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Chesapeake

$79+ 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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Aug 7 — Aug 141
Thu 8/7
Thu 8/14
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Chesapeake are usually found in September or November, 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 August 2, 2025.

Round-trip from

$223
(Mytrip)

One-way from

$79
(FlightHub)

Popular in

June

Cheapest in

September

Average price

$372
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. 3% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 2, 2025.

This Mytrip deal was found by Cheapflights users on 8/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/311:36 amORD - ORF
1 stop9h 13mSpirit Airlines
Thu 9/45:38 pmORF - ORD
2 stops23h 40mSpirit Airlines
Deal found 8/1$223
This United Airlines deal was found by Cheapflights users on 7/31. 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 8/216:30 pmORD - ORF
Nonstop2h 22mUnited Airlines
Mon 8/256:15 amORF - ORD
1 stop6h 31mUnited Airlines
Deal found 7/31$227
This FlightHub deal was found by Cheapflights users on 7/31. 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.
Mon 9/227:15 amMDW - ORF
1 stop9h 36mFrontier
Sun 9/285:47 pmORF - MDW
1 stop14h 36mFrontier
Deal found 7/31$235
This Delta deal was found by Cheapflights users on 7/31. 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 8/216:04 amMDW - ORF
1 stop7h 31mDelta
Sat 8/233:30 pmORF - MDW
1 stop6h 42mDelta
Deal found 7/31$237
This Southwest deal was found by Cheapflights users on 7/31. 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 8/2111:10 amMDW - ORF
Nonstop2h 05mSouthwest
Mon 8/256:15 pmORF - MDW
Nonstop2h 05mSouthwest
Deal found 7/31$239
This American Airlines deal was found by Cheapflights users on 7/31. 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.
Thu 8/282:24 pmORD - ORF
Nonstop2h 18mAmerican Airlines
Tue 9/26:21 pmORF - ORD
Nonstop2h 29mAmerican Airlines
Deal found 7/31$239
This CheapOair deal was found by Cheapflights users on 7/31. 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.
Sun 8/176:56 amORD - ORF
1 stop8h 43mMultiple Airlines
Sun 8/244:12 pmORF - ORD
1 stop8h 42mMultiple Airlines
Deal found 7/31$265

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 August 2, 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

Wed 9/3

11:36 am-9:49 pm

1 stop9h 13m

Norfolk

Thu 9/4

5:38 pm-5:39 pm

3 stops25h 01m

$223

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 8/21

6:30 pm-9:52 pm

Nonstop2h 22m

Norfolk

Mon 8/25

6:15 am-11:46 am

1 stop6h 31m

$227

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Mon 9/22

7:15 am-5:51 pm

1 stop9h 36m

Norfolk

Sun 9/28

5:47 pm-7:23 am

1 stop14h 36m

$235

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 8/21

6:04 am-2:35 pm

1 stop7h 31m

Norfolk

Sat 8/23

3:30 pm-9:12 pm

1 stop6h 42m

$237

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 8/21

11:10 am-2:15 pm

Nonstop2h 05m

Norfolk

Mon 8/25

6:15 pm-7:20 pm

Nonstop2h 05m

$239

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 8/28

2:24 pm-5:42 pm

Nonstop2h 18m

Norfolk

Tue 9/2

6:21 pm-7:50 pm

Nonstop2h 29m

$239

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sun 8/17

6:56 am-4:39 pm

1 stop8h 43m

Norfolk

Sun 8/24

4:12 pm-11:54 pm

1 stop8h 42m

$265

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 9/2

6:56 am-4:25 pm

1 stop8h 29m

$79

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 10/8

8:00 am-2:27 pm

1 stop5h 27m

$89

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 10/11

6:00 am-2:27 pm

1 stop7h 27m

$89

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/1

Showing 1-10 of 17 results
1
2

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 July 25, 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 March is currently the most expensive (average of $351). 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 August 2, 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 July 27, 2025.

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 evenings 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 August 2, 2025.

The most flights from CHI to C6E are scheduled on a Saturday (28 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (13 on average).

How much does it cost to fly round-trip from Chicago 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 August 2, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Chicago to Chesapeake to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,983 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,904 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Spirit Airlines
6.3
Okay
8,054 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $79 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $89 and Southwest from $109 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: Envoy Air (92%), Republic Airways (83%), GoJet (81%).

  • What are the cheapest flights from Chicago to Chesapeake?

    The cheapest flight price from Chicago to Chesapeake is $90. On average you can expect to pay $286. The most popular route, (Chicago O'Hare Intl - Norfolk), can usually be booked for $179.

  • 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 March is currently the most expensive (average of $351). 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 August 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$79Average$245FlexibilityNo cancel feeOn-time65%
DeltaCheapest$142Average$366FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$209Average$429FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$210Average$395FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$230Average$379FlexibilityNo cancel feeOn-time63%

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