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Chesapeake

$58+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
nov. 29 — déc. 61
sam. 11/29
sam. 12/6
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Chesapeake are usually found in September or February, booked 68 days in advance, depart on a Wednesday or Tuesday 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 octobre 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$110
(Frontier)

One-way from

$58
(Mytrip)

Popular in

June

Cheapest in

September

Average price

$415
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. 3% potential increase in price ($13 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 October 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 octobre 30, 2025.

This Frontier deal was found by Cheapflights users on 10/30. 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.
jeu. 11/136:30 amMDW - ORF
1 stop6h 55mFrontier
lun. 11/1711:29 amORF - MDW
1 stop11h 42mFrontier
Deal found 10/30$110
This Priceline deal was found by Cheapflights users on 10/29. 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.
jeu. 11/135:25 amORD - ORF
1 stop6h 50mFrontier
jeu. 11/133:20 pmORF - ORD
1 stop9h 51mFrontier
Deal found 10/29$110
This Priceline deal was found by Cheapflights users on 10/30. 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.
jeu. 11/135:25 amORD - ORF
1 stop6h 50mFrontier
lun. 11/1711:29 amORF - ORD
1 stop6h 27mFrontier
Deal found 10/30$127
This Priceline deal was found by Cheapflights users on 10/29. 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.
jeu. 11/65:01 amORD - ORF
1 stop4h 45mFrontier
jeu. 11/133:20 pmORF - ORD
1 stop9h 51mFrontier
Deal found 10/29$143
This Priceline deal was found by Cheapflights users on 10/29. 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.
mer. 11/1210:52 amORD - ORF
1 stop7h 06mMultiple Airlines
jeu. 11/133:20 pmORF - ORD
1 stop9h 51mMultiple Airlines
Deal found 10/29$158
This Frontier deal was found by Cheapflights users on 10/30. 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.
lun. 12/86:15 amMDW - ORF
1 stop9h 05mFrontier
ven. 12/1212:00 pmORF - MDW
1 stop8h 42mFrontier
Deal found 10/30$166
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 11/237:09 pmORD - ORF
1 stop13h 34mMultiple Airlines
mar. 12/29:26 pmORF - ORD
1 stop19h 37mMultiple Airlines
Deal found 10/29$167
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 11/206:23 pmORD - ORF
1 stop25h 08mMultiple Airlines
mar. 12/29:26 pmORF - ORD
1 stop19h 37mMultiple Airlines
Deal found 10/29$172
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 12/46:15 amORD - ORF
1 stop12h 01mMultiple Airlines
jeu. 12/118:38 amORF - ORD
1 stop6h 43mMultiple Airlines
Deal found 10/28$174
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 11/237:09 pmORD - ORF
1 stop13h 34mMultiple Airlines
lun. 12/19:26 pmORF - ORD
1 stop26h 40mMultiple Airlines
Deal found 10/29$179
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/246:48 amORD - ORF
1 stop12h 43mSpirit Airlines
mar. 12/29:26 pmORF - ORD
1 stop19h 37mSpirit Airlines
Deal found 10/29$181
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 11/206:23 pmORD - ORF
1 stop25h 08mMultiple Airlines
lun. 12/19:26 pmORF - ORD
1 stop26h 40mMultiple Airlines
Deal found 10/29$183

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 octobre 30, 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

jeu. 11/13

5:11 am-2:25 pm

1 stop8h 14m

Norfolk

lun. 11/17

11:29 am-4:56 pm

1 stop6h 27m

$150

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

mer. 11/12

2:06 pm-1:15 pm

2 stops22h 09m

Norfolk

dim. 11/16

9:03 pm-8:32 am

1 stop12h 29m

$187

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

sam. 12/6

7:10 am-7:16 pm

1 stop11h 06m

Norfolk

lun. 12/8

8:38 am-2:21 pm

1 stop6h 43m

$212

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

jeu. 12/11

5:00 am-7:16 pm

1 stop13h 16m

Norfolk

jeu. 12/18

3:01 pm-12:30 am

1 stop10h 29m

$217

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

dim. 1/18

2:12 pm-10:54 am

1 stop19h 42m

Norfolk

dim. 1/25

1:10 pm-11:25 pm

2 stops35h 15m

$237

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

mar. 11/25

6:05 am-2:55 pm

1 stop7h 50m

Norfolk

lun. 12/1

9:26 pm-8:46 am

2 stops36h 20m

$256

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

jeu. 11/13

12:17 pm-6:58 pm

3 stops29h 41m

Norfolk

lun. 11/17

7:53 pm-6:34 pm

2 stops23h 41m

$256

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

sam. 12/13

1:25 pm-4:20 pm

Nonstop1h 55m

Norfolk

sam. 1/10

11:15 am-4:55 pm

1 stop6h 40m

$285

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

mar. 11/25

5:00 am-12:28 pm

1 stop6h 28m

Norfolk

jeu. 11/27

9:56 am-2:14 pm

1 stop5h 18m

$296

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

sam. 12/6

7:10 am-2:25 pm

1 stop6h 15m

Norfolk

lun. 12/8

7:23 am-9:02 am

Nonstop2h 39m

$304

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 39 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 October 24, 2025.

The best time to book flights from Chicago to Chesapeake is 68 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, February is the cheapest month in which you can book a flight from Chicago to Chesapeake (average of $149). Flying from Chicago to Chesapeake in January is currently the most expensive (average of $270). 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 octobre 30, 2025.

One of the essential ways to save on airfare from Chicago to Chesapeake is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 18% on airfare.

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 October 26, 2025.

Travelers seeking maximum savings on their Chicago to Chesapeake flight should consider departing on Wednesday mornings 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.

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 octobre 30, 2025.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American 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
4,242 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,998 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,030 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,123 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Chicago to Chesapeake?

    For as low as $285, Frontier can have you in Chesapeake from Chicago in 1h 55m. The distance from Chicago to Chesapeake is about 702 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $95 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $114 and United Airlines from $129 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: Republic Airways (92%), Envoy Air (88%), United Airlines (83%).

  • What are the cheapest flights from Chicago to Chesapeake?

    The cheapest flight price from Chicago to Chesapeake is $115. On average you can expect to pay $322. The most popular route, (Chicago O'Hare Intl - Norfolk), can usually be booked for $141.

  • 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, February is the cheapest month in which you can book a flight from Chicago to Chesapeake (average of $149). Flying from Chicago to Chesapeake in January is currently the most expensive (average of $270). 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 Dulles Intl 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 2,558,603 searches. Data last updated octobre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$78Average$224FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$218Average$424FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$230Average$363FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$237Average$395FlexibilityNo cancel feeOn-time71%

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