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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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Nov 10 — Nov 171
Sun 11/10
Sun 11/17
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 Tuesday or Thursday and return on a Saturday

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 5, 2024.

Popular in

July

Cheapest in

January

Round-trip from

$150
(Mytrip)

One-way from

$54
(Frontier)
High demand for flights, 16% potential price rise
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Best time to find cheap flights, 18% 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 5, 2024.

This FareScan deal was found by Cheapflights users on 11/4. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/65:11 pmORD - ORF
1 stop28h 54mSpirit Airlines
Mon 12/95:45 amORF - ORD
1 stop28h 52mSpirit Airlines
Deal found 11/4$215
This Mytrip deal was found by Cheapflights users on 11/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/25:21 amORD - ORF
1 stop8h 15mFrontier
Mon 12/99:54 amORF - ORD
1 stop12h 16mFrontier
Deal found 11/3$223
This Booking.com deal was found by Cheapflights users on 11/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/59:35 amORD - ORF
1 stop23h 39mMultiple Airlines
Sat 12/75:45 amORF - ORD
1 stop11h 21mMultiple Airlines
Deal found 11/4$247
This Priceline deal was found by Cheapflights users on 11/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/87:30 amMDW - ORF
1 stop6h 07mFrontier
Mon 11/114:41 pmORF - MDW
1 stop8h 14mFrontier
Deal found 11/3$298
This American Airlines deal was found by Cheapflights users on 11/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/259:55 amORD - ORF
1 stop4h 23mAmerican Airlines
Tue 12/317:00 amORF - ORD
Nonstop2h 35mAmerican Airlines
Deal found 11/3$315
This Delta deal was found by Cheapflights users on 11/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2510:08 amMDW - ORF
1 stop5h 52mDelta
Tue 12/3110:45 amORF - MDW
1 stop4h 49mDelta
Deal found 11/3$324
This Delta deal was found by Cheapflights users on 11/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/237:05 amORD - ORF
1 stop4h 23mDelta
Sun 11/248:10 amORF - ORD
1 stop7h 15mDelta
Deal found 11/4$325
This Southwest deal was found by Cheapflights users on 11/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/246:20 pmMDW - ORF
Nonstop1h 55mSouthwest
Thu 1/27:45 pmORF - MDW
Nonstop2h 15mSouthwest
Deal found 11/5$341
This United Airlines deal was found by Cheapflights users on 11/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/246:35 pmORD - ORF
Nonstop2h 17mUnited Airlines
Thu 1/28:00 pmORF - ORD
1 stop4h 25mUnited Airlines
Deal found 11/5$350
This Southwest deal was found by Cheapflights users on 11/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2411:25 amORD - ORF
2 stops9h 25mSouthwest
Thu 1/210:05 amORF - ORD
1 stop4h 55mSouthwest
Deal found 11/5$364
This Mytrip deal was found by Cheapflights users on 11/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/146:46 pmMDW - ORF
3 stops27h 14mMultiple Airlines
Sun 11/178:06 pmORF - MDW
2 stops19h 18mMultiple Airlines
Deal found 11/5$418
This Mytrip deal was found by Cheapflights users on 11/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/305:04 pmMDW - ORF
3 stops18h 08mWestJet
Sat 1/47:10 amORF - MDW
3 stops11h 34mWestJet
Deal found 11/3$1,248

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 2,554,862 searches. Data last updated November 5, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Mon 12/9

11:33 am-6:34 pm

1 stop6h 01m

$54

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 12/10

9:58 am-8:13 pm

1 stop9h 15m

$60

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 1/23

12:00 pm-9:36 pm

1 stop8h 36m

$113

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Mon 12/16

6:07 pm-12:42 pm

1 stop17h 35m

$63

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Tue 12/24

6:20 pm-9:15 pm

Nonstop1h 55m

$153

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 11/26

7:10 pm-10:26 pm

Nonstop2h 16m

$153

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Tue 12/24

6:00 am-1:46 pm

1 stop6h 46m

$162

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sun 12/15

11:15 am-2:27 pm

Nonstop2h 12m

$188

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Fri 11/22

9:09 pm-10:55 pm

2 stops24h 46m

$136

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Tue 12/31

11:48 am-12:12 pm

3 stops23h 24m

$380

Flights are sorted by cheapest first

Deals found on 11/5

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 1, 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.

