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Chesapeake

$105+ 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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — RIC
Jul 22 — Jul 291
Wed 7/22
Wed 7/29
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 August, 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 June 22, 2026.

This CheapOair deal was found by Cheapflights users on 6/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:00 am
ORD
-
ORF
2 stops10h 12m
Multiple Airlines
Sat 8/159:34 pm
ORF
-
ORD
1 stop26h 36m
Multiple Airlines
Deal found 6/18$331
This CheapOair deal was found by Cheapflights users on 6/21. 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 9/249:26 am
ORD
-
ORF
1 stop6h 49m
Multiple Airlines
Mon 9/287:05 pm
ORF
-
ORD
2 stops17h 42m
Multiple Airlines
Deal found 6/21$332
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Tue 7/75:13 pm
ORD
-
ORF
2 stops17h 02m
Frontier
Thu 7/912:10 pm
ORF
-
ORD
1 stop8h 43m
Frontier
Deal found 6/17$333
This American Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:16 pm
ORD
-
ORF
Nonstop2h 25m
American Airlines
Sun 9/206:13 am
ORF
-
ORD
Nonstop2h 47m
American Airlines
Deal found 6/21$334
This American Airlines deal was found by Cheapflights users on 6/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/282:52 pm
ORD
-
ORF
Nonstop2h 24m
American Airlines
Sat 8/16:50 am
ORF
-
ORD
Nonstop2h 40m
American Airlines
Deal found 6/18$335
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Tue 7/75:13 pm
ORD
-
ORF
2 stops17h 02m
Frontier
Sat 7/1112:16 pm
ORF
-
ORD
1 stop8h 37m
Frontier
Deal found 6/17$336
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:45 am
ORD
-
ORF
Nonstop2h 22m
United Airlines
Sat 7/410:48 am
ORF
-
ORD
Nonstop2h 39m
United Airlines
Deal found 6/18$337
This CheapOair deal was found by Cheapflights users on 6/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/165:13 pm
ORD
-
ORF
1 stop26h 26m
Multiple Airlines
Tue 7/216:00 pm
ORF
-
ORD
2 stops24h 34m
Multiple Airlines
Deal found 6/18$338
This Kiwi.com deal was found by Cheapflights users on 6/18. 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.
Wed 7/11:29 pm
ORD
-
ORF
1 stop20h 57m
Frontier
Sat 7/412:06 pm
ORF
-
ORD
1 stop8h 44m
Frontier
Deal found 6/18$339
This Delta deal was found by Cheapflights users on 6/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:05 am
ORD
-
ORF
1 stop4h 01m
Delta
Sun 11/227:40 pm
ORF
-
ORD
1 stop5h 10m
Delta
Deal found 6/17$340
This United Airlines deal was found by Cheapflights users on 6/21. 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 7/186:45 am
ORD
-
ORF
Nonstop2h 22m
United Airlines
Sat 7/256:00 am
ORF
-
ORD
Nonstop2h 29m
United Airlines
Deal found 6/21$341
This Travelocity deal was found by Cheapflights users on 6/17. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/34:59 pm
ORD
-
ORF
1 stop25h 14m
Frontier
Mon 7/69:34 pm
ORF
-
ORD
1 stop26h 36m
Frontier
Deal found 6/17$342

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 June 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$331
(CheapOair)

One-way from

$105
(Kiwi.com)

Popular in

July

Cheapest in

January

Average price

$393
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
Search Deals
One-way flight from Chicago O'Hare Intl to Chesapeake
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in June 2026
Search Deals

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 June 22, 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

Sat 7/18

6:45 am-10:07 am

Nonstop2h 22m

Norfolk

Sat 7/25

6:00 am-7:29 am

Nonstop2h 29m

$341

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 6/30

6:45 am-10:07 am

Nonstop2h 22m

Norfolk

Sat 7/4

6:00 am-11:04 am

1 stop6h 04m

$347

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 9/1

10:55 am-2:17 pm

Nonstop2h 22m

Norfolk

Wed 9/2

1:00 pm-2:34 pm

Nonstop2h 34m

$357
Quickest round-trip

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 8/15

10:55 am-2:17 pm

Nonstop2h 22m

Norfolk

Wed 8/19

5:02 pm-6:30 pm

Nonstop2h 28m

$357

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Mon 7/20

7:14 pm-10:39 pm

Nonstop2h 25m

Norfolk

Fri 7/24

6:46 pm-8:32 pm

Nonstop2h 46m

$363

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 7/23

6:45 am-10:07 am

Nonstop2h 22m

Norfolk

Mon 7/27

6:00 am-7:29 am

Nonstop2h 29m

$363

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sun 9/13

11:30 am-2:52 pm

Nonstop2h 22m

Norfolk

Fri 9/18

5:02 pm-6:30 pm

Nonstop2h 28m

$363

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sun 7/26

5:07 am-10:35 am

1 stop4h 28m

Norfolk

Sat 8/1

6:24 pm-8:10 pm

Nonstop2h 46m

$373

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 9/4

6:15 pm-9:41 pm

Nonstop2h 26m

Norfolk

Sun 9/13

6:15 am-11:46 am

1 stop6h 31m

$373
Cheapest one-way

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sun 8/16

1:50 pm-11:15 am

1 stop20h 25m

$130

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 June 22, 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 6% 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 June 22, 2026.

The most flights from ORD to C6E are scheduled on a Monday (28 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (12 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 June 20, 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 June 22, 2026.
Read reviews from past customers who have flown United Airlines and American Airlines 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
9,868 reviews

Comfort

7.3

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
United Airlines
7.4
Good
9,868 reviews
United Airlines
7.4
Good
9,868 reviews

Comfort

7.3

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
American Airlines
7.1
Good
11,723 reviews
United Airlines
7.4
Good
9,868 reviews

Comfort

7.3

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

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 22m. United Airlines provides one of the quickest options available for as low as $341. 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 $72. American Airlines flights start at $131 while deals on United Airlines start at $133 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: Royal Jordanian (87%), Air Canada (79%), Republic Airways (79%).

  • 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 $418, our data shows the cheapest flight currently is $134. When looking at the most popular route, (Chicago O'Hare Intl - Norfolk), you can expect to pay $258 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 2 airlines flying from O'Hare Intl to Chesapeake

Discover the top 2 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 June 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$217Average$407FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$256Average$446FlexibilityNo cancel feeOn-time71%

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