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Chesapeake

$75+ Cheap flights from Chicago (CHI) 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 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Apr 8 — Apr 151
Tue 4/8
Tue 4/15
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Chesapeake are usually found in April or September, booked 73 days in advance, depart on a Tuesday or Thursday and return on a Thursday

Cheap flight deals from Chicago to Chesapeake

Keep the following information in mind while searching for Chicago to Chesapeake flight deals. Data was last updated April 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$238
(Mytrip)

One-way from

$75
(Mytrip)

Popular in

July

Cheapest in

April

Average price

$314
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 (CHI) to Chesapeake
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One-way flight from Chicago (CHI) to Chesapeake
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Highest demand for flights based on searches. 7% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Chicago to Chesapeake

Cheapest flights from Chicago to Chesapeake
Explore the most affordable flight options available from Chicago to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 3, 2025.

This Mytrip deal was found by Cheapflights users on 4/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/87:47 amORD - ORF
1 stop25h 42mSpirit Airlines
Fri 5/93:11 pmORF - ORD
2 stops29h 57mSpirit Airlines
Deal found 4/2$238
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/119:54 amORD - ORF
1 stop27h 42mFrontier
Mon 4/145:58 pmORF - ORD
1 stop26h 06mFrontier
Deal found 4/1$240
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/266:00 amMDW - ORF
1 stop9h 17mFrontier
Sat 8/25:06 pmORF - MDW
1 stop7h 15mFrontier
Deal found 4/1$242
This CheapOair deal was found by Cheapflights users on 4/2. 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.
Fri 4/256:30 amORD - ORF
1 stop7h 14mMultiple Airlines
Sat 5/36:00 amORF - ORD
1 stop12h 41mMultiple Airlines
Deal found 4/2$254
This United Airlines deal was found by Cheapflights users on 4/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/246:20 pmORD - ORF
Nonstop2h 18mUnited Airlines
Sat 5/318:05 pmORF - ORD
1 stop4h 25mUnited Airlines
Deal found 4/2$275
This American Airlines deal was found by Cheapflights users on 4/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/76:43 pmORD - ORF
Nonstop2h 27mAmerican Airlines
Sun 5/118:30 pmORF - ORD
1 stop4h 41mAmerican Airlines
Deal found 4/2$281
This Delta deal was found by Cheapflights users on 4/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/244:15 pmMDW - ORF
1 stop6h 10mDelta
Sun 5/255:35 amORF - MDW
1 stop7h 18mDelta
Deal found 4/2$285
This Delta deal was found by Cheapflights users on 4/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/208:40 amORD - ORF
1 stop7h 42mDelta
Fri 5/303:09 pmORF - ORD
1 stop7h 11mDelta
Deal found 4/2$288
This Southwest deal was found by Cheapflights users on 4/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/89:50 amMDW - ORF
1 stop7h 55mSouthwest
Sat 5/106:30 pmORF - MDW
Nonstop2h 10mSouthwest
Deal found 4/2$304
This Southwest deal was found by Cheapflights users on 4/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/31:50 pmORD - ORF
1 stop7h 05mSouthwest
Mon 6/306:15 amORF - ORD
2 stops11h 10mSouthwest
Deal found 4/2$359

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago 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 3, 2025.
Use the filters below to find and compare flights from Chicago to Chesapeake that are best for you.

