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Chesapeake

$70+ 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 6/30. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — RIC
Jun 6 — Jun 131
Sat 6/6
Sat 6/13
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 58 days in advance, depart on a Wednesday or Saturday 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 May 7, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/5. 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 5/201:59 pm
ORD
-
ORF
1 stop20h 12m
Frontier
Mon 5/2512:06 pm
ORF
-
ORD
1 stop20h 49m
Frontier
Deal found 5/5$307
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 6/301:29 pm
ORD
-
ORF
1 stop20h 57m
Frontier
Wed 7/89:35 pm
ORF
-
ORD
2 stops23h 18m
Frontier
Deal found 5/6$308
This Frontier deal was found by Cheapflights users on 5/5. 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.
Thu 5/285:11 pm
ORD
-
ORF
1 stop26h 06m
Frontier
Mon 6/112:06 pm
ORF
-
ORD
1 stop8h 45m
Frontier
Deal found 5/5$310
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/201:59 pm
ORD
-
ORF
1 stop20h 12m
Frontier
Sun 5/2412:06 pm
ORF
-
ORD
1 stop8h 35m
Frontier
Deal found 5/4$312
This Kiwi.com deal was found by Cheapflights users on 5/4. 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.
Fri 6/121:29 pm
ORD
-
ORF
1 stop20h 52m
Frontier
Mon 6/1512:21 pm
ORF
-
ORD
1 stop20h 42m
Frontier
Deal found 5/4$313
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 6/46:55 am
ORD
-
ORF
1 stop27h 16m
Frontier
Sun 6/712:06 pm
ORF
-
ORD
1 stop8h 23m
Frontier
Deal found 5/3$314
This Frontier deal was found by Cheapflights users on 5/5. 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.
Fri 6/2610:16 am
ORD
-
ORF
1 stop9h 24m
Frontier
Mon 6/2912:21 pm
ORF
-
ORD
1 stop8h 29m
Frontier
Deal found 5/5$315
This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Fri 7/31:29 pm
ORD
-
ORF
1 stop20h 52m
Frontier
Sun 7/512:21 pm
ORF
-
ORD
1 stop8h 32m
Frontier
Deal found 5/6$316
This United Airlines deal was found by Cheapflights users on 5/3. 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 6/26:45 am
ORD
-
ORF
Nonstop2h 22m
United Airlines
Tue 6/98:00 am
ORF
-
ORD
Nonstop2h 32m
United Airlines
Deal found 5/3$317
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 5/186:55 am
ORD
-
ORF
1 stop27h 16m
Frontier
Mon 5/2512:06 pm
ORF
-
ORD
1 stop20h 49m
Frontier
Deal found 5/5$318
This CheapOair deal was found by Cheapflights users on 5/2. 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 7/14:59 pm
ORD
-
ORF
1 stop26h 41m
Frontier
Mon 7/69:35 pm
ORF
-
ORD
1 stop26h 30m
Frontier
Deal found 5/2$319
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 6/158:00 pm
ORD
-
ORF
2 stops38h 26m
Frontier
Thu 6/2512:21 pm
ORF
-
ORD
1 stop8h 29m
Frontier
Deal found 5/2$320

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 May 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$307
(Kiwi.com)

One-way from

$70
(Kiwi.com)

Popular in

September

Cheapest in

January

Average price

$360
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. 2% potential increase in price ($8 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 7, 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 6/4

6:45 am-10:07 am

Nonstop2h 22m

Norfolk

Sun 6/7

6:00 am-7:28 am

Nonstop2h 28m

$359

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 7/7

10:51 am-7:22 pm

1 stop7h 31m

Norfolk

Sun 7/12

6:00 am-7:28 am

Nonstop2h 28m

$360
Quickest round-trip

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sun 7/12

12:22 pm-3:43 pm

Nonstop2h 21m

Norfolk

Sun 7/19

6:00 am-7:28 am

Nonstop2h 28m

$363

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sun 8/30

11:33 am-2:51 pm

Nonstop2h 18m

Norfolk

Sun 9/6

8:10 am-9:42 am

Nonstop2h 32m

$363

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 7/30

12:22 pm-3:43 pm

Nonstop2h 21m

Norfolk

Fri 7/31

5:00 pm-6:32 pm

Nonstop2h 32m

$363

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Mon 7/6

5:30 am-11:34 am

1 stop5h 04m

Norfolk

Tue 7/7

6:02 am-1:02 pm

1 stop8h 00m

$370

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 9/4

2:00 pm-5:18 pm

Nonstop2h 18m

Norfolk

Mon 9/7

6:20 am-9:33 am

1 stop4h 13m

$373

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sun 7/19

6:45 am-10:07 am

Nonstop2h 22m

Norfolk

Sun 7/26

6:05 am-9:36 am

1 stop4h 31m

$373

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 7/2

6:22 pm-12:42 am

1 stop5h 20m

Norfolk

Sun 7/5

10:16 am-2:29 pm

1 stop5h 13m

$383

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 6/2

9:29 pm-12:57 am

Nonstop2h 28m

Norfolk

Wed 6/3

5:44 pm-11:31 pm

1 stop6h 47m

$407

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/6

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
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

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 May 7, 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 8% 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 May 2, 2026.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Chesapeake flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday afternoons 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 May 7, 2026.

The most flights from ORD to C6E are scheduled on a Wednesday (29 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (17 on average).

How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Chesapeake?

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 May 7, 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
9,690 reviews

Entertainment

7.1

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
United Airlines
7.4
Good
9,690 reviews
United Airlines
7.4
Good
9,690 reviews

Entertainment

7.1

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
American Airlines
7.1
Good
11,669 reviews
United Airlines
7.4
Good
9,690 reviews

Entertainment

7.1

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.

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 $359. 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 $93. American Airlines flights start at $130 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: GoJet (83%), United Airlines (74%), Air Canada (74%).

  • 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 $350, our data shows the cheapest flight currently is $149. When looking at the most popular route, (Chicago O'Hare Intl - Norfolk), you can expect to pay $226 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 May 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$217Average$392FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$236Average$427FlexibilityNo cancel feeOn-time71%

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