HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chesapeake

$59+ 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
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from O'Hare Intl to Chesapeake 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 Chicago O'Hare Intl to Chesapeake are usually found in April or August, booked 43 days in advance, depart on a Tuesday or Thursday and return on a Friday

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 September 15, 2025.

Round-trip from

$200
(Priceline)

One-way from

$59
(American Airlines)

Popular in

September

Cheapest in

April

Average price

$455
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. 1% potential increase in price ($6 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 15, 2025.

This Priceline deal was found by Cheapflights users on 9/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/95:05 amORD - ORF
1 stop8h 49mMultiple Airlines
Sun 10/125:24 amORF - ORD
1 stop6h 26mMultiple Airlines
Deal found 9/13$200
This Priceline deal was found by Cheapflights users on 9/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/246:00 amORD - ORF
1 stop9h 39mSpirit Airlines
Mon 10/275:24 amORF - ORD
1 stop6h 26mSpirit Airlines
Deal found 9/12$201
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Thu 10/95:05 amORD - ORF
1 stop8h 49mFrontier
Sun 10/124:14 pmORF - ORD
2 stops24h 35mFrontier
Deal found 9/13$204
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/235:05 amORD - ORF
1 stop8h 49mMultiple Airlines
Mon 10/275:24 amORF - ORD
1 stop6h 26mMultiple Airlines
Deal found 9/15$208
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Sat 9/2712:22 pmORD - ORF
1 stop21h 57mFrontier
Thu 10/212:19 pmORF - ORD
2 stops12h 01mFrontier
Deal found 9/13$212
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Sun 9/288:49 pmORD - ORF
2 stops13h 35mMultiple Airlines
Thu 10/25:12 pmORF - ORD
1 stop24h 00mMultiple Airlines
Deal found 9/13$215
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Thu 10/25:50 pmORD - ORF
1 stop16h 34mFrontier
Sun 10/55:47 pmORF - ORD
2 stops17h 44mFrontier
Deal found 9/14$219
This Trip.com deal was found by Cheapflights users on 9/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/185:10 amORD - ORF
1 stop5h 14mFrontier
Sun 9/215:47 pmORF - ORD
1 stop26h 57mFrontier
Deal found 9/13$223
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/251:14 pmORD - ORF
2 stops18h 48mFrontier
Thu 10/301:06 pmORF - ORD
2 stops11h 22mFrontier
Deal found 9/15$224
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Thu 10/25:50 pmORD - ORF
1 stop16h 34mMultiple Airlines
Mon 10/66:53 pmORF - ORD
2 stops24h 45mMultiple Airlines
Deal found 9/13$227
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Wed 10/156:58 pmORD - ORF
1 stop13h 04mMultiple Airlines
Sun 10/195:38 pmORF - ORD
2 stops18h 40mMultiple Airlines
Deal found 9/14$232

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 September 15, 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 10/9

5:05 am-2:54 pm

1 stop8h 49m

Norfolk

Sun 10/12

5:24 am-10:50 am

1 stop6h 26m

$200

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 10/24

6:00 am-4:39 pm

1 stop9h 39m

Norfolk

Mon 10/27

5:24 am-10:50 am

1 stop6h 26m

$201

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 9/18

5:10 am-11:24 am

1 stop5h 14m

Norfolk

Sun 9/21

5:47 pm-7:44 pm

1 stop26h 57m

$223

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sun 9/28

8:49 pm-5:51 pm

2 stops20h 02m

Norfolk

Thu 10/2

5:12 pm-9:37 am

2 stops17h 25m

$247

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 12/6

10:18 am-7:37 pm

1 stop8h 19m

Norfolk

Mon 12/8

7:30 am-9:00 pm

1 stop14h 30m

$261

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 10/24

6:59 pm-12:11 am

1 stop4h 12m

Norfolk

Mon 10/27

7:45 pm-11:58 pm

1 stop5h 13m

$265

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 10/10

2:41 pm-12:27 pm

2 stops20h 46m

Norfolk

Sun 10/12

7:00 am-1:15 pm

1 stop7h 15m

$267

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Wed 10/15

11:20 am-2:40 pm

Nonstop2h 20m

Norfolk

Sat 11/1

6:00 am-10:45 am

1 stop5h 45m

$285

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 12/6

8:05 am-11:25 am

Nonstop2h 20m

Norfolk

Mon 12/8

3:13 pm-4:55 pm

Nonstop2h 42m

$294

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 10/25

6:15 pm-9:37 pm

Nonstop2h 22m

Norfolk

Thu 10/30

6:35 am-8:01 am

Nonstop2h 26m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 20 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 September 12, 2025.

The best time to book flights from Chicago O'Hare Intl Airport to Chesapeake is 43 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 $281). Flying from Chicago O'Hare Intl Airport to Chesapeake in March is currently the most expensive (average of $351). 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 September 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago O'Hare Intl Airport to Chesapeake as you normally would.

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 September 14, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Chesapeake flight should consider departing on Thursday 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 September 15, 2025.

The most flights from ORD to C6E are scheduled on a Monday (28 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (22 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 September 15, 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
8,929 reviews

Food

6.6

Crew

8.1

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,929 reviews
United Airlines
7.4
Good
8,929 reviews

Food

6.6

Crew

8.1

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,929 reviews

Food

6.6

Crew

8.1

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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 5h 14m. Spirit Airlines provides one of the quickest options available for as low as $223. 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 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 (80%), GoJet (77%), United Airlines (75%).

  • 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 $334, our data shows the cheapest flight currently is $96. When looking at the most popular route, (Chicago O'Hare Intl - Norfolk), you can expect to pay $179 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 $281). Flying from Chicago O'Hare Intl Airport to Chesapeake in March is currently the most expensive (average of $351). 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

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.

Alternative routes for O'Hare Intl to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Reagan-National flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Raleigh flights
Midway to Dulles Intl flights
O'Hare Intl to Richmond flights
Midway to Reagan-National flights
Midway to Raleigh flights
O'Hare Intl to Norfolk flights
Midway to Richmond flights
O'Hare Intl to Greensboro flights
O'Hare Intl to Charlottesville flights
O'Hare Intl to Roanoke flights
Midway to Norfolk flights
Midway to Greensboro flights
Midway to Charlottesville flights
Midway to Roanoke flights
O'Hare Intl to Blountville flights
Midway to Blountville flights
O'Hare Intl to Lynchburg flights
O'Hare Intl to Newport News flights
O'Hare Intl to Staunton flights
O'Hare Intl to Salisbury flights
O'Hare Intl to Lewisburg flights
Midway to Newport News flights

Top 4 airlines flying from O'Hare Intl to Chesapeake

Discover the top 4 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$78Average$245FlexibilityNo cancel feeOn-time65%
DeltaCheapest$142Average$366FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$217Average$435FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$229Average$395FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.