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Chesapeake

$58+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — RIC
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Chesapeake are usually found in April or August, booked 68 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

Cheap 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 October 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$110
(Priceline)

One-way from

$58
(Mytrip)

Popular in

February

Cheapest in

April

Average price

$375
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
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Highest demand for flights based on searches. 4% potential increase in price ($15 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 October 2025
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Find 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 October 30, 2025.

This Priceline deal was found by Cheapflights users on 10/29. 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.
Thu 11/135:25 amORD - ORF
1 stop6h 50mFrontier
Thu 11/133:20 pmORF - ORD
1 stop9h 51mFrontier
Deal found 10/29$110
This Priceline deal was found by Cheapflights users on 10/30. 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.
Thu 11/135:25 amORD - ORF
1 stop6h 50mFrontier
Mon 11/1711:29 amORF - ORD
1 stop6h 27mFrontier
Deal found 10/30$127
This Priceline deal was found by Cheapflights users on 10/29. 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.
Thu 11/65:01 amORD - ORF
1 stop4h 45mFrontier
Thu 11/133:20 pmORF - ORD
1 stop9h 51mFrontier
Deal found 10/29$143
This Priceline deal was found by Cheapflights users on 10/29. 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.
Wed 11/1210:52 amORD - ORF
1 stop7h 06mMultiple Airlines
Thu 11/133:20 pmORF - ORD
1 stop9h 51mMultiple Airlines
Deal found 10/29$158
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sun 11/237:09 pmORD - ORF
1 stop13h 34mMultiple Airlines
Tue 12/29:26 pmORF - ORD
1 stop19h 37mMultiple Airlines
Deal found 10/29$167
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/206:23 pmORD - ORF
1 stop25h 08mMultiple Airlines
Tue 12/29:26 pmORF - ORD
1 stop19h 37mMultiple Airlines
Deal found 10/29$172
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/46:15 amORD - ORF
1 stop12h 01mMultiple Airlines
Thu 12/118:38 amORF - ORD
1 stop6h 43mMultiple Airlines
Deal found 10/28$174
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sun 11/237:09 pmORD - ORF
1 stop13h 34mMultiple Airlines
Mon 12/19:26 pmORF - ORD
1 stop26h 40mMultiple Airlines
Deal found 10/29$179
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/246:48 amORD - ORF
1 stop12h 43mSpirit Airlines
Tue 12/29:26 pmORF - ORD
1 stop19h 37mSpirit Airlines
Deal found 10/29$181
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/206:23 pmORD - ORF
1 stop25h 08mMultiple Airlines
Mon 12/19:26 pmORF - ORD
1 stop26h 40mMultiple Airlines
Deal found 10/29$183
This Trip.com deal was found by Cheapflights users on 10/30. 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.
Thu 11/135:25 amORD - ORF
1 stop6h 50mFrontier
Sun 11/161:06 pmORF - ORD
1 stop24h 10mFrontier
Deal found 10/30$185

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 October 30, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Chesapeake that are best for you.

Fly from

O'Hare Intl

Fly to

Chesapeake

Route

Depart

Return

Price

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 11/13

5:11 am-2:25 pm

1 stop8h 14m

Norfolk

Mon 11/17

11:29 am-4:56 pm

1 stop6h 27m

$150

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 12/6

7:10 am-7:16 pm

1 stop11h 06m

Norfolk

Mon 12/8

8:38 am-2:21 pm

1 stop6h 43m

$212

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 12/11

5:00 am-7:16 pm

1 stop13h 16m

Norfolk

Thu 12/18

3:01 pm-12:30 am

1 stop10h 29m

$217

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 11/13

12:17 pm-6:58 pm

3 stops29h 41m

Norfolk

Mon 11/17

7:53 pm-6:34 pm

2 stops23h 41m

$256

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 11/25

5:00 am-12:28 pm

1 stop6h 28m

Norfolk

Thu 11/27

9:56 am-2:14 pm

1 stop5h 18m

$296

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 12/6

7:10 am-2:25 pm

1 stop6h 15m

Norfolk

Mon 12/8

7:23 am-9:02 am

Nonstop2h 39m

$304

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 11/27

3:18 pm-6:30 pm

Nonstop2h 12m

Norfolk

Thu 12/4

3:52 pm-7:27 pm

1 stop4h 35m

$305

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 12/11

5:50 pm-9:00 pm

Nonstop2h 10m

Norfolk

Thu 12/18

6:30 am-8:05 am

Nonstop2h 35m

$313

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 12/23

5:00 am-2:06 pm

1 stop8h 06m

Norfolk

Thu 1/1

3:01 pm-12:30 am

1 stop10h 29m

$320

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Mon 1/26

7:00 am-7:37 pm

1 stop11h 37m

$80

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 19 results
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

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 October 24, 2025.

The best time to book flights from Chicago O'Hare Intl Airport to Chesapeake is 68 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, February is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Chesapeake (average of $149). Flying from Chicago O'Hare Intl Airport to Chesapeake in January is currently the most expensive (average of $270). 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 October 30, 2025.

It’s typically best to fly out from Chicago O'Hare Intl Airport to Chesapeake in the evening. Doing so could potentially save you 21% on the flight price compared to flying in the morning, 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 October 26, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Chesapeake flight should consider departing on Wednesday mornings 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.

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 October 30, 2025.
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
8,998 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
8,998 reviews
United Airlines
7.4
Good
8,998 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,035 reviews
United Airlines
7.4
Good
8,998 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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 8h 14m. Frontier provides one of the quickest options available for as low as $150. 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 Spirit Airlines, which is currently one of the cheapest options available, starting at $95. Frontier flights start at $114 while deals on United Airlines start at $129 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: Republic Airways (92%), Envoy Air (88%), United Airlines (83%).

  • 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 $322, our data shows the cheapest flight currently is $115. When looking at the most popular route, (Chicago O'Hare Intl - Norfolk), you can expect to pay $141 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, February is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Chesapeake (average of $149). Flying from Chicago O'Hare Intl Airport to Chesapeake in January is currently the most expensive (average of $270). 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.

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Alternative routes for O'Hare Intl to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.
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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$78Average$224FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$218Average$424FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$237Average$395FlexibilityNo cancel feeOn-time71%

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