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Chesapeake

Cheap flights from O'Hare Intl (ORD) to Chesapeake, VA

ORD — RIC
Oct 25 — Nov 11
Sun 10/25
Sun 11/1
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 May, booked 62 days in advance, depart on a Saturday or Wednesday and return on a Thursday

Find flight deals from O'Hare Intl to Chesapeake

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

August

Cheapest in

January

Average price

$399
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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Highest demand for flights based on searches. 5% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in September 2026
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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?

It’s typically best to fly out from Chicago O'Hare Intl Airport to Chesapeake in the evening. Doing so could potentially save you 6% on the flight price compared to flying in the afternoon, which is usually more expensive.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Chesapeake?

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Chesapeake flight should consider departing on Wednesday evenings when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Chesapeake

Read reviews from past customers who have flown United Airlines,American Airlines, andFrontier 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
10,239 reviews

Food

6.7

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible
United Airlines
7.4
Good
10,239 reviews
United Airlines
7.4
Good
10,239 reviews

Food

6.7

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible
American Airlines
7.0
Good
12,089 reviews
United Airlines
7.4
Good
10,239 reviews

Food

6.7

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible
Frontier
5.6
Fair
2,576 reviews
United Airlines
7.4
Good
10,239 reviews

Food

6.7

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible

Related info for your journey

  • 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 American Airlines, which is currently one of the cheapest options available, starting at $137. United Airlines flights start at $140 while deals on Delta start at $141 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 (77%), Republic Airways (77%), United Airlines (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 $459, our data shows the cheapest flight currently is $168. When looking at the most popular route, (Chicago O'Hare Intl - Norfolk), you can expect to pay $274 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 3 airlines flying from O'Hare Intl to Chesapeake

AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$226Average$320FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$263Average$418FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$265Average$466FlexibilityNo cancel feeOn-time71%

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