Fly from

Chicago

Fly to

Chesapeake

Route

Depart

Return

Price

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 5/8

7:47 am-10:29 am

1 stop25h 42m

Norfolk

Fri 5/9

3:11 pm-8:08 pm

2 stops29h 57m

$238

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 4/11

9:54 am-2:36 pm

1 stop27h 42m

Norfolk

Mon 4/14

5:58 pm-7:04 pm

1 stop26h 06m

$240

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Sat 7/26

6:00 am-4:17 pm

1 stop9h 17m

Norfolk

Sat 8/2

5:06 pm-11:21 pm

1 stop7h 15m

$242

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 4/25

6:30 am-2:44 pm

1 stop7h 14m

Norfolk

Sat 5/3

6:00 am-5:41 pm

1 stop12h 41m

$254

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 5/24

6:20 pm-9:38 pm

Nonstop2h 18m

Norfolk

Sat 5/31

8:05 pm-11:30 pm

1 stop4h 25m

$275

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Wed 5/7

6:43 pm-10:10 pm

Nonstop2h 27m

Norfolk

Sun 5/11

8:30 pm-12:11 am

1 stop4h 41m

$281

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Sat 5/24

4:15 pm-11:25 pm

1 stop6h 10m

Norfolk

Sun 5/25

5:35 am-11:53 am

1 stop7h 18m

$285

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 5/20

8:40 am-5:22 pm

1 stop7h 42m

Norfolk

Fri 5/30

3:09 pm-9:20 pm

1 stop7h 11m

$288

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 5/8

9:50 am-6:45 pm

1 stop7h 55m

Norfolk

Sat 5/10

6:30 pm-7:40 pm

Nonstop2h 10m

$304

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 6/3

1:50 pm-9:55 pm

1 stop7h 05m

Norfolk

Mon 6/30

6:15 am-4:25 pm

2 stops11h 10m

$359

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

Showing 1-10 of 21 results
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Best time to book a flight from Chicago to Chesapeake

Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Chicago 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 to Chesapeake

How far ahead should I book a flight from Chicago to Chesapeake?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Chesapeake. Price data was last updated on March 28, 2025.

The best time to book flights from Chicago to Chesapeake is 73 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 to Chesapeake?

Currently, January is the cheapest month in which you can book a flight from Chicago to Chesapeake (average of $281). Flying from Chicago 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 CHI to C6E?

Find hourly flight availability from Chicago 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 3, 2025.

When flying from Chicago to Chesapeake, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Chicago to Chesapeake?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Chesapeake. Price data was last updated on June 30, 2024.

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

Weekly flight availability from Chicago to Chesapeake

Explore weekly flight availability from Chicago 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 3, 2025.

The most flights from CHI to C6E are scheduled on a Monday (21 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 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 3, 2025.
To help decide which airline to fly from Chicago to Chesapeake, see what other customers have to say about Southwest, Delta and United Airlines. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,274 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

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
4,274 reviews
Southwest
8.0
Very good
4,274 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

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
7,897 reviews
Southwest
8.0
Very good
4,274 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

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
4,274 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

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
4,274 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

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.
Allegiant Air
7.3
Good
732 reviews
Southwest
8.0
Very good
4,274 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

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 Chicago 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 to Chesapeake one-way?

    One-way options have recently been found by users for as low as $75 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $93 and JetBlue from $111 one-way.

  • What are the most reliable airlines from Chicago 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 to Chesapeake on time: Air Canada (80%), Air New Zealand (80%), American Airlines (78%).

  • What are the cheapest flights from Chicago to Chesapeake?

    The cheapest flight price from Chicago to Chesapeake is $139. On average you can expect to pay $291. The most popular route, (Chicago O'Hare Intl - Norfolk), can usually be booked for $193.

  • Can I find deals for flights from Chicago to Chesapeake that include hotel bookings?

    Yes. In addition to deals on Chicago to Chesapeake flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Chesapeake?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Chesapeake.

  • Can I find deals for business class flights from Chicago to Chesapeake?

    Yes. Cheapflights offers flight deals from Chicago 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 to Chesapeake?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Chesapeake (average of $281). Flying from Chicago 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.

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Alternative routes for Chicago to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Chicago to Chesapeake

Discover the top 5 airlines that operate flights from Chicago 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 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$116Average$215FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$167Average$389FlexibilityNo cancel feeOn-time63%
DeltaCheapest$175Average$459FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$200Average$374FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$207Average$418FlexibilityNo cancel feeOn-time69%

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