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Chesapeake

$54+ 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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The best prices from Chicago to Chesapeake are usually found in January or April, booked 73 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

Cheap flight deals from Chicago to Chesapeake

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Chesapeake (C6E). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 21, 2024.

Popular in

July

Cheapest in

January

Round-trip from

$218
(FlightHub)

One-way from

$54
(Frontier)
High demand for flights, 15% potential price rise
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Best time to find cheap flights, 19% potential price drop
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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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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 November 21, 2024.

This FlightHub deal was found by Cheapflights users on 11/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/61:13 pmORD - ORF
1 stop6h 11mMultiple Airlines
Mon 12/99:54 amORF - ORD
1 stop12h 16mMultiple Airlines
Deal found 11/20$218
This CheapOair deal was found by Cheapflights users on 11/20. 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 12/61:13 pmORD - ORF
1 stop6h 11mSpirit Airlines
Sun 12/89:19 pmORF - ORD
1 stop22h 31mSpirit Airlines
Deal found 11/20$252
This United Airlines deal was found by Cheapflights users on 11/19. 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.
Thu 12/126:00 amORD - ORF
1 stop4h 22mUnited Airlines
Mon 12/166:30 amORF - ORD
Nonstop2h 23mUnited Airlines
Deal found 11/19$267
This Frontier deal was found by Cheapflights users on 11/21. 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.
Mon 12/911:33 amMDW - ORF
1 stop6h 01mFrontier
Fri 12/139:54 amORF - MDW
1 stop8h 18mFrontier
Deal found 11/21$274
This Southwest deal was found by Cheapflights users on 11/20. 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.
Fri 12/1311:25 amORD - ORF
2 stops11h 00mSouthwest
Sun 12/155:30 pmORF - ORD
1 stop5h 30mSouthwest
Deal found 11/20$281
This American Airlines deal was found by Cheapflights users on 11/20. 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 12/258:40 amORD - ORF
Nonstop2h 19mAmerican Airlines
Tue 12/316:06 pmORF - ORD
1 stop4h 46mAmerican Airlines
Deal found 11/20$286
This Delta deal was found by Cheapflights users on 11/20. 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.
Thu 12/195:40 amORD - ORF
1 stop4h 37mDelta
Wed 12/256:00 amORF - ORD
1 stop7h 32mDelta
Deal found 11/20$311
This Delta deal was found by Cheapflights users on 11/20. 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.
Thu 12/196:00 amMDW - ORF
1 stop4h 17mDelta
Wed 12/2512:55 pmORF - MDW
1 stop4h 15mDelta
Deal found 11/20$317
This Frontier deal was found by Cheapflights users on 11/19. 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 11/225:15 amORD - ORF
1 stop8h 21mFrontier
Mon 11/253:46 pmORF - ORD
1 stop9h 20mFrontier
Deal found 11/19$318
This Southwest deal was found by Cheapflights users on 11/21. 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.
Fri 12/138:25 pmMDW - ORF
Nonstop1h 55mSouthwest
Wed 12/184:40 pmORF - MDW
1 stop6h 40mSouthwest
Deal found 11/21$327
This Mytrip deal was found by Cheapflights users on 11/20. 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.
Tue 12/39:30 amMDW - ORF
3 stops33h 43mMultiple Airlines
Tue 12/105:10 pmORF - MDW
3 stops26h 22mMultiple Airlines
Deal found 11/20$942

Find flights from Chicago to Chesapeake within your budget

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 2,612,795 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 12/17

11:25 am-8:13 pm

2 stops7h 48m

Norfolk

Wed 12/18

9:45 am-2:36 pm

1 stop5h 51m

$201

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Wed 12/11

11:45 am-8:13 pm

1 stop7h 28m

Norfolk

Mon 12/16

7:24 pm-10:28 am

1 stop16h 04m

$220

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 12/17

6:25 pm-9:40 pm

Nonstop2h 15m

Norfolk

Wed 12/18

3:30 pm-4:53 pm

Nonstop2h 23m

$237

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Wed 12/25

9:55 am-3:18 pm

1 stop4h 23m

Norfolk

Tue 12/31

5:52 am-11:11 am

1 stop6h 19m

$256

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Mon 1/13

5:07 pm-10:21 pm

1 stop4h 14m

Norfolk

Tue 1/28

7:30 am-12:46 pm

1 stop6h 16m

$276

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 12/12

7:20 am-12:15 pm

1 stop3h 55m

Norfolk

Sat 12/14

5:40 pm-6:55 pm

Nonstop2h 15m

$277

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 12/19

5:40 am-11:17 am

1 stop4h 37m

Norfolk

Wed 12/25

6:00 am-12:32 pm

1 stop7h 32m

$311

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sun 12/22

7:29 pm-11:02 am

1 stop14h 33m

Norfolk

Sun 12/29

9:01 pm-9:54 am

1 stop13h 53m

$323

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sun 1/5

4:00 pm-11:40 pm

1 stop6h 40m

Norfolk

Sun 1/12

2:40 pm-10:20 pm

2 stops8h 40m

$340

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 12/25

10:50 am-12:42 pm

1 stop24h 52m

Norfolk

Tue 12/31

1:42 pm-9:55 am

1 stop21h 13m

$483

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

Showing 1-10 of 23 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.

Travel insights for flights from Chicago to Chesapeake

Get recent, data-driven insights about flights from Chicago to Chesapeake including ideal travel times, pricing trends, and more.

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 November 15, 2024.

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 $279). Flying from Chicago to Chesapeake in June is currently the most expensive (average of $360). 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 November 21, 2024.

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 November 21, 2024.

The most flights from CHI to C6E are scheduled on a Thursday (21 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 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 November 21, 2024.
To help decide which airline to fly from Chicago to Chesapeake, see what other customers have to say about Spirit Airlines, American Airlines and Southwest. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,005 reviews

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,005 reviews
Southwest
8.1
Very good
5,005 reviews

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,755 reviews
Southwest
8.1
Very good
5,005 reviews

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,172 reviews
Southwest
8.1
Very good
5,005 reviews

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,811 reviews
Southwest
8.1
Very good
5,005 reviews

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
5,005 reviews

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $54 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $89 and Southwest from $119 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 Wisconsin (96%), ANA (90%), Envoy Air (88%).

  • What are the cheapest flights from Chicago to Chesapeake?

    The cheapest flight price from Chicago to Chesapeake is $174. On average you can expect to pay $358. The most popular route, (Chicago O'Hare Intl - Norfolk), can usually be booked for $160.

  • 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 $279). Flying from Chicago to Chesapeake in June is currently the most expensive (average of $360). 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.
O'Hare Intl to Dulles Intl flights
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O'Hare Intl to Staunton flights

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 2,612,795 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$116Average$205FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$117Average$384FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$191Average$403FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$200Average$360FlexibilityNo cancel feeOn-time71%
DeltaCheapest$256Average$457FlexibilityNo cancel feeOn-timeN/A
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