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Chesapeake

$73+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — RIC
Apr 17 — Apr 241
Fri 4/17
Fri 4/24
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 April, booked 75 days in advance, depart on a Tuesday 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 March 18, 2026.

This Frontier deal was found by Cheapflights users on 3/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/225:01 am
ORD
-
ORF
1 stop8h 54m
Frontier
Fri 4/2411:27 am
ORF
-
ORD
1 stop12h 12m
Frontier
Deal found 3/17$295
This CheapOair deal was found by Cheapflights users on 3/17. 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.
Thu 6/45:30 pm
ORD
-
ORF
1 stop25h 47m
Multiple Airlines
Mon 6/85:41 pm
ORF
-
ORD
1 stop7h 46m
Multiple Airlines
Deal found 3/17$296
This United Airlines deal was found by Cheapflights users on 3/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/73:35 pm
ORD
-
ORF
Nonstop2h 25m
United Airlines
Wed 4/89:45 am
ORF
-
ORD
Nonstop2h 42m
United Airlines
Deal found 3/17$297
This CheapOair deal was found by Cheapflights users on 3/17. 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.
Wed 4/159:41 am
ORD
-
ORF
1 stop23h 51m
Multiple Airlines
Sat 4/1811:27 am
ORF
-
ORD
1 stop12h 12m
Multiple Airlines
Deal found 3/17$298
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 3/317:17 am
ORD
-
ORF
1 stop11h 29m
Multiple Airlines
Mon 4/68:41 pm
ORF
-
ORD
2 stops15h 03m
Multiple Airlines
Deal found 3/14$299
This Frontier deal was found by Cheapflights users on 3/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/235:01 am
ORD
-
ORF
1 stop5h 37m
Frontier
Thu 3/2611:50 am
ORF
-
ORD
1 stop11h 49m
Frontier
Deal found 3/16$300
This CheapOair deal was found by Cheapflights users on 3/13. 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.
Sat 5/165:30 pm
ORD
-
ORF
1 stop25h 47m
Frontier
Sat 5/3012:00 pm
ORF
-
ORD
1 stop8h 51m
Frontier
Deal found 3/13$301
This United Airlines deal was found by Cheapflights users on 3/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/155:48 pm
ORD
-
ORF
Nonstop2h 20m
United Airlines
Sat 4/185:05 pm
ORF
-
ORD
Nonstop2h 42m
United Airlines
Deal found 3/13$303
This Mytrip deal was found by Cheapflights users on 3/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/247:15 pm
ORD
-
ORF
2 stops18h 05m
Spirit Airlines
Fri 5/18:57 pm
ORF
-
ORD
2 stops25h 15m
Spirit Airlines
Deal found 3/17$304
This Mytrip deal was found by Cheapflights users on 3/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1712:47 pm
ORD
-
ORF
3 stops24h 33m
Spirit Airlines
Mon 4/208:57 pm
ORF
-
ORD
2 stops14h 26m
Spirit Airlines
Deal found 3/17$305
This CheapOair deal was found by Cheapflights users on 3/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/254:18 pm
ORD
-
ORF
1 stop24h 30m
Frontier
Mon 3/3011:33 am
ORF
-
ORD
1 stop12h 06m
Frontier
Deal found 3/16$306

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 March 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$295
(Kiwi.com)

One-way from

$73
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$470
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.
Search Deals
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. 4% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 18, 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 4/23

11:00 am-2:20 pm

Nonstop2h 20m

Norfolk

Mon 4/27

6:00 am-7:31 am

Nonstop2h 31m

$297

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Wed 4/15

5:48 pm-9:08 pm

Nonstop2h 20m

Norfolk

Sat 4/18

5:05 pm-6:47 pm

Nonstop2h 42m

$303

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 4/24

5:00 am-10:12 am

1 stop4h 12m

Norfolk

Wed 5/6

8:01 pm-9:42 pm

Nonstop2h 41m

$344

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 5/1

2:40 pm-10:55 pm

2 stops7h 15m

Norfolk

Tue 5/5

6:50 am-4:05 pm

2 stops10h 15m

$350

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 4/24

2:30 pm-10:36 pm

1 stop7h 06m

Norfolk

Wed 5/6

11:05 am-4:47 pm

1 stop6h 42m

$360

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 5/15

2:40 pm-10:55 pm

2 stops7h 15m

Norfolk

Wed 5/20

6:50 am-4:05 pm

2 stops10h 15m

$364
Quickest round-trip

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 6/4

6:45 am-10:07 am

Nonstop2h 22m

Norfolk

Sun 6/7

6:00 am-7:28 am

Nonstop2h 28m

$366

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 4/16

11:00 am-2:20 pm

Nonstop2h 20m

Norfolk

Mon 4/20

6:00 am-7:31 am

Nonstop2h 31m

$367

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 5/28

2:40 pm-10:55 pm

2 stops7h 15m

Norfolk

Mon 6/1

6:05 am-2:20 pm

2 stops9h 15m

$377

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 4/17

6:00 am-4:50 pm

2 stops9h 50m

Norfolk

Tue 4/21

6:50 am-4:05 pm

2 stops10h 15m

$382

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/14

Showing 1-10 of 23 resultsSorted by cheapest first
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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

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Chesapeake?

Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to Chesapeake. Price data was last updated on March 13, 2026.

The best time to book flights from Chicago O'Hare Intl Airport to Chesapeake is 75 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 O'Hare Intl Airport to Chesapeake?

Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Chesapeake (average of $130). Flying from Chicago O'Hare Intl Airport 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 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 March 18, 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 1% on the flight price compared to flying at noon, which is usually more expensive.

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 March 14, 2026.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Chesapeake flight should consider departing on Monday evenings 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 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 March 18, 2026.

The most flights from ORD to C6E are scheduled on a Monday (22 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (11 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 March 18, 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
9,435 reviews

Boarding

7.7

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,435 reviews
United Airlines
7.4
Good
9,435 reviews

Boarding

7.7

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.1
Good
11,468 reviews
United Airlines
7.4
Good
9,435 reviews

Boarding

7.7

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 20m. United Airlines provides one of the quickest options available for as low as $297. Airlines will cover a distance of 715 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $93. American Airlines flights start at $130 while deals on United Airlines start at $132 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: Envoy Air (79%), GoJet (72%), United Airlines (70%).

  • 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 $320, 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 $196 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.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Chesapeake?

    Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Chesapeake (average of $130). Flying from Chicago O'Hare Intl Airport 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.

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 March 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$217Average$389FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$236Average$397FlexibilityNo cancel feeOn-time71%

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