights from ORD to C6E are scheduled on a Monday (24 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (24 on average).

How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Chesapeake?

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Chesapeake?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Chesapeake. Price data was last updated on July 18, 2026.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Chesapeake flight should consider departing on Tuesday at noon when fares are most often at their lowest. Tuesday 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 July 20, 2026.
Read reviews from past customers who have flown United Airlines,American Airlines, andFrontier from Chicago O'Hare Intl Airport to Chesapeake. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
10,013 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Tim,May 2023

ORD - DLH

Didn’t have to wait long for the plane and was in the lounge through that time could relax there made it nice.
United Airlines
7.4
Good
10,013 reviews
United Airlines
7.4
Good
10,013 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Tim,May 2023

ORD - DLH

Didn’t have to wait long for the plane and was in the lounge through that time could relax there made it nice.
American Airlines
7.1
Good
11,832 reviews
United Airlines
7.4
Good
10,013 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Tim,May 2023

ORD - DLH

Didn’t have to wait long for the plane and was in the lounge through that time could relax there made it nice.
Frontier
5.6
Fair
2,779 reviews
United Airlines
7.4
Good
10,013 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Tim,May 2023

ORD - DLH

Didn’t have to wait long for the plane and was in the lounge through that time could relax there made it nice.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Chesapeake. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago O'Hare Intl Airport to Chesapeake?

    A quick flight from Chicago O'Hare Intl Airport to Chesapeake can take about 2h 33m. United Airlines provides one of the quickest options available for as low as $337. Airlines will cover a distance of 715 mi. Generally, flights for this route are nonstop.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Chesapeake one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $94. American Airlines flights start at $131 while deals on United Airlines start at $137 one-way.

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Chesapeake?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago O'Hare Intl Airport to Chesapeake on time: Air Canada (81%), Envoy Air (78%), Air New Zealand (74%).

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Chesapeake?

    While on average a flight from Chicago O'Hare Intl Airport to Chesapeake is generally $643, our data shows the cheapest flight currently is $122. When looking at the most popular route, (Chicago O'Hare Intl - Norfolk), you can expect to pay $248 for that flight.

  • Can I find deals for flights from O'Hare Intl to Chesapeake that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Chesapeake flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Chesapeake?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Chesapeake.

  • Can I find deals for business class flights from O'Hare Intl to Chesapeake?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Chesapeake by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Top 3 airlines flying from O'Hare Intl to Chesapeake

Discover the top 3 airlines that operate flights from O'Hare Intl 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 July 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$102Average$267FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$219Average$409FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$256Average$451FlexibilityNo cancel feeOn-time71%

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