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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 5, 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.

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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 5, 2024.

The most flights from CHI to C6E are scheduled on a Tuesday (17 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (13 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 5, 2024.
To help decide which airline to fly from Chicago to Chesapeake, see what other customers have to say about Frontier, Spirit Airlines and American Airlines. 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
5,082 reviews

Crew

8.7

Boarding

8.3

Food

7.2

Comfort

8.1

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

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

Southwest
8.1
Very good
5,082 reviews
Southwest
8.1
Very good
5,082 reviews

Crew

8.7

Boarding

8.3

Food

7.2

Comfort

8.1

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

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

Delta
8.0
Very good
8,830 reviews
Southwest
8.1
Very good
5,082 reviews

Crew

8.7

Boarding

8.3

Food

7.2

Comfort

8.1

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

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

United Airlines
7.4
Good
9,215 reviews
Southwest
8.1
Very good
5,082 reviews

Crew

8.7

Boarding

8.3

Food

7.2

Comfort

8.1

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

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

WestJet
7.3
Good
2,800 reviews
Southwest
8.1
Very good
5,082 reviews

Crew

8.7

Boarding

8.3

Food

7.2

Comfort

8.1

Entertainment

7.7

Overall

8.1

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
5,082 reviews

Crew

8.7

Boarding

8.3

Food

7.2

Comfort

8.1

Entertainment

7.7

Overall

8.1

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.

  • Can I find flights from Chicago to Chesapeake for under $200 on Cheapflights?

    Yes, there are multiple flights from Chicago to Chesapeake for under $200. The cheapest flight booked recently is on Frontier for just $150, but on average you can expect to pay $396.

  • Are there nonstop flights from Chicago to Chesapeake for under $400 on Cheapflights?

    Cheapflights has at least 3 direct flights from Chicago to Chesapeake under $400. A good price for a nonstop flight from Chicago to Chesapeake is less than $335.

  • Are there last-minute flights available from Chicago to Chesapeake for under $300?

    There are currently 8+ open flights from Chicago to Chesapeake within the next 7 days for less than $300.

  • 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 $60 and Southwest from $153 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 (98%), Piedmont Airlines (95%), American Airlines (90%).

  • What are the cheapest flights from Chicago to Chesapeake?

    The cheapest flight price from Chicago to Chesapeake is $88. On average you can expect to pay $318. The most popular route, (Chicago O'Hare Intl - Norfolk), can usually be booked for $162.

  • What does ORD to RIC mean?

    ORD stands for Chicago O'Hare Intl Airport, while RIC stands for Richmond Byrd Intl Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry. While you’re still figuring out your travel plans, it’s not a bad idea to learn the names and codes of other airports around these areas: Norfolk Airport (ORF), Newport News Intl Airport (PHF), Pitt-Greenville Airport (PGV).

  • Can I find deals for flights from Chicago to Chesapeake that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Chesapeake flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Chesapeake with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Chesapeake flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Chicago to Chesapeake that allow pets onboard?

    Many airlines flying from Chicago to Chesapeake offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Chesapeake?

    Yes, you can often find last-minute deals on Chicago to Chesapeake flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Chesapeake flight deals updated?

    The Chicago to Chesapeake flight deals you see on this page were last updated on 11/5.

  • 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.

See more FAQs

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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 Reagan-National flights
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Top 4 airlines flying from Chicago to Chesapeake

Discover the top 4 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 2,554,862 searches. Data last updated November 5, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$116Average$197FlexibilityNo cancel feeOn-time65%
DeltaCheapest$186Average$391FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$201Average$398FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$203Average$360FlexibilityNo cancel feeOn-time71%
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