HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chesapeake

$87+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — RIC
Apr 7 — Apr 141
Mon 4/7
Mon 4/14
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 September or March, booked 38 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 April 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$238
(Mytrip)

One-way from

$87
(Mytrip)

Popular in

February

Cheapest in

September

Average price

$362
Provider with most accurate pricing for Chicago (CHI)-Norfolk flight deals.
Search Deals
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. 0% potential increase in price ($0 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 2, 2025.

This Mytrip deal was found by Cheapflights users on 3/31. 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 5/910:00 amORD - ORF
3 stops27h 16mSpirit Airlines
Sun 5/116:31 pmORF - ORD
1 stop13h 56mSpirit Airlines
Deal found 3/31$238
This Frontier deal was found by Cheapflights users on 4/1. 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 8/95:10 amORD - ORF
1 stop10h 07mFrontier
Wed 8/135:06 pmORF - ORD
1 stop8h 16mFrontier
Deal found 4/1$240
This Booking.com deal was found by Cheapflights users on 4/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/119:54 amORD - ORF
1 stop27h 42mMultiple Airlines
Wed 4/166:13 pmORF - ORD
1 stop7h 07mMultiple Airlines
Deal found 4/1$247
This United Airlines deal was found by Cheapflights users on 4/1. 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 4/226:15 pmORD - ORF
Nonstop2h 19mUnited Airlines
Wed 4/234:44 pmORF - ORD
Nonstop2h 27mUnited Airlines
Deal found 4/1$271
This Delta deal was found by Cheapflights users on 3/31. 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.
Sun 5/257:10 amORD - ORF
1 stop4h 06mDelta
Sat 5/315:35 amORF - ORD
1 stop7h 45mDelta
Deal found 3/31$285
This American Airlines deal was found by Cheapflights users on 4/1. 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 4/2212:07 pmORD - ORF
1 stop4h 20mAmerican Airlines
Thu 4/247:00 amORF - ORD
Nonstop2h 33mAmerican Airlines
Deal found 4/1$298
This Southwest deal was found by Cheapflights users on 3/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/21:50 pmORD - ORF
1 stop3h 55mSouthwest
Sat 6/76:00 amORF - ORD
2 stops11h 25mSouthwest
Deal found 3/31$370

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 April 2, 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

Fri 5/9

10:00 am-2:16 pm

3 stops27h 16m

Norfolk

Sun 5/11

6:31 pm-7:27 am

1 stop13h 56m

$238

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 8/9

5:10 am-4:17 pm

1 stop10h 07m

Norfolk

Wed 8/13

5:06 pm-12:22 am

1 stop8h 16m

$240

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 4/11

9:54 am-2:36 pm

1 stop27h 42m

Norfolk

Wed 4/16

6:13 pm-12:20 am

1 stop7h 07m

$247

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 4/22

6:15 pm-9:34 pm

Nonstop2h 19m

Norfolk

Wed 4/23

4:44 pm-6:11 pm

Nonstop2h 27m

$271

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 5/24

3:58 pm-9:17 pm

1 stop4h 19m

Norfolk

Sun 5/25

7:00 am-8:23 am

Nonstop2h 23m

$275

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sun 5/25

7:10 am-12:16 pm

1 stop4h 06m

Norfolk

Sat 5/31

5:35 am-12:20 pm

1 stop7h 45m

$285

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Mon 6/2

1:50 pm-6:45 pm

1 stop3h 55m

Norfolk

Sat 6/7

6:00 am-4:25 pm

2 stops11h 25m

$370

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 4/29

7:47 pm-12:19 am

1 stop27h 32m

$87

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 5/6

8:45 am-5:07 pm

1 stop7h 22m

$101

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 5/1

6:00 am-3:46 pm

1 stop8h 46m

$105

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 15 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 March 28, 2025.

The best time to book flights from Chicago O'Hare Intl Airport to Chesapeake is 38 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 June is currently the most expensive (average of $372). 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 April 2, 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 March 30, 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 April 2, 2025.

The most flights from ORD to C6E are scheduled on a Tuesday (20 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (8 on average).

Rainfall in Chesapeake by month

Plan your trip to Chesapeake by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chesapeake ranges from 2.9 - 5.8 inches per month. July is typically the wettest month, when rainfall can reach 5.8 in. November is typically the driest time to visit Chesapeake when rainfall is around 2.9 in.

Temperature in Chesapeake by month

Plan your trip to Chesapeake by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chesapeake, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 42.8 F).

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 April 2, 2025.
Get a feel of what it's like to fly with Southwest, Delta and United Airlines from Chicago to Chesapeake by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,898 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,616 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,922 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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.

  • 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 $87. JetBlue flights start at $101 while deals on Frontier start at $105 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: GoJet (92%), Air Canada (86%), Air New Zealand (86%).

  • 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 $291, our data shows the cheapest flight currently is $139. 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 $281). Flying from Chicago O'Hare Intl Airport to Chesapeake in June is currently the most expensive (average of $372). 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 Dulles Intl flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Raleigh flights
Midway to Dulles Intl flights
Midway to Reagan-National flights
O'Hare Intl to Norfolk flights
O'Hare Intl to Richmond flights
Midway to Raleigh flights
Midway to Norfolk flights
O'Hare Intl to Roanoke flights
O'Hare Intl to Greensboro flights
O'Hare Intl to Charlottesville flights
Midway to Richmond flights
Midway to Roanoke flights
Midway to Charlottesville flights
Midway to Greensboro flights
O'Hare Intl to Blountville flights
O'Hare Intl to Newport News flights
O'Hare Intl to Staunton flights
O'Hare Intl to Salisbury flights
Midway to Blountville flights
O'Hare Intl to Lynchburg flights
Midway to Newport News flights
O'Hare Intl to Lewisburg 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 April 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$116Average$215FlexibilityNo cancel feeOn-time65%
DeltaCheapest$175Average$366FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$200Average$374FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$207Average$418FlexibilityNo cancel feeOn-time69%

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.